Have you ever had an employee who was a pain in the neck? One who you just didn’t like interacting with, and who created more work for you than everyone else? If you’re honest, the answer is yes. Don’t feel bad, every manager has, and we won’t ask the person’s name. Your secret is safe with us.

What have you learned from them?

I recently heard that a former employee of mine had passed away. I hadn’t thought of this person very much in ten years (see: repressed memories as a coping mechanism) and when I did, the thoughts weren’t particularly kind. In fact, this was probably the most difficult person I ever had report to me in almost 27 years of leading people.

But once my mind ran down the hundred grievances, large and small, this person brought to mind, I had a second wave of thoughts. I began thinking about all the things I learned from my interactions with that person, and how that influenced my leadership behavior since then. It’s a pretty long list.

First, it was important to remember why I found him so difficult to work with. There were some key lessons just in going down that list:

  • He was there when I arrived and stayed long after I left. As someone new to the organization (and brought in during a merger) I was suspect from day one. The organization was very proud of its culture and history, and he had been there through the company’s growth years. While I considered him inflexible and unwilling to change, he thought of himself as defender of the company’s proud history.
  • He thought he was going to get the job that went to me. Let’s just say he was not prepared to give me the benefit of the doubt from the beginning, and we didn’t start off on the best footing.
  • The local management thought of him as their most valued resource, despite my appraisal of his skills and contributions to the team. As a new manager, you need accurate information on the members of your team. A lot of information was hidden from me for a long time. More importantly, as the “outsider,” the existing management tended to support the employee in most disagreements.
  • He was a remote employee, so actual face to face interaction between us was rare. We were only face to face a few times a year, so most of our interaction was by phone or email. The tone of communication, especially in writing, was a constant source of friction between us. Also, when we weren’t communicating frequently, he was the center of every bit of gossip and rumor. So by the time we did speak there was more to deal with than with other employees.
  • There were status differences between us. To be fair, this was on me as much as on him. He was twenty years older than me, had been CEO of a company, and had a PhD. Not only did he consider himself smarter and more qualified than the new kid from outside the organization with no degree, I had a beard.  To him I was obviously unprofessional and suspect (I wish I was kidding about what a big deal my facial hair was in that organization).
  • His style was confrontational and (in his words) assertive. I called it something else. In fact, not only was he blunt to the point of rudeness. The fact was, he was a bully.  Not just to me, but to others on the team.
  • He thought of himself as an advocate for the team.

What you can learn from what I learned

  • Before engaging, ask yourself, why am I struggling with this person? I would get physically anxious before every interaction with him, even when it was a mundane discussion. When I realized I was intimidated by the status differences between us, I was able to take a breath and behave in a more professional manner without reacting emotionally.
  • Consider (and confirm) the intent behind the other person’s actions. Maybe the most important lesson I learned over my time at this company was that every action a person takes makes sense to the person taking it. He really believed he was acting for the good of the organization or the customer, and that was more important than his being “subservient” (his word) to some punk kid. Sometimes he was right, and I needed to consider that.
  • Consider the rest of the team when responding to this person. Because of his seniority with the organization, and his long-standing relationships with his teammates, (and, yes, his talent) he had great influence with the team. Because of his assertive nature, he often served as a voice for other team members who were afraid of conflict or didn’t want to deal with problems. They knew he’d take up the sword. How I responded to his requests might be considered a reflection of whether or not I cared about the team’s concerns and how I treated him dictated how they worked with me.
  • While tempting, get face to face (or cam to cam) when problems arise. Don’t let them simmer longer than necessary. Especially when you work remotely, it’s easy to avoid potentially unpleasant conversations. But not addressing situations early can allow gossip and rumor to undermine the truth. And, let’s face it: the longer you avoid something you don’t want to deal with, the bigger it becomes in your own mind. Yeah, he was in my head.
  • Don’t go straight to the “I’m the boss and I said so,” card. But don’t be afraid to play it on those rare occasions it’s necessary. Feedback is a gift, but how it’s delivered and by whom is critical. It can come from a place of authority (you’re the manager), expertise (you know what you’re talking about), or relationship. When people think you are only working from your position as the boss, it’s unlikely the conversation will get the desired results. When I learned to focus on the expertise and customer outcomes, my input was received more appropriately. On the other hand, I came in to create change. And while taking input was critical, there were times what I had to do was non-negotiable. Being clear that you heard people’s concerns yet had to make another choice is a tough message. As a leader, it’s a skill you’d better learn. Management ain’t for the weak of heart.

As a leader, you will work with people who make your job difficult. But if you take the time to breathe and think about the dynamics of the relationship, you can get better results and cause yourself less stress.

I’m a better person and leader for having dealt with this person for so long. That’s what I’ll choose to remember.

It’s all about being a good teammate. That’s why this course is so important for leaders and team members alike.


Wayne Turmel--The Remote Leadership Institute

Wayne Turmel
Co-Founder and Product Line Manager

Wayne Turmel is the co-founder and Product Line Manager for the Remote Leadership Institute. For twenty years he’s been obsessed with helping managers communicate more effectively with their teams, bosses and customers. Wayne is the author of several books that demystify communicating through technology including Meet Like You Mean It – a Leader’s Guide to Painless & Productive Virtual Meetings, 10 Steps to Successful Virtual Presentations and 6 Weeks to a Great Webinar. His work appears frequently in Management-Issues.com.

Wayne, along with Kevin Eikenberry, has co-authored the definitive book on leading remotely, The Long-Distance Leader: Rules for Remarkable Remote Leadership. Wayne and Kevin’s follow-up book, The Long-Distance Teammateoffers a roadmap for success not just for leaders, but for everyone making the transition to working remotely.

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  1. Great introspection, Wayne, on this difficult employee. Your lessons learned show great personal and professional maturity.

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