Article (Cheeky Half Episode 42): Can you be a good leader AND a bad person, at the same time?

Ask whether a good leader can also be a bad person, and most people answer immediately: yes, obviously, look at any number of examples, several of them currently holding office somewhere. Ask what actually makes someone a bad person, and the answer takes considerably longer, but consensus amongst respondents should never be assumed.

The first move worth making is separating two things that get treated as one. Being liked and being good are different measurements. So are being disliked and being bad. Someone can be entirely likeable and still cross a line that matters, and someone can be a bit of a slog to sit across a table from, and still land on the right side of it. Once likability drops out of the equation, the real question surfaces: can a person cross a genuine moral line and still be regarded, without qualification, as a good leader?

The compromised artist offers a useful comparison, if a slightly overused one. Picasso’s talent and Picasso’s treatment of the women in his life sit in obvious tension, and so does Michael Jackson’s music against the allegations that shadow his legacy. Somehow, holding those two facts apart seems more available to people than doing the same with a leader. Perhaps that’s because art asks to be judged on the work, while leadership asks to be judged on the person doing the leading, which makes the two harder to separate even when the underlying shape of the question is identical.

The case that denies us a comfortable position is Jonestown. If a leader needs followers, and that’s often treated as close to a definition, then Jim Jones had followers, right up to the moment he led hundreds of them to their deaths. Whatever else that was, it wasn’t an absence of influence. It raises an uncomfortable possibility, that the capacity to move people and the moral worth of the direction in which they’re being moved are not the same capacity at all, and one can be fully present even when the other has failed completely.

There’s a harder version of this question sitting in plain sight in current geopolitics, where certain leaders appear to operate with no real accountability attached to their conduct at all, which is either evidence of extraordinary leadership or evidence of how low the bar sits when nobody’s checking. Whether that counts as a verdict on their leadership or simply a comment on who gets to hand down verdicts isn’t obvious, and probably shouldn’t be treated as though it were.

None of this resolves cleanly. There was never going to be a neat bow here, and nobody’s pretending otherwise.

Listen to Cheeky Half 42 of Leadership Decanted.