The Kentucky Derby is a whole thing in our house—homemade hats, a full menu, all of it.

But this year, something else happened.

When Golden Tempo came from dead last to win at 23-1, I was already losing my mind. And then I saw Cherie DeVaux in the winner’s circle, the first woman to train a Kentucky Derby winner in 152 years, and I felt something shift.

But the moment that really got me was the pre-race interview. Donna Brothers, a decorated former jockey whose mother was among the first women ever licensed to ride, asked Cherie DeVaux what it would mean if she made history that day.

DeVaux said she couldn’t even conceptualize it yet, and that if it happened, she’d let her know.

And then she turned it back to Brothers. Noted that she had been one of the first women jockeys to win a Triple Crown race. And said, simply: women like you are what made it easy for me.

Two women, on one of the biggest stages in sports, making the path visible in real time.

There is nothing like watching someone do the thing. Not reading about it. Not being told it’s possible. Watching it.

Seeing a real person, in real time, do something—and suddenly it’s not theoretical anymore. It’s available.

Like a path you didn’t know existed just got cleared.

And it made me realize, I’ve had versions of that moment my entire career.

I remember the first woman I knew who negotiated a part-time schedule after maternity leave. I didn’t even know that was an option. After that, I did.

I remember the first leader who said we wouldn’t schedule group meetings during carpool drop-off. She didn’t justify it. She just said it.

I remember the first peer who was genuinely tough, sharp and direct with high standards, and also warm, smiling, deeply human. She showed me you didn’t have to pick.

None of them had any idea what they were doing for me.

That’s the thing about going first. It doesn’t just change outcomes, it expands what other people believe is possible for themselves.

Who did that for you? Who’s the woman you watched do something, big or small, that quietly gave you permission?

And then the harder question: Who’s watching you right now and doesn’t know it yet?

Show them it can be done.

The Prison Scene Every Leader Should Study

I was new to the team and hadn’t even had a chance to fully introduce myself before someone talked over me during my first real contribution to the group. They cut me off and dismissed what I was saying, claiming it wasn’t relevant, without even knowing where I was going.

I didn’t know yet if this was personal or just typical behavior. But I did know one thing: if I let it slide, I’d be signaling that it was okay to treat me that way. That I was someone who could be interrupted. Dismissed. Sidelined.

So, I interrupted back. Calmly but clearly, I said, “You have no idea what I was going to say, and either way, I don’t appreciate being cut off like that.”

There was a pause. Then we moved on.

Later, he apologized. Eventually, we became great working partners. But that moment mattered. It wasn’t about being combative, it was about establishing who I was in that room.

We’ve all seen the movie: the protagonist ends up in prison. On day one, a bully steals their roll or knocks their tray to the ground. It’s a test. A signal. A power move designed to establish the pecking order.

And the hero’s response? They don’t smile politely or try to de-escalate. They flip the tray or throw the first punch. They make it crystal clear: you picked the wrong person.

Primatologist Jane Goodall observed that animals test newcomers more aggressively on first contact. I’ve seen the same dynamic play out on a lot of the male-dominated leadership team I’ve ever joined — someone will knock your metaphorical tray, interrupt you, dismiss your idea, or undermine your expertise, especially when you’re new.

The good news? This usually happens in your first few interactions, which means you have multiple chances to establish your boundaries. You don’t need to get it perfect on day one, but recognizing these early moments for what they are gives you the power to respond intentionally.

Here’s what I’ve told tens of women in this situation: your response to that first test doesn’t just handle one interaction. It establishes the character you’ll play in every future interaction with that person — and often with everyone who witnessed it.

What I’ve Learned

Your early responses in any new environment set the tone for everything that follows.

Most of the time, this isn’t about people being mean or cruel. It’s about people feeling threatened about their own position and unconsciously testing to see where you fit in the existing hierarchy. The motivation isn’t malicious — it’s often defensive or territorial.

This behavior doesn’t always happen in front of an audience either. Sometimes it’s a one-on-one conversation, a side comment, or a seemingly innocent question that feels like it’s probing your boundaries. But whether public or private, your response matters.

The cost of being “too nice” in these moments is enormous. You don’t just lose one interaction — you lose positioning, credibility, and future opportunities to be heard.

Something to Try

When you find yourself in a movie prison scene moment, try this:

• Recognize the tray-knocking moment. It usually happens early and feels like a test of your boundaries. Someone interrupts you, takes credit for your idea, makes a condescending comment, or dismisses your input without hearing you out. Trust your gut when something feels like a power play — it usually is, even if the person isn’t consciously trying to undermine you.

• Go bigger than feels comfortable. Your instinct might be to smooth things over or let it slide. Don’t. Respond with slightly more force than the situation seems to warrant. In a public setting, call it out directly: “I wasn’t finished speaking.” In a private conversation, be equally direct but perhaps more explanatory: “I need you to let me finish my thoughts before jumping in.” That discomfort you feel? It’s usually the sign you’re doing it right.

