In This Week’s Issue:
Why two leaders with the same title can lead completely differently
The difference between playing to win and playing not to lose
How fear-based leadership keeps teams stuck
What “forward leadership” actually looks like
Reader Q&A on decision-making and confidence
Setting the Stage
If you’ve led long enough, you’ve seen this: two leaders with the same job, same responsibilities, and same experience, yet completely different impact. One pushes the team forward with clarity and confidence. The other keeps the team cautious, hesitant, and waiting for permission.
The difference isn’t talent. It isn’t effort.
It’s whether the leader is playing to win or playing not to lose.
Both styles can feel responsible in the moment. But only one actually moves the team forward.
THE BIG INSIGHT
Leadership isn’t just about effort. It’s about direction.
What “Playing to Win” Looks Like
Leaders who play to win aren’t reckless. They’re decisive. They understand that momentum matters and that progress requires movement, not perfection. They take smart risks, act on the information they have, and own the outcome.
Playing to win sounds like:
This is the direction. Let’s move.
We’ll adjust along the way.
Here’s what we’re learning.
I’ll take responsibility for the decision.
These leaders pull the team forward. They create energy, clarity, and pace. People want to follow them because they make progress feel possible.
What “Playing Not to Lose” Looks Like
Leaders who play not to lose aren’t lazy or uncommitted. Most are trying to avoid mistakes. They want certainty before moving. They want perfect information. They want risks fully eliminated before taking the first step.
But the cost of that mindset is high.
Playing not to lose sounds like:
Let’s get more data first.
What if this goes wrong?
Let’s revisit this next week.
I want to make sure we don’t mess this up.
These leaders protect safety but stall progress. They create hesitation and second-guessing, even when the team is ready to move.
Why Playing Not to Lose Feels Safer (But Isn’t)
The challenge is that both mindsets feel responsible. One says, “Move.” The other says, “Be careful.” Both can sound reasonable. But only one moves the organization forward.
Teams stuck under “not to lose” leadership don’t feel safe. They feel stalled. Motion slows. Meetings multiply. Confidence drops. People stop bringing new ideas because they know the default answer is “not yet.”
Caution feels responsible in the moment. But momentum is what actually creates results.
What Great Leaders Do Differently
Great leaders don’t bet the company on every decision. They make thoughtful choices but they move. They protect the mission, not their image. And they’re willing to take accountability if something doesn’t go perfectly.
They understand a simple truth:
Teams learn more from taking the next step than waiting for the perfect one.
Here’s what playing to win looks like in practice:
Make decisions with the information you have.
Waiting for perfect clarity is how teams lose time and confidence.
Name the risk and move anyway.
You don’t need to eliminate risk. You just need to acknowledge it and prepare for it.
Test small before committing big.
Movement creates data. Data sharpens direction.
Own the decision publicly. When the leader carries the responsibility, the team carries the execution.
When leaders shift from protecting themselves to moving the mission forward, everything gets lighter, faster, and more aligned.
QUESTIONS
Q: How do I get a risk-averse team to move faster?
Start with smaller steps. Progress builds confidence, and confidence increases speed.
Q: What if I tend to overanalyze?
Set a decision deadline. Give yourself a window to consider options, then move.
Q: How do I handle a team member who always wants more data?
Clarify what’s “good enough” to act. Most people over-research because the expectation is unclear.
Takeaway
Two leaders can look the same on paper but create completely different results. The difference isn’t effort. It’s direction.
Playing to win moves the team forward. Playing not to lose keeps them spinning.
~ Chad Todd
