Latest / Career Coaching with Fexingo: Professional Coaches, Career Counselors, and Guidance for Workers / How a Career Pre-Mortem Can Prevent Your Next Mistake
Transcript
- Lucas: You know that feeling when you accept a job offer and within three weeks you realize you made a mistake? The commute is worse than you thought, the culture is off, the role isn't what was described. Luna: Oh, I think most of us have been there. It's that sinking feeling of 'I should have known better.' Lucas: Right. And the frustrating thing is — you probably could have known better. There's a tool from behavioral economics called a pre-mortem. It's used in project management and product design. But it works just as well for career decisions. Luna: A pre-mortem — so instead of a post-mortem after something fails, you imagine the failure before it happens? Lucas: Exactly. Daniel Kahneman popularized the idea. You look into a crystal ball and assume your decision has already gone terribly wrong. Then you work backward to figure out why. The key insight is that our brains are terrible at predicting risks when we're excited about something. Luna: So it's a way to bypass optimism bias. Because when you're in love with an opportunity, you naturally downplay the downsides. Lucas: That's exactly it. Let me give you a real example. A friend of mine — let's call her Sarah — was a marketing manager at a mid-sized tech firm in Austin. She got an offer from a well-known SaaS company. Big title bump, 20 percent salary increase, stock options. On paper it was a slam dunk. Luna: Sounds like a no-brainer. What went wrong? Lucas: Well, she almost took it. But before she accepted, I walked her through a pre-mortem. I said, 'It's six months from now. You're miserable in this new role. Why?' And she came up with three things. First, the commute: the office was 45 minutes away in traffic, and the company required four days in person. Second, her new boss had a reputation for micromanaging — she knew that from a former colleague but hadn't let herself dwell on it. Third, the role was less strategic than promised; it turned out to be more execution-heavy. Luna: And those were all things she could have discovered before accepting. Lucas: Exactly. The pre-mortem forced her to surface those concerns. So she did some additional research. She asked for a call with a peer in the department, she asked about the boss's management style in a second interview, and she asked to see a sample week's schedule. What she found confirmed her worst fears. She turned down the offer. Luna: That's powerful. And I bet she avoided a lot of pain. But what about the reverse? Could you do a pre-mortem on a decision you're leaning against — to make sure you're not being too cautious? Lucas: Great point. You can flip it. A success pre-mortem. Imagine you take a risk — say, starting your own consultancy — and in two years it's wildly successful. Then ask: what made it work? That can reveal hidden opportunities you're ignoring because of fear. Luna: So it's a two-sided coin. Pre-mortem for decisions you're excited about to uncover risks. Success pre-mortem for decisions you're scared of to uncover upside. Lucas: Exactly. And the process is simple. Four steps. Step one: identify a specific career decision you're facing — a job offer, a promotion, a pivot, a move. Step two: fast-forward six to twelve months and assume the decision led to a bad outcome. Step three: brainstorm all the reasons why it went wrong. Write them down. Be brutally honest. Step four: for each reason, identify one thing you could do now to prevent it. Luna: And you can do this alone, or with a coach, or even with a trusted friend who'll tell you the truth. Lucas: Right. The structure matters because it forces you to go beyond surface-level worries. Most of us stop at 'the culture might be bad' — but a pre-mortem pushes you to specify: 'the culture is bad because decisions are made top-down with no input, and I value autonomy.' That specificity is what leads to actionable safeguards. Luna: So the safeguard in Sarah's case was doing extra due diligence. What other safeguards might someone come up with? Lucas: Could be negotiating a hybrid schedule before accepting. Could be asking for a trial project to test the working relationship. Could be setting a 90-day check-in with your new manager to reassess. Could be building a financial cushion so you feel less locked in. Luna: And those safeguards are concrete actions, not vague hopes. That's the whole point. Lucas: Exactly. And here's the thing — our brains are wired to favor the narrative we've already constructed. If you've convinced yourself a job is perfect, you'll unconsciously filter out warning signs. The pre-mortem breaks that spell. Luna: I want to try this myself. I've been considering a move into a more strategic role, and I've been going back and forth. I think a pre-mortem could help me decide. Lucas: Do it. And if you want to make it even