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3 Ways to Improve Your Leadership in the Geezer’s Paradox

There comes a point in almost every leadership journey when the responsibilities of leadership become more clearly and formally defined.

You no longer lead only in the sense that “everybody” is a leader. Now you have a title. Now there are external expectations. Now coworkers who considered you a leader among peers actually report to you and call you “boss.” It’s part of your job description to give directions, provide answers, solve problems, and show the way forward.

Maybe that time already has come for you, and, if so, you know that the responsibility of leadership can bring a subtle pressure to win the approval of those you lead. It’s natural to want people to like you and support your decisions. And if your direct reports were friends before you picked up the title of “boss,” you still want them to see you as a friend. Then you discover they don’t treat you the same, because they now view you as “management.”  

In my experience, you still can be friends with the people you lead and you can be well-liked, even if you have to navigate new relationship boundaries that come with making hard decisions that everyone doesn’t like or agree with. But if you find yourself trying too hard to be the boss everybody likes, then you might want to remember the Geezer’s Paradox.

The what?

I’m not sure if I’m old enough to qualify for geezer-ship, but I am plenty old enough to appreciate this quote: “You don’t become cooler with age, but you do care progressively less about being cool, which is the only true way of being cool. This is called the Geezer’s Paradox.” (Source unknown)

I’ve written often about the fears leaders face—things like appearing incompetent, foolish, or as an underachiever—and I’ve noticed that the biggest fears are more about how the leader is perceived than about their organization and how it’s performing.

Leaders might not care about being “cool,” but they often care about how they are perceived. And, frankly, the opinions of others matter. The challenge is to give those opinions their due without allowing them to rule your life. The way to be respected, well-liked, and appreciated is to focus less on those outcomes and more on your role as a leader. That’s not always easy, but it’s not complicated. At a minimum, it involves three best practices.

Be open to feedback from sources you trust

Leaders need advisors they trust to tell them the hard truth about their flaws. But they must be trusted advisors. If your adversaries or people you’ve never met criticize your leadership, you might ask some of your closest advisors if the criticism has merit. If not, don’t lose sleep over it.

Your spouse, your mentors, your accountability partners, paid consultants, spiritual leaders, and close friends all can fill this role. The key is that they know you beyond a surface level, align with your values, and love you enough to tell you the truth when you might not like it. And for your part, of course, you have to be open to such honest feedback.

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Act on your flaws when you know them

When I was a CEO, we often used assessments to check our performance. Some of these assessments asked my direct reports to anonymously point out my weaknesses as a leader. And they did! It was painful and, in some cases, surprising, but the more I knew about how they felt, the better I could address their needs by changing in areas where I truly needed to change.

For instance, one year my direct reports consistently felt I was in a hurry and too busy for them to take up my time. That went against my value of treating people with respect, so I made a conscious effort to slow down and intentionally engage with people.

Sometimes, by the way, you have to make a point of showing that you are making such efforts. I read a story about a leader who was dinged for showing up late to meetings. For the next six months, he showed up five minutes early for every meeting he attended, and the next round of feedback about him didn’t change a bit. So over the next six months he not only showed up early but opened meetings by saying something like, “I’m glad we can get started a little early.” Only then did his engagement scores change.

Prioritize servant leadership

Leaders who want to be seen as the likable (or “cool”) boss who just happens to have a title are missing the point and the opportunity to have a positive influence. They consistently draw attention to themselves in ways that reveal their lack of self-confidence. But if they focus on serving others—providing the resources people need, for instance—then their ego can take a nap in the backseat.

Will that make them cool? I can’t answer that. But I am pretty sure it won’t matter because it will help them earn respect as a leader and, more importantly, for the right reasons.

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