Why Even the Best Bosses Have to Learn on the Job

In this series, professionals share how they embrace the entrepreneurial mindset. See the stories here, then write your own (use #BetheBoss in the post).

Even if you don’t have dreams of a corner office with hundreds of employees on your payroll, learning to be the boss — and to be a good one — is one of the smartest things you’ll ever do in business.

For many of us, it’s not something we thought we would have to learn. One friend of mine with a wildly successful small business once mentioned that not only did she never want to be the boss, but that she doesn’t even think of herself as someone who would good at it.

Is she a boss? You bet you. And she’s a great one.

Because, contrary to what she thought she wanted, she got thrown into the position when her business succeeded beyond her wildest dreams, and learned on the go how to cultivate and grow the needed qualities to lead her team. As she learned, and as many of us have seen, some of the key skills required to be a winning boss aren’t inherent, and are learned.

Whether you’re a young entrepreneur not sure you need to learn all this boss-y stuff, or someone in the thick of managing a team that could use a brush-up, here are some of the key things to remember about being a good boss:

Good Bosses Learn on the Job

The first time I became a boss, it was at the head of a nonprofit organization. Nonprofit organizations being something I had read about, volunteered in, and certainly never run. I knew next to nothing about what I was doing, and it showed. The only option — aside from admitting my cluelessness (which I did, with frequency) — was to dig deep and learn. There are different ways to do this, but I got books. Later, I got an MBA. Learning while on the job was the smartest thing I could have done at that moment in time, and it paid off in spades in the years that followed.

Good Bosses Don’t Expect to Hire a “Mini-Me”

That first time I became a boss, I did so in Kenya, a country I had first entered only months before. There were a lot of reasons that my first hire was not a “mini-me”, but the biggest, most glaring one was this: I was green as all get-out in Kenya, and needed folks who knew more than I did in a number of areas.

Over the years, sometimes I’d find myself hiring a mini-me, and sometimes I wouldn’t. But, importantly, I learned never to hunt for it, as Claire Diaz-Ortiz Junior does not know all the things.

Good Bosses Realize They May Not Be Failing the Hardest

If your venture fails, you feel it as a boss. When at the helm of an organization that hit choppy waters and shut down right after barely getting started, I felt like I failed. (Because, well, I had.) It’s at this moment that bosses are most likely to hang out in their own heads and forget about what their employees are going through. The reality is that if you were the boss, no matter how spectacular the fail you are oftentimes better positioned to get up, get going, and go after new bacon than your employees are. Understand the realities of the folks who work for you, and help. All you can. (Better yet, plan ahead for such contingencies. Employee relief funds for startups, anyone?)

Ultimately, being a good boss is a journey that should ideally start long before you ever think you’ll be one. If not, though, make a commitment to take the time out of your job managing (yes, I know you work a lot) to cultivate key qualities to help you #betheboss at work. Whether that work is at the helm of a chain of brick-and-mortar office, or on Slack with your nimble team of contractors, is entirely up to you. ;)