Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Use a Career Syndicate Strategy
Transcript
- Lucas: You know, we've talked a lot on this show about boards, coaches, mentors, peer coaching groups. But there's a model I keep hearing senior leaders use that sits right in the middle of all of them, and it doesn't really have a clean name in most career literature. Luna: I think I know where you're going. Is this the group where people share opportunities and hold each other accountable, almost like an investment syndicate but for careers? Lucas: Exactly. A career syndicate. It's a small, intentional group of peers — usually four to eight people, all at a similar seniority level — who meet regularly with a specific charter. Not just networking, not just advice. They share deal flow, they do portfolio reviews of each other's careers, and they hold each other accountable to moves they've committed to. Luna: Portfolio review — that's a great term. So it's like you're treating your career as a collection of assets and exposures, and the group helps you rebalance? Lucas: That's exactly the framing. I was talking to a former Fortune 500 CFO — let's call her Sarah — who built a syndicate about three years ago. Six members, all senior VPs or C-suite at different companies in different industries. They meet every six weeks, rotating who chairs the meeting. Each person comes with one specific ask: an introduction they need, a decision they're wrestling with, or an opportunity they're evaluating. Luna: And the results? I'm guessing it's not just feel-good peer support. Lucas: Not at all. Sarah told me that within 18 months, three of the six members landed CEO roles — two at private companies, one at a public company. She credits the syndicate with at least one of those placements directly. Another member used the group to vet a board seat she was offered and ended up declining it after they surfaced red flags she hadn't seen. Luna: That's a powerful outcome. But I imagine this only works if there's real trust and a clear structure. It's not just a bunch of executives having dinner. Lucas: Right. The structure is what separates this from a dinner club. The syndicate Sarah built has a written charter. It covers confidentiality — what stays in the room, what you can share outside. It covers expectations for attendance and participation. And crucially, it covers what they call 'deal flow.' Each member maintains a running document of opportunities they've encountered: open roles they know of, board openings, potential investors, even speaking engagements or media opportunities. Luna: So it's a curated pipeline of opportunities for the group. That's really smart. But how do you avoid it becoming transactional? Where's the line between helping each other and just trading favors? Lucas: That's the million-dollar question. Sarah said the key is that the primary currency is insight, not favors. You don't join a syndicate to get a job. You join to get better at thinking about your career. The opportunities are a byproduct. And the charter explicitly says that no member is obligated to make an introduction or recommend someone. The value is in the exposure to what's out there and the collective judgment. Luna: That makes sense. So it's about expanding your aperture — seeing moves you wouldn't have considered because you're too deep in your own industry or function. Lucas: Exactly. One of the members was a tech VP who had only ever worked at large public companies. Through the syndicate, she learned about a CEO role at a mid-market private equity-backed firm. She never would have looked there. She ended up taking it and has been in the role for two years now. The syndicate gave her the confidence to make that leap because she had people who knew her capability and could stress-test her thinking. Luna: Let's talk about composition. You mentioned different industries. Should a syndicate be cross-industry, or is it better to have people in adjacent spaces? Lucas: Sarah's view was that you want diversity on at least three dimensions: industry, function, and career stage. You don't want five people who all came up through marketing in consumer goods. You want a mix — maybe a CFO, a CTO, a chief people officer, a general manager. The more varied the lenses, the better the pattern recognition. But you also need a common denominator: everyone should be at a level where they have meaningful discretion over their own career moves. If someone is too junior, they won't have the same kind of opportunities to share. Luna: So no junior VPs trying to break into the C-suite alongside sitting CEOs? That would be a power imbalance. Lucas: Exactly. Sarah says the rule of thumb is that everyone should be within one or two steps of each other on the org chart. A sitting CEO and a senior VP might work. A CEO and a mid-level director won't. The dynamic just shifts too much. People hold back or defer. Luna: What about the meeting format? You mentioned rotating chairs. Is there an agenda? Lucas: Yes, a very structured one. Each meeting has a rotating chair who sets the agenda and keeps time. The typical format is: first, a quick check-in from each person — one win, one challenge, one ask. Then deep-dive on two members per meeting, about 30 minutes each. The deep-dive is where the real work happens. The presenting member shares their current career situation, a specific decision, and then the group spends time asking questions and offering perspectives. The rule is no advice in the first 15 minutes — only clarifying questions. It prevents premature solutions. Luna: I love that. It forces people to actually understand the context before jumping to 'you should do X.' That's rare in most executive conversations. Lucas: It is. And the final part of the meeting is deal flow — each person shares one or two opportunities they've encountered since the last meeting. These go into a shared document