Post by Brian Elliott

"The worst thing you can promise your team is certainty." Katie Burke, COO of legal AI startup Harvey, on stage at Charter's summit on Tuesday. I've been talking for years about how hard it was for me as a leader to get over the training to be "seldom wrong, never in doubt." We're taught to project confidence, have the answers, and steady the room. But when 80% of CEOs say they're afraid of losing their jobs if AI doesn't deliver, their fear spreads. Don't paper over it with promises you can't keep. Katie's example: CEOs who swore there would be no layoffs, then reversed when the business turned. The guarantee felt good for a quarter, but the broken promises linger for years. Doniel Sutton (she/her), Chief People Officer at Pinterest, talked about the human cost: "No one does their best work when they're scared." Her prescription wasn't more reassurance. It was for leaders to drop the armor first, and model the uncertainty instead of hiding it. So what replaces the promise of certainty? ⭐ Set the direction, name the bet. Harvey's framing: "This is our bet for the next three to six months. Here's what we're building. If you want to join us, we'd love to have you." Direction without a guarantee. ⭐ Leaders go first. Say your own uncertainty out loud before you ask your team about theirs. CEOs and CPOs have to get real with each other, and as Katie noted, the CPO almost always has to go first. ⭐ Stop guaranteeing outcomes you don't control. A clear bet beats a hollow promise every time—and gives people agency in the outcome. Certainty isn't the job, but honest direction is. In a lot of ways, that panel reflected the day. Charter brings together human-centered leaders with a growth mindset. They know they don’t have all the answers, but also are willing to share what they’ve learned and their struggles. 📎 Links to Charter's coverage and my latest newsletter in comments! What would shift on your team if you told them you're still figuring this out too?