Horrible Bosses is more than a movie. You don’t have to look very far to find tales of terrible managers.

Supervisors read these stories, too. So, when it’s their turn to lead, they may try to things differently—to be a cool boss. But of course, doing so at the expense of being taken seriously can lead to a host of other problems.

I’ve been lucky to work for several great people who the team still respects the heck out of. What I’ve observed is that all of these people strike a balance: They’re not dictators, but they take their managerial role seriously. Yes, they take the effort to connect with their teams, but it’s clear who’s steering the ship. Here’s what I’ve learned from them:


1. Do Be Understanding

Employees dread the notoriously inflexible boss. The one who tells you that you have to use paid leave for an early morning doctor’s appointment, rather than letting you make that hour up by staying late. The one who doesn’t sympathize that you have a family emergency or that your car broke down—when you’re dependable the rest of the time.

So long as we’re being reasonable, we want a manager who’ll be reasonable, too, and cut us some slack sometimes.


But Don’t Throw the Rulebook Away

However, a no-rules workplace isn’t the solution. How can an employee know if she’s meeting expectations if there are none? What happens when you don’t care about tardiness and people notice that some team members are rolling in hours late—and assume they’re doing less work? How can you tell someone his work isn’t up to par when he doesn’t know what he should be doing?

To find a balance, make sure that the rules of the workplace are clearly explained during the onboarding process as well as when questions arise. Then, have an “open door” policy that people can approach you if they have suggestions for something that could work better. If someone asks for increased flexibility, consider if it might benefit the entire team, or if an exception will help the employee do better work.

And if you do start making exceptions, make sure your reasoning’s sound and doesn’t change depending on the person asking. That doesn’t mean treating everyone the same, but rather having the same reason to make changes in the first place. For example: You allow people to build their own schedule for productivity purposes, rather than telling everyone they can stroll in at noon because Jim works best when he can sleep in.


2. Do Take the Time to Build a Relationship

This can be a tricky one. Many managers think that in order to be taken seriously they need to be removed from the team and refrain from discussing their personal lives in the office. However, think about yourself interacting in a variety of professional situations. Whether you’re speaking to a new networking contact or a client, don’t you try to find some common ground? Isn’t it helpful (and nice) when someone asks you how how your vacation was or how the move is going before diving into the task at hand? People are more likely to want to work hard for someone who acknowledges their common humanity—rather than an all-business, task-assigning shell of a person.


But Don’t Forget You’re a Manager First

Of course, you don’t want to become BFFs with your team. One of my favorite bosses would fall back on the refrain “I’m your boss, not your friend.” She didn’t say it in a mean or acerbic way. In Bringing Up Bébé, author Pamela Druckerman suggests parents remind children, “It’s me who decides.” It was a mantra to help the speaker (as much as the listener) remember the nature of their roles before things tilted out of balance.

For example, my former manager would come to happy hour with the team, but when she left before everyone else, she’d say it. She shared during team-building that she created a silly Christmas card each year, but none of the staff were added to list until after we’d left the organization. She brought her significant other to company events, but she never gushed (or ranted) about him.

People like to know what to expect—especially from their supervisor. So, strive to be a friendly, approachable boss all the time, instead of a person who’s sometimes a serious boss and sometimes a fun friend.


3. Do Be Encouraging

Who doesn’t like to be praised? And conversely, who doesn’t frown—even a bit—at negative feedback? Naturally, when you tell an employee how great she is, she’ll beam more than when you share what she needs to work on. And so, in the interest of being liked, it’s tempting to just share what someone’s doing right.


But Don’t Do So at the Expense of Teaching

However, positive feedback isn’t the only thing employees want. Most people also desire advancement. And if you never tell subordinates areas for improvement, it’ll be challenging for them to identify and grow the skills that’ll get them there. And you’ll find yourself only growing more frustrated as they move along without developing them.

Yes, on a morning that you give constructive criticism, you may not be earning any cool boss points. However, you’re looking out for your employee’s best interests—and in the long run that provides more value, which will be appreciated. Of course, conversations like these are much easier if you’ve already established expectations and don’t usually chat like besties.



Authority and likeability don’t have to come at the expense of one another. It’s possible to be a boss that your employees enjoy working for—and even hanging out with—and still keep your authority intact. Just don’t err too far on either extreme of being inflexible or lenient, put your role as manager first, and try to be the kind of person you’d like to work for.


Photo of cool boss courtesy of Shutterstock.