“He was one of those earnest, persevering dancers–the kind that have taken twelve correspondence lessons.”

–― P.G. Wodehouse, The Man With Two Left Feet and Other Stories

Awkward Leadership


Among the many emotions associated with leading others, one is hardly mentioned: awkwardness. And yet, time and again, the places where things can change are in the awkward moments, made up of social discomfort, imprecise words and tensions that we hope sometimes too desperately are on their way to being overcome.

We can think of awkward in different ways — as unpleasant, delicate, embarrassing — which suggest vulnerability, social exposure, maybe a subtle potential for conflict or a muted shame. We associate it with junior high or high school, as if people suddenly become graceful as adults. The deeper etymology of the word is something “turned the wrong way” or “backwards” and clumsy. This, of course, is the exact opposite of what we often unconsciously assume about anything having to do with leading — that it is always supposed to be about doing things “the right way,” “forward” and “adept.”

And yet that is a mistaken assumption, isn’t it? Effective leading — the willingness to enter the tension or embarrassment of a situation, however we name it — moves us often right into the heart of exactly what needs to be on the table. Nobody may want to go there, even as avoiding that moment potentially causes any number of problems, like failing to name an obvious but undisclosed truth. In turn this leaves the door open to ambiguity and misjudgments about one another or what’s really going on, sometimes causing hurt feelings through the very intention to avoid hurt feelings. Part of the irony of this is that we do tend to think of leaders as needing refined social skills, and yet these skills can become so refined they enable side-stepping any awkward situation we choose. This has a cost. At its core, of course, such avoidance reflects an unrealistic aversion to interpersonal risk. The awareness of this risk is what makes moving into the awkward moment a self-conscious thing.

There are common and oversimplified instances of this problem — I think of a supervisor I knew who had to tell a staff member her body odor was bothering others. But most awkward situations are not so extreme or so straightforward. Just the other day, for example, I found myself needing to bring up a discomfort I felt with the way a client had treated me in a meeting. Not a big deal, but as her coach I felt I should model taking the interpersonal risk and, truth be told, I was also dealing with my own real personal reactions. If I had not done so, I would have certainly continued to wonder what was going on and this could have undermined some of the great rapport we’ve built over time. Although bringing up what happened did create an uncomfortable moment, it also led to a healthy discussion of the larger picture of our work together and how some of that work needed to change. Was it a perfect conversation? Is it entirely finished? No, and probably not. But sometimes, as a leader I know said to his team of executives regarding how best to manage change, “raw is better.” It’s all too often our desire to avoid what is “raw” that gets us into trouble. And, as they say, that can happen little by little and then all at once.

This, too, is really a minor example, and I am aware there are major ones where awkward would be a euphemism for what people experience. There are bad conversations, for sure. And none of what I am saying here should be misconstrued to mean being overly harsh in the name of “honesty” or rejecting the notion that providing psychological safety for others is a legitimate goal. I’m speaking, rather, about what it means to be true to one’s capital S Self.

I think we have to ask ourselves, facing the awkward moments, what it is we are attempting to manifest through leading, especially in light of all the time and energy wasted on avoidance. I think we have to ask what kind of connection we want with others and how that might be achieved in the real world. I think we have to ask about our own integrity and how compassion, in fact, becomes genuine for self and others. I suspect only by learning to acknowledge and accept — and even honor — our own awkwardness, no longer trying to hide it at all, will we ever learn to get our lives and work turned the right way round.



  • Great piece. Dan. Thanks!

  • You are most welcome, Dean! Great to hear from you!

  • Wonderful article, Dan. I’d never thought about the etiology of the word “awkward.” I love the way you wove it through the article as a connecting thread.

  • Hi Jody —

    Thank you so much. The origin of the word is interesting, isn’t it?

    I hope you are doing well.

    All the best

  • Many times it’s hard for me to be raw, because I don’t want to cause problems…

  • Hi Patty

    I think that’s a common feeling for many of us. Yet there are times when being “raw” might help, especially if that means being sincere, vulnerable, and true to one’s heart — and this feels a bit awkward in the moment. I believe that if that moment shows your own humanness (not your defensiveness or harshness) then it may well do much more good than harm.

    All the best

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