• Focus on what happened, not who they are. “I don’t appreciate being cut off” lands differently than “you’re being rude” — and it keeps you on the right side of professional without softening the message.

• Don’t apologize for proportional responses. If your tray-flip matched the offense, don’t walk it back later. That undermines everything you just established and signals that you’re uncomfortable with your own boundaries.

These moments don’t come with a warning. But they do come. And how you show up in that first one is how you’ll be seen in every one that follows.

I was having a blast leading one of our rocket-ship businesses. Growth was strong, the team was energized, everything was firing. Life was good.

But there was another role in our division that had been sitting vacant for 3-4 months—similar to mine, but much bigger in scope. A team and product that needed a real turnaround. A totally different degree of difficulty.

I wasn’t the natural candidate. I wasn’t being considered. In fact, I was on the interview committee helping find the right person—which meant I knew exactly the profile we were looking for, and that my boss didn’t think I was it. All the evidence pointed one direction: stay in your lane, focus on what’s working.

For a while, I did.

But as the months passed and we still hadn’t found someone, something shifted. I’d been watching the situation closely, learning more about what the role actually required—and a tiny voice inside me kept getting louder. What if I could actually help here? I wasn’t sure. I didn’t have all the answers. But I couldn’t shake the feeling.

Then one of the sharpest women I know came to find me. She was on the leadership team of the very group that needed a leader — and she'd decided I was the right person. She didn't hint at it. She made the full case for why I should take it on, told me exactly why she thought I could do it, and didn't leave until I was convinced. Her read of the situation, and her confidence in me, was the push I needed.

I still wasn’t ready to ask for the job outright. But I raised my hand to help stabilize the team and start making progress while the search continued. My plan: empower my current leadership team to take on more so I could layer this on top.

Effectively, I would be carrying both roles at once. And showing I could handle the load turned out to be exactly what sealed it.

Six months in, I was offered the role. We promoted an internal successor for my original business, and I stepped in. Ultimately, it would open the door to the biggest job of my career, one four times larger than where I’d started.

What I Learned

That experience taught me a few things about creating your own opportunities that I keep coming back to:

• You may have to nominate yourself. Someone usually puts people forward for jobs and promotions, and sometimes that person needs to be you. We wait for others to recognize our potential. But sometimes you’re the only one who can see the connection between your skills and what’s needed. Waiting to be discovered is a strategy, just not always a good one.

• Interim roles are low-stakes auditions — for everyone. By offering to help temporarily, I got to test whether I actually wanted the role and whether I could handle it, without the pressure of a permanent decision. And my boss got to see what I could do before committing. It takes the risk off everyone.

• Current success gives you permission to take bigger swings. Because I was performing well, I had the credibility to propose an unconventional solution. Success creates options. The stronger your foundation, the more room you have to reach.

• Advocating for yourself isn’t arrogant — it’s strategic. You know your capabilities and ambitions better than anyone else does. If you see a fit that others are missing, say so. Nobody else is living inside your head.

Something to Try

Here’s how to stop waiting and start creating your own opportunities:

• Scan for the gaps nobody’s rushing to fill. Look for vacant roles, reorganizations, and messy situations that have been sitting unresolved. Those are often where you can step up in ways that wouldn’t be possible otherwise. Ask yourself: What problem does this organization have right now that nobody has claimed? Is there any version of me that could help solve it?

• Don’t disqualify yourself before anyone else does. Before you decide you’re not the right fit, ask: What’s actually driving that assumption? Is it the data—or is it a story you’re telling yourself? Sometimes the “right” candidate on paper isn’t the right person for the moment. Your read of the situation, your relationships, your approach—those count.

• Use interim roles as low-stakes auditions. Offering to help temporarily takes the pressure off everyone. You get to test whether you actually want the responsibility. They get to see what you can do. Nobody has to bet everything on a permanent decision upfront.

• Listen to the tiny voice. Before anyone else saw me in that role, I had a quiet instinct that I could help. I almost talked myself out of it. Pay attention to that signal—especially when the logical case says “stay in your lane.” That voice often knows something before the rest of you catches up.

• If someone you respect looks you in the eye and says you can do this, take it seriously. Find the people who see your potential clearly and stay close to them. When they make the case for you—listen. And if you ever see someone who could use that same push? Give it. You don't have to have all the answers or a bigger title. You just have to be willing to say: I see you, and I think you can do this.

The path I took wasn’t obvious. I wasn’t being considered. I wasn’t the natural fit. But I had a quiet instinct, a woman who believed in me, and the willingness to raise my hand before I had all the answers. That combination ultimately unlocked the biggest job of my career.

Stop waiting to be chosen. The opportunity you’re circling might already be yours to take.

