Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Use the Five-Year Backward Resume
Transcript
- Lucas: We've talked a lot on this show about how senior leaders position themselves for the next move — the narrative, the board exposure, the internal pitch. But I want to look at a different angle today: what happens when you write your resume not for the role you want now, but for the role you want in five years. Luna: That sounds like the opposite of how most people do it. Normally you're reacting to a job description that exists today, not inventing one that might exist half a decade from now. Lucas: Exactly. And that reactive approach is why so many senior leaders find themselves hitting ceilings they didn't see coming. They've got the right title, the right years of experience, but when they go for that COO role or that public company board seat, there's a gap they never anticipated. The 'five-year backward resume' forces you to see those gaps before you're in the interview. Luna: So how does it actually work? Walk me through the mechanics. Lucas: You sit down and write a resume — with dates, bullet points, quantified achievements — as if today is five years from now. So today is July 2026. You write a resume dated July 2031. You imagine the role you want to hold at that point, and you reverse-engineer the accomplishments that would need to be on that resume to justify getting that role. Luna: And you're not faking it — you're writing what you intend to have done by then. Lucas: Right. It's aspirational but concrete. Let's use a specific example. Say you're a VP of Product at a mid-stage SaaS company — maybe two hundred million in revenue, growing at 20 percent year-over-year. Your five-year goal is to become Chief Product Officer at a company scaling from five hundred million to a billion. So you write the 2031 resume for that CPO role. Luna: What would that resume look like? Lucas: It would say something like: 'Led product strategy for a $500M to $1B growth phase. Built and scaled a product organization from 40 to 120 people. Drove NRR from 110 percent to 130 percent through platform expansion. Served on two external advisory boards. Spent three years running an international product team out of London.' Luna: So the key is that you're not just writing a wish list. You're writing specific, measurable outcomes. And then you compare that to your actual resume today. Lucas: That comparison is where the value lives. Because when you lay them side by side, the gaps become obvious. Maybe today you've never managed more than a 15-person team. You've never had international P&L responsibility. You've never served on a board or advisory panel. Those aren't just nice to haves — they're table stakes for a CPO role at that scale. Luna: And if you wait until you start applying for those roles to realize those gaps, you've already lost. Building a 120-person org takes years. Getting a board seat takes networking and a track record. International experience requires relocation or extended travel. Lucas: So the exercise gives you a five-year roadmap. Now, instead of taking whatever interesting project comes along, you can be strategic. You can say: 'This year, I need to negotiate international responsibility into my role. Next year, I need to join an advisory board. The year after, I need to drive a major platform initiative that I can quantify.' Luna: It's almost like an executive development plan, but one you design yourself rather than having HR hand you a generic framework. Lucas: Exactly. And it's more honest than a traditional five-year plan, because a resume forces you to claim credit for specific outcomes. You can't write 'improved NRR' — you have to say 'improved NRR from 110 to 130 percent over three years.' That specificity forces you to think about how you'd actually get there. Luna: I want to push back a little though. Doesn't this risk becoming a very elaborate fantasy? I mean, you're writing a resume for a job that may not exist, at a company that may not exist, in a market that may change completely. Lucas: It's a fair concern. But the point isn't to predict the future perfectly. It's to identify the capabilities you'd need regardless of the specific role. The size of organization you want to operate at, the scope of responsibility, the types of initiatives. Even if the CPO role you imagine doesn't materialize, the skills you develop to get there — scaling a team, driving NRR, international leadership — transfer to whatever does come next. Luna: That makes sense. So the exercise is really about building a capability portfolio, not a specific job title. Lucas: Exactly. And I think this is particularly powerful for senior leaders who have already achieved a lot of conventional success. When you've been a VP for a while, it's easy to coast on your reputation. The five-year backward resume cuts through that because it shows you exactly where you're vulnerable. It's humbling, which is useful. Luna: Have you seen anyone actually do this and make a big career shift as a result? Lucas: Yeah. I know a former VP of Engineering who did this exercise and realized she had zero experience with public company governance — no board observer