Annie Tsai is the Chief Operating Officer of Interact, Early-Stage Investor & Advisor, Author & Columnist, and Community Builder behind “The Business Side of AI” newsletter. In this conversation, we’re talking about the most powerful AI feature most people are skipping, and why starting with “doing” instead of “thinking” costs you more than you realize.

The difference between AI that makes you faster and AI that makes you better comes down to one step most people skip entirely: planning.

Cassie: You mentioned you spent International Women’s Day volunteering with first-time builders using AI tools. What did you notice?

Annie: The same thing kept happening. Someone would show me what they were working on, and they had started building without a clear problem statement. Sometimes they’d gotten so deep into one feature that they’d lost the thread of what the thing was even supposed to do.

Every single time, I asked: “Did you go into plan mode first?”

And every single time, I got uncertainty. Plan mode had never come up. They simply hadn’t been made aware this was an option.

I left wondering: if 150 motivated builders in one room had never heard of plan mode, how many millions are opening these tools every day and going straight to “doing” because no one told them there was another way to start?

Cassie: Explain plan mode and why it matters.

Annie: Plan mode is a real capability in most major AI tools, and most people have never used it.

In Lovable, there’s a “Plan” button. Click it before your first message, and instead of immediately generating an app, it asks clarifying questions about your vision, constraints, tradeoffs. It helps you explore approaches before anything is built.

In Cursor, you hit Shift + Tab to trigger it. In Claude and ChatGPT, there’s no button—you have to prompt your way into it. And that’s the problem, because most people don’t know to do it.

Cassie: This feels so foundational—something product managers know really well but most people skip entirely.

Annie: Exactly. The single most important lesson I keep relearning: the most expensive mistake you can make is solving the wrong problem efficiently.

In product, we call this being solution-focused versus problem-obsessed. Solution-focused is when you start building toward a feature. Problem-obsessed is when you slow down to ask—what problem am I solving, for whom, and how will I know when I’ve solved it?

Teams that skip this build things that are technically impressive and functionally off.

Teams that do this well ship faster, with less rework, and end up with products people actually use.

AI tools only accelerate this dynamic. If you’re problem-obsessed before you prompt, outputs are dramatically better. If you’re solution-focused, you generate your way into the wrong thing at unprecedented speed.

Cassie: For someone without a product management background, how do you actually do this?

Annie: Before I build anything meaningful with AI, I write a rough PRD—a product requirements document. It’s more a thinking document than a handoff doc.

I think through: what problem am I solving, who is it for, what does success look like, what are the constraints?

I work through that with my AI as a thought partner, not a builder. By the time I’m done, I have a brief I can execute against.

Every output downstream is better for it.

Cassie: What if your tool doesn’t have a “plan mode” button?

Annie: Here are prompts that shift the mode:

“Before we build anything, I want to make sure I’m focusing on the right problem. Ask me questions until you can summarize my actual goal, who it’s for, and what success looks like.”

“What assumptions am I making that are most likely to be wrong?”

“Help me write a one-page brief for this before we start. What do you need to know from me?”

“What am I probably not thinking about? What are the most common failure modes for something like this?”

Every one of these asks your AI to help you think before you ask it to produce. That’s the whole move.

Cassie: For someone who wants to start using AI this way, what’s one thing they could do this week?

Annie: Before you ask AI to write, build, or generate anything, spend fifteen minutes in planning mode.

If you’re building something: “I want to build [thing]. Before we write any code, help me work through the problem. Who has this problem? What have they tried? What does a good solution need to do?”

If you’re making a decision: “I’m trying to decide [decision]. Help me map the assumptions I’m making and identify the ones most likely to be wrong.”

If you’re creating content: “I need to write [piece]. Before you draft anything, help me get clear on the one thing I want the reader to feel or do.”

The planning conversation becomes the brief, the brief becomes the prompt, and the output much more closely meets your expectations.

Plan first, build second. Everything downstream gets better.

Cassie: Thanks, Annie. The most expensive mistake you can make is solving the wrong problem efficiently—and AI will help you do exactly that unless you slow down first.

Want more from Annie on using AI strategically? Subscribe to The Business Side of AI for practical insights that actually work in the real world.

Emily Parkhurst is the founder of Formidable, a media and membership company dedicated to getting more women’s voices into the press and onto stages. A former journalist with nearly 20 years in newsrooms—including as Publisher and President of the Puget Sound Business Journal—Emily saw firsthand how underrepresented women are as expert sources. She founded Formidable to change that. In this conversation, we’re talking about why women struggle to position themselves as experts, and how to actually build relationships with journalists that open doors.

A few weeks ago, I published a conversation with Stephiney Foley about building a personal brand without feeling like a self-promoter. The feedback I heard most often: “This is great, but I’m not ready.”

That’s exactly why this conversation with Emily matters. Because “not ready” is the thing holding women back from being visible, from being heard, and from building the influence we deserve.

Cassie: Let’s start with Formidable. You founded it because you saw how underrepresented women are in media coverage. What were you seeing in newsrooms that made you realize this needed to change?

Emily: The vast majority of media coverage has been and continues to be written through a male lens. As a result, readership often skews male, as do media leadership teams. This became a self-fulfilling prophecy that traditional media companies have struggled to reverse. Women’s issues were often relegated to lifestyle sections rather than being integrated into comprehensive news coverage.

As a journalist, I spent years actively trying to diversify my sources. I would call people, reach out, search for women experts. And what I kept finding was that women were waiting to be asked. And even when you asked, they’d often decline to speak to me. They were waiting to be “ready.”

Reporters want diverse sources. They need them. But if you’re not visible, if you’re not putting yourself out there, they can’t find you. And that’s a problem we can actually fix.

Cassie: You’ve said that one of the key things holding women back from being heard more is being comfortable telling our story and positioning ourselves as experts. Why do you think women struggle with this more than men?

Emily: Women are constantly trying to check all the boxes before they feel qualified to speak up. We think we need one more certification, one more year of experience, one more credential before we’re “ready” to be an expert.

Men don’t do that. They see an opportunity and they take it. They recommend each other based on potential, not just proven track record.

And here’s the thing: journalists don’t need you to be the world’s foremost expert on a topic. They need you to have a perspective, to be able to speak intelligently about something in real time, and to be responsive when they’re on deadline.

If you have three things you can talk about for 10 minutes with zero preparation, you’re an expert. You don’t need permission. You don’t need to wait until you feel “ready.” You just need to start.

Cassie: For women who want to get more visible but feel uncomfortable with self-promotion, what’s the most important mindset shift they need to make?

Emily: Stop thinking about it as self-promotion. Think about it as service.

Journalists are people. They’re overwhelmed. They’re on tight deadlines. They’re looking for good sources who can help them tell important stories. If you have expertise that can help them do their job better, you’re not bothering them by reaching out—you’re helping them.

The other shift is understanding that visibility isn’t about being loud or performative. It’s about being useful. It’s about building relationships before you need something. It’s about treating journalists like human beings, not just people who can give you coverage.

Follow journalists on social media. Engage with their work. Comment on their stories. Send them an email that says, “Hey, I really loved your piece on X. Thanks for covering this.” You’ll make their day. And when you do eventually reach out with a pitch or an idea, they’ll actually remember you.

Cassie: And practically speaking—if someone reading this wants to start building relationships with journalists in their industry, what’s one thing they could do this week?

Emily: Pick three journalists who cover your industry or your area of expertise. Follow them on LinkedIn and other social channels. Read their recent work. Then send each of them a short, genuine email that says something like:

“Hi [Name], I’ve been following your coverage of [topic] and really appreciated your recent piece on [specific story]. I work in this space and would love to be a resource for you if you’re ever looking for sources or perspectives on [your area of expertise]. No pitch, just wanted to introduce myself.”

That’s it. Don’t ask for anything. Don’t pitch yourself. Just introduce yourself as someone who appreciates their work and is willing to be helpful.

Most people never do this. And the ones who do? They’re the ones journalists remember when they need an expert on deadline.

Cassie: This is exactly what I mean when I talk about influence without losing yourself. Getting visible isn’t about being loud or self-promotional. It’s about recognizing that your expertise has value—and that staying quiet doesn’t serve anyone.

Emily’s right: journalists are actively looking for women experts. They want to diversify their sources. But if you’re waiting to be ‘ready’ or waiting for permission, you’re making their job harder and yours invisible.

Want to learn more? Formidable helps women build media strategies, develop their personal brands, and get their voices heard. I highly recommend getting it in your inbox. Learn more and subscribe here!

April Rinne is a global change navigator, trusted advisor to the world’s leading organizations, and author of FLUX: 8 Superpowers for Thriving in Constant Change. Her career portfolio includes speaker, author, futurist, advisor, lawyer, hiking guide, global development executive, investor, and yoga practitioner. April and I met years ago through a shared passion: working to create better conditions for people charting self-employed paths. She’s brilliant, generous, and one of those rare thinkers who sees what’s coming before the rest of us do. In this conversation, we explore why the career ladder is broken, what a career portfolio actually is, and how to build one that brings out your best.

Fifteen years into my career, I made what felt like a risky move: leaving communications for business operations and product leadership. Twenty-five years later, I’m building a different kind of portfolio—executive advisor, board member, speaker, Career Hack. Each transition looked uncertain from the inside. Looking back, they weren’t disruptions to my career. They were the career.

April Rinne has a name for this. She calls it a “career portfolio”—one of the 8 Flux Superpowers in her book FLUX. This conversation gave me language for what I’ve lived, and a framework for what comes next. If your path has been anything but linear, you’ll find yours here too.

Cassie: Let’s start with the fundamental shift. Why is the career ladder model broken, and what’s a career portfolio?

April: The career ladder assumes a predictable, linear path: start at the bottom, work your way up, reach the top (where “success” is supposed to be). But that’s not how the world works anymore—and honestly, it never fully captured how people build meaningful, successful careers.

A career portfolio is your unique combination of everything you can do that adds value to society. It is so much more than your resume or LinkedIn profile! It’s holistic, ever-evolving, and future-fit. It acknowledges that you’re not just one thing, that your skills and interests intersect in unique ways, and that the future of work requires flexibility and continuous learning.

Unlike the ladder, a career portfolio brings out your best and maximizes your potential. It’s also extremely helpful for navigating times of change and uncertainty, both in the workplace and the broader world.

Cassie: This feels liberating and also a little scary. Most of us were raised on the ladder model. When did you first realize it didn’t work for you?

April: Even as a child, the career ladder felt odd. When people asked what I wanted to do when I grew up, I never had one answer. I wanted to do things that hadn’t been done before, to constantly learn, and to stay open to change. My parents were both teachers – and for a long time I thought I might teach too, because it would allow me to keep learning – but I was really interested in what was happening all over the place, not just in the classroom.

When I was 20 and studying overseas, the unthinkable happened: Both of my parents died in a car crash. In an instant, my entire life changed – including how I thought about my career development. I had to grow up fast and figure out: What really mattered to me, and how would I take care of myself?

As you might imagine, this experience had a profound effect on me – and continues to shape my work and life today. I realized how short and fragile life could be. I looked around and paid attention to who was truly thriving. I imagined if I were to die tomorrow… and I realized I didn’t want to be stuck on a rung of the ladder, waiting for someone else to tell me when I’d reached success. I wanted to build something different. (A portfolio, but I didn’t have that term yet.)

For the past 25 years, I’ve been curating my own portfolio. In the beginning, I got flak for it. Even though I’d been through a lot personally, I was still told that my career made no sense, that I wasn’t serious, that my goals would crash… that I should climb the ladder. And yet, quite the opposite was true.

Today my portfolio includes speaker, author, futurist, advisor, lawyer, hiking guide, global development executive, investor, yoga practitioner—and also orphan, globetrotter, trail runner, insatiable hand-stander, and mental health advocate.

People used to say doing so many things was a sign of ADHD or simply impossible. Today they ask how they can do it too.

