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The Inner Circle: Building Your Personal Executive Advisory Group 4:12 Jackson: I'm fascinated by this idea of an "Executive Advisory Circle." It sounds so formal—like you're recruiting your own personal board of directors. But in reality, it’s a small, carefully selected group of three to five people, right?
4:27 Miles: Exactly. It’s about quality over quantity. Instead of having five hundred "connections," you have five deep, consistent relationships with people like VPs, founders, or C-level leaders. These are the people who help you navigate office politics and—this is the big one—teach you the language of the C-suite. We're talking profitability, risk management, and capital allocation.
4:52 Jackson: So it’s not just a mentorship thing where they tell you "good job." It’s a strategic sounding board. But how do you actually start one? You can't just walk up to a VP and say, "Hey, want to be on my personal board?"
5:05 Miles: No, that would be a total career-limiting move. You have to be intentional. The research suggests looking for alignment between their career path and where you want to go. If you’re a Senior PM aiming for a Director role, find a VP who scaled a similar product. Then, you start by engaging with their public work—commenting on their LinkedIn posts or asking a really sharp question during a webinar they’re hosting.
5:29 Jackson: And when you finally reach out for that first "chat," you have to be incredibly specific. You don't ask to "pick their brain." You say something like, "I saw how you framed that market pivot to your board, and I’d love twenty minutes to understand your thinking process behind that." It shows you’ve done your homework.
5:47 Miles: Right, and then the magic happens in the follow-up. You recap their advice, show them how you acted on it, and then—weeks later—share the results. That’s how you build trust. Eventually, you ask for a recurring check-in, maybe once a quarter.
6:01 Jackson: It’s interesting how the sources suggest a balance of internal and external advisors. Internal leaders provide the context—they know where the bodies are buried in your company. But external advisors give you that unbiased industry perspective. They can tell you if your company's strategy is actually out of sync with the rest of the market.
6:20 Miles: And for the execs, there’s actually value for them too. A Senior PM can offer "ground truth" insights from the front lines—customer trends or team morale—that the VP might not be getting from their direct reports. It’s a reciprocal relationship.
6:32 Jackson: But there are risks, right? If you’re meeting with an external advisor who’s on a competitor’s board, you have to be incredibly careful about confidentiality. You have to anonymize data and stick to general principles.
6:46 Miles: Absolutely. And you have to manage the "political risk" internally. If your boss sees you constantly meeting with their boss, they might think you’re trying to bypass them. The trick is to frame it as mentorship and keep your manager in the loop. "Hey, I’m meeting with the VP of Sales to learn more about the revenue side of the business"—it makes you look proactive, not sneaky.
7:06 Jackson: It’s a two-year investment, really. The first six months are just making connections. Six to twenty-four months is establishing that rhythm. And after two years, that’s when you get the high-value stuff—introductions to boards, investors, or senior roles.
7:20 Miles: It’s essentially building your own "executive graph." And while those private circles are great for depth, if you want scale, you have to look at Thought Leadership platforms.