more powerful, write down your assumptions before you start the pre-mortem. Then compare. You'll likely see that your optimistic story left out half the picture. Luna: One thing I've noticed: people often resist the pre-mortem because it feels negative. Like you're jinxing yourself. But it's actually the opposite — you're giving yourself a chance to prevent the bad outcome. Lucas: That's a great way to frame it. It's not pessimism. It's pragmatic optimism. You're so committed to a good outcome that you're willing to confront the obstacles upfront. Luna: And speaking of pragmatic — there's something else that's been on my mind. We've been doing this show for a while now, and I've noticed that the listeners who get the most out of it are often the ones who engage actively, whether by trying the tools or by supporting the show. Lucas: Yeah, that's a good point. And honestly, the reason we can keep making episodes like this — ad-free, no sponsors, just straight career strategy — is that a small group of listeners chips in monthly through buy me a coffee dot com slash fexingo. It's not a big ask. It's just what keeps the lights on. Luna: If this show has helped you think through a career move or saved you from a bad decision, that's the kind of thing that makes supporting feel meaningful. No pressure, but we're grateful for those who do. Lucas: Alright, back to the pre-mortem. One more nuance: timing matters. Don't do a pre-mortem when you're exhausted or stressed. Do it when you have 15 minutes of clear headspace. And do it before you've emotionally committed — once you've told your friends 'I'm taking the job,' it's harder to be objective. Luna: So ideally, you run the pre-mortem while the decision is still in the evaluation phase, before the offer letter is signed. Lucas: Exactly. And if you're already in a role that's not working, you can still do a pre-mortem on your decision to stay. Imagine it's a year from now and you're still in the same job, still frustrated. Why? That can motivate you to make a change. Luna: I love that. It turns regret into foresight. You're basically borrowing wisdom from your future self. Lucas: That's a perfect way to put it. And the research backs this up. Studies show that when people imagine a negative outcome in detail, they become more accurate at assessing risks. It's called the 'prospective hindsight' effect. Luna: Let's talk about how to make this a habit. Should people do a pre-mortem for every career decision, big or small? Lucas: I'd say reserve it for decisions that have significant consequences — job changes, promotions, major pivots, accepting a relocation. For smaller stuff, like which project to take on, a simpler pros and cons list might suffice. But if the decision will affect your life for months or years, the pre-mortem is worth the 15 minutes. Luna: And if you're in a coaching relationship, you could ask your coach to guide you through one. Or you could swap with a peer — you do a pre-mortem for each other's decisions. Lucas: That's a great idea. External perspective is valuable because your own blind spots are, well, blind to you. A friend might say, 'You keep mentioning that the commute is long but then you say it's fine — that seems like a red flag you're ignoring.' Luna: Exactly. So let's recap the steps: one, pick a decision. Two, assume failure in six to twelve months. Three, list all possible reasons. Four, create safeguards for each reason. Lucas: And bonus step: after you implement the safeguards, revisit the pre-mortem in a month to see if new risks have emerged. Because circumstances change. Luna: This is one of those tools that sounds too simple to work, but in practice it's incredibly effective. I've used it myself and it saved me from taking a role that would have been a mismatch. Lucas: Oh really? What was the situation? Luna: A few years ago, I was considering a director-level position at a large media company. The title was great, the pay was great, but I had a nagging feeling. I did a pre-mortem and realized the main risk was that the role required managing a team of 20, and I'd always preferred smaller, more agile teams. I dodged a bullet. Lucas: See, that's exactly the kind of insight that a pre-mortem surfaces. It's not about finding flaws in the opportunity — it's about finding mismatches between the opportunity and your own values, preferences, and strengths. Luna: And that's the kind of clarity you can't get from a spreadsheet. It's emotional and cognitive at the same time. Lucas: Alright, so here's my challenge to listeners: before you make your next career decision — whether it's taking a job, turning one down, or deciding whether to stay put — spend 15 minutes on a pre-mortem. Write it down. You might be surprised at what you discover. Luna: And if you do it, we'd love to hear how it went. You can reach us on the show's social channels. We're @fexingo on most platforms. Lucas: Until next time, keep making intentional moves.