Don't be a Bad Loser: 7 Questions to Ask When You Don't Win

In a recent Winning Well interview, Bob Morris asked, “You talk about Winning Well, but what does it mean to lose well? David and I both laughed the kind of half-hearted chuckle that comes only after enough distance from the pain.

And as timing would have it, I’ve recently been helping both of my children process through disappointing losses on the college political front and the baseball field.

The truth is, you can’t win well, without losing well–repeatedly. If you’re not losing some of the time, you’re not winning.

Getting good at resilience and recovery is all part of the Winning Well game .

As we answered his questions, we began sharing stories of times we’d lost, and had to rally our teams in the midst of severe disappointment.

7 Questions to Ask When You Don’t Win – This Time

“I never thought of losing, but now that it’ s happened, the only thing is to do it right. That’s my obligation to all the people who believe in me. We all have to take defeats in life.” - Muhammad Ali

As with most leadership challenges, there’s hardly a better strategy for helping your team lose well than asking great questions. Here are a few questions to get you started.

1) What are we feeling now and why?

Chances are this will be met with crickets–wait for it. Linger. Discuss. Process. Shut the door. Allow emotion. Before you open the door. It’s okay to share that you’re disappointed too, but do your best to role model a calm exploration and discussion of your feelings.

2) What are we most proud of?

Even the worst defeats generally come with moments of success, smart plays, and even ingenious effort. Help your team to step back and celebrate the elements of good.

3) What must we do to show up as gracious losers?


In order to win well the next time, it’s so important to not show up as bad sports. Help your team brainstorm the mostimportant behaviors here. Perhaps it’s a congratulatory phone call or two, or a simple offering of “How can I help?” Remember Winning Well is a marathon.

4) What can we learn here?

This is the most important question, but resist the urge to jump in and start with this one. You’ll get better thinking if you start with 1 and 2.

5) How can we invest in (and build bridges with) the winners?

Our current political arena gives us plenty of examples of how to do this well–and how to screw it up.

6) How do we stay focused on our MIT (Most Important Thing)?

You may have lost a battle, but don’t give up on your bigger vision. This is a vital question to as before the final question…

7) What’s next?

It’s not over. Help your team craft a clear path forward.

When you’re the most frustrated, chances are, so is your team. Most situations get better with conversation.