Why Aren’t There More Best Bosses?

Ask people to describe the best boss they ever had, and most can do it in seconds. Ask them how many bosses like that they have worked for, and the number is usually one. Maybe two.

So here is the honest question. If almost everyone agrees on what a great boss looks like, and almost everyone wants to be one, why are there so few?

It is tempting to reach for character. Most people just don’t care enough about their people. But that answer does not hold up. Plenty of decent, well-meaning leaders still end up bossing in the ordinary way. The reason is not a shortage of good hearts. It is that almost every arrow in the system points in the other direction.

Start with how people get the job. Someone becomes a boss by being excellent at something else. They hit their own numbers, so they are handed a team. But the skill that earned the promotion, personal performance, is not the skill the new role requires, which is growing other people.

Gallup’s research puts numbers on the gap: only about one in ten people have real talent for managing, and organizations pick the wrong person for the role most of the time.(1)

We are promoting for the wrong thing, at scale.

Then look at what gets measured. The scoreboard rewards this quarter’s output. Developing a person is slow, quiet work that rarely shows up on a dashboard, and often pays off only after you have moved on. So, the rewarded move is always to lean on people for results now, rather than build them for later. Traditional bossing is not a failure of the system. It is what the system asks for.

And the pull gets stronger the higher you climb. More pressure, bigger numbers, less room for the patient work of people. That is exactly why Best Bosses grow rarer near the top, and rarest of all in the chair that runs the whole company. By the time someone reaches the level where they shape a whole culture, the incentives that carried them there have spent years pulling the other way.

Put it together, and a hard truth emerges. Good people default to traditional bossing because everything around them makes it the path of least resistance. Choosing people first is not the natural move. It is the deliberate one, made against the grain.

Which is the hopeful part. If the shortage were about who people are, there would be little to do. But it is about what they have learned and been rewarded for doing. And that can change.

No one is born a Best Boss. The right behaviors can be built on purpose, which is exactly why you can do it.

Diane Scott, PCC & Aaron Bujnowski, DSc, are co-authors of The Best Boss Effect: Becoming the Positive Leader People Never Forget, which will be released in late 2026.

(1) Gallup, State of the American Manager: Analytics and Advice for Leaders (Gallup, 2015), 36.