Latest / Executive Careers with Fexingo: VP, C-Suite, and Senior Leadership Career Strategy / How Senior Leaders Vet Culture Before They Sign
Transcript
- Lucas: So you've got the offer. The comp package is right, the title is right, the mandate is clear. But here's the question that keeps executives up at night in August 2026: what is the culture actually like once you're in the seat? Not the culture the recruiter described, not the culture in the glossy deck — the culture that runs on a Tuesday afternoon. Luna: That's the part that's almost impossible to vet from the outside. You can read the financials, you can talk to the board, but the unwritten rules of how things actually operate? That's a whole other animal. Lucas: Right. And I think a lot of senior leaders make a mistake here. They spend hours on the business case, the strategy, the market opportunity, but they treat culture as a soft skill they'll figure out once they're there. Then six months in, they find themselves in a team meeting where no one disagrees with the CEO, and they realize the culture is a monolith — and they're the only one who thought dissent was welcome. Luna: Six months is an expensive learning curve at that level. So what's the alternative? How do you do cultural due diligence before you sign? Lucas: There's a framework I've seen work well — I call it the three-conversation method. Before you accept, you need three specific conversations: one with someone who left the company, one with someone who joined recently, and one with someone who's been there a long time. Each conversation tells you something different about the culture. Luna: The leaver — that's the exit interview proxy. But how do you talk to someone who left without it feeling awkward or like you're digging for dirt? Lucas: You frame it as, 'I'm considering joining a company you know well — I'd love your read on what it's really like to work there.' Most people, if they're not under a non-disparagement agreement, will give you a surprisingly honest answer. The key is to ask about specific behaviors, not general impressions. Not 'was the culture good?' but 'how are decisions actually made around here?' Luna: That's a great question. Because every company says they're data-driven, but some make decisions by committee and others by one person's gut. Lucas: Exactly. And the recent hire — someone who's been there under a year — can tell you what the onboarding process actually felt like. Did they get real context, or were they thrown into the deep end? That tells you a lot about how the organization treats its people. Luna: And the long-timer? The person who's been there a decade or more. Lucas: That's your culture anchor. They've seen the cycles, they know where the bodies are buried, and they can tell you what's actually changed versus what's stayed the same. If the long-timer says, 'We've always done it this way,' that's a red flag. If they say, 'We've evolved how we do X,' that's a sign the culture is alive. Luna: So those are the conversations. But what about the meeting audit? You mentioned that earlier — is that when you actually sit in on meetings before you join? Lucas: You can't always do that, and it can be awkward to ask. But you can do a proxy: ask to see a recent board deck or an operating review. Or listen carefully to how people describe a typical weekly staff meeting. The real audit happens when you ask, 'Can you tell me about a recent decision that was made — what was the process, who was in the room, how did it land?' Luna: That's clever. Because the way they describe that one decision reveals the operating system. Lucas: Yeah. And here's a concrete tell: how does bad news travel? In a healthy culture, bad news goes up fast and gets addressed head-on. In a toxic culture, people sugarcoat it, or they shoot the messenger. Ask the recent hire, 'When something went wrong, what happened? How was it handled?' Luna: That's a great question. And I've heard a lot of executives say you should also look at how the company talks about its failures publicly — like in earnings calls or press releases. Are they admitting mistakes? Lucas: That's a good external signal, but it's filtered. The internal signal is stronger. You want to know what happens in the room when a number is missed. If the response is 'we need to understand what happened,' that's one culture. If it's 'who's responsible?' that's another. Luna: And let's not forget the dress code. I know it sounds superficial, but how people dress can tell you a lot about hierarchy and conformity. Lucas: That's a real thing. I once talked to a VP who joined a company where the CEO wore a hoodie and jeans, but everyone else on the exec team wore suits. That mismatch signaled a lot about the informal power structure. It's not about the clothes themselves — it's about what they signal regarding who's allowed to be different. Luna: So the meeting audit, the dress code, the bad news test — but how do you actually get all this without sounding like you're interrogating the recruiter? Lucas: You ask for a second round of conversations, not with the board or the CEO, but with people who would be your peers and direct reports. You say, 'I'd love to meet a few of the people who'd be on the team — to get a sense of how we'd work together.' That's a normal request for a senior hire. And in those conversations, you just have a real conversation. Don't make it an interrogation. Ask about their week, what they're working on, what they're frustrated by. Luna: And what if they give you the polished answer? 