Cassie: For someone who’s been on the traditional path, starting a portfolio can feel overwhelming—even irresponsible. How do you actually begin, especially if you’re not ready to blow up your career?

April: The first thing to remember is: you already have one—even if you don’t realize it, even if you’ve never had a paid job. I love this, because “beginning” is already underway.

The simplest first step is to map out your current portfolio. What is every skill you have that can be helpful to others? Write it down. Map it out. Draw connections between skills. Don’t overthink it; just get an inventory of everything that’s there.

Include any role or activity where you’ve created value and served others: traditional jobs, yes, but also freelance work, volunteering, side hustles, passion projects, caregiving, supporting family and friends.

Your portfolio should also include experiences that are customarily left off your resume, yet fundamentally make you, you. For example, my status as an orphan, globetrotter, and mental health advocate are essential components of my portfolio. They power the work that I do.

Remember: Your portfolio is created by you, not determined by hiring managers. It includes your unique combination of skills, experiences, and talents that can be mixed, matched, and blended in different ways.

Start with a simple list. Then make connections between the things in it—that’s where the real value lives.

Cassie: Once you’ve identified what’s in your portfolio, how do you talk about it in a way that makes employers see value instead of chaos?

April: Employers are hungry to hire talent with non-traditional backgrounds, but they often need help. Your portfolio narrative is the link—it’s the story you tell to make connections between the skills people are hiring for and the skills you’ve developed. Just like creating your portfolio, you are responsible for writing your narrative – and doing so well can open more doors than you might expect.

When I was a hiking and biking guide, some people said my career looked frivolous. What they didn’t see was that I was working 18-hour days, learning how to project manage, balance budgets, build teams, ensure safety, and spark joy. I got a practical mini-MBA on the trail and perspective that shaped the rest of my life.

Often, I had to fill in these gaps for others. I did this in my narrative. Being able to explain why my experience was valuable didn’t just shape my portfolio. It helped me stand out from other candidates.

Telling a good portfolio narrative requires understanding how the different things in your portfolio enhance one another. I like to think of this as “1+1=11”: Your combination of skills is far more valuable than any of them on their own. Tell a story about when skills from unrelated parts of your life were helpful in unexpected ways. For example, how something you learned as part of a hobby – perhaps teamwork, or discipline, or following your curiosity – served you well in a professional setting, or how being a parent has changed you as a leader.Cassie: You’ve said it’s never been easier to build a career portfolio—and also never been more necessary, especially in the AI era. Why now?

April: The macro forces driving the future of work demand independent and adaptable thinkers. Automation, the Great Resignation, hybrid offices—it’s clear the time is ripe to rethink what a successful career path looks like. This has been the case for many years, even a couple decades already.

And yet, here’s the real kicker: despite having worked on this concept for 20+ years, it has never been more necessary, more relevant, or more valuable than in today’s era of AI. AI is shifting the value of a portfolio from “nice to have” to “must-have.”

The skills at the heart of your portfolio are often the ones that can’t be eliminated by technology. They’re uniquely human. And yet, all too often they’re not even on your resume, yet they shape and define your professional success—and will do so even more moving forward. So it’s really important for people to know this about you!

Those who build a career portfolio now will be more prepared to pitch themselves for—and even create—new opportunities, as they’ll be well-practiced at making creative connections between their skills and the jobs they want to pursue.

Cassie: For people who feel like they need to have their whole portfolio mapped out before they can start, or worry they’re “too late” to build one, what would you say?

April: You don’t need to have it all figured out. That’s the beauty of a portfolio. Because it’s not focused on a singular end, it gives you more space to test out different things and find your way.

For all the things you can’t control in today’s world, taking ownership of your portfolio is one that you can. You can start today.

Cassie: This conversation shifted something for me. For years, I thought my non-linear path was a liability. But April’s framework reframes all of it. None of the moves were detours. They were the portfolio. And the “1+1=11” principle is exactly right—the combination of those experiences is what makes me valuable, not any single one.

For women especially, this matters. We’re so often told to specialize, to stay in our lane, to prove ourselves in one domain before we’re allowed to expand. But the future doesn’t reward narrow expertise. It rewards people who can connect dots, cross-pollinate ideas, and adapt.

Your portfolio is already being built. The question is whether you’re tracking it, telling its story well, and using it strategically—not just to build a career you like, but to design a life you love.

Want to dive deeper? Check out April’s book FLUX: 8 Superpowers for Thriving in Constant Change and follow her on LinkedIn for insights on navigating the future of work.

Stephiney Foley is the Founder and CEO (Chief Mom!) at Yuzi, a maternal care platform focused on supporting mothers through postpartum. She’s been featured in Vogue, Parents, and military family magazines, and was recently named to the Puget Sound Business Journal’s 40 under 40. In this conversation, we’re talking about how to get comfortable with visibility, build a support system that works, and use media strategically.

Cassie: Your work matters so much—so many new mothers suffer silently with postpartum depression, anxiety, and isolation. Getting the word out about Yuzi and maternal care is part of the mission. But you shared that you didn’t start out comfortable with self-promotion. How did you get over that?

Stephiney: I’m still working on it, honestly. The shift for me was realizing that if I truly believe in what I’m building, if I believe maternal care matters, then staying quiet isn’t noble. It’s just letting the status quo win.

I also learned that authenticity is everything. The posts that got the most engagement were the most honest ones about what I was actually experiencing.

People can tell the difference between genuine content and performative stuff. So, write about things that are relevant to your experience right now. Be honest about what’s hard. That’s what resonates.

Cassie: What’s your actual strategy for staying visible without burning out?

Stephiney: Build a support system. For a while, I had a group of four or five women founders in a WhatsApp channel. Every time one of us posted something, we’d be the first to engage with it.

We did that for about a month, and all of us saw tremendous uptick. There’s this “golden hour” after you post where if you don’t get early engagement, it disappears.

Women don’t ask for help enough. Men recommend each other constantly. Women wait until someone has checked every box.

Find your people. Support each other. Show up for them with real comments that add to the conversation.

I also don’t try to be everywhere. I focus on LinkedIn because that’s where my audience is. Pick one thing that feels natural and go deep on that.

Cassie: How has media visibility actually moved the needle for your business?

Stephiney: Media coverage led to our biggest strategic pivot. Last year, a healthcare system reached out after seeing our coverage and said, “We need your software.” That completely changed our business model from direct-to-consumer to B2B.

You have no idea who’s reading your coverage. One publication picks you up, then another sees it, then another. It compounds.

And real customers find us through it. People read an article and say, “This exists? I need this.”

Cassie: Building a personal brand isn’t about performing or being loud. It’s about showing up authentically and supporting each other.

If you see another woman doing good work, say it out loud. Comment. Share. Build the support system Stephiney describes.

You don’t know who’s watching. One article can open a door you didn’t even know existed.

Want to learn more about Yuzi’s mission? After experiencing postpartum depression herself, Stephiney realized how many mothers suffer silently—up to 85% of women experience some type of mood disturbance after giving birth and 67% of parents with young children feel isolated. Yuzi is building the world’s largest maternal care platform to change how society supports mothers and families, erase silent suffering, and foster connection. Check out Yuzi and follow Stephiney on LinkedIn.

These are Career Hack’s first 10 female guest mentors. Each one brought something that stuck with me, and I think will stick with you too. I’ve organized them around the quality that stood out most. This is what intentional, generous, optimistic leadership actually looks like. In their own words.

CLARITY Tracy Stone on letting go of comparison and defining success your way

Tracy opened by doing something most career coaches won’t: she told us to slow down before we strategize. The comparison trap isn’t just a mindset problem, she argued — it’s a navigation problem. When you’re running toward someone else’s finish line, all the hustle in the world won’t get you where you actually want to go.

“What are you chasing because you actually want it, and what are you chasing because you think you should want it?”

CONFIDENCE Jolawn Victor on three types of confidence for advancing your career

Jolawn reframed confidence in a way I hadn’t heard before. She broke it into three distinct types — and showed that the reason so many smart, capable women still feel like they’re faking it is because they’ve been trying to build the wrong kind. This piece comes with a quiz. I’ve seen readers go back to it again and again.

“Over time, I learned that while over-performing is important early on, long-term success depends just as much on your ability to navigate politics, build alliances, and develop organizational savvy.”

PERMISSION Ruchi Pinniger on how your desire for more isn’t greed, it’s growth

Ruchi’s piece hit something deep. So many of the women I’ve mentored carry this quiet guilt about ambition, about wanting more money, more influence, more recognition. Ruchi names it, traces it back to where it comes from, and then gently dismantles it. She also introduced the RIR method: Recognize, Interrupt, Reframe, as a practical tool for the moment a limiting belief shows up. One of the most-forwarded pieces we’ve published.

“Every new chapter of your life will ask for a bigger version of you. And that’s a good thing.”

MOMENTUM La Toya Haynes on making career decisions without endless overthinking

La Toya works with high-achieving women who want to make better decisions, faster — without second-guessing themselves into paralysis. Her Clarity Compass is a three-step framework that sounds almost too simple until you try it. Define your non-negotiables. Set a decision window. Trust the smallest next step. The magic, she says, is in moving. Momentum itself reduces doubt.

“Instead of asking, “What if I make the wrong choice?” I ask, “Which option moves you closer to your goals and aligns with your values?”

STORYTELLING Patti Sanchez on the two stories every leader driving change needs

Patti brought a framework I’ve shared more times than I can count since her piece ran. She’s spent decades helping leaders communicate through change, and her diagnosis of why change fails is precise: we skip the grief. We jump straight to the vision without acknowledging what people are losing. Once you see it, you can’t unsee it.

“When we hear a compelling story, something wonderful happens—we experience “narrative transportation.” The critical part of our brain quiets down and the creative part kicks in. In that creative space, we become more open and receptive to new ideas. We even start to imagine ourselves living in that world.”

DISCERNMENT Gold Truong about the importance of having a good sounding board at work

Gold’s piece is deceptively practical. She talks about how to navigate ambiguity at work — not by having better answers, but by getting better at knowing who to think out loud with. Her framework for finding the right sounding board has quietly become one of the most useful things I’ve shared with mentees. Especially relevant for people moving into senior roles where there are fewer safe spaces to not know.

“The key is being proactive about creating clarity rather than waiting for it to arrive. That’s what leadership in ambiguous situations looks like. And, while the natural temptation can be to go slow, speed is your friend here!

ADAPTABILITY Annie Tsai on staying AI-fluent and leading through it

Annie has given Career Hack two pieces, and together they make a complete argument. The first mapped the six skills that actually matter in the AI economy — and none of them are technical. Agent design, product thinking, emotional intelligence, sense-making, change leadership, and above all: the ability to learn how to learn. That last one, she says, is your long-term career moat. The second piece went deeper on one of them: writing. Her take is the most grounded I’ve encountered — not breathless, not fearful. The future belongs to people who keep learning, and who use new tools to amplify their thinking rather than replace it.

“In 2026, the people who win will break out of the “job title” box and be fluent in both technical and creative spaces. Most importantly, they’ll build the bridge between AI and real work. You still have time to build your toolbox.”

CURIOSITY Eileen Fagan on finding peers at any level

Who in your life is still pushing your thinking? Not validating it — actually expanding it? Eileen’s piece starts there, and it reorients how you build your network from the ground up. Her reframe is simple and quietly radical: stop organizing your network around hierarchy and start organizing it around learning energy. This one is especially important for anyone who’s been in their industry for a while.

“I think the mistake people make is looking for peers who match their level instead of peers who match their learning or creative energy. My closest peers aren’t necessarily in the same role — they’re people who are deeply curious, constantly learning, and asking big questions about how things work. That’s what keeps me growing.”

INITIATIVE Anirma Gupta on building the community YOU need

In 2005, Anirma was one of only seven women serving as chief IP counsel at major Silicon Valley tech companies. There was no network for them. So they built one — starting with informal lunches to compare notes on challenges no one else understood. Twenty years later, ChIPs has over 9,000 members across the globe. Her story is a masterclass in not waiting for someone else to solve the problem you’re living.