You’re Always Teaching Something (Make It Count)

On a vacation one year, my husband suggested we kayak in open ocean waters around a remote island home to a large bat colony. We had taken a boat to get there—completely isolated, no people anywhere near us, just waves. I had kayaked plenty of times where the shore was visible and the water was calm. But this was different.

The idea terrified me. I was about to say my husband and daughter could try it when I caught myself. My daughter was watching me to see if I would do it—trying to gauge whether this was actually scary or just looked scary. I could see her glancing at the endless waves, then back at me, calibrating.

That’s when it hit me: this wasn’t just about kayaking. It felt like I was representing all of womankind. Like my daughter was going to base her entire understanding of female capability on whether her mom could handle a kayak in choppy water.

So I said yes. Not because I was feeling brave, but because she was watching. Because I was teaching her something about how women handle fear, how we approach challenges, whether we’re willing to try hard things.

This dynamic shows up everywhere once you notice it. At work, your team is watching how you handle the difficult client call, whether you admit when you don’t know something, how you respond when a project goes sideways. They’re not just observing; they’re calibrating what’s expected, what’s possible, and what kind of leader you are.

Even if you don't manage people, you're demonstrating what you bring and setting the standard for what's valued. Your colleagues notice whether you speak up in meetings, how you handle feedback, whether you help when someone’s struggling.

The uncomfortable truth? You’re always teaching something, whether you mean to or not.

What I’ve Learned

That experience reminded me of something important about leadership that applies far beyond parenting:

You have invisible influence. People notice what you do when you think no one’s watching. How you handle being wrong in meetings. Your reaction to bad news. Whether you follow through on commitments when it’s inconvenient. Your team is constantly learning from these moments what behavior is actually valued, not just what’s written in the company handbook.

Your response to challenge sets the standard. When you volunteer for the challenging project, take on the initiative no one else wants, or admit a strategy isn’t working, you’re modeling risk tolerance, problem-solving, and authenticity. When you avoid hard conversations or only propose sure-thing initiatives, you’re teaching that too.

Admitting difficulty builds psychological safety. When you name that something is challenging while still moving forward, you create space for others to be honest about their own struggles. Teams need to see that competent people can feel uncertain and still perform.

Consistency matters more than perfection. People aren’t looking for flawless leaders; they’re looking for predictable ones. When your actions align with your stated values consistently, even when it’s hard, you build trust and credibility.

Small moments matter as much as big decisions. How you handle interruptions in meetings, whether you give credit generously, your response to someone’s mistake—these everyday interactions shape culture more than quarterly presentations.

Something to Try

Here’s how to become more intentional about the leadership lessons you’re teaching:

• Do a quick audit. Ask yourself: What behaviors might my team be copying from me right now? Consider these areas: Risk tolerance: Do you only propose initiatives with guaranteed success? Problem-solving: Do you stay steady under pressure or visibly panic? Growth mindset: Do you take ownership when things go wrong or find others to blame? Communication: Do you admit when you don’t know something or pretend to have all the answers?

• Identify your “modeling moments.” These are situations where you can intentionally demonstrate the behavior you want to see: The first person to acknowledge when a strategy isn’t working or ask for help publicly when you need expertise outside your wheelhouse • Taking on stretch assignments that scare you but could benefit the team • Responding calmly to unexpected problems during high-stakes situations

• Practice visible learning. Share moments when you took a risk that scared you and what you learned. This normalizes calculated risk-taking and creates permission for others to try new approaches.

• Change up your questions. Instead of “What would make this project successful?” try “What’s one risk we should take that could significantly improve outcomes?” This signals that thoughtful risk-taking is valued.

• Name the modeling explicitly. Tell your team: “I want us to be the kind of group that tackles hard problems, so I’m going to volunteer for this difficult client situation. Not because I have all the answers, but because I want us to practice being willing to try.”

In that kayaking moment, I realized my daughter wasn’t just watching to see if I was brave. She was learning what was possible for someone like her. Your team is doing the same thing. They’re watching how you navigate uncertainty, handle failure, and approach challenges to understand what’s expected and what’s achievable.

You're always modeling something. Make sure it's worth copying.

Try ‘Permission to Speak Freely’

When we were kids, our dad came home one day carrying a big box with a grin on his face. Our local independent video store was closing, and he’d bought a whole stash of VHS tapes from the clearance bin. Suddenly, we had real movies instead of grainy recordings we’d captured on weekends when pay channels went free. Thanks to my dad being a Navy vet, many were war films

One phrase from those movies lodged in my memory: “Permission to speak freely?” In the military context, it’s what a subordinate uses to ask a superior for space to raise a dissenting or potentially uncomfortable opinion. It doesn’t shield the speaker from consequences, but it creates a temporary pause in the usual etiquette of hierarchy so that something important can be voiced.

Years later in corporate settings, I noticed the same dynamic—rooms where disagreement felt risky, leaders who didn’t naturally invite opposing views. That’s when I started borrowing the spirit of that military phrase.

