America’s Founding Fathers engaged in intense debates about how the government of the United States should be structured. Many of the towering figures of that era were in nearly violent disagreement with each other for years. But they managed to build a disparate band of former colonies into a nation.
Decades later, the newly-elected Abraham Lincoln brought several of his most intense and capable opponents into his cabinet. During the biggest crisis the nation ever faced, he encouraged vigorous debate. At times the cabinet members were at each other’s throats. But he cleverly pulled the best ideas out of those disagreements. Under Lincoln’s leadership, the nation survived.
Hiring people who agree with you makes your life as a leader easier. You seldom get into arguments about your decisions. Nobody challenges you.
Nobody challenges you is another way of saying nobody tests your assumptions. Nobody vigorously examines your direction. Nobody pushes you to come up with better plans. Nobody is helping you be as good as you can be at whatever it is you are doing.
Years ago I led the development of a secure web application that was designed for internal corporate communication. One of the team members was a born contrarian. He’d tell us why a particular feature wouldn’t work. He’d point out how a nefarious user could game the system. I admit that at first this grated on me. But then I realized the full value of his criticism. He was revealing problems that would manifest if we didn’t change the design of the application. What seemed like sand in the gears was really a big lighthouse beacon, warning away from dangerous shores.
Thankfully he raised his concerns early in the development process. As we reworked the system, I explicitly placed him in an OPFOR role. His job was to pretend to be a malicious user. He analyzed the system accordingly, and as he brought flaws to the surface, we fixed them. This was a huge learning event for me, but more importantly, the development process actually went faster and more smoothly. We delivered the project ahead of schedule, and the client was thrilled.
If you’re in charge, having in-house skeptics may seem like a challenge to your authority. But if you’re secure in your role and can keep those skeptics focused on sharpshooting ideas rather than people, they can help you exceed your own limitations.