“You start by identifying who is there, even if the group is small…We were creating the support system we didn’t have. What mattered wasn’t scale or formality—it was intention. Find your people, however few, and start talking.”

CARE Kara Fitzpatrick on leading without authority, and how to make people want to work with you again

Kara has spent her career leading through influence — building teams and moving projects forward in environments where relationships matter more than org charts. Her secret isn’t structure, though she uses it well. It’s care. Throughout one 11-month project, she sent notes, flowers, and small gestures to team leads during the hardest moments. One reply said it all: “I was ready to walk away today. Then your note showed up.” Her advice for anyone leading this way:

“Love your team, believe in them with all your heart, and do everything in your power to set them up for success.”

What I notice, looking at this list

These women didn’t just share frameworks. They shared how they think. And when I look at what runs through all ten of them — clarity, confidence, permission, momentum, storytelling, discernment, adaptability, curiosity, initiative, care — what I see is a map.

A map of how to grow, and get ahead, without losing yourself in the process. How to build influence that doesn’t require anyone to shrink. How to lead from what you actually have, not from what you think you’re supposed to perform.

That’s what Career Hack is built to do. And these women are proof that it’s possible.

If any of these pieces spoke to where you are right now, go read the full conversation. Every link is worth the click.

To the women in this list, and to everyone reading this, thank you for being here!

Training AI to Tell Your Story Better – with Guest Mentor Annie Tsai

Annie Tsai is the Chief Operating Officer of Interact, Early-Stage Investor & Advisor, Author & Columnist, and Community Builder behind “The Business Side of AI” newsletter. In this conversation, we’re breaking down how to train AI to help you write better and faster, how to protect your authentic voice, and why the future belongs to people who can use AI as a partner rather than a replacement.

I’ve been sharing more lately about the stories that shape us—the narratives we tell ourselves, the ones we tell others, and increasingly, the ones we’re training AI to tell on our behalf.

Writing isn’t just how we communicate, it’s how we demonstrate our thinking, influence decisions, and build authority. And here’s the question I keep getting: “How do I use AI strategically for my career without losing my voice in the process?”

It’s the right question. Because the story AI tells about you, in your LinkedIn profile, your cover letters, your presentations, works best when it authentically represents who you are and what you bring.

Annie’s approach: don’t hand over your story. Teach AI to help you tell it better.

Cassie: I keep getting asked how to use AI strategically for career growth without sounding like everyone else. For professionally ls who want AI to amplify their voice rather than replace it, where should they start?

Annie: Writing with AI is a leverage play. The most competitive people heading into 2026 will be the ones who understand how to use their tools to scale their thinking into clear, fast, high-quality communication across channels, formats, and teams—without generating more content or hiring more people to get the job done.

The trick is not to hand over the writing. Instead, you need to teach your tools how you think so they can meet you at the edge of execution.

Here’s what high-performing AI writing assistance looks like:

Feed it your best writing to establish the baseline. Make sure there’s enough variety and quantity to cover multiple variations of similar styles. Include different content types—memos, articles, blog posts, sales pitches, presentations, product documentation, all of it. Show the system what “great” and “accurate” looks like.

Be explicit about your voice, including when your voice has variation. Add a sentence in every prompt that clarifies the tone you’re targeting upfront. Examples: “Use a curious, sharp, and slightly irreverent tone,” “Use simple, punchy sentences and avoid acronyms or confusing industry terminology,” or “Use a more personal tone with longer sentences, but keep the target reader as an industry marketer.” The more consistently you reinforce your voice and writing style, the faster AI can reflect it accurately.

Give feedback in the edit. Active feedback helps all AI models improve their output targeting, so don’t just delete paragraphs you don’t like. Tell your LLM why it didn’t work. Was it too generic? Did it sound like an AI wrote it and not you? If the latter, write it how you would write it and include that as feedback. The feedback signals over time are what separate finely-tuned partners from poor outputs.

Pair it with your real workflow. Have your AI tools draft internal updates, restructure your deck outlines, rewrite your LinkedIn posts to learn. The fastest way to get better output is to put the system inside your actual content stream and learn with real-time editing. Iterate inside of the chat flow so it can keep learning.

Cassie: How do you know when AI is working well versus when it’s taking over your voice?

Annie: It’s still pretty easy to tell when content is AI-generated. AI is very good at injecting subtle tells in not-so-subtle ways:

• Using corporate clichés in ways you never would (”cutting-edge solutions,” “dynamic synergies”)

• Saying something and nothing at the same time (”In today’s fast-paced world, innovation is key”)

• Hedging everything to exhaustion (”While x is true, y is also worth noting”—and doing this four times in one output)

• “Isn’t” to “Is” framing (”The problem isn’t AI. The problem is you.”)

• Repeating everything in threes (”We believe AI helps. AI is useful. It can be helpful.”)

• Really short sentences in series (”You tried. I tried. We all tried the ice cream. And nothing.”)

• Using specific words (“quietly” is the current LLM favorite) consistently in separate pieces when it was sparsely found in one’s content prior

• Closing with an empty call-to-action (”So, let’s embrace the future—together.”)

Now, I’ll be the first to admit I do some of these things in my natural writing. I write a Tuesday column for the Daily Journal in the San Francisco Bay Area, and I like examples in threes because it gives me the opportunity to use an Oxford comma—and I will take every chance I get to inject an Oxford comma into my writing.

The real tell is the repeated combination of these writing structures plus certain formatting decisions. Your content starts to scream “AI WROTE ME!”

The goal is not to turn over your writing entirely to AI while you sip a cocktail. Instead, think of AI as the tool that helps you organize your thinking, compress your synthesizing time, and edit to satisfaction faster and better than you ever have before.

Cassie: For someone who wants to start building their own AI writing system, what are the practical first steps?

Annie: Start with this:

Pick several pieces you’re proud of. Feed them as inputs into whatever AI tool you prefer and ask it to summarize your tone, writing style, structure, and for each piece, ask it to describe the target audience. Work with your AI to establish writing personas if there are variants you want to use as style outputs. Give each persona a name you can reference in the future. This step is the most important as you are setting the context, and context will make or break how effective your AI is at outputting something you’re happy with.

Create one prompt you can reuse weekly for a status update, a post, report, or something else that’s relatively low-stakes.

Test your AI on content pieces that are small but real—an intro paragraph, a cold email, a bio summary rewrite, translating notes to insight outputs.

The mistake is trying to replace the work of writing with AI. Instead, train your AI tools to work with you. The writers and operators who build this stack now will ship faster, more cohesive, and compelling content that gets the job done.

Cassie: This is exactly what I mean when I talk about stories that shape us. The narratives we craft—about our expertise, our leadership, our value—create the foundation for how others see us and how we see ourselves.

Your voice is part of your influence. The clarity and confidence in how you communicate shapes how people perceive your authority. When you train AI to work with you rather than for you, you’re not just writing faster—you’re building a system that helps you tell your story more consistently and compellingly across every platform.

This is the same principle behind Ron Ricci’s free Career Story Builder. It doesn’t write your career story for you—it helps you articulate your unique strengths and value in a way that’s authentically yours. You teach it how you think, what you’ve accomplished, and what makes you different. Then it helps you communicate that powerfully in interviews, on LinkedIn, and in career conversations.

The question isn’t whether to use AI. It’s whether you’re using it to amplify your story or obscure it.

Want more from Annie on using AI strategically? Subscribe to The Business Side of AI for practical insights that actually work in the real world.

And if you’re ready to build your own career story with AI as a partner: Try Ron’s Career Story Builder and see what’s possible when you train AI to understand what makes you exceptional.

Hugh Molotsi serves on the boards of Barloworld and Mozilla and is co-author of The Intrapreneur’s Journey. He was formerly President and CTO of BuyNothing and VP of Innovation and Engineering Fellow at Intuit. In this conversation, he talks about one of the most underrated career skills: receiving feedback well, especially when your brain is screaming that the feedback is wrong.

We all know feedback is critical for growth. But here’s the hard truth: how you receive feedback matters as much as the feedback itself. When you get defensive, shut down, or argue back, you train people not to be honest with you. The problem? Our brains are wired to see feedback as a threat. So how do you stay gracious when every instinct is telling you to fight back—especially when you think the feedback is wrong?

Cassie: We all know feedback is important for growth, but most of us still get defensive when we receive it. What’s actually happening when we react that way?

Hugh: When we receive constructive feedback, we naturally feel attacked. The pesky amygdala part of our brain takes over and we go into fight-or-flight mode. We’re no longer listening and treat the feedback giver as our adversary. It’s particularly hard to listen to feedback when we disagree with it.

Let’s face it—you’re going to receive feedback that is based on misunderstanding, incomplete or incorrect information from time to time. But here’s the thing: receiving feedback graciously doesn’t mean you have to agree with all of it or take action on it. I liken it to receiving a Christmas sweater from your grandmother. You should sincerely thank her for the gift, but you don’t have to wear a sweater you don’t like. Keeping in mind that you always get to decide what you do with the feedback will hopefully help you be gracious and keep the amygdala at bay!

Cassie: That’s such a helpful reframe. So when you’re in that moment receiving feedback—especially feedback you think is wrong—what’s your process for staying gracious?

Hugh: Here are some steps that may help:

• Listen actively – Let the feedback giver talk without interruption and then play back to them what you just heard in your own words.

• Thank the person giving you feedback – Even when you completely disagree with the feedback, you can be thankful that the person has taken the uncomfortable step to deliver a difficult message. The easier route would have been to complain or gossip to someone else. Your positive response also builds trust with this person and builds your personal brand that you receive feedback well.

• Acknowledge the portions of the feedback that resonate – Listen carefully to the full content of the message being delivered and call out the parts you agree with. Being vulnerable in this way goes a long way in making the experience for the feedback giver a good one. It also signals your genuine desire to improve and that the whole exercise won’t be a waste of time.

• Ask questions to gain clarity – For the portions of the feedback you don’t agree with, allow for the possibility that you may be the one who misunderstands or has incomplete or incorrect information. Ask clarifying questions that work back down the ladder of inference without being accusatory.

Cassie: What about when the feedback involves something you did that hurt someone—even if you think their reaction wasn’t reasonable?

Hugh: Apologize sincerely (when appropriate) – When your actions have hurt someone’s feelings (whether or not you feel their reaction is reasonable), you can always apologize for how you made them feel (and mean it!).

Share your perspective – Only after you have achieved the goodwill of the earlier steps should you offer to share your own perspective and provide missing information or correct any misinformation. Use this opportunity to express what was going on emotionally below the surface for you. When the feedback is about an interaction (”you were rude to Tanya”), you can provide valuable insight by sharing what you were feeling (”I was worried the meeting I was facilitating wouldn’t end on time when I cut her off”).

Share what you will do to follow up (when appropriate) – If there is a specific action you need to take, share your commitment to follow through with a specific timeframe. If you are committing to improving behavior, ask the feedback giver to provide ongoing feedback to help you.

An absolute no-no: Don’t use this interaction as an opportunity to give the feedback giver your own feedback. This is classic defensive behavior and is unlikely to be helpful. Anything you say will likely be interpreted as unfair retaliation. If you do have genuine feedback to share, wait for an opportunity in the future to give it.

Cassie: This is so practical. For someone who struggles with receiving feedback, what’s the one mindset shift that makes the biggest difference?

Hugh: Remember that if you don’t make the experience for the person giving you feedback a pleasant one, they are less likely to give you candid and direct feedback in the future—which is only to your own detriment. And here’s the liberating part: receiving feedback graciously doesn’t mean you have to agree with all of it or take action on it. You always get to decide what you do with the feedback. That mindset shift—knowing you’re in control of what happens next—helps you stay gracious in the moment.

Thanks, Hugh, for the reminder that receiving feedback well is a career superpower—and that we always get to decide what we do with it.