I’ve used variations of this approach with leaders who aren’t known for welcoming pushback. Instead of jumping into concerns about their strategy, I’ll ask, “Would it be okay if I shared a different perspective on how to make this successful?” The shift in body language is usually immediate—suddenly they’re listening instead of preparing to defend.

What I’ve Learned

When you ask permission to raise a concern or share tough feedback, you’re signaling two things at once: courage and respect. You’re showing that you trust the other person enough to share something potentially uncomfortable—and that act of trust often softens their stance. It puts them in a more open frame to listen rather than defend, flipping the dynamic from challenge to collaboration.

In meetings with leaders who aren’t known for inviting disagreement, asking permission creates a small opening that signals you recognize the dynamic and still want to engage constructively.

Something to Try

I’ll be honest—as a woman, I’m not usually a fan of asking for permission. We’re already conditioned to soften our opinions and defer to authority. But this is different. You’re not asking if you’re allowed to speak; you’re signaling that what you’re about to say matters enough to create space for it. It’s strategic, not deferential.

This approach works best in certain situations:

With leaders who don’t naturally invite opposing views. In rooms where dissent feels risky, asking permission creates a small opening and signals you want to engage constructively.

When raising delicate issues where tone matters as much as content. If the way you say something could land as strongly as what you’re saying, a permission phrase sets the right tone. It softens the entry without softening your point.

As a way to frame potentially unwelcome truths as respect and shared responsibility. Sometimes the hardest messages are the most important. By prefacing them as an act of partnership, you frame your input as care for the bigger picture, not personal critique.

When working with a new leader. Early interactions set the tone for your relationship. Using a permission phrase can test the waters, showing how open they are to feedback, while also establishing you as someone who speaks up thoughtfully from the start.

Here are ways to borrow the spirit of “permission to speak freely,” ideally paired with a tone that signals curiosity rather than confrontation:

• “Would it be okay if I offered a different point of view?”

• “I have a perspective that might shift the conversation—would now be a good time to share it?”

• “May I speak freely on something that could help us think about this differently?”

• “I want to offer [a different take/raise something unpopular/share my experience which has been quite different]—are you open to hearing it?”

In practice, I’ve found that no one ever says no. Even the leaders I suspected were not interested in hearing a challenge responded with “of course.” That small act of asking both shows respect and gently shifts the dynamic—it makes people more open to listening, and creates space for ideas that might otherwise go unheard.

Influence isn’t just about the substance of your point; it’s about creating the conditions for it to be heard. Like those old military movies taught me, sometimes the most powerful thing you can do is ask permission first, not because you need it, but because it opens the door for what comes next.

Why You Need a Bad B*tch Alter Ego (and how to claim yours)

Yesterday the LeanIn/McKinsey 11th Women in the Workplace report came out showing progress for women is slowing and support is slipping, and my feed was filled with posts about what companies should do.

So, I wrote five different essays last night— one about how waiting for companies to fix things is modern-day Prince Charming energy, and us princesses are going to have to save our damn selves, one about how much energy is spent debating what women should be (lean in or lean out? girlboss or soft life? tradwife or executive?) and not enough invested in helping women hold power, and a couple more rant-adjacent pieces I’ll spare you. All of them held something I believe to be true: progress doesn’t only come from programs, policies, or corporate statements — it comes from us. From the versions of ourselves that take the meeting, ask for the money, challenge the room, and refuse to shrink.

Which is what led me here. Not to another think piece, but to something more personal. Because the truth is, sometimes work requires a softer version of us…and sometimes it requires the tough b*tch who doesn’t flinch, doesn’t fold, and takes what’s hers.

Here’s something I never thought I’d broadcast: I had a sixth-grade nickname called Trashy Cassie. And she’s tougher than I’ll ever be.

Let me back up.

How Trashy Cassie Was Born

In sixth grade, I was an awkward girl with a Dorothy Hamill haircut, a mouth full of dental hardware, and about a foot of height more than most of the others. It wasn’t a phase I was growing into gracefully. The centerpiece of it all was my bionator, a device that clipped onto both my upper and lower teeth to correct my overbite. As you’re realizing right now, there’s nothing more socially assuring in middle school than being tall, weird-looking, and mute.

One day at lunch, I finished eating and walked my tray to the garbage can. What I didn’t realize, until I got back to class, was that I’d tossed my bionator away with the leftover tater tots.

I called my mom from the nurse’s office, humiliated but hoping she’d tell me it was fine. She reminded me that the bionator had cost $150, which at the time may as well have been a million, and that I had to find it.

So, I went back to the cafeteria. And then into the dumpster. With the janitor. The good news, he told me, was that it was a new dumpster—this would be quick and no problem.

We found it.

It was sterilized and went on to keep torturing me. Unfortunately, word of my dumpster adventure got out. Garbage Pail Kids were having a pop culture moment, and someone quickly decided “Trashy Cassie” was the perfect nickname. It stuck. The bionator may have been disinfected, but my reputation was not.

