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False Positives

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For the past several years, I’ve had an ongoing, internal debate raging: Is it possible to be a kind and caring leader and still be effective? Several of the models of leadership I inherited from a family with generational roots in the military hold that leaders can choose to be either kind and ineffective, or demanding and effective.

I want to admit upfront that in an effort to challenge the notion that only highly demanding leaders can be effective, I often overswing. I have overcompensated with what one previous U.S. president called a “kinder, gentler” approach.

In many ways, I’ve flourished in this industry. I think I have proven to myself that different approaches to leadership can work as I’ve crafted a style of leadership that tends toward the kind and gentle.

What I have also learned more recently, though, is that any approach can be taken too far and become a weakness. There truly is a shadow side to the kinder, gentler approach, if not kept in check. I’ve also become aware that my internal “kindness vs. demanding” debate is a false dichotomy. It’s not an either/or—it’s a both/and. Several books in recent years like “Fierce Conversations,” “Radical Candor,” and “Crucial Conversations” discuss the creative tension of this “both/and” approach. The authors argue that being kind and understanding while holding your team to a high standard is more effective than one or the other. Both are needed.

But can there be too much kindness, too much empathy? I am coming to learn that the answer is a clear “yes.”

Think about encouragement. We all want to encourage our teams and the individual members to perform at their highest. And we’ve seen the crazy example— and maybe even visited there ourselves!—of the yelling and screaming and carrying on manager who thinks that the louder they yell, or the meaner they are, the more people will perform. In an effort to move away from that nonsense we decide to become an encouraging presence, pointing out every possible positive that we can find, all the while ignoring all the shortcomings of any given team member. We can become like the parody of a 1950s housewife whose child is a complete psychopath and wants to burn their house to the ground, and mom says things like, “Oh, he’s just being a rambunctious little boy!” In an effort to be positive and encouraging, we can start to lose touch with the first job of any leader, defining reality.

Flattery is another part of the shadow side of encouragement. Flattery is not really about helping the other person do a great job or develop their skills. Rather, flattery is for us. It actually is a tool of manipulation. We flatter people so they will like us and do what we want them to do. There’s an old proverb that says, “The wounds of a friend are better than the kisses of an enemy.” Flattery only gives people a false sense of accomplishment. It doesn’t help anyone become better.

I’ve shared in recent columns that we recently hired a COO. In learning to work alongside someone with a very different, but complementary style to mine, I’ve seen how my approach has gotten in the way of his. We had recently gotten some good feedback from a customer and I wanted to share that with a team member. So I did. I praised him and thanked him somewhat publicly for a job well done. I didn’t let it slip into flattery. It was sincere and tied to a specific example of good performance. What could be wrong with that, right?

What was wrong with it was that it wasn’t coordinated with my new co-pilot. He was getting ready to challenge this team member in several areas where his performance was lackluster. Nothing huge. Just some things that needed to be shored up. But I inadvertently short-circuited that. I had accidentally set us up in roles of “good cop and bad cop,” as opposed to allowing my COO to have a single, fuller conversation that involved both encouragement and challenge.

Being too positive, too encouraging, and yes, even too kind is not good. It must be kept in check with things like holding your team accountable and having hard conversations when effort and performance lag. Calling those you lead to become great and holding them to a higher standard is actually the most caring thing you, as a leader, can do. They will become better for it.

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