Anirma Gupta is co-founder of ChIPs, a global nonprofit with over 9,000 members and 30 chapters supporting the advancement of women across technology, law, and policy. She’s also a longtime legal executive across public companies and high-growth technology businesses. In this conversation, we talk about what to do when you’re navigating leadership without real peers—and why building community is sometimes the most practical form of leadership.

ChIPs started with seven women at a lunch table. Today, it’s a global organization supporting women leaders in tech, law, and policy. But it didn’t begin with a strategic plan or an ambition to scale. It began because something essential was missing: peers who understood the work.

Recently, Eileen Fagan spoke about the importance of true peers—people who expand how you think, not just validate your title. But what happens when those peers aren’t available? When you’re operating alone, with no ready-made network that understands your context?

Sometimes you have to build what you need.

Cassie: In 2005, you were one of only seven women serving as chief IP counsel at major Silicon Valley tech companies. Many leaders today experience similar isolation. When there’s no existing network to join, where do you start?

Anirma: You start by identifying who is there, even if the group is small. In our case, there were seven of us—at companies like Apple, Google, Intuit, eBay, and Sun Microsystems. We began with lunch meetups as an opportunity to support one another and compare notes on challenges unique to the role that we were all navigating. We were creating the support system we didn’t have. What mattered wasn’t scale or formality—it was intention. Find your people, however few, and start talking.

Cassie: ChIPs grew from those informal lunches into a global organization. How did you scale without losing what made it meaningful?

Anirma: We anchored everything in a simple principle: pay it forward. None of us succeed on our own, and those who have benefited from opportunity have a responsibility to extend it to others. That belief has shaped the organization to be what it is today.

ChIPs was designed to be a community built on important ideas, grounded in relationships. As we expanded, we brought in people from law firms, judges, policymakers, and leaders from adjacent fields, because innovation improves when more perspectives are in the room.

At the same time, the mission stayed constant: advancing and connecting women in technology, law, and policy, and accelerating innovation through diversity of thought and participation. We were clear about what mattered, and growth followed over time.

Cassie: What has building ChIPs made possible—and what would you say to leaders who are unsure whether they’re equipped to create community themselves?

Anirma: I’ve watched our community members support each other through inflection points, step into general counsel roles, build companies and funds, and reshape leadership teams from the inside. What stands out most is the generosity—people offering time, perspective, and access to make the path more navigable for others.

For leaders considering whether to build community, my advice is simple: start small and start now. You don’t need a fully formed plan. Just believe the community is worth creating and take responsibility for the first step. Invite a few people to lunch. Create space for honest exchange.

If you’re in a position to bring people together, to shape the room, then what you create is likely to have a lasting effect– often more than you expect!

Eileen Fagan is a longtime executive and change leader known for her systems thinking, people-first approach, and deep experience driving transformation at scale. She is one of my favorite thought partners—the type of person who makes me want to be so much better. (Those are the best peers: they don’t just support you, they elevate you!) In this conversation, we explore a subtle but essential topic: how to find true peers at any level, why “like title” isn’t the same as “like mind,” and what it takes to keep learning and growing throughout your career.

The higher you go in your career, the fewer natural peers you have. The hallway chats disappear, your calendar fills with obligations, and fewer people will challenge you directly. But Eileen has a powerful reframe that applies whether you’re a senior leader or mid-career professional: real peers aren’t defined by hierarchy—they’re defined by curiosity.

Cassie: Once you get to a certain level, it’s easy to feel like there are fewer people to think with — fewer true peers. How do you approach that?

Eileen: I think the mistake people make is looking for peers who match their level instead of peers who match their learning or creative energy. My closest peers aren’t necessarily in the same role — they’re people who are deeply curious, constantly learning, and asking big questions about how things work. That’s what keeps me growing. It’s less about “Do you sit where I sit?” and more about “Are you still awake to possibility?”

Cassie: That’s such a great way to put it — that “learning energy” is what makes a peer. What happens when people don’t do this work of finding learning peers?

Eileen: You have to be intentional. You won’t necessarily just bump into them in your own hallway anymore. I look for learning communities — people in different industries who share a sense of curiosity and generosity. I’ll join a learning salon or organization, go to events, or even just start a small group or meetup where we exchange ideas every month. Especially as you grow in your career or reach more senior roles, you can’t wait for your company to create your peer network for you — you have to build your own.

Cassie: I love that. You’re naming something that I think a lot of leaders feel quietly, that sense of being the only one asking the questions. What’s the risk of not doing this work of finding peers?

Eileen: It’s a kind of isolation that sneaks up on you. You get so focused on leading your teams that you stop feeding your own curiosity. Over time, that can turn into stagnation — or worse, defensiveness. The best leaders I know are learners first. They protect their energy by surrounding themselves with people who expand their thinking, not just validate it.

Cassie: This is so practical and empowering. Thanks, Eileen, for reminding us that peer relationships aren’t about matching titles, they’re about matching energy and curiosity.

For everyone reading: whether you’re a senior leader feeling isolated or a mid-career professional wondering where your thought partners are, the answer is the same. Look for learning energy. Be intentional. Build your own network of curious, generous people who expand your thinking. Don’t wait for your company to create it for you.

Kara Fitzpatrick is Sr. Director & Chief of Staff for the Bank, Business, & Card Experience Design Team at Capital One. She’s a dynamic leader and force multiplier who has worked on global stages like the Super Bowl, Oscars, and Women’s World Cup, and served in two White Houses under Presidents Biden and Obama.

You need to get something done. You need a team to execute. But here’s the catch: none of them report to you. No boxes on an org chart connecting you to them. No formal authority. So how do you lead successfully when no one technically has to listen to you? And how do you do it in a way that makes people actually want to work with you again?

Cassie: You’ve built an incredible career leading high-stakes teams—from the Super Bowl to the White House—and people keep wanting to work with you again. What’s remarkable is that in many cases, not a single person on those teams reported to you. How do you lead successfully when you don’t have formal authority?

Kara: It is possible to lead high-stakes work and drive real impact without formal authority—I’ve done it for over 10 years, leading teams as small as 5 and as big as 60, putting on successful shows, creating leadership development programs, launching products, reimagining processes, and redesigning organizations. One common link across many of them is that in a lot of cases, not a single one of those people reported to me. In the “boxes on org charts” sense.

Here’s what it takes:

The short answer: Love your team, believe in them with all your heart, and do everything in your power to set them up for success.

The long answer: Give them a goal, rally them around a shared vision, work with them to set up their plan for how they’re going to deliver their part, provide air cover when they need help or when there’s conflict or roadblocks, then make sure they know you believe they can do it.

The key bit involves creating an environment where people feel they’re in a safe space to do some of the best work of their career.

Cassie: Let’s talk about what “setting people up for success” actually looks like in practice when you’re leading without authority?

Kara: First, structure matters—even in informal leadership. I design the team with clear verticals and identify the key areas needed. For a small show with 250 attendees, we had four verticals: communications, experience design, production, and talent.

Here’s what most people miss: I choicefully gave the different leads titles that mattered for each vertical. So even if their day-to-day title was Writer, for this show they were Communications Manager. Why?

Whether we like it or not, titles matter.

Doing this empowers them, gives them a feeling of ownership, and ultimately they want to succeed because they feel responsible to the rest of the team and the deliverable for their area of expertise. People responded to this action and rose to the occasion. They knocked it out of the park.

Beyond titles, you need documentation of who’s responsible for what. I create what I call the Roles and Responsibilities doc. In a case of glaringly easy simplicity, that’s exactly what it’s called. This is great not only for clarity between teams, but also an easy way for new people coming on to understand who does what. It prevents wasted work when someone—with all good intent—asks the wrong person to do something.

Cassie: Structure makes sense—titles, clear roles. I can hear the naysayers now: “You can’t make anyone do anything if they don’t report to you.” So how do you actually get people to care and go above and beyond?

Kara: It takes time, but a big key to success is really taking the time to know what makes folks tick—find out what’s intrinsically motivating for your team. This can be accomplished via an icebreaker activity at the beginning of a project or sprint. Or take them out to coffee, or you know, just pay attention to what they say or how they act.

Find out: why did they choose to do this kind of work? How can you align the team’s shared goals with its members’ individual ones? Then use this knowledge to build them up. Give them confidence. Show them you’ve got their back and that you believe in them.

A former manager used to say, “Give them enough rope to take risks, but not to hang themselves.” While that’s a bit grim, you get the point. Make sure they know they can come to you—and that sooner is better than later. Tell them risks are good and valued, and also when to pull you in to help them out.

Throughout one large project I led—11 months from kickoff to finish—I would send flowers, wine, beer, chocolate, or most times, a simple note to the team leads at various points that I knew were stressful or intense. In one, I just wrote, “Thank you for doing that this week! YOU ROCK.”

Their reply ended up rocking me: “You always seem to reach out just when I need it most, and I didn’t know I needed to hear it. I was ready to walk away today, then your note showed up.”

You never know the difference a small gesture can make. Be kind. Care. And show it through actions and words.

Cassie: One thing I’ve noticed about great leaders, like you, who operate without formal authority is that people keep wanting to work with them again. What creates that repeat collaborator phenomenon?

Kara: A happy, functioning team equals a great atmosphere, solid culture, and a great product.

When you demonstrate that you trust people to do what they’re there to do, and you’re not in the weeds day in and day out micromanaging, people feel empowered. When you show them you believe in them, give them meaningful ownership, and support them when they need it—they remember that.

Empowering the team doesn’t just mean you set things up and then never check in. What it means is that you demonstrate that you trust them to do what they’re there to do. As a leader, you’re responsible for the overall end-to-end experience, for sure. But it helps no one if you’re in the weeds day in and day out.

People responded to feeling valued, having clear ownership, and knowing I had their back. And when the next project came up? They wanted to be part of it again.

Cassie: For someone who needs to lead without formal authority—whether it’s a cross-functional project, a matrix organization, or just trying to drive change—where should they start?

Kara: Start with structure and clarity, even if it feels informal. Create clear roles and responsibilities. Give people meaningful ownership—even if it’s just for this project. Figure out what makes each person tick and align the work with what motivates them.

Then do the harder work: show them you believe in them. Give them air cover when they need it. Send the note. Make the gesture. Care about them as humans, not just workers.

And remember: your job isn’t to have all the answers or be in the weeds. Your job is to set them up for success, make sure they know you’ve got their back, and cheer them on.

When you do that well, people don’t just deliver great work. They want to work with you again.

Thanks, Kara, for showing us that influence doesn’t require authority—it requires trust, clarity, and genuine care for the humans doing the work.

Want more insights on leadership and creating healthy, high-performing teams? Check out Kara’s site.

P.S. A note on the Career Hack publishing cadence:

I’m testing out some changes to when and how I publish. Alpha Insights will still come on Mondays, but now as notes in the Substack app. My columns (formerly Wednesdays) move to Tuesdays, and Guest Mentor conversations (formerly Fridays) move to Thursdays.

Feedback always welcome—just reply and let me know what you think!

Ron Ricci is the author of “How to be a Great Manager in the Age of Uncertainty: Be a Career Dot Connector”; creator of the Career Story Builder, an AI-powered tool to help people craft compelling career narratives; and writer of Managing in the Age of Uncertainty Substack. In this conversation, we’re exploring why the corporate ladder is dead, how to build your career story based on your strengths, and why self-awareness is the foundation of career success.

AI’s biggest impact? Making the career ladder an artifact of the boomer generation. As every function and job role rethinks itself around AI, the predictable path of climbing step-by-step up a hierarchy doesn’t reflect how careers actually work anymore. Instead, we’re building what some call “portfolio careers”—a collection of chapters and experiences that tell a coherent story about who you are and what you do exceptionally well. The challenge? Most people don’t start with the right foundation: their actual strengths.

Cassie: You’ve said the corporate ladder is dead and we need to think in terms of career stories instead. What does that shift actually mean for how we think about our careers?

Ron: The age of the predictable career ladder—where you took clear steps up a hierarchy over the course of decades and often with the same manager—is over. We’re now in what I call the “Age of Uncertainty,” where there’s no obvious ladder and no predictable path because everything in every organization is being reimagined by AI.

