Hire Yourself as the Opposition

A Viewpoint on Perspective, Conviction, and the Discipline of Understanding

In leadership, there is a quiet habit that does more damage than most policies ever will. It is the habit of being certain. In boardrooms, in management meetings, and in personal relationships alike, I often see intelligent and well intentioned people become deeply attached to their position. The language is polished. The reasoning sounds rational. The conviction feels justified. I have been guilty of it myself. When we are convinced we are right, something subtle happens. We stop trying to understand and begin trying to win.

The difficulty is that most meaningful conflicts are not between right and wrong. They are between two people who each believe they are protecting something important. Over time, I have adopted a simple discipline that helps create space in those moments. I call it hiring yourself as the opposition’s attorney. If you were required to defend the other person’s position, could you do it convincingly? Not sarcastically. Not reluctantly. But thoughtfully and credibly.

Most of us resist that exercise. Our heels are dug in. We feel the stakes. We feel misunderstood. We want the other side to concede first. But perspective rarely emerges from escalation. It emerges from effort.

During the pandemic, I had a conversation with a former colleague that made this lesson tangible. She had elderly parents and was understandably concerned about their health. Her brother wanted the family to gather for a holiday. In her mind, the risk was unnecessary and potentially dangerous, and she was firm in her opposition. What complicated the situation was that her parents were supportive of the gathering. That tension created anxiety and frustration. She felt unheard and perhaps alone in her caution.

I asked her a question that did not land easily. Could she defend her brother’s point of view? Not to agree with it and not to surrender her concern, but simply to articulate it fairly. At first, the answer was no. Her position felt too justified and the risk felt too real. But after a few days, she returned to the conversation differently. She had tried the exercise. She began to recognize what her brother might have been protecting. He was not dismissing risk. He was grieving lost time. He was afraid of prolonged isolation. He valued shared moments while they were still possible.

Seeing that did not eliminate her concern, but it reframed it. Instead of two fixed positions, there were now two legitimate values in tension: safety and connection. That shift changed the tone of the conversation. It allowed for compromise. The family found a way to gather with precautions that respected both priorities. Nothing about the facts had changed. Only perspective had.

In governance and organizational life, the same pattern appears frequently. A board member pushes for stricter financial controls while a manager advocates for more flexibility. A committee wants to preserve tradition while another pushes for modernization. Each position usually contains a rational fear: loss of quality, loss of identity, loss of control, or loss of opportunity. When leaders refuse to step into the opposing argument, conflict hardens. When they discipline themselves to defend it, understanding often follows.

Hiring yourself as the opposition’s attorney does not mean abandoning conviction. It means stress testing it. It forces you to articulate the other side’s reasoning in a way that would satisfy them, not you. That standard matters. If you cannot explain their position in a way they would recognize as fair, you probably do not understand it yet.

In my experience, this exercise lowers emotional temperature, exposes assumptions that may not be as solid as they feel, and often reveals common ground that was obscured by posture. It is not easy. It requires humility and time, and it requires the willingness to admit that your view may be incomplete.

Before your next difficult conversation, try the exercise. Imagine you have been formally retained to defend the other person’s position. Build their case. Strengthen it. Speak it out loud. You may still disagree, but you will disagree with clarity rather than caricature. And more often than we expect, once we understand what the other person is truly protecting, we find that we are not as far apart as we thought.