Take Longer Vacations

We often measure leaders by their dedication. We measure them by their commitment to being available at all hours, and by how many people depend on them.

In other words: we measure them exactly wrong.

I propose that instead we should measure them based on how long their vacations are: the longer the better.

Think about the rising star on a team. Their peers begin coming to them for guidance. Managers recognize the employee’s emergent leadership and encourage more people to rely on them.

Before long the employee has to backfill their own role because they’re spending so much time directing work. Their leadership growth to this point has been impressive but suddenly hits a wall. They no longer have time to invest in their own development, which is how they came to be seen as a leader in the first place.

If leadership really means being relied upon by more people every day, then it has a very low ceiling. Leadership like this just doesn’t scale past a certain point.

Instead, I believe that your leadership is best measured by what people do when you aren't around.

Leadership at scale requires a clear shared vision with a consistent strategy that people can rely on it without you having to get involved. Leadership is when people are faced with a novel problem and can reliably guess how to proceed because of consistent application of basic principles. The more complex challenges they can tackle without you, the more effective your leadership has been.

I once asked a bunch of leaders across Facebook how long their last vacations were and how things went while they were gone. Good junior managers and engineers could leave for a week without anything going wrong. Good directors and tech leads could leave for a month. The better people were, the longer they could be away.

True leadership is giving people the tools to make good decisions locally. Leadership means sharing a vision of the future, not consulting an oracle. If you want to test your leadership, take longer vacations.