'Oh, everything's great, we love it here.' Lucas: Then you dig one level deeper. Say, 'I know every company has things that are hard — what's the thing that's hardest for you right now?' If they say 'we're growing so fast, it's hard to keep up,' that's a good sign — it's a specific challenge. If they say 'nothing comes to mind,' that's a red flag. Every healthy organization has pain points. Luna: Let me play devil's advocate for a second. Isn't there a risk of over-analyzing? You can't really know a culture until you live it. Some executives just take the leap and trust their gut. Lucas: There's definitely a limit. No amount of pre-hire research will tell you what it's like to work for a board that changes its mind every month, or a founder who says one thing and does another. But the point of cultural due diligence isn't to eliminate all risk — it's to reduce the chances of a catastrophic mismatch. And it's also about knowing what you're walking into so you can set realistic expectations. Luna: So sometimes it's not about avoiding a culture clash — it's about choosing a clash you can handle. Lucas: Exactly. Some cultures are tough but you can work with them. The question is whether the specific friction points are ones you're equipped for. I remember an executive who joined a company with a very aggressive, high-pressure culture. He knew it before he signed. He had a background in turnarounds, so he actually thrived in that environment. The culture wasn't a good fit for everyone, but it was for him. Luna: So it's about self-awareness too. Knowing your own operating style and what you can tolerate. That's a big part of the equation. Lucas: Right. And that's why the three conversations include the long-timer — they can give you a sense of whether the culture is stable or in flux. If the culture is changing, you might be coming in at a pivotal moment where you can shape it. That's an opportunity, not a warning. Luna: Makes sense. So before we go further — and this might sound odd — but if today's conversation has given you a useful framework for thinking about your own next move, that's exactly what we hope for. And if it was worth the price of a coffee, that's the link you'll find — buy me a coffee dot com slash fexingo. Lucas: Yeah, it's a tiny way to keep this show going without ads. No pressure, but if you find these episodes helpful, it makes a real difference. Now, back to the culture audit — there's one more signal I want to talk about, and it's the one most people miss. Luna: What's that? Lucas: How the company treats time. Not just your time in the interview process, but how they talk about time in general. Do they respect boundaries? Are meetings stacked back to back? Do they expect you to answer emails at nine at night? That's a cultural value in action. Luna: That's a good point. You can ask about it directly, but you can also observe it. If the interview process drags on for months with no clear timeline, that says something about their decision-making speed. Lucas: It does. And here's a subtle one: what does the company's vocabulary reveal? Do they talk about 'employees' or 'people'? Do they say 'resources' or 'team members'? The language they use internally is a window into how they think about humans. Luna: I've noticed that too. When a company talks about 'headcount' like it's a commodity, that's a tell. Lucas: Yes. So, to wrap this up: cultural due diligence isn't about finding a perfect culture — it's about understanding the real one before you commit. The three conversations, the meeting audit, the bad news test, the time signal, the language — these are all clues. But the most important thing is to be honest with yourself about what you're seeing, even if it's not what you hoped. Luna: And that honesty extends to the second step: comparing what you see to what you need. Sometimes the hardest part is walking away from a great offer because the culture isn't right for you. Lucas: It's a tough call, but it's better to find out now than a year into the role. So my challenge to our listeners is this: before you sign that next offer, do the three conversations. Ask the hard questions. And if you're not sure, ask more questions. Your future self will thank you.