One of the clearest signs of a healthy organization is a strong pipeline of talent—people who have grown through the ranks, deepened their skills, and are genuinely ready to step into leadership. It’s something worth celebrating when it happens. But there’s a lesser-discussed challenge that comes with that strength: what do you do when you have more than one exceptional candidate competing for a single role?
A Real-World Succession Planning Scenario
This came up recently in a Winslow debrief I led with a manager who was evaluating five strong candidates for one open leadership position – three internal, two external. After reviewing the behavioral and technical profiles of the external candidates, they were ruled out; strong, but not quite as well-suited as the internal three.
What remained were three highly capable, well-respected individuals with remarkably similar profiles. Any one of them could have stepped into the role and succeeded. This is an enviable position to be in, and also a genuinely difficult one. When the data is nearly equal, the decision then needs to shift from analysis to leadership judgment.
The Coaching Questions That Cut Through the Tie
My client wanted me to simply tell him who to pick, and honestly, I couldn’t have gone wrong with any of them. But that’s not how my support works. I learned years ago that when coaching (helping people make a decision or plan of action), the goal is always to help the individual arrive at their own decision with clarity and confidence.
So instead of giving an answer, I asked four questions:
- Who do you believe will grow most into this role over the next several years? Not just who is ready now, but who has the trajectory.
- Who can hold the team together after this decision is made? Whoever is chosen, two strong people will be passed over. The right leader will help those individuals stay engaged and moving forward.
- If this person leaves because they weren’t selected, can you live with that? I asked this about each candidate. It’s a clarifying question—the answer often reveals where someone’s instincts are quietly pointing.
- When you look at all the data and set aside the uncertainty—who do you know is right for this? Most leaders already have a sense of the answer. They’re not unsure of the decision; they’re unsure whether they should act on it.
The best succession planning doesn’t just ask “who is ready?”—it also asks, “have we created the conditions for the right people to emerge?”
The Takeaway for Leaders Facing This Decision
Any one of these candidates will be an asset. But the more important point is this: when the data narrows to a near-tie, the work isn’t over – it just shifts. The manager still has to lead in this decision. And the right questions can make the difference between a decision that feels made for them and one they own completely.
