LinkedIn Post Ideas for Board Advisors

A board meeting last quarter, and the most useful thing I did was say nothing for forty minutes. The CEO was working through a pricing decision live in front of the board — thinking out loud, second-guessing herself, circling back to a point she'd already made. I had a clean answer ready within the first five minutes. I could have shortcut the entire discussion. I didn't. I'd watched her make harder calls than this one before, correctly, when given the room. Jumping in with my answer would have solved this meeting and cost her something bigger: the board's confidence that she could work through ambiguity in front of them without an advisor rescuing her. She landed on almost exactly what I'd have said, twenty-five minutes later, having gotten there herself, in front of the people whose confidence in her actually matters long-term. Afterward, she thanked me specifically for staying quiet — she'd noticed I had something to say and hadn't said it, and she read that correctly as trust, not disengagement. The instinct every advisor has to fight is that our value is measured by how much we say. Sometimes the most valuable thing in the room is watching someone else's judgment hold up under pressure, unassisted, especially when the audience is the one that needs to believe in that judgment going forward. Advisory craft is mostly knowing when your intervention costs more than it saves.

Most advisory boards are decoration. Here's the test I use on my own arrangements, and I'd encourage every founder and advisor to run it honestly. The question: in the last twelve months, name one specific decision that went differently because of something an advisor said. Not "they were helpful to talk to." Not "they gave good general perspective." One decision, changed. I ran this test on my own five advisory seats last year. Two passed cleanly — I could point to a specific hiring call and a specific pricing decision that went differently because of a conversation I'd had with the founder. One was borderline; I'd given input that was directionally used but I couldn't honestly claim it changed the outcome. Two failed the test outright. I was a name on a deck and a monthly call that produced pleasant conversation and zero changed decisions. I resigned from one of those two. The other I renegotiated — tighter scope, a specific problem to work on for two quarters, a real checkpoint to re-run this same test. Founders keep advisors as decoration because a name looks good to investors. Advisors let it happen because the equity vests regardless of whether the advice lands. Neither party benefits from being honest about it, which is exactly why almost nobody runs this test. If you're on an advisory board right now, or have one, name the decision. If you can't, you already have your answer.

How I structure advisor engagements now, after getting the mechanics wrong more than once early in my advising career. Scope: defined narrowly, in writing, before I say yes. Not "general strategic advice" — a specific domain, like pricing strategy or enterprise sales motion, that matches what I actually have pattern recognition on. Vague scope is the single biggest predictor of a decorative arrangement. Cadence: one structured call a month, minimum 45 minutes, plus availability for urgent asks between sessions — capped, explicitly, at a reasonable number so it doesn't quietly become a part-time job I'm not compensated for. Equity versus retainer: for early-stage companies, typically 0.1-0.25% vesting over two years, with a real cliff. For later-stage or profitable companies, I now push for a modest cash retainer alongside any equity, because equity alone in a company already generating revenue undervalues the actual time cost. The 90-day checkpoint: an explicit, calendared conversation at day 90 where either side can end the arrangement without hard feelings. This single mechanism has killed more zombie arrangements for me than anything else — it gives both sides permission to admit, early, that the fit isn't right, before two years of equity vests on a relationship that stopped producing value in month four. Most advisory relationships are negotiated on vibes and never revisited. Building in the exit before you need it is what makes the whole arrangement honest.

I advise five companies right now. Here's what an actual hour looks like, and the numbers behind how I run a portfolio of advisory relationships without any of them going stale. Prep, 15 minutes before each call: I re-read my notes from the last session, plus whatever metrics snapshot the founder sent that week. If nothing was sent, that's itself informative — I note it. The opening question, every single time, regardless of company: "What's the decision you're most unsure about right now?" Not "how's it going" — that invites a status update. This invites the actual thing I'm there for. The hour itself: roughly 35 minutes on their named decision, 15 minutes on whatever I noticed in their metrics that they didn't bring up themselves, 10 minutes on anything time-sensitive I'm tracking across my other portfolio companies that might be relevant to them (patterns, not confidential specifics). The follow-up note, sent within 24 hours: three bullet points, always the same structure — what we discussed, what they committed to, what I committed to. This is the artifact that makes the next session useful instead of a repeat of this one. Across five companies, that's roughly five hours of calls monthly plus another three of prep and follow-up. The actual leverage isn't the hour itself. It's the pattern recognition I bring from seeing the same problem show up differently across all five.

A founder I advise ignored my clearest, most confident advice last year. She was right. I was wrong. My advice: don't raise a Series A yet, the metrics weren't there by the benchmark I'd seen work across a dozen similar companies, and premature fundraising at weak metrics typically means a down round or worse eighteen months later. She raised anyway, at a valuation I privately thought was unsustainable given where the business actually stood. Eighteen months later: the round gave her the capital to make a hire that unlocked a product direction neither of us had seen coming, and the company's metrics caught up to and then exceeded the valuation within a year. My pattern recognition, built on companies that looked similar on paper, missed the specific thing about her market timing that she understood better than I did. I told her, directly, that I'd been wrong and that her conviction had been the correct call against my experience. That conversation did more for the relationship than any advice I'd given her that actually worked. Advisors who only tell the stories where they were right are giving you half the picture, and founders can tell. The honest version of pattern recognition includes knowing it's pattern recognition, not certainty — and being willing to say so when the founder's specific read beats your general one.

