Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Use Pre-Written Resignation Letters
Transcript
- Lucas: So here's something I keep seeing among senior leaders who really control their own narratives: they draft their resignation letter before they accept the job. Luna: Wait — before they even start? Lucas: Yes. I know it sounds counterintuitive, maybe even a little morbid. But I've now heard this from three different C-suite executives who do it consistently. And the logic is surprisingly tight. Luna: Okay, I'm curious. Walk me through it. Lucas: The basic idea is this: you write the letter when you are calm, when you are objective, and when you are not under any emotional pressure. You are not angry at a boss, you are not frustrated with a board, you are not in the middle of a failed project. You are evaluating an opportunity with a clear head. Luna: So you're essentially defining in advance what would make you leave. Lucas: Exactly. The letter becomes a personal document that lists the concrete conditions under which you would walk away. And by writing it before you say yes, you force yourself to be honest about what really matters to you in the role. Luna: What kind of conditions are we talking about? Lucas: I've seen people write things like: 'I'm resigning because the board has not followed through on the governance commitments we agreed upon,' or 'I'm leaving because the company's growth strategy has shifted away from the long-term value creation we discussed.' Specific, principled, and tied directly to the promises made during the hiring process. Luna: That's almost like a pre-nup for an executive role. Lucas: That's exactly what it is. And the interesting thing is, a handful of listeners make this show possible — they support us through buy me a coffee dot com slash fexingo, and that's what keeps these episodes ad-free and focused on real tactics like this. So if you find value in these conversations, that's where you can chip in. Luna: Yeah, and it's a small group that makes a big difference. No pressure, but if this kind of practical strategy helps you, it's worth checking out. Lucas: Anyway, back to the pre-written resignation. I spoke with a chief revenue officer at a mid-cap SaaS company — let's call her Sarah — who did this in 2024 when she was considering an offer from a competitor. Luna: What did her letter look like? Lucas: She wrote two versions. One was a standard professional resignation — 'I've decided to pursue a new opportunity, effective X date.' But the second version was a negotiation letter. It said something like: 'I'm willing to stay for a phased transition of up to six weeks, provided that my unvested equity is accelerated to the date of my departure and that I am not required to participate in any post-exit non-compete enforcement.' Luna: So she used the letter as leverage before she even resigned. Lucas: Yes. She brought that letter — or rather, the terms in it — to the CEO and the board chair during her exit conversation. And because she had thought through her deal-breakers in advance, she was able to negotiate a clean departure that protected her financial interests. Luna: Did she get the equity acceleration? Lucas: She got a partial acceleration — 75 percent of her unvested options — and a three-week consulting agreement at her full salary. The CEO later told her that her preparedness made the conversation easier because he knew exactly what she needed to feel okay about leaving. Luna: There is a kind of emotional intelligence in that. You are removing ambiguity from a situation that is usually full of it. Lucas: Right. And the other benefit is that it changes your relationship with the role from day one. Sarah told me that every time something went wrong in the first year — a missed forecast, a strategy pivot — she would mentally revisit her letter and ask: 'Is this one of the conditions I wrote down?' Luna: That has to be grounding. Lucas: It is. It prevents the slow erosion of boundaries. Because when you are in the middle of a tough quarter, it is easy to convince yourself that things are worse than they are. But if you have a written document from your calm self, you have an anchor. Luna: Is there any research on this? Or is it just anecdotal? Lucas: There is actually some interesting data. The Institute for Executive Transitions published a study in 2025 that tracked 340 senior leaders who changed roles. They found that those who drafted explicit exit criteria — either in writing or as a formal memo to themselves — reported 23 percent higher satisfaction in their first 90 days compared to those who did not. Luna: Because they had clearer expectations going in. Lucas: Exactly. The study also showed that these leaders were more likely to raise concerns early — within the first 30 days — if something was off. They had a benchmark. Luna: So the letter is not really about leaving. It's about staying with your eyes open. Lucas: That is a perfect way to put it. And I think that is the real power of this tool. It is not a resignation letter in the traditional sense. It is a self-accountability document. Luna: What would you put in yours if you were writing one today? Lucas: I think I would write it around three categories. First, governance and autonomy — do I have the decision rights I was promised? Second, strategic alignment — is the company still pursuing the same long-term value thesis we discussed? Third, personal sustainability — am I able to maintain my health and relationships while doing this job? Luna: That last one is often overlooked until it is too late. Lucas: It is. And it is the hardest to include because it feels selfish. But senior leaders burn out at alarming rates. A pre-written resignation that includes a health or family boundary forces you to take that seriously from the start. Luna: So if a listener wants to try this, what is the practical first step? Lucas: Open a blank document. Do not call it a resignation letter. Call it 'My Terms.' Write down three to five concrete conditions that, if violated, would make you start looking for your next role. Then put it in a drawer. Check it every six months. And when you do decide to leave, you will already have the language ready. Luna: I like that. It is proactive without being paranoid. Lucas: Exactly. And it ensures that when you do write that actual resignation letter, it comes from a place of clarity, not frustration. That is a much better position to negotiate from. Luna: Alright, I'm going to try this. Not because I'm planning to leave, but because I want to know what I actually value. Lucas: That is the whole point. And maybe in a future episode, we will talk about what happens when you hand that letter over and the board asks you to stay. Luna: I think that is a whole other episode. Lucas: Absolutely. For now, try the pre-written resignation. It might change how you think about your current role. Luna: Or your next one.