At the time, it felt like the worst thing that could possibly happen. I asked my mom if not going back to school was an option. It wasn’t. Something about surviving that moment gave me an unexpected kind of resilience.

Fast forward 20 years into my corporate career, and I found myself in a situation that triggered that exact same feeling.

When Nice Stops Working

I was dealing with a senior executive who was making my life miserable. Classic undermining behavior—questioning my decisions in meetings, calling my boss to complain about my aggressive behavior, the whole playbook. And I had that exact same feeling. I didn’t want to go to that next meeting. I wanted to avoid him the way sixth-grade me wanted to avoid school.

Except now I’m driving a multi-million-dollar growth initiative, and “avoiding” isn’t an option.

Here’s what nobody tells you in leadership training, but every woman knows once she gets there: there are moments that require a level of directness and toughness that might not come naturally to you.

I needed to stand up to this executive directly. Tell him his behavior was unacceptable. Set a hard boundary. The version of me who wants everyone to like her? She wasn’t equipped for that conversation.

But you know who was? Trashy Cassie.

So that’s who I channeled. I texted him asking for 5 minutes. I was direct: “Here’s what’s happening, here’s why it needs to stop, here’s what happens if it doesn’t.” No apologies. No softening. Just clear boundaries delivered calmly.

It worked.

Another time, a peer complained to leadership that I had “too much” responsibility. His definition of “too much”? More than he had. Not more than I could handle. Just... more than him.

His proposed solution? He should take on part of my portfolio. The political version of me wanted to smooth this over, but I called on Trashy Cassie. I went into that conversation with leadership with complete clarity about my portfolio, my performance, and why the current distribution made business sense. I kept my portfolio. He waited a year before trying again.

What I’ve Learned

Here’s my take on why the alter ego approach is so effective:

It creates distance from the discomfort. When you’re channeling someone else—even a past version of yourself—you’re not carrying the full emotional weight. You’re playing a role, which somehow makes the tough stuff more doable.

It’s based on real evidence. You’re not imagining some fictional badass. You’re calling on a version of yourself that already survived something hard. You have proof that this person exists within you. I literally dug through garbage and came back the next day. If I can do that, I can have a difficult conversation with a peer.

It feels temporary. I don’t have to be Trashy Cassie all the time. I wouldn’t want to be. But knowing I can access that energy when I need it? That’s the key. It’s armor you put on for specific battles, not a personality transplant.

It shortcuts the internal debate. Instead of spending energy convincing yourself you can be tough, you just... channel the person who already was. Less mental overhead, faster action.

The moments that define your career aren’t usually the ones where you’re playing to your natural strengths. They’re the moments that require something extra. Something harder. Something that doesn’t feel like “you.”

Having a version of yourself you can call on in those moments? That’s not fake. That’s strategic.

Something to Try

Think back to a time you survived something difficult. Not necessarily traumatic—mine was dumpster diving in sixth grade, for crying out loud. But something where you showed up anyway. Where you pushed through discomfort and came out the other side.

Maybe you were the new kid who ate lunch alone for three months. Maybe you survived cancer treatment, or caring for a dying parent, or a divorce that tried to break you. Maybe you got cut from the team, laid off without warning, or had your presentation fall apart in front of the board.

That person who survived it? That’s your alter ego.

Give them a name if it helps. The point is to make them distinct enough that you can consciously shift into that mode when you need to.

Next time you’re facing a moment that requires toughness you’re not sure you have, ask yourself: what would that version of me do? The one who already proved they could handle hard things?

If I can survive being called Trashy Cassie, you can absolutely handle whatever’s in front of you right now.

What moment taught you that you’re tougher than you think? Or share your alter ego name! Comment, or reply and tell me—I read every response.

Create a Personal ‘Service Level Agreement’

Early in my corporate career, I found myself working with a very senior executive who would email me questions or feedback on our shared work when he got around to reviewing it. Whenever I saw his name in my inbox, I would drop everything—pause mid-meeting, interrupt whatever project I was working on—and respond immediately.

At first, this felt like good relationship management. But I started noticing a pattern: the faster I replied, the faster additional requests would come.

One particular morning, this cycle completely hijacked my schedule. A simple question at 9 AM turned into hours of continuous email exchanges, pulling me away from an important project deadline and making me late for other commitments. I felt frustrated and started thinking he was being unreasonable with his expectations.

Then it hit me: I had created this dynamic. I was the one training both of us that I was available for immediate, constant back and forth communication. I had set an impossibly high bar for myself that was unrealistic to maintain and ultimately counterproductive.

What I’ve Learned

Over the years, I’ve watched this same pattern play out repeatedly, especially with women who feel pressure to be overly accommodating. We create unrealistic expectations for ourselves and train others to expect constant availability, simply because we haven’t thoughtfully considered how we want to manage our professional communication. I’ve also seen how everyone can fall victim to the idea that response speed equals value.

