Sink or Swim: How to move from being a buddy to being a boss

—This is the first Sink or Swim advice column from Nancy Vonk and Janet Kestin. To learn more about the column, and Nancy and Janet, read the introduction here.—  

Q. Dear Swim, I was promoted several months ago and now one of my best friends at work is reporting to me. I realize I’m not always totally honest with him about his ideas to avoid hurting his feelings. Obviously not ideal. Your advice on keeping the friendship when you’re the boss? 

A. The transition from “friend” to “boss” is one of the most difficult challenges for newer leaders (and even some very seasoned ones). One day you’re peers and drinking buddies, and suddenly you’re their superior.

How do you help them accept your leader status when they may not see you as “better” than they are? (Immediately after we were promoted to CCO’s, one of our star writers resigned, saying bluntly: “I didn’t sign on to work for you.”) How do you keep up the valued friendship?

The answer to the latter could be, well, you can’t. As one fellow CCO once put it, “You aren’t going to the wedding anymore.” Now you’re in a position to make the call on your friend’s work, to give him performance feedback, to set expectations and hold him accountable (all fundamental to the role)—and if you allow the friendship to colour your judgment, enable bad behaviour or avoid conflict, you’re heading straight to “bad boss” status.

If you hold back the tough news that their work’s not there yet, don’t share honestly about where they need to improve, and don’t call them out on their bullshit, you’re doing them no favours and definitely harming yourself. All of those classic—and unfortunate—choices lead straight to mediocre work and stalled development. If you don’t hold them to the same standards and expectations as everyone else, not only will your friend lose respect for you, but you’ll be risking the same from your entire department.

Friendships can survive the new “I’m the boss of you” dynamic, but it may take a little time for the two of you to find a new way to relate. If you lead them to their best work, that’s a reward for everyone. But be prepared to let go.

Q. Dear Swim, I didn’t realize when I started a leader role how much I’d miss doing the work. I’m having second thoughts about my role. So far it seems like a thankless job. Should I step back and accept that less money and a smaller title are worth it to be happy?

A. The leader role comes with a very different type of reward from creating work. It’s hard in the first place to realize that there’s a very sharp turn in the road from “maker” to leader—it’s just not a smooth or natural change for many people.

One of the big reasons for that is the realization that there’s no medal for being a good leader. In fact, people who do it really well often perform their most valuable service behind the curtain. That can mean people assume you’re doing, well, nothing.

We know because we used to make those assumptions. We didn’t realize how much our bosses did on the quiet (like navigating client issues, championing us, dealing with agency politics), until we were in that job ourselves. What you may find, if you hang in there, is that some of the greatest rewards of your career come from having the power to help people grow.

Empowering people to step up into their true potential might mean the most when you look back on your career. We found there’s nothing like the moment of “Thanks for what you’ve done for me.” Using your position to drive positive change brings deep satisfaction. In time you may find the pluses of leadership outweigh the more tangible rewards of the past job.

Or maybe not.

Not everyone is cut out for leading. Getting the promotion may reveal that you don’t actually want it. And that’s fine. Life is too short. Be happy. We do suggest you give it some time first. Becoming an effective leader, fully in touch with your impact, requires more than a simple flick of a switch. Seek out mentors and don’t be afraid to ask questions. They can help you negotiate that steep learning curve.

**Are you an emerging (or even experienced) leader facing a challenge in your role? Nancy and Janet have advice based on working with thousands of people from around the globe. Email your question to

Janet Kestin and Nancy Vonk are the co-founders of Swim, a “creative leadership lab” that supports the success of leaders at every level around the globe. They were co-chief creative officers of Ogilvy Toronto (1998-2012).