Embracing Intelligent Failure for Leadership Growth

Todd Curzon

Alright Daniel, let me just kick us off with a story that’s been stuck in my mind all week. So—last Tuesday, I get this call from a VP of Engineering, Alex, he’s four months into his new role at this Series C SaaS company, about sixty people reporting up. He goes, “Todd, I need help. I just finished Q1—everything's perfect. Hit every metric, got praise from the CEO, zero big mistakes.” But then he just sighs and says, “I feel... empty. Like I didn’t actually learn anything new.”

Daniel Carter

Oh, that is familiar. There’s almost nothing worse than what I call a ‘hollow victory’, right? I’ve had more than a few execs tell me that after a 'perfect quarter', they actually wonder if they're cut out for this.

Todd Curzon

Exactly! And he did all the stuff every playbook says—“first 90 days, show credibility, execute, prove you belong.” He did it. And—it totally backfired when it came to growing as a new leader. Which, actually, fits with what Amy Edmondson found in her latest research, that came out last year. She tracked VPs through their early transitions and—get this—folks who eliminated every single failure in a quarter? Their learning velocity was 54% lower than VPs willing to try a few things and, have the occasional flop.

Daniel Carter

Fifty-four percent? That is not a rounding error. That’s like… playing chess against yourself every day. Sure, you never lose, but you never really get better. Actually Todd, you know me, I like a board game analogy and that is what you always get with tic-tac-toe against yourself: it’s a draw, but you’ve learned exactly nothing new and nobody’s having any fun.

Todd Curzon

I have literally done that. And it’s exactly Alex’s problem. He only did things he was already sure about. Zero intelligent failure, zero experiments—meant zero new learning. And honestly, that’s probably way more common than we realize for new execs.

Todd Curzon

So, let’s unpack why this happens, Daniel—when you made your jump up to executive coaching, what did it feel like around... y’know, making mistakes?

Daniel Carter

Oh man, so much pressure. In the early years, especially with a new title, you just do not want your first big call to be the wrong one—that mindset of, “Only swing at the obvious pitches.” Which, honestly, is just a recipe for staying stuck.

Todd Curzon

Yeah, and that’s where Edmondson’s research really clicks into place. She breaks out three types of failures: basic failures, which are the classic mistakes, right? Forgot the process, dropped the ball—avoidable stuff. Then you’ve got complex failures, where the system just breaks down. But the real secret sauce: intelligent failures. Those are the risks in uncharted territory, experiments that might flop—but they’re where learning lives!

Daniel Carter

But so often, we treat all road bumps the same way. Just ‘failure is failure,’ sweep it under the rug, never try again… and suddenly, everything exciting just gets locked out.

Todd Curzon

I see that constantly! Like Alex—he lumped intelligent failures in with the ones you’re supposed to avoid, so he never tested what he didn’t already know. Which ends up being a perfect way to build a team that only brings you safe bets and—let’s just say—doesn’t bring you problems until they’re on fire.

Daniel Carter

And it’s not just theory. Edmondson’s work shows psychological safety predicts team performance three times better than an error-avoidance culture. I’ve had clients who mistook calm seas for trust, only to find out later it was the silence before the storm. Nobody’s surfacing issues—they’re just hiding them better.

Todd Curzon

Yes! When you create that “never be wrong” culture, the safest move for your team is to be quiet. Wait ‘til the issue is massive before surfacing it. And the worst part: the moment perfection is valued above learning, innovation is officially on life-support—because everyone is playing not to lose rather than playing to learn.

Daniel Carter

So, Todd, just to bring this home—Alex’s team started protecting him from problems, right?

Todd Curzon

Yep. He hadn’t heard about a major snag for nearly a month, because his folks didn’t want to bring him bad news and risk being seen as failing. That’s the exact opposite of psychological safety. Instead of issues being early warnings, they’re last-minute fire drills.

Daniel Carter

And like we talked about a few weeks ago—if you can't distinguish between a smart experiment gone wrong and a plain-old mistake, your team’s just gonna keep their heads down and hope nothing blows up on their watch. Which means the learning really stops for everyone, top to bottom.

Todd Curzon

Alright, let’s get practical—here’s how Alex turned this ship around. First, I walked him through reframing his Q2 goals. Instead of “Execute flawlessly,” it was “Run three experiments and learn.” Edmondson’s research shows this sort of framing actually changes behavior, not just the words on the slide. Alex rewrote his big bets as: “We’re testing if [approach] works by [date] to learn [a specific thing].” Learning metrics, check-in dates, clear hypotheses. A whole different vibe from the standard ‘get it done or else’ approach.

Daniel Carter

That shift is huge. Most new VPs write quarterly goals as commitments, not learning hypotheses. The magic is, if you learn what works and what doesn’t—you win either way, because you’re gathering data, not just chasing check-boxes.

Todd Curzon

Exactly! And step two: Alex started modeling what Edmondson calls intelligent failure—in meetings, he just named what he didn’t know. “I’m running these three experiments, here’s what I’m not sure about, here’s what I’m testing.” The change was instant—his senior engineer basically said, “Okay, now I can share my own doubts.” That’s psychological safety happening, right out loud.

Daniel Carter

It’s rarely easy, especially for leaders who want to appear in control, but it really works. And then—the kicker: when Alex made a misstep two weeks later, he openly called it an intelligent failure. He used Edmondson’s actual phrase, “I got this wrong, here’s what I’m learning.” That alone shifted her CEO’s perception—instead of doubting, he doubled down on his trust in her leadership.

Todd Curzon

And last one—change up your questions. Stop asking, “Will this work?” and instead, "What do we need to learn to know if this could work?” Edmondson tracked these language shifts and they change team behavior far quicker than a fresh mission statement ever could. Sarah tweaked just three questions and suddenly she had engineers proposing bold new pilots. Because she’d set the expectation that uncertainty was normal, not dangerous.

Daniel Carter

It’s one of those things I wish I’d heard at the start of my own career: your questions dictate what your team feels allowed to try. Creating that safety for experimentation is how you build real, adaptive teams—especially in a new VP seat.

Todd Curzon

So if you’re listening and think, “Wow, that’s me—I had the ‘perfect’ Q1 but feel stuck,” start here: rewrite just one major initiative as an experiment, share out loud something you’re not sure about, and ask what you need to learn rather than demanding certainty. That’s not just theory—Edmondson’s research and a dozen execs I’ve coached back it up.

Daniel Carter

And if you want more on this shift from flawless execution to intelligent failure, reach out—like seriously, don’t wait six months and realize you’re still stuck in perfection mode. Or, subscribe for next time, because we’re diving into network positioning and why your hidden connections are more important than ever, especially in your first year as a new exec.

Todd Curzon

Couldn’t have said it better, Daniel. And for everyone out there—just remember, sometimes the “perfect” quarter is your biggest learning trap. Give yourself, and your team, room to run the right kind of wrong. Daniel, always a pleasure—see you next time?

Daniel Carter

You bet, Todd. Thanks for tuning in, everyone. Take care!