roles, no SEC reporting knowledge, nothing. She was targeting a CTO role at a public company. So she spent the next two years joining two private company advisory boards, taking a governance course at Stanford, and volunteering for the audit committee of a nonprofit. When the CTO role opened up, she was ready. Her future resume had become her actual resume. Luna: That's a great example. And it's not just about technical skills — it's about network and reputation too. Advisory boards, speaking engagements, published thought leadership — those all show up on a five-year resume. Lucas: Absolutely. One thing I'd add: you need to write the future resume in the same format as your actual resume. Same font, same structure, same level of detail. If you just jot down bullet points on a napkin, it won't have the same psychological weight. You need to see it as a real document that could be submitted. Luna: And then you share it with someone you trust — a mentor, a coach, a peer — to reality-check it. Otherwise you might be too ambitious or not ambitious enough. Lucas: Right. And that leads to something I want to mention, because it ties into how this show works. We keep Executive Careers free of ads, and we hear from listeners that this kind of practical, specific advice is exactly why they tune in. If you've found value in episodes like this one — or any of the previous 87 — and you want to support keeping this resource open and independent, you can do that at buy me a coffee dot com slash fexingo. No pressure, just a way to keep the show sustainable. Luna: Yeah, it's a small gesture that goes a long way. We don't sell your data, we don't run sponsored segments, and we keep the focus on what actually helps senior leaders. Lucas: So back to the five-year backward resume. Once you've written it and identified the gaps, the next step is to prioritize. Not all gaps are equal. Some are what I'd call 'table stakes' — you absolutely must close them to be credible. Others are 'differentiators' — they'd set you apart but aren't mandatory. Luna: Can you give an example of each? Lucas: For a VP of Product aiming for CPO at a scaling company, table stakes might be: having managed a team of at least 50, having direct P&L ownership, and having driven at least one major platform transformation. Differentiators might be: having a published book on product strategy, having a strong personal brand on LinkedIn, or having spoken at five industry conferences. Luna: So you close the table stakes first, and then you invest in the differentiators when you have time. Lucas: Exactly. And the timeline matters. Some table stakes — like international experience — might take a year or more to arrange. You can't just decide to have it in three months. So the five-year window gives you enough runway to make those big moves. Luna: What about the risk that you over-invest in one specific future and miss opportunities that don't fit that narrative? Lucas: That's a real risk. The antidote is to update the future resume every six months. The world changes, you change, your ambitions change. Maybe in year two you realize you'd rather be a board director than a CPO. That's fine — rewrite the resume. The discipline of the exercise is more important than the specific target. Luna: So it's a living document, not a one-time thing. Lucas: Exactly. And if you do it consistently, you start to notice patterns. Maybe every version of your future resume includes 'sits on two public company boards' — that tells you that board service is a genuine priority, not a passing thought. Luna: That's a useful signal. I also think this exercise helps with the emotional side of career planning. When you're a senior leader, it's easy to feel like you've 'arrived' and the next move is just a matter of timing. The backward resume can be a wake-up call that you still have real gaps to fill. Lucas: It's humbling in the best way. And it gives you agency. Instead of waiting for a headhunter to tell you what you're missing, you discover it yourself and start working on it proactively. That's a much more powerful position to be in. Luna: So for a listener who wants to try this today, what's the first step? Lucas: Block out two hours this week. Open your current resume. Save it as a new file called '2031 Resume Draft'. Pick a role you genuinely aspire to — not what you think is realistic, but what you'd love to have. Write the bullet points as if you've already done them. Then set it aside for 24 hours. Come back and compare it to your current resume. Write down the top three gaps. That's your starting point. Luna: And then share it with someone you trust to call you on your blind spots. Lucas: Exactly. And if that conversation leads to a new insight or a new connection — which it often does — you've already gotten more value from the two hours than most career planning exercises provide. Luna: I think this might be one of those ideas that sounds simple but is actually quite difficult to do well. It requires real honesty about where you are and where you want to be. Lucas: It does. But the payoff is clarity. And for senior leaders, clarity about the next chapter is arguably the most scarce resource there is.