Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / Senior Leaders Who Hire Their Own Bosses
Transcript
- Lucas: There is a move that senior leaders make — rarely discussed, but when it works, it can reshape the next five years of a career. It's the decision to hire your own boss. Luna: Hire your own boss. That sounds like you're engineering the situation where you choose who you report to, before they're even in the role. Lucas: Exactly. I'm thinking of a specific case. A VP of Product at a Fortune 500 technology company — let's call her Sarah. She'd been in the role for about three years, and her CEO told her they were bringing in a Chief Product Officer above her. Standard growth move. Most people in that situation brace for impact. Luna: Right, you get ready to be managed by someone you didn't pick, with their own agenda. Lucas: Sarah did something different. She asked the CEO if she could draft the job description for the CPO role. And not just the generic one — she wrote a detailed profile, including the specific gaps she saw in the product organization that she couldn't fill herself. She framed it as 'I want to make sure we get someone who complements my weaknesses, not someone who duplicates my strengths.' Luna: That's a smart framing. It's not about control — it's about organizational fit. Lucas: The CEO agreed. Sarah then used her network to identify three candidates, and she briefed the CEO on each one before the formal interviews happened. She didn't make the final decision, but she shaped the pool. The person they hired — a woman from a different industry with deep data infrastructure experience — was exactly what Sarah needed. And because Sarah had been part of the process, the dynamic from day one was collaborative, not adversarial. Luna: So the new boss knew that Sarah had a hand in bringing her in. That changes the power balance immediately. Lucas: It does. And it's not a power play in a negative sense — it's actually a sign of strategic maturity. The VP recognized that a new boss could either be a threat or an accelerant, and she chose to make it an accelerant. Luna: Let's talk about the specific steps, because I think the instinct for most executives is to wait and see who arrives, and then react. How do you actually initiate this conversation? Lucas: The first step is what I call the gap audit. You need to honestly assess what you're not good at — or what you don't have time for — that a boss above you could bring. In Sarah's case, she was strong on product vision and customer research, but weak on data architecture and scaling analytics infrastructure. She wrote that down. Luna: So she was essentially writing a job description for someone who would fill her gaps, not someone who would replace her. Lucas: Exactly. Then the second step is the framing conversation with your current boss — usually the CEO or the person above the new hire. You don't say 'I want to pick my boss.' You say something like: 'I want to make sure this new role sets us up for success. Can I help define the profile so we attract the right person?' The language matters a lot. Luna: And then the third step — the actual recruitment. You're essentially doing the early sourcing. Lucas: Right. You use your network, you identify candidates, you do informal conversations before the formal process. But you have to be careful not to overstep. You're not the hiring manager — you're the scout. The CEO still makes the call. Luna: What about the risk? I can imagine a scenario where the CEO feels like you're trying to run the show, and that backfires. Lucas: That's real. The key is the framing. If you come across as someone who wants to control their own destiny in a constructive way, most CEOs appreciate that. But if you seem like you're trying to install a puppet, it will blow up. I've seen that happen too. Luna: Can you give an example of a backfire? Lucas: A CFO I know tried to do this. He was a very strong finance leader, but he had a blind spot — he didn't see that his relationship with the board was deteriorating. When the CEO said they were bringing in a new CFO — wait, that would be a new peer, not a boss. Let me adjust. I know a different case: a CTO who was told they'd get a new VP of Engineering above them. The CTO drafted a profile that basically described a clone of himself — same background, same technology stack, same architectural philosophy. The CEO saw through it and hired someone completely different, and the CTO lost credibility. Luna: So the mistake was trying to replicate himself instead of complementing. Lucas: Exactly. The gap audit has to be honest. If you're not willing to admit your weaknesses, this move will fail. And the CEO will notice that you're being defensive. Luna: Let's step back. How common is this? Are there senior leaders who actively look for this kind of opportunity? Lucas: It's not common, but it's more common than people think. I've spoken to a few executive recruiters who say that in about 15 to 20 percent of senior-level searches, the person who will report to the new hire has some influence on the profile. But only about 5 percent of the time does that influence extend to actually sourcing candidates. Luna: And those are the ones who really understand organizational dynamics. Lucas: Yeah, they're the ones who see that a new boss isn't just a person — it's a structural change in your career trajectory. If you can shape that structure, you're playing a different game. Luna: I want to pick up on something you said earlier about the language. Can