Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Manage Career Regret
Transcript
- Lucas: There's a number I keep coming back to from a Harvard Business Review study published earlier this year. They surveyed two hundred C-suite executives, and sixty-two percent said they regret at least one major career move. Not a minor tactical misstep, but a decision that changed their trajectory. Luna: Sixty-two percent. That's nearly two out of three. And these are people who, by any external measure, made it. Lucas: Exactly. And the most common regret wasn't taking a bad job. It was staying too long in a role that no longer stretched them. That's a really interesting finding because it flips the conventional wisdom that regret is about a wrong turn. A lot of senior leaders look back and wish they'd left earlier. Luna: I've seen that with a former client who was a CFO at a mid-cap firm. She told me she stayed two years too long because she felt loyal to the CEO who'd hired her. By the time she left, her network had atrophied and she was competing against candidates who'd been more proactive. Lucas: That loyalty trap is real, especially at the senior level where relationships are deeply personal. But what I find useful is to treat regret not as an emotion to suppress, but as data. If you can name the specific decision you regret, you've already identified a signal about what you value. Luna: Right. Regret is a compass. It points to what matters to you. Lucas: Exactly. So the question becomes how to use that compass before you make the next move. That's where I think a structured tool like a Decision Audit can help. It's a simple retrospective — you write down a past decision you regret, then list the assumptions you made at the time, the information you had, and what you'd do differently. Luna: And you do that before the next big decision, not after. Lucas: That's the key. Most leaders do post-mortems after a failure, but they rarely do a pre-mortem informed by past regret. The CFO I mentioned — she did a Decision Audit before her next move. She realized that in her previous role, she'd prioritized stability over growth because she was worried about her kids' college tuition. That was a legitimate concern, but she never questioned whether it was still the right priority. Luna: So the audit surfaced an unexamined assumption. What did she change? Lucas: She decided that her next role had to offer a clear stretch assignment within the first twelve months. She ended up taking a board seat at a growth-stage company — something she'd never considered before — and she told me the risk actually energized her. The regret from the past became a criterion for the future. Luna: I think there's also a second layer here, which is the regret of inaction. The HBR study mentioned that the second most common regret was not taking a risky opportunity. That's harder to audit because there's no concrete outcome to analyze. Lucas: That's a great point. Regret of omission versus commission. For omission, I find it helpful to ask a counterfactual: 'If I had taken that opportunity, what's the best thing that could have happened?' Then ask, 'What's the worst?' Often the worst isn't as bad as we imagine. The missed opportunity becomes less daunting. Luna: And that exercise itself can reduce the emotional weight. It turns vague regret into a concrete lesson. Lucas: Right. The goal isn't to eliminate regret — it's to make it productive. One technique I've seen work well is the 'regret journal.' A senior leader I know keeps a running list of decisions he wishes he'd handled differently. Once a quarter he reviews it and looks for patterns. Last year he noticed that three of his five regrets involved moving too quickly without consulting his team. That insight changed how he approaches major calls now. Luna: It's like a personal retrospective. I think there's a lot of value in that. The hard part is creating the discipline to actually do it. Lucas: That's why I recommend pairing it with something you already do. Tie the review to your quarterly planning session or your annual performance review. Make it a recurring habit, not a one-time exercise. Luna: So let's say a listener is in a role right now and they feel the early twinge of regret — that sense that they might be staying too long. What's the first step? Lucas: First, name it. Don't dismiss it as just burnout or a bad week. Ask yourself: 'If I stay another year, what am I giving up?' Be specific. Maybe it's the chance to build a new skill, or to work with a different leadership team, or to enter a growing industry. Then ask: 'What's the cost of leaving now?' Sometimes the cost is smaller than you think. Luna: And if the regret is about something you didn't do — a missed opportunity — can you still act on it? Or is it truly gone? Lucas: That's the crucial question. Some doors close permanently. But many reopen in different forms. The executive who regretted not taking a Silicon Valley role ten years ago can't go back in time, but she can look for a role in a tech-forward company now. The regret becomes a directional signal. It tells you where to aim next. Luna: I like that framing. Regret as a signal, not a verdict. Lucas: Exactly. And that's really the takeaway for senior leaders. You have enough experience to have accumulated regrets. That's not a weakness — it's a resource. The question is whether you mine it for insights or let it sit as background noise. Luna: You know, this conversation reminds me of something I've been thinking about. A lot of what we talk about on this show is about making better decisions. And I think one of the things that helps us keep doing this show ad-free, and keep having these conversations, is listener support. If you've found value in any of these frameworks — the Decision Audit, or anything else — you can support the show at buy me a coffee dot com slash fexingo. Lucas: Yeah, it's a small way to keep this resource available to everyone. And honestly, every bit helps us maintain the independence to explore topics like this without any outside pressure. Luna: Exactly. So back to regret as a signal — I think the biggest challenge for senior leaders is that they're supposed to project confidence. Admitting regret can feel like admitting weakness. But the most self-aware leaders I've worked with are the ones who can say, 'I got that one wrong, and here's what I learned.' Lucas: That level of self-awareness actually builds trust with boards and teams. A leader who can acknowledge a past mistake and show how they've adapted is more credible than one who pretends they have no regrets. So if there's one concrete action from this episode, it's this: take thirty minutes this week to write down one career decision you regret, and ask yourself what it tells you about what you want next. Luna: And if you do that, you might find that regret is just a signpost pointing toward a better move. Lucas: Exactly. Thanks for listening.