An Odd Secret About Leadership

A master’s student recently interviewed me for a paper he’s writing.  He is writing a case based on his experience as a head of a small private school and the leadership dilemmas he faced, and he wanted my take on what the antagonist in the case could have done differently. His passion for the paper and for the work he used to do is remarkable. He is a bright, caring, experienced, insightful person who – like so many people who gravitate to work they care about – was completely unprepared for the brutal realization that doing work that you find deeply meaningful can be agonizing in unexpected ways.

If you are tapped to lead because you are seen as being competent, caring about what you do and having a resilient work ethic, I congratulate you.  There are lists and guides for all the things you will need to do well as a leader: you must develop your business acumen, your interpersonal skills and your instinct for how to make projects work.  All of this will be valuable and it will feel exhilarating as your leadership skills grow and serve your goals.  You will work hard and persevere and put in the long hours and the effort and you will help build something that works and about which you feel proud.  

But there is a key element that that people who ask you to lead don’t tell you. They don’t tell you because not many people can name it.  The secret that that no one shares is that leadership, done well, can break your heart. It can break your heart because the humans you work with will disappoint you. Circumstances will change beyond your control. You will screw-up, make weird choices and you will disappoint others. If you keep true to the reasons you were chosen to lead in the first place – because you care and are competent and have a passion for what you do – you and your teams will recover and manage to thrive.

Leading people is fabulous and risky and sometimes heartbreaking. Know that. Accept it. And go and do it anyway. The risk of not leading, not trying will break your heart even more.


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