Celebrating the Challenging Boss

Over the course of a career, we work with dozens of bosses. We often look at bosses with a sense of wonderment because they have some magical powers bestowed upon them by their titles and we believe they hold our future in their hands. It follows that our experiences with our bosses become memorable. More than that, they help form the foundation of who we become as leaders.

Most of us are grateful to the bosses that propped us up, told us we were better than we thought we were, had our backs in tight situations, consistently did what they said they would do, and connected with us as individuals. The bosses who coached, mentored, and urged us toward personal growth earned our respect. I have a long list of such bosses to whom I’m grateful.

But there are also bosses that we didn’t hold in such high regard as we experienced them. It is only after the fact, sometimes months or years later, that we allow ourselves to consider the contribution these bosses had to who we became as leaders.

Some examples:

  • I had a boss who threw a chair across the room at an employee and missed. Happily, there was no second attempt to improve his accuracy.
  • I had bosses who spent time counting floor-to-ceiling windows in offices to make sure the wrong people didn’t have too many. Such matters consumed their days.
  • Bosses who reduce employees to tears with profanity-laced tirades followed by “I’m sorry.” Until the next time.
  • Bosses who hid bad news from their employees until it was too late to react and get out of the situation.
  • I heard about a boss who shut the blinds, turned off his lights, and hid under his desk while HR fired most of the people on his team. His turn came only a few months later.
  • A boss that didn’t know employee names sitting fifty feet from his office.

In the heat of the moment, I did not often have the perspective that time and distance eventually provides. I didn’t always see the lessons in it for me, nor did I know how those experiences changed me as a leader.

When we want to strengthen our heart and lungs, we run, bike, or swim. When we want to improve our body, we do resistance training. Our physical strength expands as we demand more of ourselves.

It’s the same with our leadership abilities. Presented with challenges that create dissonance and discomfort, we put in the effort and expand our ability to handle more complex situations in the future. We augment our toolkit and increase our ability to influence our teams.

Lessons Learned

Some things I learned along the way:

1. Our styles under stress vary widely. Some of us wear our emotions on our sleeves, and others display a level of monk-like equanimity that leaves those of us in the first category in awe. Recognizing, controlling, and channeling our emotions lead to better outcomes.

2. Reverse role models are valuable. Those of us with older siblings had at least two advantages growing up. First, we could learn from their mistakes and tell ourselves, “Let’s not try that one.” Second, by the time we reached adolescence, our worn-out parents allowed us to get away with more. Hypothetically, of course.

3. When we experience these situations, we tend to react in one of two ways—we become stronger, or experience learned helplessness. In the former, we become leaders determined to do things differently to serve the team and company. In the latter, we struggle to lead ourselves and make decisions because we have not exercised our decision-making muscles over time.

4. Commitment wins over vicious compliance. Employees reward us with their commitment only after they feel safe, trust their leaders, and feel like they are part of something bigger. Vicious compliance may get things done in the short term, but creates a toxic environment that destroys teams and companies over time.

5. Bullying behavior exists in companies and life. It shows up due to insecurity and scarcity. Our survival instincts drive us to move away from this behavior. If you decide to stay and help instead and believe you have the coaching skills to assist, a transformation is sometimes possible. Establishing rapport, holding up a mirror, and not making them wrong, are a few steps to start. Bullying behavior often leads to feelings of shame, so it’s important to help a person feel safe while not letting them off the hook for their behavior. The goal is to help create more resourceful behavior and not allow “I’m sorry” to be the last word. In bullying situations, targets don’t want to hear an apology; they want to experience different behavior.

6. All leaders are in the people business. Learning the first names of employees is a simple but powerful way to connect. It lets people know you cared enough to learn their name, sure, but also that your messages merit their attention. Ideally, over time, it also opens the door to earning their trust.

Activating Questions

As with all experiences, we have the freedom to choose what each means to us. Take the time you need to shake off the negative feelings from the experience and ask yourself:

1. What else could this mean? Why is he behaving this way?

2. What can I do to help this leader? What can I do to help the team?

3. How can this experience serve me?

4. What am I willing to do to make things the way I want them? What am I ready to stop doing to make things the way I want them?

5. Do I exhibit some of these counterproductive behaviors? If so, what do I need to do differently to be more effective?

6. How has this experience made me stronger?

7. What are the lessons from challenging bosses that I can share with others to help them on their leadership journey?

Takeaway: It’s easy for us to have a bad experience, become the victim, and make the offending person the villain. But lessons are always available to us once we start asking better questions and remain open to learning. All leaders struggle during their personal journey, and it’s a gift to experience those people who challenge us along with those that help us through the challenges.