Why Smart Leaders Stay Too Long on Losing Bets

Todd Curzon

Alright, let’s crack this open with Annie Duke’s concept of 'collective knowledge lag.' If you haven’t read her stuff, she’s got this wildly accurate lens on why teams bail on ideas—mentally—way before their leaders get the memo. Daniel, do you remember that story about the VP we both coached last year? The one whose team mentally checked out like six weeks before she did?

Daniel Carter

Yeah, I do. It’s actually more common than people think. Leaders get so focused on steering the ship, they miss when everyone else has already packed their bags for shore. It’s like—the warning signs are subtle, you know? Like when teams—suddenly—they just…stop asking questions in meetings. That’s an early warning flare right there.

Todd Curzon

Yeah, and it’s funny—or tragic, depending on your mood—‘cause I always imagine a board game night, where you’re the only one still moving your piece and everyone else is just scrolling their phones. That’s what this VP was doing: charging ahead, thinking the silence meant buy-in. But man, the whole group had mentally called it quits weeks ago and she had no clue. I mean, that's a classic losing bet, right?

Daniel Carter

Absolutely. There’s research that shows on average, failing projects in tech stick around four to six weeks longer than they should. Everyone sees it coming, but nobody pulls the plug. Maybe it’s the optimism bias, or maybe people just don’t want to be the one to break the bad news. And as Annie Duke puts it, by the time leadership catches up, the team’s already drifted—checked out emotionally, if not physically.

Todd Curzon

And what’s wild—just to layer on here—is, it’s not even malice or laziness. It’s, like, basic psychology. Everyone wants to move on to the next shiny thing, but nobody wants to look like the quitter. But, meanwhile, the real risk is festering. That’s what we see over and over at the leadership level, especially with folks newly promoted from technical roles. And, not to beat a dead horse, but in last month’s episode, we hammered home how reflection and feedback loops make all the difference—here’s where that rubber meets the road.

Daniel Carter

Exactly. Spotting those drop-offs in engagement becomes a survival skill at the leadership table. You have to look for the silence—those non-questions. If you notice that... it’s usually not buy-in, it’s something way worse: quiet quitting on the idea. That’s when the six-week clock starts, whether you know it or not.

Daniel Carter

So, if we’re talking traps, Annie Duke’s research on escalation of commitment is downright sobering. Newly promoted execs—and I’ve seen this so many times—they’ll double-down, triple-down. Some folks lose over six months defending a failing decision. That’s a third of a fiscal year, just stuck on a zombie project.

Todd Curzon

Yeah, I gotta admit—I fell right into that with my first VP gig. I clung to a product pivot way past the expiration date. I kept coming up with new reasons, little tweaks—I convinced myself it was grit, not…well, stubbornness. It’s embarrassing now, but once I finally let go, it was like—instantly—the team breathed out. The meeting rooms felt lighter. I was the last one to realize we were just pouring time into a lost cause.

Daniel Carter

You’re not alone—I hear stories like that almost every week. What’s so interesting is that this escalation isn’t just about protecting your ego. It gets tangled up in your identity. You think, "If I give up now, I’m not the leader I thought I was." But the research is super clear—by clinging to those bets, you don’t just lose time. Duke says losses can intensify by 340% because you’re missing other, better opportunities along the way. It’s like missing every train at the station because you’re still arguing about the first ticket.

Todd Curzon

Wait, can we circle back to that framing trick Duke talks about? Because, look, I am obsessed with this. If you label it "my strategy," your brain ties it to your identity. But if you call it an "experiment," suddenly, changing course isn’t personal, it’s just data. That tiny shift? Research shows it can speed up course corrections by, what, nearly five months on average?

Daniel Carter

Yeah, that's the number Annie Duke landed on. And, honestly, I think a lot of our listeners are battling this every day. Especially VPs who were just promoted—they feel like they need to prove themselves, show grit. But grit at the wrong time just becomes stubbornness by another name. Grit for the win, yeah—except when it’s really…just you refusing to fold in a poker game with no good cards left.

Todd Curzon

That’s a terrible poker analogy—oh wait, no, it’s actually perfect since Duke is a championship poker player, ha! But, yeah, lesson learned: create room for experiments, invite the team to poke holes, and don’t take a course correction as a referendum on you. Otherwise, you’re just stuck defending the indefensible and dragging everyone with you.

Todd Curzon

So let's talk about the escape hatch, right—the science, and the nitty-gritty playbook for quitting well. Annie Duke gives us this great question: "Would you start this today, knowing what you know now?" If the answer’s nope, you have your answer for next steps. Not what you sunk into it last quarter, not the original pitch—just what makes sense now.

Daniel Carter

That’s what we call focusing on opportunity cost, not sunk cost. And her concept of 'kill criteria'—setting clear signals for when it’s time to stop before emotions cloud your judgment—is super practical. I had a VP client who used anonymous confidence ratings from the team, kind of a quick pulse-check. When trust in the initiative tanked, it was a sign to re-evaluate before more time was wasted.

Todd Curzon

That’s genius. And we should mention—Boards, counter to what a lot of VPs fear, actually reward real transparency and quick course-corrects. The research backs this: when an exec publicly pivots with evidence-based language—"Here’s the data, here’s what changed, here’s why"—it’s seen as maturity, not flakiness. Consistency is great, but only if you’re consistent with reality, not just with the original plan.

Daniel Carter

Remember that VP I coached, the one who rewrote her all-hands update after we worked on Duke’s script for pivots? She thought she was walking into career suicide. Instead, the board promoted her to COO for, in their words, ‘demonstrating mature judgment and not blind optimism.’ It was all about clarity and making that evolution public, not just in private.

Todd Curzon

Love that. So, for everyone listening, quitting isn’t losing. Sometimes the smartest move is knowing when to walk and having a process that de-risks that decision. Otherwise, you’re just stuck in that imaginary board game, playing by yourself. And trust me, nobody wins that one.

Daniel Carter

Well said, Todd. We’ll keep digging into the playbooks and frameworks for these tough calls in upcoming episodes, so you’re never stuck guessing on your own. Until next time, thanks for joining us.

Todd Curzon

Thanks for tuning in, Daniel, and to everyone charting your leadership path—don’t be afraid to fold a hand now and then. See you next week!