What Leading Through AI Uncertainty Actually Requires (It’s Not What You Think)

In this week’s episode of Voices of Search, we spoke with Jennifer Doty, speaker, author, and executive mentor whose career spans nearly two decades at MetLife, where she held a series of increasingly senior roles before ultimately leading all of group benefits in the US with more than 1,400 people reporting to her. Since leaving corporate life, Jennifer has built a portfolio career that includes leading customer operations at ThreeFlow, a group insurance technology startup, while also coaching leaders and professionals through career transitions, speaking, and writing.

Our conversation covered the mindset shifts required to lead through periods of massive technological change, why vulnerability is a competitive advantage rather than a liability, and what it actually looks like to help a team adopt AI without losing the human fabric of the organization in the process.

Key Takeaways From This Episode:

• Leading through AI adoption requires three separate skill sets: figuring out how to use it yourself, enabling your team to use it, and integrating it as a business strategy. Conflating them causes real problems.
• Admitting “I don’t know” and asking for help are among the most powerful tools available to leaders navigating unfamiliar territory.
• The stories people tell themselves are the primary obstacle to growth—and because the brain can’t distinguish a true story from a false one, those narratives can be deliberately rewritten.
• People outgrow roles gradually, not overnight. The shift usually happens well before you notice it.
• The “get ready to be ready” approach—using periods of stagnation to build clarity and skills for the next move—is more practical than waiting for the perfect moment to leave.

You Don’t Need to Be the Expert in the Room

When MetLife asked Jennifer to lead the IT integration for its acquisition of a large piece of AIG, her reaction was immediate. “Steve, you do know I can turn on my laptop and call the help desk,” she told the senior leader on the phone. “That is like how knowledgeable I am around technology.”

The job turned out to have nothing to do with technical knowledge. There was one IT team, 25 business teams, and a complete inability to communicate across the divide. Jennifer’s role was translation, and learning to do it well became the foundation of everything that followed.

What Leading With Zero Expertise Actually Looks Like

The tactics she relied on in that integration are the same ones she coaches leaders through today:

• Listen more than you talk. Walking into a room as the least knowledgeable person is an advantage if you use it.
• Be visibly vulnerable. She asked people to explain things “like you’re explaining to your grandmother”—which made the work clearer for everyone, not just her.
• Say “I need your help.” She found those words consistently disarmed skeptics who questioned why she was there at all.

The parallel to AI adoption is hard to miss. Most leaders aren’t AI experts. That’s not the point. “If you didn’t need me, I wouldn’t be here,” she told the team members who doubted her—and the same logic applies to any leader navigating a transformation they didn’t train for.

AI Adoption Is Three Different Problems, Not One

Jennifer’s most practically useful framework is also her simplest: leading through AI requires three separate skill sets, and most organizations are treating them as one.

“You need to figure out how to use it by yourself. You need to get a team to figure out how to use it every day. And then you have to figure out how you’re going to embed it as a strategy in your business,” she said. “And those are three different things.”

Making Room for Where People Actually Are

The team enablement layer is where Jennifer spends most of her coaching energy—and where she sees leaders fail most often. The anxiety is real. People wonder whether their jobs will still exist. They default to old habits. They open a Word document when they meant to start in Claude.

Her response isn’t to push past those feelings. It’s to normalize them. “It’s sort of like brushing your teeth every day until it becomes routine,” she said. “It’s okay where you are, and you need to, as a leader, be supportive of people as they work through that change.”

At ThreeFlow, every employee has a Claude seat and has been asked to explore how to use it in their own role. The framing Jennifer uses with her team is forward-looking: learn this now, because AI fluency is a resume builder regardless of where your career goes next. “I’m more apt to retain people who can help me figure out how to leverage AI than the people who are going to say, ‘My job’s just going to go away, so why do I bother?'”

The Stories You Tell Yourself Are the Obstacle

Arguably, the most important part of the conversation wasn’t about AI at all. It was about the internal narratives that prevent professionals from moving forward—and how to change them.

“99% of the things that challenge people in the way they operate on a daily basis are the beliefs that go on between these two ears,” Jennifer said. “The beautiful thing about your brain is it doesn’t know if a story is true or not.”

Reframing Is a Daily Practice, Not a One-Time Fix

The stories that hold most professionals back tend to sound like this: you can only be successful at one thing at a time, or you don’t deserve to build a career around what actually excites you. Jennifer’s position is that none of those are true—but they function as true until they’re deliberately replaced.

She’s applied this to her own career consistently over the past five years, building a portfolio life that looks nothing like the single-track corporate path she started on. “I’ve practiced this time and time again to create the life I want, to build the existence I want to be in.” The practice also includes gratitude—not as a soft concept, but as a functional tool. The more you name what’s working, she argues, the more of it you tend to see.

Outgrowing a Role Happens Before You Notice It

For anyone navigating the current job market, Jennifer’s observations on career transitions are some of the most grounded in the conversation.

“It doesn’t just dramatically shift overnight and all of a sudden you wake up, and you’re like, ‘This isn’t for me,'” she said. “It happens gradually, and you don’t see it because it’s happening so slowly.”

Get Ready to Be Ready

The trap most people fall into is justifying why they should stay—the salary is good, things are stable, it’s fine enough. Her therapist’s framing has stuck with her: things are good until they’re not, and when they’re not, you know.

For people who recognize the shift but aren’t yet in a position to leave, her advice is to use the time actively. “Why don’t you use that time to help create the next thing?” she said. Build the skills, make the connections, develop the clarity—so that when the moment arrives to move, you’re already ready for it.

The Swiss Army Knife Is More Valuable Than the Specialist

In a business environment that prizes deep expertise, Jennifer makes a deliberate case for breadth. She describes herself as a Swiss Army knife—and in moments of transformation, she argues, that’s the more durable competitive advantage.

The skills that transfer aren’t domain knowledge. They’re the ability to be humble in the face of the unknown, to name what nobody else will say in a room, and to make people feel genuinely seen. “We all wear a sign around our neck every day that says, ‘Make me feel important today,'” she said. “If you can help someone feel like their feelings and concerns are important, that goes a long way in gaining trust.”

Rebuilding Connection in a Digital Environment

One of the practical challenges Jennifer addresses is the loss of informal connection in remote and hybrid work. The hallway conversation—the quick check-in that turns into a real discussion—was a primary vehicle for trust-building and career development. That infrastructure is largely gone.

Be Intentional, or It Won’t Happen

Her answer is to recreate it deliberately, using the tools that already exist:

• Text people directly, outside of company channels. Personal outreach lands differently than a Slack message everyone can see.
• Use audio messages. Whether via text or Slack, hearing someone’s voice conveys warmth and nuance that written words can’t. “They can hear your concern. They can hear your excitement. Emotion matters.”
• Check in on people as people, not just as colleagues—with no agenda beyond seeing how they’re doing.

“You have to be intentional about it because it will not happen,” she said. In a distributed environment, connection is a leadership priority, not a byproduct.

The through-line of the whole conversation is that the skills required to lead through AI transformation are not primarily technical. They’re the same skills that have always separated effective leaders from ineffective ones: the willingness to be vulnerable, the ability to create psychological safety, and the discipline to examine the stories you’re telling yourself about what’s possible. 

The technology changes. Those fundamentals don’t.

Voices of Search is a daily SEO and content marketing podcast hosted by Jordan Keone and Tyson Stockton. The show delivers actionable strategies and data-driven insights to help marketers navigate the ever-evolving world of search engine optimization and content marketing. New episodes air weekly, covering everything from technical SEO to AI discovery, featuring industry leaders and practitioners sharing real-world frameworks and proven tactics.

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