That early experience taught me something valuable: We already know how to set communication expectations—we just haven’t applied them to ourselves. In business, Service Level Agreements (SLAs) do one simple thing: they eliminate the guessing game. Customer support responds within two hours during business hours. Shipping takes 3-5 days. The same framework that prevents chaos in business relationships can transform our professional communication.

Consistency builds trust, not speed. In business, SLAs create predictability. When you establish clear response time expectations, you eliminate the guesswork that creates anxiety on both sides.

Workflow protection drives real productivity. Business SLAs prevent service interruptions. Your personal communication standards serve the same function for your actual work. When you commit to responding within reasonable timeframes rather than immediately, you create space for deep work and strategic thinking, or what Stephen Covey called putting first things first.

Breaking the “always available” expectation prevents burnout. Just as business SLAs normalize that service providers aren’t available 24/7 unless explicitly contracted that way, your personal standards help colleagues understand that constant availability isn’t sustainable or necessary.

Distinguishing real urgency from manufactured pressure. When people know your response framework, they’re more likely to communicate actual priorities clearly instead of assuming everything needs immediate attention.

Here’s what I actually do: I tell people I work closely with that I don’t monitor email and Slack minute-by-minute, and if something’s truly urgent, text me. This simple boundary has prevented countless unnecessary interruptions while ensuring real emergencies still get immediate attention.

Finally, as a leader, be very careful about the expectations you set as a rapid responder for people on your team. Your communication habits can easily become unspoken performance standards.

Something to Try

You don’t need to send a formal announcement (please don’t), but having your own internal framework keeps you consistent and trains others through your actions. This isn’t about creating rigid rules you have to follow perfectly. It’s about giving yourself permission to be in control of your time instead of letting every ping dictate your day.

• Think through service level agreements for your communication. Just as businesses set different response times for different types of clients, you might establish different timeframes for different relationships—perhaps faster for your boss or team, more reasonable for general colleagues.

• Decide when you’ll actually respond rather than reacting in real-time. Scheduling specific times during your day for responses, rather than constantly interrupting your work or checking messages during meetings. The goal is to be responsive without being reactive.

• Establish what kinds of communication warrant immediate attention versus what can wait. Not everything marked “urgent” actually is, and having your own framework helps you make those distinctions more thoughtfully.

• Think about your “business hours” for different types of communication. Establish when you’re available for routine communication versus when you’re offline. You might look at messages outside work hours or even draft responses but use scheduled send features to deliver them during business hours unless someone alerts you directly for something urgent.

• Be transparent with close collaborators. Let key colleagues know you don’t monitor communication constantly and establish alternative channels (like texting) for true emergencies.

• If you’re worried your boss or company actually expects immediate responses, start small. Respond within an hour instead of within minutes. Batch responses instead of one-off replies. Most people won’t even notice the shift. This isn’t just for senior people, it’s actually more important when you’re earlier in your career. When you have less organizational capital, training people to expect sustainable responsiveness protects you from burnout.

The key is being intentional about these choices rather than defaulting to whatever feels most accommodating in the moment.

In that executive relationship, I almost burned myself out trying to be the perfect, always-available employee. But then I realized I was the only one who could change this dynamic.

Personal SLAs aren’t about being unresponsive—they’re about being strategically responsive in ways that protect your effectiveness and well-being. In a world that treats everything as urgent, having clear standards for what actually deserves immediate attention becomes a competitive advantage.

Choose Your Mode Before Responding

During an important operating meeting, I was focused on making a case for a particular direction when, afterwards, I saw a Slack message from a fellow Senior Vice President that read, “What’s your background?”

My stomach dropped. What’s your background? Had I said something that made him question my expertise? Had I lost credibility? I started mentally cataloging every qualification I had, every reason I belonged in that room, preparing to prove myself.

I responded awkwardly with a joke about why he was asking and then launched into a full explanation of my experience and qualifications. Later, he replied, “I was asking about your Zoom background,” referring to the virtual background image I was using, not my professional history.

In that moment, I realized how completely I’d created a story about his intentions with zero evidence. Brené Brown talks about the stories we tell ourselves, and this was a perfect example—I’d written an entire narrative about being inadequate based on three innocent words.

In this example, I was telling myself a story about my colleague thinking I was less than. But, why? We were relatively new colleagues, though he’d been nothing but gracious and supportive in every interaction.

What I’ve learned

While I have practiced noticing what story I am telling myself, it hasn’t necessarily helped me decide how to move forward. So, I have worked on consciously making a decision what “mode” to operate from.

I’ve learned to be strategic about what information to use when choosing my mode. If I have nothing to go on, these are perfect moments for curiosity. Other times, people explicitly state their intentions, giving you clear data to work with. The skill is recognizing which situation you’re in and choosing your response accordingly.

