What Does It Mean to Win?

How you define “winning” may be informing your life in ways you are not aware of. And your strategy for “winning” could be costing you, and others, more than you think.

I once coached a senior leader who personally defined winning as always being the guy with the right answer. He spoke first in meetings in a confident and convincing manner. Since he usually had solid answers, most discussions ended there and his ideas were implemented. He felt very successful when this happened.

What he didn’t notice was what his strategy for “winning,” as he defined it, was costing him and his organization. People found it hard to collaborate with him, and were often frustrated that they couldn’t get their own ideas considered, let alone acted upon. Worse, there were no leaders in his organization who were ready to be promoted because the most talented people left as quickly as they could. The ones who remained were never given the support and stretch opportunities they needed to build their confidence and hone their leadership skills. His division had become a leadership desert. But he didn’t notice, because he was “winning” his game, his way.

This leader and I talked deeply about what winning really meant for him, and what the organization needed from him in order to be successful, in both the short term and the long term. He started to notice how his leadership style impacted his team and his organization. What he saw inspired him to redefine “winning” as supporting others to evolve their leadership capabilities to serve the greater good of the entire organization. He enjoyed the challenge of transforming how he approached all relationships, and he used what he learned to coach others to be better leaders. Over time his division began to flourish again, and attracted talented people who wanted to learn and grow.

When you are coaching someone, really spend time understanding what winning—and losing—looks like for that person. If you can expand the person’s definition of winning, the behavior changes needed to fulfill that aspiration unfold with greater speed and ease, and continues to deepen as the person experiences the rewards of “winning” in new ways.

Change the game to change the experience. This holds for individuals, teams and entire organizations. Perhaps it’s time to step back and ask yourself, “Are you really winning at the game you’re playing, or is it time to redefine what winning means for you and design a new game that brings out the best in you and others?”

Dianna Anderson, MCC
CEO, Cylient

Join the Conversation

What unintended consequences have you noticed in your, or other people’s, strategies for winning?

2 thoughts on “What Does It Mean to Win?

    EJL says: September 14, 2016 at 2:30 pm

    New environments have made old games and old ways of “winning” obsolete. Your comment “change the game to change the experience” is certainly true and your leadership advice is excellent. A game that brings out the best in others is an experience that endures long after the game is over. It is one of the best experiences, and it lingers…

    Dianna Anderson says: September 14, 2016 at 7:15 pm

    So true. I think that one of the most powerful things we can do with coaching is to re-mind people that, regardless of their circumstances, they have the power create their own games, and invite others to play with them, in ways that elevate everyone. Thank you for your thoughtful comment.


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