Hiring Your First Manager

There are many milestones in the life of a startup, but the first time you think, “Maybe we need to hire someone to manage this team,” is a defining moment for your company.

The stakes are higher for a manager, much higher than with an individual contributor, because they’re going to be leading a whole team. And these stakes are compounded by the fact that you will only be able to really judge their performance by looking at the second-order consequences — the way in which their team performs. If you haven’t done that before, it’ll require new judgement on your part. At the same time, you need them to directly represent your company’s mission and values, since in a lot of ways they’re going to act as a proxy for yourself in that regard. Their reports will interpret you THROUGH the manager’s influence.

All of which means that making a bad management hire is even worse than making a bad hire is usually said to be. Here are three easy techniques to reduce that risk.


Hire for Fit First

A manager’s effectiveness depends on their cultural fit, much more so than for an individual contributor. If your new manager can’t work comfortably with the team, if they aren’t aligned on values or expectations, then this is never going to work, no matter how skilled they may be.

Structure your interview process so that you get as many points of view on this person. It’s not crazy talk to have every member of the team get a chance to meet them — all of that input will really help to clarify if the candidate is going to be able to fit in with the team. Remember you’re not looking for someone who operates the same way the team does now. It’s great if the candidate brings some new perspective or attitude, but they need to be able to meet your team where they are right now.


Contain Their Scope

Don’t hire top-level managers first. Build up from the bottom, hiring team leads before VPs. Keep the scope of the management role as small as you can, especially for your first few hires of this type. That will enable you to learn what works and what doesn’t, while limiting your risk.

Smaller scope is easier to explain and easier to keep clear for the rest of the team. And clarity is crucial.


Transparent Reporting

Communicate to everyone what you expect the reporting structure will be. Don’t try to be vague or “we’ll figure it out one day”. Remember that for the people on the team, getting a new boss can be very stressful, even if they approve of the hire. Make it clear who will report to this position, and who will not. Some people will be unaffected — let them know.

It’s really best if it feels like a very small change to most people. Don’t trumpet this as a big transformation, that only adds to the stress. Point out who’s going to have a new boss, and what you hope that will bring to them (more attention, mostly).

When hiring your first manager, focus on their fit with your existing culture, make sure to be clear about their scope, and be as transparent with the team as you possibly can about how this is going to change things for them.


Craig Whitehead

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