Rock-solid individual contributors win — a lot. Winning becomes their reputation, and you hear it in how others describe them. “They get things done.” “They figure things out.” “I can trust that, if I give it to them, I know it will get done.” For these individual contributors, their value – and what you reward – is dependability. They know how to run on a pre-defined path where success is clear-cut. That’s their superpower.

Leaders lose. Not a lot, necessarily, but they lose a lot more often than their rock-solid individual contributors. They make a strategic mistake, or hire the wrong person, or invest in the wrong thing. For leaders, their value – with little reward beyond the intrinsic – is in their ability to maximize wins, minimize the cost of losses, and persist independent of outcome. Leaders understand how to set a course in the face of uncertainty, providing that pre-defined path that enables others’ success. Even the nature of “win” and “loss” changes.

The challenge: no one wants to win less, much less redefine a win to something less concrete.

In my coaching of next leaders, I tend to see the contributor-to-leader transition getting messy at the point where winning is no longer a linear function of effort, but a complex algorithm of factors both within and outside of their control. Their instinct is to abandon ship since the thing that has made them so successful – winning – doesn’t work anymore. I’ve found this to be a point of identity, and a core reason why those identified or groomed to be next leaders either struggle with the transition or pass up the opportunity entirely.

Talk to your next leaders. Ask them how they define wins and losses, and challenge them to look at the organization from a wider view. The more their identity becomes wrapped up in organizational rather than individual success, the more capable they are likely to be at taking charge when it’s their turn.