Is there any more difficult choice for a leader than the one to step aside and let others take over?
It is the exceptional leader who makes this choice when things are good – who sets themselves up to leave under their own terms. Who plans for the “after”, not as an escape, or a reward… but rather sees it as the next adventure.
When assessing leadership, I like to look at the people immediately around the individual in charge. Not the “executive team” or “advisory council” – who is the person next to them in big meetings? There’s a lot to learn by looking at the qualities of the people just to the side of the central hub, sort of how looking just to the side of a star in the night sky can make it more visible.
Take a close look at the leader’s go-to person. Are they an amplifier of the leader’s personality, carrying the same messages and styles in their own work? Are they a shield? Ready to give the tough feedback, hold space in difficult meetings, stand and delivery bad news like layoffs, taking the hits in reputation while their boss stays above it? Or are they a foil? The funny person to the leader’s seriousness, or the relaxed person in a tense situation? I’m guessing you’ve experienced some or all of these and others, and probably with specific spins on each.
Most importantly – does the go-to person look like someone who is being trained to take over? Are they being coached up? Are they growing and evolving with the leader, or are they a fixed point of constancy? What does that say about them, and the leader?
Opinion: a good leader is thinking about, and more importantly doing something about, continuity – every day from their first day in charge until the day they leave. Smart leaders have their person picked out, communicate this to them, actively encourage them and delegate authority to them. Brave leaders share the spotlight and find ways, however small, to step aside when they can. They know that if they’ve done the work well, the enterprise or the team will go on without them, and hopefully do even better.