The new path to growth and advancement is rooted in your ability to tell a career story – where each job role is a chapter in a longer story that sets you up for the next step.

This is especially true for millennials and Gen Z who are replacing boomers and Gen X in the workforce. It’s also having a major impact on the role of managers. The best managers today are what I call “career dot-connectors”—meaning they help people on a team connect the dots between their current role and their future career opportunities. In the end, top performers should be able to write a best-selling story to make themselves irresistible candidates for the next opportunity.

Cassie: You’ve developed the Career Story Builder tool, and the very first question it asks is “What do you do better than anyone else in your field?” Talk about why that’s where we should start.

Ron: Every great story is told in three acts. In a career story, the first act is about establishing yourself – who you are and what makes you special. Best-selling career stories are based on someone’s strengths, the unique talents someone brings to the table.

The other two acts of your career story focus on differentiation and relevance, both of which are grounded in your strengths. You can’t differentiate yourself or stay relevant if you’re not playing to what you genuinely do better than others. And, it’s a lot easier to show up with confidence if you’re playing to your strengths.

The role of managers today is to make sure everyone on a team is in a job role aligned with their strengths. I have a favorite phrase as a manager: “Everyone has a source of greatness.” Great managers ensure their people are self-aware enough to know theirs. As managers, it’s important to recognize that sometimes people want to be better at something than they really are. That’s why I never liked it when people would say “I want to be more strategic.” I always saw that as an indicator they weren’t in touch with their true self.

Cassie: How do you develop that self-awareness? What if you genuinely don’t know what your greatest strengths are, or how to talk about them?

Ron: Former United Airlines CEO Oscar Munoz gave me the best advice on this. He calls knowing yourself “knowledge of contribution.” And he has a test that he says has proven 100-percent effective: ask your spouse or partner if feedback you’ve received at work is accurate.

It starts with feedback. Hearing candid feedback is the foundation of growth. Talk to people you work with and talk to your manager. In fact, ask anyone in your close orbit. The main goal is to get perspective on yourself. I always say the best people “fall in love” with their strengths and embrace them instead of trying to reshape them.

Managing your career requires self-awareness. It goes beyond career trajectory—it brings peace of mind as you approach your growth. I genuinely believe playing to your strengths will make you happier, more self-assured and confident, especially in job interviews. It’s easier to be an expert in something if you know it is true.

Cassie: For women specifically, I see a pattern where they downplay their strengths or focus on areas they want to improve rather than what they’re already great at. What’s your advice for women who struggle to claim their strengths confidently?

Ron: I would say knowing your strengths sets you free to be the best of yourself. It’s liberating to know you do something special when other people know it, too. It’s not bragging or shining a light on yourself. It’s just the truth.

I’d add that self-awareness plays a big role here. Knowing that you have weaknesses is as important as knowing your strengths. The best storytellers understand how to compartmentalize their weaknesses and focus on their greatness. There’s nothing inauthentic about this because everyone has things they aren’t good at. It also helps you frame areas to improve on your terms, if asked.

If you’re in a job transition or trying to advance your career, your job is to write a best-seller – to make you an irresistible candidate for the next opportunity. Confidence is the key to making your story better than others. Don’t focus on what you think you should be good at or what sounds impressive. Showing up believing in the best of yourself will make you, frankly, the more interesting candidate.

In the era of the corporate ladder, there was a bias toward being a generalist or general manager. Not so today. If you want to differentiate yourself in the Age of Uncertainty, focus on what makes you exceptional at things you’re naturally great at and build a career story around that.

Cassie: Let’s talk about how to put this into practice. Where should our members start?

Ron: I created the Career Story Builder specifically to guide people through this process. It’s a free, AI-powered tool that helps you craft a compelling career narrative starting with your strengths.

The tool walks you through a series of thought-provoking questions and gives you recommendations you can use immediately—in your LinkedIn summary, in interviews, in conversations about your career. One of my former Cisco colleagues, Ken Carrasco, used the tool and told me it was easy to use, quick to complete, and gave him a result he could use immediately without editing.

If you’re struggling to articulate your strengths or tell your career story with confidence, try the Career Story Builder. It’s free and unlimited, and I’d love to hear your feedback on how to make it better.

Cassie: Thanks, Ron, for showing us how to build our career stories from a foundation of strengths.

Now women, when you answer “What do you do better than anyone else?” I’m giving you permission to channel your inner overconfident white guy. Don’t downplay, don’t hedge, just state your greatness. :-)

Ready to build your career story? Try Ron’s free Career Story Builder tool and discover how to articulate your strengths with confidence.

Try Career Storybuilder

La Toya Haynes is the founder and CEO of The Talent Practice, with over 27 years of experience in human resources, leadership coaching, and organizational development. She holds an MBA in Organizational Development and Executive Coaching and has helped startups and established enterprises build leadership pipelines and achieve strategic goals. In this conversation, we’re talking about why overthinking keeps ambitious women stuck, how to shift from paralysis to clarity, and the three-step framework that helps you make decisions with confidence.

Smart, accomplished women (and men) get stuck all the time—not because they lack options, but because they’re drowning in them. The “what-ifs” pile up, analysis turns into paralysis, and momentum stalls. Sound familiar? Here’s how to break the cycle and start making decisions that move you forward.

Cassie: I see so many accomplished women get stuck in analysis paralysis when facing big career decisions. What’s actually happening when we overthink ourselves into inaction?

La Toya: Overthinking career decisions is exhausting. It keeps smart, ambitious women stuck—spinning on “what-ifs” instead of moving forward. I help clients shift from paralysis to clarity by reframing decision-making: instead of asking, “What if I make the wrong choice?” I ask, “Which option moves you closer to your goals and aligns with your values?”

This mindset works because it shifts focus from fear to forward momentum. It gives space for intuition to meet practical analysis, so decisions are strategic—not paralyzed by “what-ifs.”

Cassie: That reframe from “wrong choice” to “aligned choice” is powerful. So, when you’re facing a decision and spiraling, what’s the actual process to get unstuck?

La Toya: I use a three-step approach I call the “Clarity Compass.”

First, define your non-negotiables: values, priorities, and deal-breakers.

Second, set a decision window—a specific, short timeline for making the choice to prevent endless rumination.

Third, trust the smallest next step: pick the option that aligns most with your values and take one concrete action, even if it feels small.

The magic is in moving—momentum itself reduces doubt.

Cassie: What changes for people when they actually start using this approach?

La Toya: Clients who adopt this approach experience a profound shift. They feel lighter, more confident, and less stressed because they’re no longer stuck in cycles of overthinking. Instead of letting fear dictate their career path, they act decisively and authentically.

And often, opportunities open up in ways that weren’t visible when they were overanalyzing—because clarity attracts the right paths.

Cassie: Thanks, La Toya, for the reminder that momentum breaks overthinking—and that deciding with our values creates clarity.

Want more career insights from La Toya? Follow her on LinkedIn or go directly to The Talent Practice website.

Brian Divine is the co-founder and head of sales and partnerships at Pangea, an AI-powered, end-to-end FX management company. Before tech, he spent 18 years in hospitality, including running two of his own businesses. He’s also my brother—someone I deeply admire for how he thinks about identity, worth, and what it means to live from a foundation of knowing who you are rather than proving what you can do.

Most of us root our worth in what we produce. Our résumés become our scorecards. But what happens when the role changes, the company fails, or the promotion doesn’t come? In this conversation, we talk about separating who you are from what you do—and why that shift might be the most useful career move you never thought to make.

This captures the kind of conversation Brian and I have late at night after our families go to sleep—wine in hand, working through ideas that matter. What he shared hit me hard: we all inherently know our worth isn’t tied to our output, but we forget it constantly. I asked him to expand on it here.

Cassie: You’ve said that confidence has evolved over time. What do you mean by that—and why does it matter?

Brian: We talk a lot about confidence in business, but the word has drifted a long way from its original meaning. Confidence comes from the Latin verb confidere, which literally means to trust fully.

Historically, confidence wasn’t something you generated internally—it was trust placed outside yourself. People trusted God, tradition, community, and disciplined work. Confidence was faithfulness to something larger than you.

Over time, that meaning flipped inward. Confidence became something you manufacture through achievement, status, and approval—transactional, fragile, always at risk of collapse. Amplified by social media, it’s turned into performance against self-imposed standards and curated lives.

What we end up with is a world of people who look confident but carry anxiety, exhaustion, and self-doubt inside. It’s a house of cards. The only way to be free is to anchor confidence in something more durable than performance—something bigger than titles, trophies, and bonuses.

Whether you’re wearing a shark costume in high school or walking into an executive boardroom, your worth doesn’t change. You may have skills to demonstrate, but you don’t have inherent value to prove.

Cassie: It’s so easy to tie your worth to what you accomplish—it feels good, the recognition is real, and most high achievers do it without realizing. What’s the danger in that, and how do you untangle those two things?

Brian: There are two fundamental problems with grounding your worth in what you do, what you have, or what people say about you.

First, the next promotion or raise is never enough. You reach the top of one mountain only to discover a taller one across the valley—and you set out again. It may feel motivating, but an identity built on achievement is rarely satisfying. It produces a quiet, chronic sense of insufficiency.

Second, success is temporary. Even the most accomplished person will one day find themselves in a bed, unable to produce, unable to climb, unable to prove anything more. Then what? Will your eulogy read: “Died with more to accomplish. Survived by a list of achievements few remember”?

I don’t want that for my life, or for my kids, or for anyone else.

Cassie: If most of us are doing this without realizing it, how do you know when your confidence is rooted in your achievements instead of something more solid?

Brian: One of my boys’ favorite movies is Cool Runnings, a great story about a hero who doesn’t technically win.

Before the final run, Derice asks his coach, Irv Blitzer, why he cheated. Irv’s response is gold (pun intended):

“A gold medal is a wonderful thing. But if you’re not enough without it, you’ll never be enough with it.”

Derice asks, “How will I know if I’m enough?”
Irv replies, “When you cross that finish line, you’ll know.”

When it comes to where we derive our confidence, that insight lands close to home. Most of the time, we do know.

• When you won that award, did your joy quietly become, “Now I’m worthy”?

• When you didn’t get the promotion, did the disappointment turn into, “I’m not enough”?

• When you received negative feedback, did it feel like a threat to your identity rather than a critique of your work?

Those reactions are telltale signs. They reveal that confidence is coming from the wrong place—and that something is out of balance.

Cassie: That’s the hard part, isn’t it? Most of us have spent decades building an identity around what we do. Where do you even start untangling that?

Brian: Ultimately, confidence has to come from a source with real authority or credibility—God, a parent, a trusted leader or friend, or a truth that holds across time and circumstance.

One of the greatest gifts we received from our parents—especially from our dad, the “chief grace officer” of our family—was this message: you are not what you do. Your value is not tied to your accomplishments.

Yes, you have potential, and we expect you to do meaningful things. But your worth exists before you do any of them.

When you’re rooted in that truth, success doesn’t inflate you and failure doesn’t destroy you. Both become teachers, signposts along the journey, not statements about who you are.

That kind of confidence has to be supported by what you actually believe is true—your worldview shapes your identity. If you want clarity on identity, you need clarity on your worldview: What stories do you tell? How do you act in the world? What do you enjoy? What do you value? What do you believe?

For our family, much of our worldview was shaped by faith—and for me, it remains the foundation of my identity as I stumble my way through life. If God formed you, set you apart, and created you with immeasurable value before you achieved anything, that’s a compelling basis for identity—and a radically different story than the one the world usually offers.

Cassie: When your worth isn’t on the line anymore, what does that free you to do as a leader?

Brian: It changes everything. When your worth is separate from your accomplishments, your decisions start from “Who am I and what do I want?” instead of “What will make me successful, approved, or worthy?” or “How do I build a well-regarded image?”

You take risks and speak up because failure doesn’t diminish your value.
You set boundaries because your identity isn’t rooted in approval.
You lead without needing to dominate—because you have nothing to prove.

