Sometimes it's worth to lose

I heard once, that the best end of any situation, any action or discussion is when everyone are a winners. I know that it sounds great and for most of us such a positive endings are something that we are dreaming about.
But is it always right? Should we always be focused on winning? Should we always be a winner? Maybe opposite side don't have to be a winner as well? Not because we want to lose or we want to hurt our opponent, no, that's not the reason.
Maybe sometimes win-win situation isn't the best choice? Maybe sometimes it's better to lose, even when we are focused on benefits for both sides?

win-lose situation

When is worth to lose and leave our oponent with the lovely taste of victory?

Let's assume, that we are teaching someone to take our position in near future. We see, that he found himself pretty well in new role, he's active and willing to improve further and learn more. But something still is missing.
In minds of your's former team members you are still the leader (of course it's also something good, but in this particular case - that's an issue). They got no problem with new leader, they're follow his ideas, but somehow he feels uncertainty and even you noticed that almost always team waits for your comment.

This is good place to met a small challenge and fail. But your failure is only a part of the success, you need also help him succeed in a place where you lost. You need to help him to achieve victory.

win-lose once again

What in case when you are the winning side? How it could be something good for all participated people?

If your manager is using micro management and doesn't allow for any improvements in your team, it's worth to win with him on team scope. Thanks to this, he will knew that's not a problem to leave the team itself and let you to take care of them.
You will win place for improvements, no one will argue with team ideas and manager will have more time for his work.

But in such a situation you need to be extremally careful and keep on mind, that the main goal is achieve benefits for, in longer term. You don't want to offend him.

lose-lose

It's good to lose from time to time, it builds our character and teaches us how to react in problematic situations.

Sometimes it's worth to make such an "exercise" in your team.
Maybe you want to show them how important is their opinion and their suggestions, that not everything depends on you and their also should take a responsibility.
You want to build trust and teach them what to do in crisis. You want to teach them, that they also can make decisions, even if it will turn out at the end, that was wrong decision.

As a leader you should help others to became a leaders as well and sometimes losing with them can help them to see their own leadership skills.

be focus on goal

It's important to be focus on goal.
When you clarify your goal, think how you can reach it and succeed. Be open for solutions and analyze problem carefully. It will show you, that sometimes the best way to (main) success is to lose in smaller battles.