What Makes a Great Boss?

Managing is an art form. True leadership takes even more hard work.

learn more about Steve Tobak

By Steve Tobak

Opinions expressed by Entrepreneur contributors are their own.

I was not a great boss. There, I said it. Do I feel badly about that? Not really. After all, nobody's perfect. Besides, I don't think I was a terrible boss; it just wasn't what I excelled at.

Just so we're clear, when I say "boss' I mean managing people.

Don't get me wrong. The executive management teams I was part of and the organizations I led accomplished some great things. But the truth is I cared more about the business – about achieving and winning – than I did about the people. So as a boss I have to give myself a C+, maybe a B-.

So what inspired me to write this? The few great bosses I've had the good fortune to work with over the years and, of course, all the crappy ones. Consider this a tribute to the former and a wakeup call for the latter.

They tell you what you need to get to the next level, even if it hurts. I was sort of a fair-weather boss, as most are. I never liked telling people what I knew would be hard for them to swallow. I didn't sugarcoat the hard truth; it was more of an avoidance strategy.

Tough love is always the hardest thing to do but great bosses do what has to be done to help their people grow. More than anything that includes wasting no time telling them what's holding them back.

I used to have a CEO that would take me aside right after a meeting and tell me when I was being a royal pain in the you-know-what. I know I can be sort of intimidating so I always respected him for that. And you know, we're still friends after all these years.

Related: Want to Be Happy? Quit Trying to Be So Happy.

They hold themselves and others accountable. This is probably the one attribute I actually got right. I always held myself and my direct reports to the highest standards.

If you want your people to do great things, you have to set the bar high. If you accept a challenge and set a goal, you do whatever it takes to make it happen. Just don't forget we live in a competitive world and winning is never easy. Failing is OK as long as you give it your best. That goes for you and your people.

Great bosses always lead their teams into battle. If they win, they sing everyone's praises. If they lose, they take the heat. They own it. The buck always stops with them. If some of their folks could have done better, they tell them in private.

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They're transparent about goals and metrics … and they follow up. There's nothing less motivating for a good employee than a boss who keeps moving the target. I mean, how can you win the game when the rules keep changing?

Goals and metrics should be clear, set in stone at the beginning of the time period and measured at the end. Some bosses set objectives but fail to follow up. That's a critical mistake. People are smart. If they know you're not going to circle back, then where's the incentive to break their butts to make it happen?

Long ago I had a mercurial (a euphemism for dysfunctional) CEO who was always full of surprises and not in a good way. He was notorious for what we called strategy du jour – changing the plan at a moment's notice and with little cause. We were a pretty hot startup for a while. Then he hit a wall and so did the company.

They manage up effectively. Sideways, too. A key attribute of teams that accomplish great things is a boss that keeps upper management off their backs, removes barriers, and provides what they need to do their jobs. That comes across loud and clear in Organizing Genius: The Secrets of Creative Collaboration, an excellent book by the late great Warren Bennis.

It is so important to manage up, to sell your organization's capabilities to fight for projects, headcount and other resources. You also have to ensure that the needs of your peers and other stakeholders are met, or at least heard. Take it from me, it's always the folks you don't think about that end up being the political animals that do you in. I learned that lesson the hard way.

They have a sense of humor and humility. Ironically, it takes maturity and empathy to have a well-developed sense of humor and humility. The reason is simple. When we're young, we think the world revolves around us. We think we have all the answers. We're full of ourselves and take ourselves too seriously. Our skin is thin and we wear our hearts on our sleeves.

In time, as we mature, we come to know how much we don't know. We come to realize that the world is a very big place and we're not superhuman. We cease to be dominated by our egos and become more empathetic. Granted, you want to strike a balance, but the best bosses know themselves pretty well. They're comfortable in their own skin. And they treat others with the respect they deserve – no more, no less.

One of the best men I've ever known was a CEO who met all those qualities, especially the last one. Before he was my boss he was our company's CFO and my peer.

Once on an evening flight after a long day of tough meetings, our CEO and I had a bit too much to drink and got into a pretty heated argument. Seated behind us, Jay – that was his name – jumped in, got us to lighten up and probably kept me from getting fired. That's just the kind of guy he was. He always had your back. And he made one hell of a boss.

Related: Want to Impress? Don't Do This.

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at stevetobak.com, where you can contact him and learn more.

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