Six red flags I check for before joining any advisory board, learned from saying yes without checking enough of them early on. 1. A vague ask. "We'd love your strategic input" with no specific problem named is the clearest predictor of a decorative seat. 2. No board exposure offered. If I'm meant to help at the governance level, and I'm never in the room or briefed on what the actual board discusses, my input is operating in a vacuum. 3. Equity cliffs shorter than six months, or no cliff at all. It signals the company hasn't thought seriously about the arrangement, or worse, expects to churn advisors quickly. 4. Founder defensiveness in the first call. If a founder bristles at a mild, well-intentioned challenge during the courtship conversation, that's the best version of them I'll ever see. It gets worse once equity is real. 5. No other advisors I can talk to. A founder unwilling to connect me with an existing advisor for a reference check is asking me to trust blind. 6. A problem that's actually an operating role in disguise. If the real ask is closer to fractional executive work than advisory input, that's a different conversation, different compensation, and a different relationship entirely. Any one of these is a conversation, not necessarily a dealbreaker. Two or more together, and I walk. Save this list for your first advisor offer — I wish I'd had it for mine.

Every board I sit on is now expected to have an AI oversight opinion. Most are asking the wrong questions, or none at all. The questions I now raise at every board where AI is part of the product or the operations: Data provenance: where did the training or fine-tuning data actually come from, and do we have the rights we think we have? I've seen this go unasked until a customer's legal team asked it first, which is the wrong order. Model risk: what happens when the underlying model changes or degrades in a way outside our control? Most companies have zero contingency plan for a vendor model update that silently changes output quality. Vendor lock-in: if our core AI vendor doubled their price tomorrow, what's our actual leverage? "None" is a common, underexamined answer. Displacement claims: if the company is telling customers or investors that AI eliminates a category of labor, is that claim actually validated, or is it a sales narrative that creates liability if it's wrong? I raise these not because I think AI is uniquely dangerous, but because boards are pattern-matching this the way they pattern-matched cloud migration a decade ago — as a technology question, when it's actually a governance and risk question wearing a technology costume. Few boards ask these until something breaks. The value of an advisor at the intersection of trend and oversight is asking them before it does.

What's actually in my prep stack before a quarterly advisory session, not the idealized version. The metrics snapshot: whatever the founder sends, usually a one-pager of revenue, burn, and the two or three KPIs specific to their business. I read this twice — once for the numbers, once for what's missing compared to last quarter's snapshot, which is often more informative than what's included. My own notes from the last session: specifically what they committed to and what I committed to. If either of us didn't follow through, that's the first thing I raise, gently, before we move to new topics. One customer call, if I can get it. I ask the founder, at least once a quarter, to let me sit in on or listen to a recording of one customer conversation — ideally not a hand-picked happy customer, a real one. This tells me more about product-market fit than any dashboard the founder curates for me. Whatever's in the news about their competitive landscape that quarter, fifteen minutes of searching, not deep research — enough to ask an informed question, not enough to pretend I know their market better than they do. What I don't do: read every Slack message or internal doc I have access to. That's operating-level involvement disguised as diligence, and it's not my role. The gap between showing up prepared and showing up useful is usually just this: knowing what happened since last time, and having heard one real customer.

I took an advisory seat, with equity, in a company I didn't actually believe in. I knew it within the first real conversation. I said yes anyway. Why: the founder was someone I liked personally, the intro came through a friend I didn't want to disappoint, and there was a quiet FOMO — a well-known investor had just backed the round, and some part of me assumed their diligence meant mine wasn't necessary. None of those are real reasons to advise a company. All three are real reasons people say yes anyway, and I'd be lying if I said this was the only time. The actual cost wasn't the equity, which is probably worth close to nothing today. It was the opportunity cost of the hours — roughly four hours a month for a year and a half, close to fifty hours — that could have gone to a company I actually believed in, one that would have valued my specific pattern recognition instead of a name on a deck. I finally exited the arrangement honestly, telling the founder directly that my conviction wasn't where it needed to be for either of us to get real value from the relationship. That conversation should have happened at month two, not month eighteen. Advisor attention is a scarce resource, same as any other kind of capital. Spending it on flattery, FOMO, or a friendly founder instead of genuine conviction is the least discussed and most common misallocation in this business.

Advisors — should you ever go around the CEO directly to the board? I've thought about this line more than almost any other question in advising, and I want to hear where others draw it. My own line: only if I believe there's a genuine risk to the company or its stakeholders that the CEO isn't addressing after I've raised it directly, at least twice, and given them real room to act. I've come close to crossing it once. A CEO I advised was, in my read, materially misrepresenting the company's runway to the board in a way that went beyond optimistic framing into something closer to concealment. I raised it with her directly, privately, twice. The second conversation was hard — she pushed back, I held my position, and eventually she corrected the number herself in the next board update, without me needing to escalate. I don't know what I'd have done if she hadn't. I think I would have gone to the board chair. I'm honestly not fully certain, and I don't think anyone who claims total certainty on this question has actually faced it. The advisor-versus-employee line matters here: I have no operating authority to force a correction. Going around someone is a serious act that can end the relationship and your reputation with the founder community, deservedly, if you're wrong about the severity. Where do you draw this line, and has anyone actually had to cross it?