How I Was Able to Turn a Work Enemy Into an Ally–Twice

Have you ever gotten the feeling that someone has it out for you, but you don’t know why?

That’s happened to me a couple of times in my career. The first time happened eight years ago. One of my colleagues who was very well-liked in the department seemed to hold a vendetta against me from nearly my first week on the team.

“Kara” was smart, tenured, and quick-witted — all traits that you don’t want in an enemy.

During meetings, Kara would occasionally throw out comments like, “Do you even know what you’re doing?” or “How do you not know how to do this? It’s so easy.” She accompanied some of her biting comments with a good-natured chuckle, so for a while I just thought she had a strange sense of humor.

Then the comments ratcheted up a bit. It felt like she was trying to use me as a stepping stone for social validation, like a bully in an elementary cafeteria. With each cheeky comment she made to me and each nice comment she said to someone else, my confusion deepened.

I had never had a work enemy before. Most of my friends and colleagues would describe me as an optimistic guy who tries to be nice to everyone, so I was entirely clueless as to how to handle this situation. I wasn’t used to political infighting or using verbal ammunition against anyone.

I finally decided to approach my buddy Eric for help. I explained the situation and told him that I was getting tired of all the jabs and right hooks. I told Eric I was planning to pull my colleague aside and just ask her one-on-one what she had against me.

But Eric cautioned me against that approach: “That might embolden her. Then she’ll know she’s getting to you, and she doesn’t sound like the type of person who would lighten up if you call her out on it.”

Eric suggested a different approach: I should go out of my way to treat Kara with respect and even treat her as a mentor. Ask her for help. People love to be needed, so I should make it clear that I needed her. Who knows…maybe she would come around and soften a bit if she perceived me as more of a mentee and less of a threat?

The following week, I sought out Kara’s help on a new project. I had a good idea of how I wanted to run the project, but I figured it wouldn’t hurt to humble myself and ask for Kara’s opinion.

At first, Kara acted a bit surprised that I needed her help. Then she softened and said, “You know what? A couple of years ago, I ran a similar project. I tried X and it really didn’t work. I think you should do Y instead.”

A week later, I swung by her desk to let her know that her advice paid off and really helped me out. I continued this process for the next few months: seeking out Kara’s help, even when I was 95 percent sure what I needed to do.

In a remarkably short amount of time, we actually became friends. She viewed me as a mentee, and I viewed her as a mentor. I worked to genuinely keep an open mind every time I asked for her guidance.

The result was that we each saw each other in a new way. Rather than seeing her as a bully or a jerk, I focused on her expertise, intelligence, and practical insights. And she came to see me as an eager learner who wanted to build a great product for our clients. Even though I constantly asked Kara questions, she could see the depth of thought in the questions I asked, which helped her appreciate what I could bring to the table as a member of the team.

A few years later, after both she and I had left the company, we actually met up to grab drinks together. Our friendship was such that we were genuinely excited to see each other and catch up on life.

The second time I found myself with a work enemy, I decided to try a similar tactic. This time, it was a colleague who had trouble getting along with a lot of people on the team — not just me.

“Mark” was a manager of another department within the company. He was also a perfectionist who had an opinion about everything. Anytime I brought a new idea to a manager meeting, Mark was the first person to shoot it down. He didn’t agree with me on much of anything.

The trouble was, Mark had a very loud and convincing presence in those manager meetings. If he disagreed with an idea, others lined up behind him because they were scared to get in his crosshairs. They’d prefer to be on Mark’s side as opposed to debating against him.

For a while, I let my frustration get the better of me. I stewed about how unfair it was that every decision had to go through Mark as the de-facto voice of our managers' group. I wallowed. I got angry. I complained to my wife and my friends. (You know, the typical mature responses.)

Then I remembered what happened with Kara a few years prior. I wondered if a similar approach could work with Mark, so I decided to give it a shot.

The next cross-team project I led, I walked over to Mark’s desk a few days before the manager discussion and asked for his help. I told him that he always had great ideas for how to improve projects (which was true) and that my proposal could really benefit from his help. I asked if he had time to review the project proposal and get back to me with his feedback.

Mark said he’d be glad to do that. The proposal came back with a ton of comments — way more than I expected. Even though I was not eager to make so many changes to my proposal late in the project, I looked over his comments and many of the changes he recommended made sense. So I made the edits he suggested, then presented the proposal in the next managers’ meeting.

Not only did Mark not shoot down the proposal, but he actually chimed in saying that he thought it was a great idea. His involvement and ownership in the project turned him into a co-conspirator rather than a detractor. He now had skin in the game, and he used his powerful voice in that meeting to convince others how great of an idea the project was.

Going forward, Mark became a huge ally of mine in the company. Not only did I keep going to him for ideas, but he also began to come to me for ideas. We became a powerful duo, pushing the same direction on many key company initiatives. And we also became friends along the way.

Now, I don’t tell you these stories to encourage you to be manipulative or disingenuous. These two examples worked because I genuinely respected what these colleagues had to offer. I knew Kara was smart and creative. I valued Mark’s sharp eye for detail and persuasiveness in meetings.

When I asked for their help, I honestly wanted it. I knew they could improve upon my ideas. If I didn’t know that in my gut, Kara and Mark would have smelled something fishy.

These two situations were a great learning experience for me. I realized that the best way to win someone over to your side is often not to try to convince them of anything but to instead realize the value of what they bring to the table. To humble yourself. To seek mutual respect rather than revenge. To ask for advice rather than prepare for battle.

As the saying goes, “You can catch more flies with honey than you can with vinegar.”

Do you need to use more honey in one of your work relationships this week?