Seek the Challengers

Photo by Shelagh Murphy on Unsplash

Many years ago, I had a junior person on my product team who was:

  • Constantly questioning why she “had” to be at meetings
  • Pushing back against tasks and responsibilities assigned to her, saying they were a waste of time
  • Constantly questioning long-established company culture
  • And, by pushing and questioning, being annoying.

Knowing only those things, a lot of people would say, “That person doesn’t seem like a good culture fit; you should get rid of her.”

But this same person was also:

  • Hardworking beyond belief
  • A brilliant product manager
  • A flawless executor
  • Beloved by engineers and designers.

She was (and is) awesome. She made the whole company better by launching an incredibly important product that the community loved, and which drove real revenue. She had a massive impact on all the organizations where she worked. And on top of that, she went on to become a dear friend.

People like that—I call them challengers—can often be the smartest people in the room. They question because they want to understand the logic and thinking behind ingrained cultural habits. They want to use their time well, and they want to make a big impact.

These are the people who push organizations to be better. Organizations that don’t have these challengers don’t succeed in the long term, because being challenged is what leads to growth. Every organization needs at least a handful of these people. They don’t have to win every fight, but they shouldn’t lose every fight either.

Yes, they can also be incredibly annoying, require a fair amount of time to manage, and drive you to distraction. That’s the price the organization pays, in terms of friction and time, for having dissenters in the ranks. But those dissenters are worth their weight in gold. If every employee is drinking the kool-aid, the company won’t question long-held beliefs, challenge itself, or stretch in new and interesting ways.

So when you recruit, look beyond the pre-converted. Hire the people who have some doubts or reservations. When you do have a challenger on your team, don’t crush their spirit. They will point out that maybe you aren’t the best thing since sliced bread, and the outside world may view your “brilliant and fair” idea through a different lens. Challengers teach you to be open to questioning yourself and changing your mind, and that’s how you grow.

To tie this in to current events: big systems, and societies, need challengers, too. Instead of seeing the challengers as annoyances who are not worth your time, try to listen to their point of view. Regardless of which “side” they may be on, there may be times when you agree with them. And if you don’t entirely agree, if you are willing to listen, you might be able to arrive at a solution that incorporates good ideas from different constituents.