As you know, our company Pangea helps global organizations move money around the world. Last year, one of our client success associates made a mistake that could have been very costly if we hadn’t caught it in time. When I met with him, he genuinely believed he might be fired—or worse. He felt terrible.

After explaining the seriousness of the situation, I told him: “Two things are true. First, you made a mistake, and we need systems in place to ensure it never happens again. More importantly, you are not your mistakes. You’re doing good work and I’m glad we hired you. You’re forgiven. Now let’s move on.”

That response was grounded in two realities. First, I didn’t need to assert authority or leverage his failure to make myself feel bigger. Second, he isn’t defined by what he does. Even after a significant mistake, his worth—and his standing as an employee—remained unchanged.

We fixed the system, not the person. And as a result, his trust in the company, and in leadership, grew.

Cassie: That’s exactly it. And that groundedness opens up something else—the ability to lead from service rather than ego. My view is that success is the byproduct of serving something bigger than yourself. When you’re working on a cause bigger than yourself, it becomes easier to speak up and push forward because you’re not advocating for you—you’re advocating for what’s right.

Brian: Completely. When you’re no longer protecting your image or trying to prove your value, you can see more clearly and focus on what actually matters. With fewer distractions, more energy goes toward advancing the mission.

You become generous with your knowledge, your connections, and your attention, without keeping score. You’re gracious when others fall short. You give praise freely and build people up, knowing your own standing isn’t at risk.

These aren’t just nice-to-haves; they’re competitive advantages. When you operate with nothing to fear, nothing to lose, and nothing to prove—trusting that a rising tide can lift all boats—everyone around you gets better. Over time, you develop a reputation for creating value beyond yourself. That reputation becomes currency.

But this kind of leadership can’t come from striving.
It only grows out of a secure identity.

Cassie: For someone who realizes they’ve built their identity on achievement, where do they start untangling that? Especially for women, who are often conditioned to prove themselves over and over?

Brian: Start by noticing the story you’re living from. Practice separating your identity from what you do, what you have, and what people say about you. You may be an executive, a parent, a partner—important roles, but not who you are. You might live in a beautiful neighborhood, have a well-designed home, or be well regarded by others. Those are all good things, but they’re roles, possessions, and reputation—not identity.

Now ask the harder questions. What if those things went away? What if you were laid off, divorced, or lost your home? What if people stopped speaking well of you? Confidence (or trust) placed in what’s temporary will always be fragile.

Next, invite perspective from people you trust—people who care about you, not just your output. Ask them what they see as core to who you are. Spend time with Scripture (or your sacred text) that speaks directly to identity. Ask your parents, friends, or partner a simple question: If everything fell apart, who would I still be? Their responses can offer a helpful starting point.

If they can’t answer, or if their answers are all about what you do, that tells you something important. It might also mean you need outside support, someone like a professional counselor, to help you build an identity that isn’t dependent on performance.

Once you start to separate who you are from what you do, you can turn your attention to what you actually believe and value. That clarity helps you build the rhythms and habits that support the person you want to become—not the person you think you need to be.

Cassie: I love that. This work is especially important for women because it sits at a deeper intersection—identity, expectation, caregiving, ambition, and the unspoken pressure to hold everything together without showing the strain.

Untangling worth from achievement isn’t a mindset shift you complete once. It’s a daily practice. I have to constantly notice the story I’m operating from and ask myself: Am I doing this because it’s true to me, or because it will validate me?

When you lead from knowing who you are, you stop grasping for validation and start creating real impact. You take risks you wouldn’t have taken. You speak truth you would have softened. You build influence that actually lasts.

Bonus from Brian:

If You’re Wrestling With These Questions, Brian’s Picks for Movies About Identity

For young families: Cars (especially Cars 1 and 3) and Planes (Planes and Fire & Rescue) tell stories where the hero is forced to find an identity beyond success.

For thoughtful viewing: Little Women (the Winona Ryder / Susan Sarandon version) beautifully explores the diverse personalities of Marmee, Jo, and her sisters, and the different ways each wrestles with purpose and identity.

For everyone: Good Will Hunting is a powerful exploration of identity, shame, and freedom. Will has to untangle a complicated origin story, a brilliant mind, deep pain, and relentless self-doubt. The scene where Sean dismantles Will’s shame with the repeated, unwavering “It’s not your fault” is a masterclass in breakthrough—and a reminder of how healing identity often comes through grace, not achievement.

Now is such a great time to slow down and invest in yourself. If you’re looking for tactical career guidance without the pressure of a full course, here’s every Guest Mentor piece we’ve published so far—each one offering frameworks and practices you can actually use.

📌 Stop Comparing and Start Defining Career Success on Your Terms – Tracy Stone For when you’re caught in the LinkedIn comparison trap. Tracy reframes what success actually means when you stop running someone else’s race.

📌 Building Corporate Confidence – Jolawn Victor The three essential types of confidence for career advancement, how to assess where you are with each, and how to strategically build what you need for your next move. Plus, a quiz for tailored results!

📌 Your Desire for More Isn’t Greed, It’s Growth – Ruchi Pinniger On replacing guilt with growth, reframing your relationship with money, and building self-trust as your financial foundation.

📌 Six Must-Have Skills in the AI Economy – Annie Tsai The skills that actually matter for 2026, how to build them without overwhelm, and why the future belongs to people who bridge AI and real work.

📌 Why Change Fails (And How to Diagnose the Real Problem) – Patti Sanchez The three types of resistance you’ll encounter when leading change and the two essential stories that make change stick.

📌 Ping! On Leaning on Others to Navigate Ambiguity – Gold Truong How to find the right sounding board at work—the people who help you see what you can’t see on your own.

📌 Ping! On the Three-Step Practice That Reframes Limiting Beliefs – Ruchi Pinniger A quick exchange on the RIR method (Recognize, Interrupt, Reframe) and how to rewrite the limiting beliefs that hold you back.

Pick what speaks to where you are right now. Bookmark what you want to come back to. And if something resonates, share it with someone who needs it.

Here’s to ending the year with clarity and starting 2026 with intention.

Want to be a Guest Mentor?

Career Hack features accomplished leaders who share tactical frameworks, hard-won insights, and honest perspectives on navigating the messy realities of work. Our Guest Mentors come from diverse industries and backgrounds, united by a commitment to helping women grow their influence and lead without losing themselves in the process. Most are women, I’m intentionally keeping men to about a third of our mentors, the same space women currently hold in leadership and tech, but everyone is welcome!

If you have expertise to share—whether through a quick “Ping” exchange, a deep-dive Q&A, or repurposing existing content—we’d love to hear from you.

Express Your Interest

Happy New Year! I’ll resume regular publishing the week of January 5th.

Tracy Stone is a certified leadership coach and consultant with years of executive leadership experience in tech, and the voice behind Carving Her Path, a Substack about navigating your career with intention. In this conversation, we’re talking about the comparison trap that keeps so many of us running races we never signed up for, and how to define success that actually fits your life.

You can spend your career chasing what success is supposed to look like, or you can define what it actually means for you. The first path is exhausting. The second is liberating. This conversation is about making that shift.

Cassie: Let’s talk about that feeling when you see someone else’s success and suddenly feel like you’re falling behind. What’s really happening?

Tracy: Oh, I know that feeling. You’re scrolling LinkedIn during lunch. Another promotion. Another impressive title. You hit the like button and genuinely mean it. But underneath that happiness sits something else: How did they get that? What do they have that I don’t? Why am I still here while everyone else races ahead?

Here’s the truth: as humans, comparison is natural. When there are visible markers of success—titles, promotions, awards—it’s hard not to measure yourself against them. It’s hard not to wonder if you’re behind, if you’re not progressing the way you “should,” if you’re missing something everyone else seems to have figured out.

I lived it myself. I had three kids in five years. My colleagues were sprinting toward big executive titles while I was recalibrating what success even meant. Then I made a decision that felt like career suicide: I left the corporate workforce entirely to be home with my kids.

I was thrilled to get the time, but I also found myself feeling frustrated with my career progress. I spent a lot of time watching my former colleagues’ trajectories soar. Director. Senior Director. VP. Each LinkedIn announcement felt like a reminder of where I “should” be and wasn’t. I wasn’t just running in place anymore. I had pulled myself out of the race completely. I was absolutely playing the comparison game. And I was losing.

Cassie: We’ve all been told not to compare ourselves, but that doesn’t stop the feeling. How do you actually use comparison productively?

Tracy: I recently read Mel Robbins’ book The Let Them Theory, and she reframes the comparison beautifully.

Use comparison as a mirror first. When you see someone’s success and feel that pang of jealousy, pause. Ask yourself: What is this showing me about what I actually want? What’s holding me back from going after it?

Then use it as fuel. Let their success inspire you. Let it show you what’s possible. But don’t let it eat away at you.

Here’s what Robbins emphasizes: success isn’t a zero-sum game. There isn’t one finite pie we’re all competing for. Let them have their success. And let yourself define and chase yours.

That shift—from scarcity to abundance, from competition to inspiration—changes everything.

Cassie: When you returned to work, how did you define success on your own terms instead of trying to catch up?

Tracy: I had a choice. I could try to “catch up” to where I thought I should be, chasing titles that looked good on paper. Or I could define what success actually meant for me. I chose the latter.

I went from being highly technical and strategic, managing a large team as the right-hand person to the GM of a $1.5B business to building women in tech programs. Definitely not a typical career path, but one that fueled and excited me like nothing else. It was my path.

Here’s what I learned:

Progress isn’t always upward. Sometimes the best move is lateral, backward to go forward, or completely sideways into something unexpected.

Slowing down can mean speeding up later. That “pause” gave me clarity and perspective that accelerated everything that came after.

The impressive title might come with a cost you’re not willing to pay. Someone else’s dream job might be your nightmare. And that’s okay.

LinkedIn shows the highlight reel, not the behind-the-scenes. You’re comparing your messy middle to someone else’s polished ending.

Your path doesn’t have to look like anyone else’s. Think of career paths like clothes. That dress might look stunning on someone else, but it doesn’t fit you.

Cassie: For someone caught in the comparison trap right now, what questions should they ask themselves?

Tracy: What does success actually look like for you? Not your boss, not the person with the impressive LinkedIn title. You.

What impact do you want to make? What kind of work energizes you? What matters most when you look at the whole landscape of your life—not just your career?

And here’s the harder question: What are you chasing because you actually want it, and what are you chasing because you think you should want it?

When you can answer those questions honestly, you stop running someone else’s race. You start carving your own path. Your career path doesn’t have to follow anyone else’s timeline or trajectory. It just has to be yours.

Cassie: Thank you, Tracy, for reminding us that success isn’t a one-size-fits-all race. Sometimes the bravest move is defining it on your own terms.

Want more insights on carving your career path and guidance for defining success on your own terms? Subscribe to Carving Her Path and reach out to Tracy to help you unlock your potential and carve your career path.

Jolawn Victor is the CEO of Telematics at Radius, a global fleet management company. She’s built an incredible career scaling international businesses at Intuit and Headspace and serving on boards across three continents. In this conversation, we’re breaking down the three essential types of confidence crucial for career advancement, how to assess where you are with each, and how to strategically invest in building the confidence you need for your next move.

Confidence isn’t one-size-fits-all, and the type of confidence that got you to where you are today might not be what you need for where you’re going next. Whether you’re positioning yourself for a promotion, stepping into a board role, or taking on P&L responsibility for the first time, understanding which type of confidence to build—and how to build it strategically—can be the difference between feeling stuck and feeling unstoppable.

Cassie: You’ve built an incredible career—Chief Growth Officer at GoCardless, served on boards, scaled international businesses at Intuit and Headspace, and now you’re a newly appointed CEO at Radius. Looking back at your journey from engineer to C-suite executive across three continents, what role has confidence played in your advancement?