This framework is especially crucial for digital communication—Slack, email, and text messages where tone is invisible, and context is minimal. Without facial expressions or voice inflection, our brains fill in the blanks, often with our worst fears. A simple “Can we talk?” message can send us spiraling when it might just mean “I have a quick logistical question.”

Something to Try

Instead of letting your default reactive patterns take control, you pause and choose:

• Curious Mode: To explore the why behind the question. Seeking to understand the broader context/intent before assuming.

• Clarifying Mode: To decode what the question actually is.

• Confident Mode: Responding from what you know or can contribute.

Here’s how it works in practice:

Curious mode questions: “Can you help me understand what you’re looking for?” “What prompted that question?” “I want to make sure I’m addressing what you really need - can you tell me more?” “What would be most helpful for you to know?” “I’m curious about the context behind your question”

Clarifying Mode questions: “What did you mean by [specific phrase]?” “Can you clarify what you’re referring to?” “I want to make sure I understand - are you asking about X or Y?” “Could you be more specific?”

Confident Mode questions: “Based on my experience with [specific area], here’s what I’ve found...” “I can speak to that - in similar situations I’ve seen...” “That’s actually an area where our team has strong data...” “I’m well-positioned to address that because...”

For digital messages that trigger defensiveness:

• Read the message twice before responding

• Ask yourself: “What’s the most neutral interpretation of this?”

• When in doubt, default to clarifying mode rather than assuming intent

• Remember: the sender may be rushed, distracted, or simply bad at digital tone

Dear reader, I wish I had simply clarified what he meant before responding. And if you can believe it, I made it worse.

After the initial conversation, my colleague thanked me with a joke, saying he was ‘glad to get that little personal ad.’ Delighted with my own wittiness and barely containing my laughter at what I was sure would be comedy gold, I gave a nod to the 1979 hit that my BFFs and I had inexplicably loved, ‘Escape (The Piña Colada Song),’ and replied: I like piña coladas and getting caught in the rain.

He responded with something equally random back. He hadn’t gotten the reference, he’d just felt compelled to match my energy with... something. I could practically hear the ‘what is happening?’ through his message. Apparently, my deep knowledge of vintage soft rock hits is not universally appreciated in corporate America.

The moral of the story? Take a beat and decide which mode to reply in before opening your mouth. Sometimes the best response is the simplest one: ‘What did you mean?’ It’s a lot less embarrassing than accidentally serenading your colleagues with Rupert Holmes lyrics.

Please tell me I’m not the only one. What’s a time you overthought a response and made it accidentally weird?

Find out “Why not you?”

When I first joined a new division as a leader, I set up a casual coffee with the GM, my boss’s boss. He was someone I respected immensely—sharp, thoughtful, and not prone to flattery. In prior conversations, he’d been generous with praise about my leadership style and overall impact at the company. It all sounded great but was pretty broad and I wasn’t clear where I stood in his mind.

So, I decided to ask a more direct question, not about how I was doing, but about what might be holding me back.

I asked: “If a leadership role on your staff became available, why wouldn’t I be a candidate for it?”

He didn’t hesitate: “Because you have no skills. Or at least, I have no idea what they are.”

I nearly fell out of my chair.

He quickly clarified: “I have no doubt that you’re a great leader. But I don’t know what depth or domain you really own. What situation would I confidently hand over to you?”

His directness and that level of clarity stunned me. It was exactly what I needed to hear. I realized that while I had built a career leading across functions—first in communications, then business operations, both classic generalist ‘Swiss Army knife’ roles—I hadn’t done the work to name what I was uniquely great at or what kinds of problems I was best suited to lead. Unlike someone who’d grown up in product or marketing with a clear lane, I was a strong generalist and relationship builder, but I needed a sharper narrative.

Over time, I learned to define and articulate my edge while also deliberately building deeper expertise, all in a way that mattered to the business. But that moment only came because I asked a very specific, and very uncomfortable, question.

What I’ve Learned

If you ask a general question, you’ll usually get a general answer. That’s fine for positive reinforcement, but not if you’re trying to grow.

Asking a specific question puts a finer point on the feedback you get. It narrows the field, makes it safer for the other person to be honest, and helps you pinpoint what’s actually standing in your way.

More importantly, it surfaces how others perceive you in the context of opportunities that actually matter, giving you actionable insights rather than pleasant, but often unhelpful, generalities.

Something to Try

Start with something real you want— a project, a promotion, a stretch opportunity. Then ask a bold, direct question like:

• “If this role opened up, what would make you hesitant to put me in it?”

• “What situations [related to this role/project] would you not trust me to lead?”

• “If you had to describe what I’m uniquely great at, would you know what to say?”

Then: listen. Take notes. Don’t defend. Let the discomfort do its job.

The goal isn’t just to get what you want, it’s to learn, grow, and contribute meaningfully. Asking the right question is often the fastest way there.

Amplified

Reshma Saujani, founder of Girls Who Code, knows exactly what keeps women from asking questions like this.

