Category Archives: Leadership

So, you’re on the executive staff of a startup and you’ve been asked to present at an upcoming board meeting.  That’s great news. Board exposure is a key benefit of working on the e-staff. You’re getting the chance to build relationships with the venture capitalists and independent directors who sit on your board. These people can help you in many ways, e.g., providing tactical advice, acting more generally as mentors, helping you extend your network, approving your future promotion to a more important position, presenting you with outside board or advisory opportunities, and — when the time comes for it — helping you find your next company.

The board can be a tailwind accelerating your career or a headwind slowing it down. Let’s talk today about how to make a good impression in board meetings and how to start building good relationships with the members of your board.

Here are six tips:

1. Lose the baggage. If you have authority issues or PTSD from prior board experiences, you need to lose the baggage. That may not be easy — and you may need a therapist to do it — but boards can easily sense passive aggression and inauthentic interactions. I worked with one CRO who viewed board meetings as a necessary evil, something to survive so we can all get back to work. If you feel this way, the odds are the board can tell. (Our board certainly could, and it limited his tenure as a result.)
2. Make your presentation from scratch. Bad board sessions start with bad slides. Usually, they’re too long and detailed. This typically positions the exec as either “in the weeds” (ergo too junior and in need of an upgrade) or “stonewalling” (i.e., deliberately making an overwhelming deck to stifle conversation). The path to hell begins in the slide sorter, so do not start there. Start with a blank outline to avoid the number one mistake — starting with what you have instead of what the audience needs. Doing so is a false economy and, for chrissake, it’s your board: if anyone deserves a custom presentation, it’s them. So make a custom slides, from scratch.
3. Cut to the chase. Boards are notoriously impatient. Individual sessions are usually pretty short. There’s no time to warm up with “How ’bout those Yankees?” or several introductory slides, including the tired highlights / lowlights slide. (That slide is appropriate once in a board deck, in the CEO’s update, and if there’s something particularly good or bad in a functional area, it should have already been raised there.) If we’ve had insufficient pipeline for the past two quarters, go immediately to the reasons why and the remediation plan. If you’re not sure what the hot issues are — itself a yellow flag — ask the CEO. Nothing will infuriate a board more than endless warm-up slides that don’t cover the important issues. Beware saying: “Great question, but we’ll get to that on slide 27.” With some boards, you may not still be employed by slide 27.
4. Make slides that facilitate discussion. Board members like to talk, so let them. Build slides that facilitate a discussion. That usually means first baselining the board with key facts and metrics. (Remember, they might sit on 5 to 10 other boards, so they’re not going to remember everything you talked about last meeting.) Then tee-up a discussion using techniques such as: (i) making a proposal and asking for feedback, (ii) outlining three options (if you really can’t decide) and requesting input on them, or (iii) asking three questions that will help you make the decision. Be authentic. Don’t propose three options if two are patently absurd. This wastes the board’s time and they’ll see through it.
5. ATFQ (answer the effing question). If, at any time during the meeting, the board asks you a question: answer it. Read this — among the top five Kellblog posts of all time — for advice on how to do so. If asked for your opinion, offer it. Don’t stare at the CEO and then toe the company line. The board is fully aware of the disagree-and-commit principle. They assume you’re committed. They’re asking if you agree.
6. Ask for relevant follow-up meetings. If you’re the CRO and one of your directors is a former-CRO, ask them for an offline meeting to discuss a hot sales-related topic. While you should spend most of that meeting discussing the advertised topic, you should take a bit of time to get to know each other and start building a relationship. Invite them to a coffee if you can, as opposed to a Zoom. Drive to their office if they invite you.

If you follow this advice, you’ll make a better impression on your board than most and you’ll start to leverage board meetings to set up offline conversations that will hopefully lead to a few career-long and career-changing relationships.

As CJ Gustafson replied when we discussed the idea of building relationships, “oh, you could find a relationship like Scorsese and DiCaprio.” Yes, exactly. That worked out pretty well for both of them.