Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Use Personal Playbooks for Career Decisions
Transcript
- Lucas: Luna, I was talking to a friend last week — VP of Product at a mid-size SaaS company, great role, solid team, but he got approached for a CEO gig at a smaller startup. And he was genuinely torn. Not because the money was wildly different, but because he couldn't figure out which move actually served his career two or three steps down the line. Luna: That's a classic senior leader dilemma. When you're that close to the top, the options get more complex, not simpler. A lot of people default to the title or the comp, but those are often the wrong signals. Lucas: Exactly. Which is why I want to talk about something that's surprisingly rare even among very experienced executives: having a personal decision playbook. Not a pros and cons list on a napkin, but a structured framework you've built in advance, before the offer even lands. Luna: A playbook for your own career. I love that. What's in it? Lucas: I think the best ones have four components. First, a values audit — not the vague 'integrity and innovation' kind, but specific, rank-ordered priorities. Like: autonomy, geographic flexibility, depth of impact, learning velocity, financial upside. You actually list them and force-rank them. Luna: And that ranking changes over time. What mattered at thirty-five might not matter at forty-five. So you're supposed to revisit it, right? Lucas: Exactly. At least annually. The second component is scenario mapping. Before a fork appears, you sketch out the two or three most likely paths your career could take — same company, different company, adjacent industry, maybe starting something. And you write down what each path would actually look like: the day-to-day, the trade-offs, the risks. Luna: So when an offer lands, you're not reacting in a vacuum. You already have a map of the terrain. That's smart. What's third? Lucas: Decision criteria with explicit weights. Let's say you value learning velocity at 40 percent, financial upside at 30, geographic flexibility at 20, and brand prestige at 10. You plug the opportunity into that framework, and you get a score. It forces you to be honest about what you actually prioritize. Luna: I've done something like that, but I'll admit I didn't use it when I should have. A few years ago I had an offer to join a fast-growing fintech as head of marketing. Great title, decent comp. But I skipped the playbook. Six months in, I realized I hated the culture — it was all speed, no reflection. And that wasn't on my criteria list at all. I had no 'culture red flag' filter. Lucas: That's the fourth component — a personal red flag list. Things you know from experience will make you miserable. For me, it's any role where the founder or CEO has a pattern of public outbursts. I've seen it, I've lived it, and I will never do it again. So that gets a hard veto. Luna: A hard veto. No weighting, no scoring — just no. That's powerful. And it's the opposite of what most people do, which is to rationalize away the red flags because the package looks good. Lucas: Right. So let's apply this to my VP friend. He built a playbook in about forty-five minutes one Saturday morning. His top value was learning velocity — he wanted to be in an environment where he'd be stretched. Second was ownership over a full P&L, because he'd only had product P&L before. Third was geographic flexibility — he wanted to stay in Austin. Luna: Okay, so how did the two options score? The CEO role at the startup versus staying for a potential COO track. Lucas: The CEO role scored high on learning velocity — running a whole company is a massive stretch. And it gave him full P&L ownership. But it failed on geographic flexibility — the startup was based in San Francisco, and they wanted him in office four days a week. So that was a 10 percent weight, but it was a dealbreaker under his red flag list: he'd promised his family they wouldn't relocate again. Luna: So the red flag overrode the scoring. That's exactly how it should work. What about the COO track? Lucas: The COO path scored medium on learning velocity — he'd done operations-adjacent work before — but high on P&L ownership, and obviously high on geography because he'd stay put. No red flags. But the timeline was unclear. The CEO hadn't committed to a transition date. So his playbook told him: the startup CEO role is exciting but vetoed. The COO path is solid but needs a timeline commitment. He ended up negotiating a concrete eighteen-month timeline for the COO transition, and the CEO agreed. He stayed. Luna: And he probably would have made a different call without the playbook. The startup CEO title is shiny. The playbook cut through that. Lucas: Exactly. And look, I think the playbook is also useful for the smaller decisions — should I take that speaking gig? Should I join that advisory board? Should I mentor that person? If you run them through your values and criteria, you avoid the trap of saying yes to everything because it feels good. Luna: It's also a great tool for saying no gracefully. When you have a clear framework, you can say 'this doesn't align with my current priorities' instead of 'I'm too busy' or making up an excuse. It's more honest. Lucas: And that honesty, I think, is part of what builds your reputation as a thoughtful leader. People notice when you make deliberate choices. It actually makes them trust you more. Luna: Speaking of building trust and reputation — Lucas, I know we talk a lot about tools and frameworks on this show, and I think many of our listeners have gotten real value from them. If that's you, and you've found episodes like this one useful, a couple of dollars a month is genuinely what keeps these going. Buy me a coffee dot com slash fexingo — if you've gotten something out of them, it makes a real difference. Lucas: Yeah, it's a small gesture that adds up. We don't run ads, and listener support is what makes that possible. So if you're in a position to chip in, we appreciate it. And if not, no worries — the episodes stay free. Luna: Exactly. Okay, back to playbooks. One thing I want to add: a playbook isn't a one-and-done document. It should evolve. I revisit mine every six months, usually at the start of a new quarter. And I've added a section called 'energy audit' — I track which activities drain me and which energize me, and I use that to refine my criteria. Lucas: That's a great addition. Because your values might shift subtly. Maybe after a year in a role, you realize you actually crave more collaboration, not more autonomy. The playbook catches that. Luna: So if someone wants to build their own playbook today, what's the fastest way to start? Lucas: I'd say set a timer for thirty minutes. First ten minutes: write down your top five values as they are right now. Not what you think they should be. Be brutally honest. Next ten minutes: list three scenarios your career could realistically take in the next two years. Last ten minutes: write down three non-negotiable red flags from past experience. That's your starter playbook. You can refine it later. Luna: I love that it's a low-friction start. The hardest part is actually sitting down to do it. But once it's there, you have a tool that can save you from a really expensive mistake. Lucas: And not just financially expensive — the time cost, the emotional cost, the relationship cost. I've seen executives burn two years in a role they knew was wrong within the first month, just because they didn't have a framework to say no. Luna: Right. So the playbook is really a commitment device to your own priorities. It's a way to make sure your career is being shaped by your deliberate choices, not by the noise of opportunity. Lucas: That's the whole point. You stop being reactive. You become the author of your own career narrative. Luna: I think that's a great note to end on. Next time, I'd love to talk about how senior leaders actually use these playbooks in real-time negotiation — like when a counteroffer comes in mid-conversation. Lucas: Perfect. That's a whole episode on its own. We'll dig into that next week.