Jolawn: Whenever I spoke with a woman preparing for a career change, a familiar pattern emerged. She was either going back to school for another degree, considering a lateral move, or even accepting a demotion to break into a new industry, function, or company. I say this without judgment because I have done it myself.

When I moved from manufacturing engineering into brand marketing, I went back to school and earned an MBA. Later, when I transitioned from marketing to product management in fintech, I took a step down in title to gain experience in a new function and industry.

But when I looked around at my male counterparts, I did not see the same pattern. Research from the Russell Sage Foundation shows that in most developed countries, women are actually more educated than men. That made me wonder why. Why do women, and I am generalizing here, often feel the need to collect more credentials, more accolades, more proof of their capability, while others seem able to pivot freely into bigger, better opportunities without the same burden of extra degrees, time, and cost?

For me, the answer came down to confidence. It is about how confident we feel stepping into something new. Can we trust that we will figure it out, or do we freeze under the weight of imposter syndrome? I have come to believe that many of us are playing the corporate game with the wrong strategy, and that makes it almost impossible to win.

Carla Harris, a senior advisor at Morgan Stanley, often speaks about the difference between performance currency and relationship currency. Early in your career, you are taught to put your head down and deliver great results, trusting that merit alone will be rewarded. But as your career progresses, performance currency has diminishing returns. What becomes critical is relationship currency, which is the trust, advocacy, and influence you build with others.

Over time, I learned that while overperforming is important early on, long-term success depends just as much on your ability to navigate politics, build alliances, and develop organizational savvy.

Cassie: That’s such an important distinction—performance currency versus relationship currency. When did you first realize you needed to shift your strategy? Was there a specific moment where it clicked?

Fast forward 15 years into my career. I wanted to make another pivot, this time from product management into my first general management role. But I was not going back to school for what would have been my fourth degree. Instead, I built a plan to strengthen my political confidence, and when the time was right, I went straight to the CEO and made my case.
And guess what? I got the job.The key is that once I had a clear plan to build confidence in the right way, career pivots started to happen much faster.

After two decades in my career, I have realized that there are three distinct types of confidence every woman needs to cultivate. Understanding which one you are lacking is the first step toward accelerating your career growth.

Cassie: Three types? Most people think of confidence as just one thing. Break that down for us.

Jolawn: Confidence matters in every area of life, from home, to the office, to the gym. When it comes to your career, believing that you can shape your own outcomes is essential. There are three key areas that form the foundation of career confidence:

Functional Confidence
Functional Confidence is the belief that you are capable of handling the technical aspects of your role. It means knowing you have the intelligence, skills, and expertise to perform effectively in your day-to-day work.

Social Confidence
Social Confidence is the belief in your ability to build and maintain healthy relationships with colleagues. It is the ability to build relationships, establish trust, and create a strong network of support.

Political Confidence
Political Confidence is the belief that you can influence situations and outcomes. It is about knowing how to leverage relationships, communicate effectively, and navigate organizational dynamics to achieve your career goals.

Cassie: This is so clarifying. How can women assess where they currently are with each type of confidence? What are the signs that you might be strong in one area but lacking in another?

Jolawn: To understand where you currently stand in each of these areas, take the Career Confidence Quiz and discover your personal confidence scores.

​​When I first took the career confidence quiz, I found that my strongest area was functional confidence, while my political confidence was my weakest. My immediate question was, “How in the world do I gain more political confidence?”

The engineer in me believed there had to be a process, so I created an action plan. Based on your own confidence profile, you will be able to identify which dimensions you scored highest and lowest in and notice any recurring themes or patterns.

After reviewing my results, I committed to two things. First, I subscribed to several industry publications to continue strengthening my functional expertise. Second, I built a political action plan that was tied to a specific business goal.

Cassie: Let’s talk about that political action plan. You mentioned it was tied to a specific business goal—what was the situation, and walk me through what your plan actually looked like.

Jolawn: At the time, I was leading an innovation launch within a highly matrixed Fortune 50 company. It was similar to two previous launches that had required disproportionate resources, time, and energy relative to the outcome. Both were ultimately viewed as failures—the first one, because it was painful to execute and did not succeed long term, and the other because the launch was cancelled extremely late in the process.

Success in my role was directly proportional to the success of this innovation launch so the stakes were high. My political action plan needed two components. First was a stakeholder analysis, where I mapped out the interests and sometimes unspoken expectations of each executive and cross-functional stakeholder involved in or impacted by the launch. Second, I built an engagement plan that highlighted gaps between the current innovation design and each stakeholder’s priorities, along with initial ideas for how to close those gaps.

One of the most effective parts of the engagement plan focused on the product’s taste. For this particular brand, product-concept fit was critical, and one of the earlier failed projects had struggled in that area. This time, the new innovation perfectly captured the brand’s taste guardrails, which had been built over more than 80 years. I wanted to remove any lingering doubt about that. So I kept product samples with me at all times, and whenever I ran into a stakeholder in the office, I offered them one. That simple gesture helped eliminate one of the biggest unspoken concerns about the project and built trust and excitement across the team.

Cassie: That’s brilliant, and so helpful and specific. When you think about other pivotal moments in your career—stepping into board roles, for example—how did you apply this framework? Did you use the same approach of identifying which type of confidence you needed to build?

Jolawn: During the pandemic, I took time to reflect on my long-term career goals and realized I wanted to learn more about serving on corporate boards. When I thought about who could guide me, one name immediately came to mind, Merline Saintil, a former colleague from Intuit. Merline’s board bio is impressive, including service on multiple Fortune 100 boards, successfully taking six companies to IPO as an investor, in addition to being a venture capital limited partner. Her wealth of knowledge and experience was an ideal profile of who to learn from.

At that point, I knew board service was an area where I had much to learn. Rather than jumping straight into a board readiness program like Stanford Directors College or Santa Clara’s Black Corporate Board Readiness program to increase my “functional confidence”, instead, I decided to join the organization Merline co-founded named Black Women on Boards (BWOB). BWOB focuses on building political confidence when it comes to board service, inclusive of preparation, placement, and on-going board development for their members serving on both private and public company boards. After reaching out to her, Merline generously shared her own board experiences and, just as importantly, offered to support me as I began my own journey.

As a result, BWOB was instrumental in my first independent board appointment at Jebbit, a Vista Equity Partners portfolio company. BWOB strengthened my candidacy by expanding my network, connected me with opportunities, and helped to demystify the board placement process.

Cassie: I love it. So, instead of getting another degree or certification, you built political confidence by joining BWOB and expanding your network. That’s exactly the pattern you noticed at the beginning of our conversation. Looking back now, what would you say to women who are still stuck in that cycle of collecting more credentials before making their move?

Jolawn: Looking back, I realize that every time I went back to school or took a step down, I was building the wrong kind of confidence. I already had the functional skills—what I needed was political confidence. Once I understood that distinction and started being strategic about which type of confidence to build, everything changed. My advice? Before you sign up for another degree or accept a lateral move, ask yourself: what kind of confidence am I actually missing? Because the answer to that question will save you years.

Cassie: Thank you so much for sharing this framework and your stories—this is exactly the kind of specific, actionable insight our members need. Really grateful for your time and wisdom!

Want to discover your own confidence profile?

Take the Career Confidence Quiz to assess where you are across functional, social, and political confidence—and get a personalized action plan for building the confidence you need for your next career move.

Patti Sanchez is a strategic storytelling expert, author, and the creator of “Crafting Compelling Change Stories,” an on-demand course on using narrative to drive organizational transformation. In this conversation, we’re breaking down why change initiatives fail, the three types of resistance you’ll encounter, and the two essential stories every change leader needs to tell.

You’ve prepared the perfect presentation. Your slides are packed with data proving why this transformation is crucial. But as you present, you see blank faces, worried looks, and eye-rolls. Sound familiar? According to Gartner, nearly 80% of employees don’t trust that organizational change will succeed—and they’re not wrong, since only 1 in 3 leaders report successful adoption of change. The problem isn’t your strategy; it’s that most leaders fail to get people emotionally invested in change. The solution? Storytelling that transforms abstract strategies into compelling narratives people can see themselves in.

Cassie: You’ve written that most corporate transformations fail not because the strategy is wrong, but because leaders fail to get people emotionally invested. What’s actually happening when we encounter resistance to change?

Patti: Resistance to change is completely natural—it’s literally how our brains are wired. When we encounter change, our brains see it as a threat, like a hungry tiger ready to pounce. The amygdala, which regulates emotional reactions, unleashes stress hormones to help us react quickly. But those same hormones cause the prefrontal cortex—the part that handles rational thinking—to essentially shut down, leaving the emotional amygdala to run wild.

This biological process explains why even smart, dedicated employees can become seemingly irrational when faced with change. They’re not being difficult; they’re being human. I’ve learned to reframe resistance as a learning opportunity, because it contains seeds of insight that can actually improve your strategy. Resistance is feedback. It tells you what your stakeholders want, need, and value. Simply asking for that feedback makes people feel heard, which helps defuse uncomfortable emotions.

Cassie: That’s such an important reframe. When you’re listening to that feedback, how do you diagnose what type of resistance you’re actually facing?

Patti: Resistance typically shows up in three distinct ways: intellectual, emotional, and relational. You can gauge which type you’re facing by the language people use. Change consultant Rick Maurer identifies three key phrases:

• “I don’t get it” indicates intellectual resistance—people don’t understand the change or why it’s necessary.

• “I don’t like it” indicates emotional resistance—they understand it intellectually but have negative feelings about what it means for them.

• “I don’t like you” indicates relational resistance—there’s a trust issue with leadership or the messenger.

Each type demands a different approach, but they all have one thing in common: they’re asking you to help people make sense of the change and their role in it. One of the most potent tools for sense-making is story. Persuasive change stories don’t spew facts; they make meaning. They connect transformation to something people already care about—their customers, colleagues, community, or craft.

Cassie: You talk about two specific types of stories every change leader should tell. Walk us through what those are and why both matter?

Patti: The first is a strategic change story—this is your big-picture narrative that puts your change in context. It follows a classic three-act structure:

The beginning describes today’s reality, where there’s a problem to be solved that carries consequences for key stakeholders.

The middle describes the change that needs to be made, how you plan to implement it, and critically—the benefits to people whose support you need.

The end describes the brighter future your change will create, where the problem has been resolved and promised benefits have been realized.

The strategic story answers three critical questions: Why is change necessary? Why is it good for your audience? And why should they trust you to lead them there?

The second type is a personal change story—this is where you reveal your own experiences with change to help others navigate the journey. It’s based on the hero’s journey structure: you had a goal, faced roadblocks and were tempted to quit, but with help you persisted and ultimately triumphed. The most important part of a personal story, though, is the lesson. Along the way, you gained insights that changed you forever – and sharing those insights with others will help them succeed, too.

Together, these narratives humanize you as a leader and provide a roadmap for how others can navigate change successfully. I worked with a software CEO who shared a cautionary tale about a past product launch that failed because he didn’t listen to criticism from his team. By owning his mistake and sharing what he learned, he built trust that he was truly committed to hearing feedback.

Cassie: This is so actionable and valuable. For those leading change, whether it’s a major transformation or just trying to shift how their team works, where should they start?

Patti: Start by understanding that different audiences need different versions of your story. Managers need to understand why the change is good for the business and how it benefits their specific teams. Employees care about one thing above all: what’s in it for them personally.

Think beyond the big announcement. How will you reinforce your story through multiple touch points? What experiences will you create to let people step into the narrative? When we hear a compelling story, something wonderful happens—we experience “narrative transportation.” The critical part of our brain quiets down and the creative part kicks in. In that creative space, we become more open and receptive to new ideas. We even start to imagine ourselves living in that world.

The organizations that succeed at change don’t just tell better stories; they create story-driven cultures where everyone understands their role in the transformation narrative.

Want to master the frameworks for crafting compelling change stories? Patti has created a comprehensive 90-minute on-demand course where you’ll learn practical frameworks and practice applying them to real scenarios. Learn more about “Crafting Compelling Change Stories” here.