In her book Brave, Not Perfect, Saujani writes that perfectionism isn’t about excellence—it’s about protection. It’s the belief that if we look perfect, do everything perfectly, we can avoid criticism and rejection. But that shield also keeps us from the very feedback that helps us grow.

Asking “why not me?” requires exactly the kind of bravery Saujani champions: the willingness to hear an answer you might not like in service of growth you actually need. It’s choosing clarity over comfort, action over avoidance.

Watch her TED Talk: Teach girls bravery, not perfection

Reframe in Realtime

I had been invited to speak at an internal offsite, an event for our legal, compliance and government team held at a hotel about 45 minutes from the office. They wanted me to share trends we were seeing with a key customer segment. I was deep in the work and had a lot of insight to bring, so I said yes.

At the time, I was also in the middle of my pumping schedule. I had just returned from maternity leave, and anyone who’s been through that stretch knows timing is everything. I looked at the event time and figured I could make it work with one ask: I needed a private room to pump before I spoke.

Everyone was gracious about it. A colleague made sure the hotel’s event coordinator would set me up with a space. On the drive over, I pictured an unused guest room or maybe a quiet suite.

Instead, I got the janitor’s office. And I’m using “office” loosely. There was a desk and a chair, but also mop buckets, cleaning chemicals, and that distinct smell of industrial disinfectant. Still, I had asked for a room, and this was technically a room. I set up my pump.

About halfway through, the door opened. The janitor, one of the few people with a master key, walked right in. I don’t know who was more shocked, him or me. For anyone who’s pumped before, you know there are days you feel like a life-giving superhero.

This wasn’t one of those days.

I felt rattled, exposed, and like a complete mess. And in 20 minutes, I was supposed to stand up in front of more than a hundred colleagues and speak as an expert.

I froze. I could feel the tears threatening. I hated the idea that this moment would ruin my session. And then something snapped into place. I told myself a new story.

It wasn’t the story of a struggling new mom barely holding it together in a janitor’s closet. It was a story where I had just accidentally flashed the janitor. Mortifying? Yes. But also kind of funny.

And weirdly, that made me feel powerful again. Because if I could take that moment and make it mine, I could do anything.

So, I laughed to myself, packed up, and walked onstage to deliver my talk.

What I’ve Learned

Sometimes, the hardest part of showing up is not what happens around you, it’s the swirl of what happens inside you. The temptation to spiral. To turn a small disruption into a story about inadequacy or failure.

Here’s what that moment taught me about owning your story and turning chaos into control:

• The ability to reset your own internal narrative, especially when no one else knows what just happened, is very powerful.

• Finding the absurd angle in a mortifying situation can instantly shift you from feeling like a victim to someone in control of their story.

• There’s a critical difference between what happens TO you and what you DO with what happens to you.

Once I changed the mental story, my physical composure and confidence naturally followed.

Something to Try

Here’s how to build your own story-rewriting superpower:

• Practice the “Only I Know” pause, when something embarrassing or deflating happens, remind yourself that you’re likely the only one aware of the full context, and use that privacy as power rather than shame.

• When you feel rattled, ask yourself “What’s actually ridiculous about this situation?” Sometimes humor is the fastest route back to feeling capable and in control.

• Choose your carrying story by deciding which part of what happened serves you going forward and which part you can leave behind in that moment. Use physical transitions to signal a reset to yourself—after a tough moment, walk to the bathroom, take deep breaths, adjust your posture to tell your body you’re moving into a new chapter.

• Finally, practice the “plot twist” mindset: instead of asking “Why is this happening to me?” ask “How does this make my story more interesting?” This small shift in perspective can transform obstacles into character-building moments that actually strengthen your presence and resilience.

In that closet, I almost unraveled. I had every reason to feel off. But then I realized: I was the only one who knew what had just happened. I had total control over how the next part of the story would go.

Remember: you always have more control than you think. Not over what happens, but over what it means. In those moments when everything feels like it’s falling apart, the most powerful question isn’t ‘Why me?’ but ‘What now?’ Because the story you tell yourself determines everything that follows.

Amplified

What shifted things for me in that closet wasn’t composure, it was narration. I could’ve told the story one way and fallen apart, or told it another and kept moving. Lori Gottlieb, psychotherapist and author of Maybe You Should Talk to Someone, knows exactly what’s at stake in moments like that:

“If I’ve learned anything, it’s that we are all unreliable narrators of our own lives… Stories are the way we make sense of our lives. But what happens when the stories we tell are misleading or incomplete or just wrong? … We assume that our circumstances shape our stories. But what I’ve found time and again is that the exact opposite happens. The way we narrate our lives shapes what they become.”

That’s the whole muscle: interrupting the version that shrinks us and choosing one we can live inside of. I’m including the clip of her TED Talk so you can hear her say it in context — it lands even harder out loud.

Hang tight, a guest voice is up next to show us how they reframe in real time, too.

— Cassie