Where do you see yourself going at Startup Inc.?

One of the funniest moments of my education as a founder was the time one of our devs, a valuable guy, came into my office and said with a completely straight face:

I’ve been here a year and a half now and haven’t gotten a review yet.

And of course, as I’m sitting there, a handful of inappropriate responses flit through my brain.

I’ve been here three years and neither have I, welcome to the club.

You’re great. Get back to work.

You suck. Get back to work.


Fortunately, what I actually said was

Uuuuuuhhhhhhhhhhhhhh – okay we’ll do one.

Think Butthead on a bad day. Then I went off and tried to figure out what I was gonna say to this guy because up to that exact moment I had never realized that I’d have to have these kinds of conversations with people.

In companies with an actual HR department, full of actual HR professionals who set actual policies based on actual HR science (is there such a thing?) what they tell you to do in reviews is ask people “where do you see yourself going at XYZ Co.?”

This question looks perfectly reasonable until the first time you ask it at a startup.

Mr. Founder: “So where do you see yourself going at Startup Inc?”
Mr. Employee: “Well, I could have your job.”

This is usually followed by an awkward silence where both of you regret coming to work that day.

Truth is, in the way of a bigger title, more responsibility, authority and salary, there is usually no place to go at a startup. If you’re doing it right, you’ve maxed people out along all those lines.  You can be a founder, or one of the guys.  So the only way to have the review conversation is to start by admitting that, even in the short term, people may have to leave the company to realize their personal goals.

Loyalty at a startup is a complicated thing.   Your guys bleed for you and all you can give them in return is options, flex-time and a foosball table. In the end most of these guys will be working somewhere else.  And that’s okay.  That reality doesn’t relieve you of your responsibility to help your guys get where they want to go.

So what do you do? You take a mortal risk (probably the third one of the week) and try honesty:

Hey, your best future might not be here but I’ll help you get there anyway.

This is something you can give people that managers at a big company can’t.  So do it.  Loyalty’s a two-way street, so take a ride down your side and see where it gets you.