Ruchi Pinniger is the Founder and CEO of Watch Her Prosper®, a former hedge fund CFO on Wall Street, venture capital investor, and serves on the executive board of Savvy Ladies. In this conversation, we explore how to replace guilt with growth, reframe your relationship with money, and build self-trust as the foundation for financial confidence.

Many accomplished women have encountered the narrative, or direct feedback, that ambition makes us ungrateful, that wanting more means we’re never satisfied, and that dreaming bigger is somehow greedy. There’s also a hard truth: growing your income doesn’t automatically translate to growing your wealth. Without a healthy money mindset and intentional habits, even high earners find themselves feeling stuck or unclear about their financial futures.

Cassie: I’ve seen so many accomplished women hit their goals and then feel... stuck. They’ve achieved what they set out to do, but instead of celebrating, they’re wondering ‘what’s next?’ and feeling almost guilty for wanting more. What do you say to women who worry that wanting to dream bigger means they’re being greedy or ungrateful?

Ruchi: Let’s start here: you are allowed to want more.

Not because what you have isn’t enough, but because you are evolving. Your dreams were never meant to have an endpoint. They were meant to expand as you do.

We’ve been told that ambition makes us ungrateful. That dreaming bigger means we’re dissatisfied. But the truth? Every new chapter of your life will ask for a bigger version of you. And that’s a good thing.

You hit your goals early because you’re capable of more than you imagined. That doesn’t make you selfish. It makes you a visionary.

Cassie: Love this! How do we shift from that guilty “what’s next?” to something more empowering?

Ruchi: Instead of asking “What’s next?” with fear or guilt, ask:

• What would feel exciting?

• What impact do I want to make now?

• What would it look like to grow in a way that also feels spacious and aligned?

At Watch Her Prosper®, we believe money and business aren’t just about numbers on a spreadsheet, they’re about the prosperous life you want to create and the impact you want to leave.

You don’t have to apologize for wanting more. You don’t have to shrink to make others comfortable. You get to expand, and you don’t have to do it alone.

Your “next level” isn’t a destination—it’s an invitation.

Cassie: That permission to want more is so powerful. But I know many of our members also struggle with feeling ‘behind’ financially or comparing themselves to others in the here and now. How can we develop a healthier relationship with money when we’re constantly bombarded with messages about what we ‘should’ be doing?

Ruchi: This gets exactly to my first money rule, and is so important. How is your relationship with money? Pay attention to the thoughts and emotions that come up when you think about finances. If they lean negative, it’s time to reframe them with prosperity-driven beliefs. Try this mantra: “Every day, I trust myself more and more with money. Money flows easily to me.”

Cassie: I love that mantra. What else can we do practically to shift that relationship?

Ruchi: Remember, money isn’t just about numbers; it’s about how we think, feel, and act when it comes to our finances. The way we manage and feel about our money can directly impact our sense of security, freedom, and overall happiness.

Here’s a practical step to start shifting that relationship: make money check-ins a habit! Whether it’s Money Mondays or Finance Fridays, schedule a weekly date with your finances. Review your accounts, check your expenses, and track your income—no stress, no judgement, just awareness. Information is power!

Cassie: Let’s talk about something a lot of women want but hesitate to ask for: more money. Whether it’s negotiating salary, asking for a raise, or making investment decisions, I hear women struggle with trusting their instincts. How can we build the confidence to trust ourselves with these big financial decisions?

Ruchi: This might be one of the most important money rules. You don’t need to have all the answers, but you can trust yourself to make the right choices. Whether it’s hiring the right team or making big financial moves, self-trust is the foundation of financial success.

I often say to women asking for more money, “It’s not the number, it’s your nervous system.” Meaning do you believe inside that you are worthy of that number. If you are, it will be more likely you’ll receive it.

Cassie: Thanks, Ruchi, for reminding us that our desire for more isn’t greed, it’s growth.

Ready to practice what Ruchi shared? Don’t miss her upcoming Redefining Prosperity™ Workshop — a live virtual session on Dec 3 to help you reframe your money mindset and start attracting abundance.

Details here. And follow Ruchi on Instagram @watchherprosper for more mindset shifts!

A quick text exchange with an accomplished leader on a practice that makes a difference. Today’s is with Gold Truong, Director of Product Management at Amazon who talks about the importance of having a good sounding board at work. When you’re navigating complex problems, it’s easy to get stuck in your own perspective—having the right people to lean on unlocks breakthroughs you can’t see on your own.

Cassie: When you take on a big job or stretch role, what helps you navigate complex, unfamiliar problems?

Gold: Complex problems that require cross-functional collaboration can get really noisy, especially as I’m figuring out my approach. It is helpful to have people I trust around me who will provide a constructive, neutral perspective on the problem.

Cassie: How do you find those people? What’s your process for identifying the right sounding board?

Gold: I start from who I already know and consider what has me feeling stuck. When I think about how to seek perspectives to keep me grounded (and focused), I try to find colleagues who have solved similar problems to mine. Even if there isn’t someone who has solved a similar problem, which I’ve found rare, I’ll ask around to find someone who worked through similar levels of ambiguity. Just finding someone who can empathize can help problems feel more solvable and approachable.

Cassie: What’s changed for you since you started intentionally building these sounding board relationships?

Gold: Having someone I trust give me a fresh perspective has helped me unlock teams in a rut. When you’re deep in a problem, you can’t see your own blind spots. I use my sounding board as a safe place to let me think out loud, comfortably. As a recovering perfectionist, these safe spaces let me test ideas I have and also get high quality feedback on my approach.

Cassie: Thanks, Gold, for the reminder that we don’t have to figure everything out alone!

This connects to a question from a Career Hack member about navigating ambiguity and unclear expectations.

Member Q&A

Q: “My role involves a lot of ambiguity and unclear expectations. How do I figure out what ‘good’ looks like and navigate successfully when there’s no clear roadmap?”

A: This is such a common challenge, especially as you step into more senior roles where the roadmap disappears, or when your team or business is in a state of change.

My first advice: push on where there’s actual ambiguity versus where you could get some clarity from someone like your boss. Not everything has to be ambiguous. If the expectations around the outcomes you’re driving aren’t clear, or the timeline for those outcomes isn’t clear, have that conversation. Get as much clarity as you can upfront.

For the things that remain unclear? I like to think of ambiguity as opportunity. When things aren’t defined, you have space to define the role or the success you’ll have. It’s a great opportunity to demonstrate leadership and strategic thinking. Don’t wait for clarity to be handed to you, create it!

Here’s how:

1. Find your anchors. Even in ambiguity, there are usually a few clear points:

• What ARE the clear expectations (even if it’s just 1-2 things)?

• What does your manager care most about?

• What problems does the business need solved right now?

• What does this ladder up to in terms of your team’s, business’s, or company’s bigger goals?

Start with those anchors and work outward.

2. Put Gold’s advice to use. Find people who are close to the problem you’re solving or who have navigated something similar before. Ask them how they figured out what “good” looked like and what they wish they’d known earlier. You don’t have to figure this out alone.

3. Over-communicate and create feedback loops. Share your thinking and approach regularly. Ask “Is this the right direction?” Make your process visible so people can course-correct you. And if no one gave you clear expectations or timing, propose your own, then use these regular check-ins to validate and adjust. Assume you’re going to need to iterate…you won’t get it perfect from the start, and that’s okay.

The key is being proactive about creating clarity rather than waiting for it to arrive. That’s what leadership in ambiguous situations looks like. And, while the natural temptation can be to go slow, speed is your friend here!

If you have a question, add it to any article, or submit this feedback form.

Subscribe now

Annie Tsai is the Chief Operating Officer of Interact, Early-Stage Investor & Advisor, Author & Columnist, and Community Builder behind “The Business Side of AI” newsletter. In this conversation, we’re breaking down the six must-have skills for 2026, how to build them without getting overwhelmed, and why the future belongs to people who can bridge the gap between AI and real work.

AI is redefining what every role requires—whether you’re in operations, marketing, finance, or leadership. The opportunity is tremendous: those who learn to work effectively with AI will position themselves for influence, impact, and career growth. But knowing where to start can feel overwhelming when the technology is moving this fast and the advice feels either too technical or too vague.

Cassie: The AI era is changing what’s expected of everyone at work. What does that transformation actually look like?

Annie: In the AI era, your title may not say “product manager,” but your job increasingly requires a product manager’s mindset: extracting insights, framing problems, scoping solutions, orchestrating tools, and communicating clearly across stakeholders. The acceleration of agent-based workflows and generative tooling means everyone is now a builder of workflows, decisions, internal products, and narratives. And as more execution shifts to machines, the value of human skills like empathy, insight extraction, sense-making, storytelling, emotional intelligence, and leadership grows exponentially.

Cassie: That makes sense, we’re all becoming builders in some way. If someone wants to position themselves for success in this new landscape, what skills should they prioritize?

Annie: I break it down into six core areas. First, agent and AI system design - learning to design, orchestrate, and monitor AI agents, which are becoming the new unit of work. Second, product thinking - focusing on the right problems, scoping ruthlessly, and iterating effectively. Third, emotional intelligence - AI can’t build trust, read the room, or lead humans through change. Fourth, insight extraction and sense-making - models generate output, but interpreting and translating that into action is uniquely human. Fifth, change leadership - AI adoption is messy and requires leaders who can build trust and navigate uncertainty. And finally, adaptability and meta-learning - the ability to learn how to learn quickly is your long-term career moat.

Cassie: Love it, these are all critical skills. For someone ready to invest in their development, how would you recommend structuring their learning to make real progress?

Annie: Don’t try to do everything at once. Pick two “moonshot” skills for the next six months - one technical like agent design or product thinking, and one relational like insight extraction or empathy. Depth beats breadth. Then design a micro-project to apply each skill immediately. Build a simple AI agent, interview team members about AI pain points, or translate an internal tool into a stakeholder narrative. Create 30-day feedback loops to reflect on what worked and what surprised you. Once your micro-project works, embed it into a team process or present it to leadership - you need to both create value and show value.

Cassie: What advice do you have for people who feel like they’re already stretched thin and now need to add AI skills on top of everything else?

Annie: Here’s the reframe: In 2026, the people who win will break out of the “job title” box and be fluent in both technical and creative spaces. Most importantly, they’ll build the bridge between AI and real work. You still have time to build your toolbox. Start with one agent project and one human skill to deepen between now and year-end. Use low-cost or free resources to create a high-impact learning loop. The key question is: What am I “shipping” next month that improves how my team works or how our customers live?

Cassie: Thank you Annie for guiding us through how to build influence and impact in this fast-changing world.

Want Annie’s full framework, including her curated list of free and low-cost courses across all six skill areas? Read more here and subscribe to her newsletter, The Business Side of AI, for more insights on building the future at work.

Insights from Steve Kerr and Sam Altman Event on Innovation & Leadership

On Monday night, I attended the sold-out, ticketed event At the Table: A Conversation on Leadership, Innovation & San Francisco, where Manny Yekutiel hosted a lively discussion with Sam Altman, CEO of OpenAI, and Steve Kerr, head coach of the Golden State Warriors. Two leaders from wildly different worlds found common ground in how they build teams, handle adversity, and stay true to their values. Here are five lessons that stood out:

1. Culture matters above all. It’s not just what you say, but how it shows up every day.

2. Great teams rely on multipliers. A few exceptional individuals can amplify the performance of everyone around them.

3. Clarity beats inspiration in a crisis. Knowing exactly what to do is more powerful than speeches or pep talks.

4. Lead with conscience and conviction. Values and ethics shape decisions and influence teams in tangible ways.

5. Pair vision with practical guidance. Ambitious goals only succeed when there is both vision from the leader AND experienced team members help translate vision into action.

Paid members: I’m sharing my detailed take-aways for each of these lessons, along with a full recap of the evening, including stories and insights that didn’t make it into the headlines. These are the kinds of insights worth passing along. Feel free to share these notes with your team or anyone in your organization who’d benefit from them.

Read more