The Easiest/Hardest Way to Become a Great Boss

I’m interviewing people for an article right now, and stumbled upon a cluster of similar answers to the question: How do you hire someone for a position if you don’t have that skill set?

Bosses who were successful—their companies were afloat, had grown considerably (over 100 employees), and, most importantly, whose original employees were still working for them, had one thing in common, when they were bootstrapping:

Yes, for a brief time, they actually did the jobs that they’re now managing. One person did logistics, HR, marketing, administrative work.

I’ve had amazing work experiences and shitty ones, and one of the biggest factors differentiating shitty bosses from non-shitty bosses is how well they actually want to understand the job. Not how well they do understand it (not everyone can code or be an accountant), but the extent to which they’ve tried to do the work.

Bosses who aren’t interested in even trying to do the work of their employees usually means one of a few things:

  • They think they’re above the job. Thinking you’re above a job can disguise itself in many ways, like saying, “I’ll just leave that to the experts!”
  • They don’t have the time, aren’t willing to make it, or don’t know how to manage their own time.
  • They’re not curious about how a part of their company works.
  • They’re not capable of doing the job, but don’t want to lose face by trying. Insecurity can also disguise itself in many ways, like saying, “I’ll just leave that to the experts!”

The best way to underestimate the amount of work needed to complete a task is to think about it from a theoretical standpoint, rather than a practical one. The closer you get to the work itself, the more you understand what it entails, and what somebody attempting that task will need in order to succeed.

If you really want to understand your company, or even just a part of it that’s not working, do all the jobs.

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