A few weeks ago, I had breakfast with a friend who spent twenty years as a senior engineer at Intel. Ten years ago, Apple lured him away to build a new engineering team.
Knowing Intel has lost roughly 67 % of its market cap in the last five years—while NVIDIA has sprinted ahead—I asked him, “What happened?”
He didn’t hesitate.
“They wouldn’t risk killing the x86 cash cow, so the world passed them by. Classic Innovator’s Dilemma.”
That one sentence says it all. Intel’s leaders were playing not to lose instead of playing to win – and they paid dearly. The trap isn’t limited to semiconductors; executive teams in every industry have to stay on offense, not defense.
So, how do you make sure you and your team are playing to win instead of playing not to lose?
The Diagnostics
First, let’s look at some key indicators of each:
| Playing Not to Lose | Playing to Win |
| Avoidance goals: “Don’t miss guidance.” | Achievement goals: “Grow NPS by 10 points.” |
| Tight control & approval layers | Delegated ownership with guardrails |
| Success = absence of error | Success = creation of new value |
Why Leaders Get Stuck
Next, let’s get real about the reasons you and your team might be stuck playing defense:
Exposure at the top: Compensation, reputation, and investor scrutiny attach a high price tag to public mistakes, so leaders often default to loss‑avoidance.
Cognitive load: Constant high‑stakes decision cycles narrow attention to “what could go wrong,” reinforcing the threat bias that comes from chronic fight or flight.
Cultural signals: If smart failure is punished faster than bold success is rewarded, leaders up and down the organization naturally armor up and protect for the downside. A culture of low psychological safety sharply increases defensive decision‑making among managers.
Signals You’re Playing to Win
Then, send intentional signals that you’re playing to win:
Place bets on the upside: Set aside a small portion of your annual operating budget to fund ring-fenced experiments that may fail but may also pay off big. This kind of approach fosters a culture of intelligent risk taking.
Shorten the feedback loop: Balance the big project bets with small sprints that shorten the performance feedback loop with a rapid test-and-learn approach.
Promote psychological safety from the top: Through your words and, especially, your actions, show that questions, debates, and course-corrections are both encouraged and expected.
Manage Yourself
Finally, as a senior leader, manage yourself to win:
Take micro-breaks: Three rounds of deep breathing and five minutes of movement between meetings lowers your cortisol level and preps your prefrontal cortex for creative problem solving.
Get your white space: Schedule one 90‑minute “white‑space” block each week – no email, no email and no meetings so you can think on the business, not in it.
Whole‑self routines: Leaders who intentionally practice the physical, mental, relational, and spiritual routines that support their peak performance have higher resilience and lower reactivity.
The teams that win in 2025 will be the ones brave enough to disrupt themselves before someone else does.
What have I missed? Share your best practices on making the shift from playing not to lose to playing to win – send me an email or leave a comment on LinkedIn.
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