So … you looked far and wide to find that VP you really needed.  And you finally made the hire!  And you … well … you think they will work out.  But you aren’t 100% sure.

No VP is perfect, and no VP can do it all.  So you have to make sure you both back them, and do everything possible to make them succeed.  But also, if you have some doubt, make sure you are looking for the right flags.  Especially if you saw some of them during the hiring process.

So let me outline the negative aspects of managers that in my experience have, 99.99% of the time, led to them leaving / quitting / washing out in 3–9 months:

  • Can’t meet deadlines. This may be OK in junior employees, I guess. But never in a manager.
  • Doesn’t understand the mission. This may be your fault as CEO, but if any leaders don’t get the mission you are on (or really anyone), it won’t work out.
  • Doesn’t want to grow. Anyone that doesn’t want to add new skills won’t work out in a startup < 200 employees or so.
  • Too threatened by new VPs and leaders. This makes perfect sense in BigCos, but in start-ups, if a VP/Director/Manager is too threatened by a new hire / new role, something isn’t going to work out here.
  • Too much of a “player”. If they talk too much about how amazing it was to work at Slack or DropBox, how terrific Stewart Butterfield was to work for … well, that’s great. But that’s a derivative effect. Not the game itself.  Or if they spend way too much time on their own podcast, and never quite get the one for the company done.  Etc. etc.
  • Can’t hire anyone great in first 30–60 days. All great managers can.
  • Too defensive re: their poor performers. A great manager is highly aware and transparent re: who on their team is the best, mid-pack, and not performing. If they are too defensive about their non-performers, that’s a sign of a manager that can neither deliver nor scale.
  • Lack of 100% ownership and too many excuses. You already know this. If they don’t own something in their area, really, they own nothing.

When you see this behavior in your managers/directors/VPs, at least plan on the fact you’ll need to hire a replacement in a single-digit number of months.

This is also a checklist to go down if a VP starts off strong, but the quality seems to decline.  Do they stop hiring great folks?  Do they stop owning things?  Do they stop understanding the mission?  Sometimes, folks just lose the engagement they once had.  When that happens, I’ve rarely seen them get it back.  It’s time to move on.

Now the flip side is, some “negative” characteristics actually can be an asset in a start-up. Here’s my list of things not to see as flags, more as areas you can help and backfill on as they grow:

  • Frustrated with other leaders not delivering. This just comes with ownership. It’s your job as CEO to fix this, somehow. As you upgrade the team, this should fade a bit.
  • Can only hire folks that are a junior version of themselves. Yes, this is a sign of a new / green manager. But you can help them open their eyes to a more diverse set of backgrounds, experiences, and hires. You need to start ASAP and early, though. By hire #3.
  • Mainly doing / focused on what they are good at. If you are a first-time VP of something, you won’t be great at everything. No one is. It’s OK if your stretch VP mainly focuses on the areas she’s great at … as long as she also takes accountability for the areas she is weak at. They will grow, and you are getting leverage here. Find a way to help backfill their weaknesses.

Quietly go through this checklist re: all your existing managers, and if you can, any you are about to hire.

At least slow the hire down if you see these flags.  And if you’ve already hired them?  Be worried.  At least, be aware.

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