The Confidence to Say I Don't Know Has to Be Earned

In The Wall Street Journal's CEO Brief, Lila MacLellan talks with Linda Yaccarino about what she calls the sophomore year of her healthcare career. In The 'Extremely Valuable' Question Linda Yaccarino Asks Her Team, MacLellan explains how Yaccarino became CEO of eMed Population Health in 2025, a digital health platform that helps employers give people access to GLP-1 medications. Before that she spent two years running X, and before that she was a senior advertising executive at NBCUniversal, where she helped launch Peacock.

Yaccarino doesn't see the move as a strange pivot. She says she has always been drawn to industries at a turning point. She describes her time at X as a stress test of resilience, relationships and values. And she shares the question she relies on most as a newcomer to healthcare, one she calls extremely valuable for a CEO in a new company. Sitting with her team, she tells them, "I don't know, teach me."

Confidence That Doesn't Need to Pretend

Most leaders entering a new industry feel pressure to prove they belong. They speak early, use the vocabulary they just learned and hide what they don't understand. It looks like confidence. It is usually borrowed confidence, the kind that depends on appearing to know.

What Yaccarino describes is different. She says her body of work, including her failures, is what gives her the confidence to admit what she doesn't know. That is exactly the right order. People who have earned their conviction through years of hard decisions don't need to fake expertise, because their sense of who they are doesn't rest on having every answer. They can afford to be students again.

I have always believed that conviction comes before confidence. Confidence that arrives first tends to be fragile, because it is built on how things look. Confidence that grows out of conviction is sturdier, because it is built on what you have lived through and what you stand for. I wrote about the difference between what can be faked and what has to be earned in AI Can Fake the Catch. It Can't Fake What You Earned.

What Actually Travels Between Industries

Yaccarino makes another point that deserves attention. She describes leadership skills as portable, something you can carry from one business to another. I agree, with one addition. What travels is not just a set of skills. It is a sense of who you are and what you naturally solve for.

Yaccarino says she has always gravitated toward industries at strategic turning points, from the rise of streaming at NBCUniversal to a new class of medications today. That pattern is more revealing than any job title on her résumé. It suggests that what she solves for has stayed remarkably consistent even as the industries changed around her. That kind of self-knowledge is what makes a reinvention feel like a continuation rather than a gamble, and it keeps evolving with every chapter.

When she weighed her next move, she says the question she asked was how she could keep doing something meaningful. That is a better question than which job pays most or which title sounds biggest. It points toward the parts of yourself you want to carry forward. I described how that thread runs through every chapter of a career in The Only Constant in a Multichapter Career Is You.

Why Not Knowing Builds Trust

There is a practical payoff to Yaccarino's approach. When a new leader says "teach me," the team stops performing for the boss and starts contributing. People who have spent years learning the business finally get to share what they know. The leader gets a faster education, and the team learns that honesty is welcome.

It also sets a standard everyone can follow. When the person at the top admits what they don't know, it becomes safe for others to do the same. That doesn't replace expertise or discipline. Healthcare runs on rigorous standards, and a CEO still has to master the business. It simply means the learning happens in the open, where it helps everyone.

A Few Moves to Make Now

For professionals considering a career change: before you list your skills, list the problems you have loved solving across every role. If a pattern shows up, that is what you will carry into the next industry.

For leaders stepping into a new role: in your first month, choose one meeting where you ask more than you tell. Notice who speaks up and what you learn.

For anyone feeling like an outsider: ask whether you are hiding what you don't know to protect your image. The people around you can usually tell, and they would rather teach you than watch you pretend.

Yaccarino's lesson isn't really about healthcare. It is about the kind of confidence that lets you walk into any room as yourself.

When you know who you are, admitting what you don't know becomes a strength rather than a risk.

Want to explore these ideas further? Learn more about my work on leadership, identity and conviction at www.theglennllopis.com.