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

Љۥ 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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