
Hard Conversations, Held Well
June 5, 2026The People You’re Developing (Or Aren’t)
Succession is a current-quarter issue, not a future one
Most leaders treat succession as a future problem. They will think about it next year, after the current initiative wraps, when the team is more stable, when there is room to breathe. The trouble is that the version of you who will do that thinking next year is the same version who has been postponing it this year, and the year before that. Future-you is rarely a more disciplined leader. Future-you is just present-you, with one more year of accumulated avoidance.
The leaders whose organizations outlast their tenure understand something the others miss. Developing people is not a future activity. It is a current-quarter discipline, woven into the texture of the work itself. And the leaders who skip it are not saving time. They are just borrowing it from a future where the bill will come due all at once.
“If your organization cannot function without you, you have not built a leader. You have built a dependency.”
Three principles for developing the people who are already in front of you
1. Identify the two or three you are actually investing in
Most leaders say they invest in their people, and most leaders, when pressed, cannot name the specific two or three they are deliberately developing this quarter. Generic investment in everyone is, in practice, deep investment in no one. Pick two or three people. Write their names on a piece of paper that only you see. Then ask, for each one, what specific stretch they need this quarter, what conversation you owe them, and what experience you can engineer for them in the next ninety days. If the answers are vague, the development is not happening.
2. Give them work that is genuinely uncomfortable
People do not develop from doing what they are already good at. They develop from being given work that is one step beyond their current capacity, with the support to figure it out. The hardest part of this for leaders is not identifying the work — it is resisting the urge to take the work back when the person stumbles. The stumble is the development. If you rescue them every time, you are protecting their comfort and stunting their growth, and they can feel the difference even when they cannot name it.
3. Talk about their future, not just their performance
Performance conversations look at what someone has done. Development conversations look at who they are becoming. Most leaders have plenty of the first kind and almost none of the second. Once a quarter, sit down with each of your two or three and have a conversation that has nothing to do with this week’s deliverables. Ask, “Where do you want to be in three years? What is in your way? What am I doing that helps, and what am I doing that hinders?” The answers will tell you whether you are actually developing them, or just managing them.
Leadership Reflection
• Who are the two or three people you are deliberately developing this quarter? Could you write their names without thinking?
• What recent stretch assignment have you given each of them, and how did you handle the moment they stumbled?
• When was the last development conversation you had that was about who someone is becoming, not just what they have produced?
The succession that already exists
Whether you are deliberate about it or not, succession is happening in your organization right now. Someone is being prepared to take on more, by your investment or by the absence of it. Someone is learning what your judgment looks like, by watching you exercise it. Someone is forming an internal model of how a senior leader carries the weight, and that model will shape them for decades.
The only question is whether you are doing the shaping on purpose, or letting it happen by accident. Both produce results. Only one produces leaders.
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Stuck on a decision that matters? That’s what the MSG Resources Leadership Advisory is built for — a private, invitation-oriented space for senior leaders who need clarity on the decisions that shape everything else. Learn more at connect.msgresources.com/leadership-advisory.

