What It Takes to Be a Great Boss

Experience, perspective and alignment are the three essentials to becoming a great leader.

learn more about Steve Tobak

By Steve Tobak

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Opinions expressed by Entrepreneur contributors are their own.

Great bosses are hard to come by. I should know. Over a 30-year career, I've had the pleasure of working for and alongside hundreds of top executives at companies big and small. For more than 20 years, I was one myself. Of all those leaders, few are what I would call great bosses. To be honest, I'm not one of them.

Great bosses are not easy to come by. If you ask 10 people to describe the perfect boss, you'll likely get 10 different descriptions. Just as our image of the perfect spouse, parents, friends -- anyone important in our lives -- are rarely the same, it's no different for the person we report to on a daily basis.

Now flip that around and consider what it must be like to try to meet the expectations of dozens, maybe even hundreds of distinct individuals. Therein lies the rub.

You've probably heard the expression, "Try to please all and you please none." Well, that definitely applies to managing people. You can drive yourself nuts trying to be the boss you think others want you to be and only end up making things worse for yourself, your employees and your company.

Think of it in terms of today's popular memes. If you try too hard to get people to like you, you're likely to end up as a doormat. If you twist yourself into a pretzel in an effort to be genuine, you'll probably come across as fake. If you're not willing to be straight with people -- tell them the cold hard truth and make tough calls for fear of offending someone -- you're not doing anyone any favors.

Look, leading a team, managing a group, or running a company is not a popularity contest. Instead of trying to be liked, admired or even respected by individuals who work for you, do what real executives do to become great bosses: gain experience, perspective and alignment.

Related: The Fine Art of Being a Great Boss


The way we learn to be good at our jobs is by observing others and learning what works and doesn't work. Then we try it out and see how it goes. Learning to manage people and lead is no different. It's all about gaining exposure to role models good and bad, getting real world experience in a broad range of scenarios, and of course, trial and error. Throw in a little mentorship and you're good to go. Rinse and repeat.

Related: 7 Things That Make Great Bosses Unforgettable


Most young up-and-comers are know-it-alls out to conquer the world. It's only after years of experience and getting some real successes and failures under our belts that we realize just how much we don't know -- about the business world and ourselves. Discovering we don't have nearly the self-awareness we think we have is always a revelation. That's where 360-degree feedback from employees, bosses and peers comes into play. It brings perspective.

I wouldn't take any any single comment to heart, but if several people you interact with have the same feedback, it's probably a good idea to give it some serious consideration. Business is all about relationships, and when it comes to relationships, perception is reality.

Related: The 5 Secrets of Great Bosses


Every successful company has a unique purpose, strategic goals and a culture that reflects how each employee is expected to behave. The key is to ensure the entire organization is strategically aligned and executes within that framework, and each boss plays a critical role in that process, from the executive team on down.

That may sound overly structured, but keep in mind that the best-run companies have cultures that foster innovation. That means employees are encouraged to challenge the status quo and come up with better ways to do things. That process helps the company adapt to changing conditions, overcome obstacles and grow.

The point is, you can be the nicest guy in the world who treats his employees like gold. But, if you and your team are not cutting it in the eyes of your company and its stakeholders, I don't care how likable, friendly, giving, sharing, approachable, communicative or empathetic toward your employees you are, you're still a lousy boss.

If, on the other hand, you challenge your employees to excel at their jobs and lead your team to exceed expectations on a consistent basis, you're probably well on your way to becoming a great boss.

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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