Who You Are Is How You Lead: A Conversation on Leading Through Massive Change

The kind where a former Fortune 500 CMO admits she sat down with her VC friend three weeks ago, looked across the breakfast table, and said, "I'm terrified."

That somebody was Tara Sharp — former Google exec, former Sonic and Viasat CMO, board member at a dozen companies, UN advisor on AI policy, and one of the heroes of Maya Shankar's The Other Side of Change. She's the kind of person whose résumé makes you sit up a little straighter. And she was the one telling us, in real time, that real change still scares her.

But the résumé isn't the story. What Tara has done with her power is the story.

She helped provide free internet access to public schools in Latin America — kids who often struggled to get textbooks now had the internet on a laptop. The day after the firestorms tore through Sonoma County and dozens of schools burned down, she was able to get a semi truck of Google laptops and hotspots there in days.

And before any of that — before the title, before the platform — there is the moment that to me is the actual definition of leadership showing up.

When Tara was six months pregnant, doctors shared that her daughter had half a heart and nothing connecting her heart and lungs, and that her baby would not survive. Over and over, that was the answer. Tara didn't like that answer. She went and found doctors who would fight with her. Surgeons who thought - maybe - they could save her daughter's life. She found them.

Her daughter is fourteen now. She plays three sports and just graduated eighth grade. Stanford Children's Hospital considers her a miracle.

Don’t settle. Fight. Find the people who want to fight with you. Identify how you want to make a difference. And then share it all back.

That's what this whole session was about.

We've been so deep in the what of this moment — the AI roadmaps, the ROI decks, the team restructures, the diagnostics for the CFO — that we're ignoring the part that drives it all. Who are we being and who are we becoming through all of this? How are we actually showing up? And, since no one is coming to save us (Thank you, Lauren)… what kind of leaders do we want to be?

Here's what I'm sitting with.

The mask comes off, or you stay stuck.

When Tara was 25, she was running rooms full of people twice her age. Wine industry, Sonoma County, golden ticket. And she told us, with a kind of tender horror you only get from looking back twenty years later, that she had been walking around pretending to be a 60-year-old man.

Not on purpose. She was just emulating Jess Jackson, the Kendall Jackson founder who'd taken her under his wing. He was the model of "successful." So she became a small, perhaps awkward, Xerox of him.

Then came the years at Stanford Children's Hospital. Tara was watching nurses save babies' lives — including her daughter's — and shared with us,

"I just didn't have the energy anymore to pretend to be somebody I wasn't."

Crisis stripped the mask off. And once it was off, the career and the impact I described above is what came next. She walked away from a top job in wine, into tech cold, and within seven years was at the very top of a brand new industry — using the seat to do things that mattered.

Most of us won’t have a hospital moment force our masks off. But we are in a moment of massive change anyway. And the leaders who make it through this aren't going to be the ones with the best impressions of someone else. They're going to be the ones brave enough to show up as themselves — even when "themselves" still has a wobble in it.

Say it out loud.

Tara's idea for a new AI company has been sitting on her chest for months. She went quiet. A close friend took her to breakfast and asked what was going on.

"I'm terrified."

He looked at her and said, "I know. What you're talking about doing is big, and it's scary. You do this part. I'll do that part."

That's the whole story. Not a TED talk. Not a framework. Just one human telling another human she was scared, and the other human stepping in where they were needed.

If someone as accomplished as Tara — after a career of public wins — is still saying "I'm terrified" out loud, then so can you. Pretending you have all the answers is the slowest possible way through change. Telling a trusted person what's actually going on inside you is one of the fastest.

A few weeks ago Tara presented to the Gap Inc. exec team. She asked the room how many of them felt anxious when she said the word AI. Only a few hands went up. But she could read every face. They were terrified — they were just terrified of admitting they were terrified.

If you can't say "I don't know" or "this scares me" in the rooms you're in, that's the first leadership problem to solve. Not your AI roadmap.

Don't do it alone. Don't even try.

Tara's playbook for navigating change is old-fashioned, and quite frankly, delightful.

Build a personal board of directors. Some are mentors. Some are operators with skills you don't have. Some are cheerleaders who will pick up the phone when you're in bed at noon convinced you're a fraud. Lauren’s tip: many of the highest-impact mentors are women you've never met, who would say yes if you asked. Women get asked to mentor at less than half the rate men do. Ask! Wouldn’t you be honored?

