Startup VPs sometimes lament that their CEOs don’t really know the people on their teams, don’t realize how smart and talented they are, or fully appreciate the value of their teams’ work. How, they wonder, can they build a better bridge between their boss and their teams?
The answer is simple: invite the CEO to something. To what?
- Your staff meeting
- A departmental town hall Q&A session
- Your team’s planning offsite
- A quarterly business review (QBR) or equivalent
Social gatherings (e.g., team buildings, after-work drinks) are fine a complement, but they don’t actually solve the problem I’m addressing — how to build a bridge between your team and your boss. This is not about knowing their spouses’ names and how many children they have. This is about seeing them at work, in the workplace.
That the answer is so simple and that so few VP actually do it reveals something :
- Some VPs like to complain about the problem. These folks likely harbor insecurity about their teams because they are, in the end, afraid to put the CEO in a room alone with them. They are afraid their teams may look stupid, or worse yet receive direct feedback that they worry their teams can’t handle. These VPs would never invite the CEO unprompted, and even when prompted, reply with, “yes, we should do that one day” but somehow that day never seems to come. These VPs are weak and will likely get stuck in their careers unless they have have more confidence in their teams (or hire better teams, as indicated) and more confidence in their boss.
- Some VPs like to fix it. These people typically don’t need to be told to build a strong relationship between their team (particularly their direct reports) and their boss. It’s good for everyone, and the company overall, when such relationships are in place. These people aren’t afraid their team will embarrass themselves because they know they’ve hired smart, quality people. These people aren’t afraid that their team will wilt under a bit of direct, executive feedback either — probably because they’re not afraid to deliver such feedback themselves. If they don’t think of the idea themselves, when prompted, they jump on the idea — and not just once for show — but by building such invites into their standard operating cadence.
My strong advice is that you want to be the second type of VP. If you’re not trying to build a better relationship between your team overall, your directs, and your boss, then you are failing everyone — including yourself.
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 Now you could argue I’m projecting here because I’m not a highly invite-able CEO, but I can say across 12 years of CEO experience at two different companies, it was a relatively rare experience to be spontaneously invited by my direct reports to such events. (And when it did happen, it was always the same VPs doing the inviting.) What’s more, I can also say across more than a decade of CMO experience at two different companies, I didn’t see a lot of my peers do it, either.