Are You Playing to Win or Playing Not to Lose?

I’m working with a C-suite executive at a mid-sized company, and the organization is going through some changes. Given his position, my client is privy to what’s happening and savvy enough to see the writing on the wall — what’s coming down the pike doesn’t look good, and his days may be numbered.

We agreed that it’s time to start exploring other opportunities. And that’s when it became clear that his confidence was shaken.

“Maybe I should target VP roles,” he said. “Perhaps a senior director position at a bigger company makes sense. Should I step out of leadership and go into consulting? I think I should cast a wide net.”

Here we go again, I thought. I’m never surprised but always disappointed when this happens.

I’m sitting across from a brilliant, driven, highly-accomplished C-suite executive, and just because his employer is taking an unexpected turn, he’s suddenly questioning his status and worth.

So I asked him: “Are you playing to WIN? Or are you playing not to lose?”

It’s a powerful question. One of my coaches has asked me! What about you? Are you playing to WIN? Or are you playing not to lose?

Because let me tell you what I know for sure, as I did with him…

Volunteering to step down a few rungs on a ladder you’ve already climbed is playing not to lose.

Looking for a lower-level role through a lower-risk search is playing not to lose.

Taking a pay cut to avoid the competition is playing not to lose.

Playing not to lose is accepting less than you deserve, which is a guaranteed “L” by any meaningful measure.

Here’s how my client can play to win instead —
Leverage his C-suite experience to land an even better position.

That goes for you too —
If circumstances threaten to bring you down, aim higher.

Never sell yourself short. Kick it up a notch! Shoot for the ultimate. What do YOU want? 

• A job at a bigger organization with higher pay, excellent benefits, and more support.
• A position that fosters growth and prepares you for the next level.
• A seat at the table with more visibility and a chance to make a name for yourself.
• An opportunity to make an impact and leave a legacy.
• A role that values your expertise more than your time and presence, so you can prioritize life outside of work.

It’s up to you. What do you want to WIN? Challenge yourself to go after that.

Too many people mistake aiming lower for taking the easier route with less risk. But playing not to lose never wins.