For the leader with people-pleasing tendencies, one of the most challenging questions is one that Esther Perel recently asked on a podcast: Are you leading people or are you trying to please people? I have often mistaken the two, calculating the effectiveness of my leadership with the self-serving fuzzy math of wanting to be liked. It’s possible we consider ourselves far better leaders than we actually are when we dismiss any brand of leadership that makes space for conflict, confrontation, or prolonged periods of discomfort.
David Shore, a professor of organizational development at Harvard, says “managing change is about upsetting people only at a rate that they can tolerate.” This is supremely hard to get right. The people-pleasing leader won’t upset people at a fast enough rate and things won’t change. The hard-charging leader will upset people at too fast a rate and the people will leave. I’m not sure I’ve ever reached this elusive Goldilocks zone of leadership. It requires the dissonance of both deep sensitivity to the human consequences of upsetting your people, along with enough detachment from those human consequences to allow the necessary, low-grade discomfort to persist. The most enlightened leaders, I believe, are often the most patient: they’re not anxious to escape the discomfort in themselves or in their team, but rather are capable of standing firm in that lonely and necessary liminality.