that the group maintains. Sarah told me that document has become one of the most valuable assets for the group. It's not just job openings — it's board seats, speaking gigs, potential co-investors, even dissertation topics for one member who was considering a doctorate. Luna: That's incredible breadth. But at the same time, isn't there a risk of groupthink? If six smart executives all validate each other's moves, you might miss the contrarian perspective that could save you from a bad decision. Lucas: That's a real risk, and Sarah acknowledged it. Her group fights it by occasionally inviting an outsider to a meeting — someone who's not a member but has relevant expertise. They also have a norm of assigning a 'devil's advocate' for each deep-dive. That person's job is to push back on the presenting member's assumptions, even if everyone else agrees. It's not comfortable, but it's valuable. Luna: So there's a deliberate effort to inject friction into the process. That's smart. How do they handle confidentiality? If someone shares a potential board opportunity, and another member is also qualified, what happens? Lucas: The charter addresses that. For any shared opportunity, the person who brought it has the right of first refusal for a week. After that, it becomes available to the group. And no one is allowed to pursue an opportunity that another member is actively being considered for, unless that member explicitly gives permission. It sounds formal, but Sarah says it actually reduces tension because everyone knows the rules upfront. Luna: That makes a lot of sense. It's like a gentleman's agreement, but written down. Lucas: Precisely. And the final piece is accountability. After each meeting, members commit to two or three actions they'll take before the next meeting. These are logged in the shared document, and the next meeting starts with a review of whether people followed through. Not in a punitive way — but the social contract is real. Sarah says she's never seen a member miss a commitment twice. Luna: Because nobody wants to be the person who doesn't follow through in front of peers they respect. That's a powerful motivator. Lucas: Exactly. And that's where a syndicate beats a coach or a mentor one-on-one. A coach holds you accountable to your goals, but it's a paid relationship. A syndicate is peer-based. The accountability comes from mutual respect and the desire to not let the group down. It's different. Luna: I want to ask about who shouldn't do this. Are there profiles of senior leaders for whom a syndicate might not be the right fit? Lucas: Sarah mentioned a couple. First, if you're not willing to be vulnerable and share your real challenges — not just your wins — you'll get limited value. The group can only help if they know what's actually going on. Second, if you're in a highly competitive field where you're likely to directly compete with members for the same roles, it's probably not ideal. Although Sarah's group has managed that by being in different industries. Third, if you're not willing to give as much as you get. Free-riders get detected quickly and the group usually self-corrects. Luna: So it requires a certain generosity of spirit. But the payoff seems huge. Lucas: It is. And one more thing Sarah said that stuck with me: she views her syndicate as a form of 'career insurance.' Not in the sense of a safety net, but as a way to diversify her exposure to opportunities and perspectives. She said she's made better decisions in the last three years than in the ten before it, largely because of the group. Luna: That's a powerful endorsement. For someone listening right now who thinks this might be for them, what's the first step? How do you even find five or six peers to form a syndicate? Lucas: Sarah's advice is to start with two or three people you already trust and respect. Have an honest conversation about the idea. If they're interested, each of you brings one or two additional people you vouch for. That way, the initial trust is built through existing relationships. Don't try to recruit strangers from LinkedIn. The trust is the foundation. Luna: And once you have the group, invest time in the charter upfront. That seems to be what makes it durable. Lucas: Absolutely. Spend the first meeting not on deep-dives but on setting norms. What's confidential? How often will you meet? What's the commitment? Who can join later? Get that right, and the syndicate can run for years. Sarah's group just renewed its charter for another two years. Luna: It's really a model that maps onto how senior leaders think — systematic, structured, and long-term. I think a lot of our listeners might already have the seeds of a syndicate in their network without realising it. Lucas: That's exactly the insight. You might have five former peers you respect. You might already meet for drinks twice a year. Formalise that. Add a little structure. You'd be surprised what emerges. Luna: And if people find this kind of strategic career thinking useful, we should mention that this show is supported entirely by listener contributions. We don't run ads, and that's intentional. If the show has helped you think about your career more clearly, you can support it at buy me a coffee dot com slash fexingo. It's a small way to keep this kind of content available to everyone. Lucas: Appreciate that, Luna. And it genuinely helps us keep the focus on substance. So, back to the syndicate — one final thought. Sarah told me that the single best decision she made was to include people who disagreed with her on major strategic questions. She says it made her a better leader, not just a better networker. Luna: That's a great note to end on. A syndicate isn't an echo chamber — it's a sounding board with texture. Thanks, Lucas. Lucas: Thanks, Luna. And to our listeners — if you're thinking about building a syndicate, start small, set clear norms, and see where it takes you.