If you are a sports fan at all, you've probably seen games in which the team participating was playing to win, being assertive and creative, and then you may have seen teams that were playing not to lose, just trying to hold on, being slow and deliberate attempting to maintain their grip on the game until time runs out.
If you are playing not to lose, you are ahead in the game. Right now, you are winning. That's where complacency creeps in. You begin playing defense, protecting what they believe already belongs to them. On the other hand, I have seen too many sports games (and business ones too) where the trends and momentum change with twists and turns which leaves teams shocked, surprised, and disappointed.
Playing not to lose takes away your thirst for risk, innovation, and courage. You begin to settle, not moving into areas you haven't been to before. You start being guarded because what has worked for you in the past is comfortable and seems to be adequate. Being on the defensive makes you paranoid, fear starts to set in which means while you are trying to protect the market share you believe is yours by right, your lead starts to slowly slip away. Customer behavior and expectations are constantly evolving and changing, while you are doing everything you can think of to maintain the status quo. This helps your challengers' momentum and hurts your chances of maintaining your market share.
Executive teams who are playing to win on the other hand are not just looking at the score. They are actually playing against themselves, trying to be better versions of themselves and their organizations every day. They are playing against the team they were yesterday, striving to be better today. They are being bold in their execution and constantly improving on what they know is needed to gain ground.
Teams like this respect and honor everyone's contribution. Teams that are winning know it's not about the individual accomplishments unless it contributes to the team effort. They know when you rise, you need to take everyone along and help them increase as well.
So, is your team playing to win consistently? Or have you started, slowly but surely, playing not to lose?