you give us a specific script for the initial conversation? Lucas: Sure. You're sitting with your CEO. They've just told you that a new layer is coming. You say: 'I think this is a great move for the organization. I want to make sure we get someone who really complements what we're building. I know my own gaps — I've been thinking about where I need support. Could I help draft a profile that captures what we need?' Luna: That's very direct, but it's humble. Lucas: It is. And the CEO will typically say yes because you're making their job easier. Then you follow up with a one-page document that lists three to five specific capabilities the new person should have — and why those are important for the business. Not why they're important for you. Luna: So the framing is always about the business, never about yourself. Lucas: Exactly. And that's what separates the people who succeed at this from the ones who come across as political. Luna: Let's talk about the post-hire dynamic. Once the new boss is in place, how do you manage that relationship? Because you've been part of their hiring, but they're still your boss. Lucas: This is the most delicate part. You have to immediately transition from being a collaborator in the hiring process to being a direct report. You don't want to create a situation where the new boss feels like you're still trying to manage them. The way Sarah handled it was to schedule a series of transition meetings in the first 30 days where she explicitly handed over the agenda. Luna: What does that mean practically? Lucas: She said: 'Here's everything I've been working on. Here's where I think we need to go. But your role is to decide what changes. I'm here to support that.' She didn't cling to her previous autonomy. She made it clear that the new boss had the authority to redirect things. Luna: That's a sign of confidence. A less secure leader would have tried to protect their turf. Lucas: Absolutely. And because she did that, the new boss trusted her more. Within six months, Sarah's scope actually expanded — she got two additional product lines under her because the new CPO saw her as a partner, not a threat. Luna: So the long-term payoff is real. But I imagine not every situation lends itself to this move. Lucas: Right. You need a few conditions. First, you need to have enough credibility with your current boss that they trust your judgment. Second, the new role has to be genuinely open — not a pre-ordained hire where the CEO already has someone in mind. And third, you need to be willing to honestly assess your own weaknesses. Luna: That last one is probably the hardest for senior leaders. We're not wired to advertise our gaps. Lucas: No, we're not. But the ones who can do it — and do it strategically — end up in much stronger positions. It's one of those counterintuitive career moves that looks risky but actually reduces risk. Luna: It reminds me of something we talked about in an earlier episode — the idea of shaping your own role through an offer-stage memo. This is similar, but it's about shaping the person above you. Lucas: Exactly. And in both cases, the principle is the same: don't be a passive recipient of organizational decisions. If you can influence the structure you work in, you should. Luna: Yeah, that's a good way to put it. Lucas: You know, we talk a lot on this show about specific tactics that can shift a career trajectory. And one thing I appreciate is that we can have these conversations without any commercial interruptions. We deliberately don't run ads on these episodes because we want you to get the full value without being sold to. Luna: Right, and that's a choice we make. If you find these episodes useful and want to support that choice, you can find us at buy me a coffee dot com slash fexingo. It's a simple way to keep the show ad-free. Lucas: And it really does make a difference. So back to the topic — let's talk about one more nuance. What happens if you try this move and the CEO says no? Luna: That's a tough spot. What do you do then? Lucas: If the CEO says no, you have to accept it gracefully. But you also have information. It tells you that the CEO either doesn't trust your judgment or has a specific person in mind. Either way, you now know that your influence in the organization is more limited than you thought. That's useful data for your own career planning. Luna: So it's a diagnostic tool as much as a strategic move. Lucas: Exactly. If they say no, you have a choice: adapt to the new boss as best you can, or start thinking about whether this is the right environment for you long-term. Either way, you're acting from a position of awareness, not surprise. Luna: I like that. It takes the emotional sting out of the rejection and turns it into data. Lucas: And that's really the theme of this whole approach. Senior leaders who succeed over the long term are the ones who see organizational moves as things they can shape, not just things that happen to them. Hiring your own boss is one of the most powerful examples of that mindset. Luna: So if listeners take one thing from this episode, what should it be? Lucas: Next time you hear that a new layer is coming above you, don't brace for impact. Ask yourself: what gaps does my future boss need to fill? And then have the conversation. The worst that can happen is they say no — and you learn something about your standing. The best that can happen is you get a boss who makes you better. Luna: That's a good place to leave it. Thanks, Lucas. Lucas: Thanks, Luna. See you next time.