Get a therapist. Get a coach. If your ego won't let you call them therapists or coaches, call them Zoom Friends and pay for them anyway. Tara was clear: she would not be where she is without both.

And yes, talk to Claude. But don't just talk to Claude. Get out of the chat window and go talk to humans, too.

This sounds like basic life advice, and it is. But notice: every piece of it is about not going through change alone. The ego trap — doing it solo so you can say you did it — was the thing Tara most wished she could go back and slap out of her younger self.

Change requires grief. Even small changes.

This was a fun fact: In studies, people will choose a guaranteed electric shock over sitting in uncertainty about whether one might come. We would rather know the bad thing is happening than not know if and when.

"Biologically, we are all hardwired to seek comfort, familiarity, and stay with our tribe."

We know intellectually that greater returns come from new things. Biology is just working against us.

Tara's practical fix: remind yourself you can go back. When she left the wine industry, she held onto the knowledge that she could return if tech didn't work out. That soft landing is what made the leap possible.

"It gives you a lot of comfort to know that you can come back to what is already familiar."

And even with a soft landing in your back pocket, real change still takes something from you.

Halfway through the conversation, Tara held up her favorite pen. Battered, comfortable, ink running out. Then she held up a new pen and said, "I will actually grieve this pen."

It sounds silly until you really think about it. Every change worth making takes something with it — a version of yourself, a future you'd planned, an identity you were proud of. If you don't make space for that grief, it doesn't disappear. It just leaks out sideways.

Lauren said something here I loved: there's a version of your future you've already pictured for yourself, and any meaningful change asks you to grieve that version before you can build the next one.

The leaders who try to muscle through are the ones who flinch in the middle of a transformation. Or worse, the ones who drag a team that hasn't been allowed to feel anything either.

If your team is going through a restructure, an AI rollout, a strategy reset — they are grieving something. Acknowledge it before you brief them on the new operating model. And let's be honest here. WE ALL ARE.

Be the helper.

This one I loved because I deeply believe in the power of community in all of its forms. (hello, Futureproof Project.) It's a question Tara's mother used to ask her: What's the kindness you can do for your community?

When Tara feels overwhelmed by the news cycle, the AI cycle, the political cycle — any of the existential weather we're all carrying around — she does something small and kind for someone she knows. The night before our call, she had a dozen moms she'd never met over for cheese and crackers, because their kids were all about to land at the same high school. They walked out with new friends.

That's it. We are not built for our newsfeeds. We're built for communities of less than 200 people. The leaders I see navigating this moment well are not the ones with the strongest macro takes. They're the ones still doing small kindnesses, still asking how you really are, still choosing the human version of every interaction even when they could have been “efficient" instead. Also, if you’re not intrinsically motivated to help, just remember, statistically, givers win (Thank you, Adam Grant.).

Let go of what you can't carry

Pick something you can't control. Put it down. Not solve it. Not reframe it. Just set it down.

Because nobody can lead a team through massive change while also white-knuckling everything that's actually outside their hands. The leaders coming out of this period stronger are going to be the ones who learned to put a few things down, on purpose, so they had hands free for the work right in front of them. What is in your locus of control?

So here's where we land.

This isn't necessarily the content people are asking us for right now. They're panicked, they want a silver bullet, and — well, we know there isn't one. So we have to take care of the whole package. We get asked about AI maturity, about org redesign, about productivity gains. Those are real questions and we're going to keep helping with them.

But the leaders we've watched come out the other side of massive change — the ones whose teams still trust them, the ones whose businesses still feel like them — got there by being two things at once. Insatiably curious. Quietly responsible. Curious enough to ask the dumb question, run the experiment, learn the new tool, be the dumbest person in the room on purpose. Responsible enough to make room for the grief, the fear, the teammate who isn't sure they're going to make it.

So here we go!

Stay curious. Stay responsible. Take the mask off. Take the hard but right path. Ask for help you're embarrassed to need. Do one small kind thing today. Build the people around you up while you build the thing.

Our decks can wait. Our humanity can't.

Who you are is how you lead. Especially now.