Losing Well: 7 Questions to Ask When You Don't Get the Win

A Winning Well post with David Dye

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 most important 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.

The Power of A Second Chance

The planners of the 2015 National Speaker’s Association Influence conference had every reason to believe he was up to the challenge. After all “Sam” had just received the coveted CSP (certified speaking professional) certification (proving he was a seasoned speaking master). But as Sam took the stage in front of 1700 of his speaking peers for his five minutes of NSA fame, he went blank. After a few stumbles and restarts, he uttered the words that drew an audible gasp from the supportive crowd, “I knew this would happen.”

He’d just committed professional speaking sin #37 “When you screw up, for God’s sake don’t draw attention to it and make it worse. Keep going.” We all were watching our worst speaking nightmare play out before our eyes. Nothing worse than bombing in front of your professional community.

By Tuesday morning so much was going on, our brains were full, and “Sam’s” five minutes of angst had faded for most of us. What happened next sent tears down my face (I looked around it… wasn’t just me).

The music blared and large screens spread the message, “Welcome to Redemption Island.” The screens then REPLAYED that horrible moment where “Sam” had let his inside voice out, “I knew this would happen.” The MC announced, and “We are here to give him another shot.”

The crowd went wild.

He gave the speech. Flawlessly. He ended with thanking his peer who had encouraged him to give it another go, in fact he said “I love you.” (There’s nothing more powerful at work than peers who truly love you-with a little “l” and no sex.)

The Power of a Second Chance

First some context.

In yesterday’s keynote,  Mel Robbins described the NSA like this “It’s like you’re going camping by yourself and stumble upon a huge party down by the river with all kinds of people just like you who invite you to come play” (I may be paraphrasing, but that’s close… please don’t quote me, quoting her). So what’s surprising is not that they got to this answer, but how few other organizations I’ve been a part of would have handled it this way.

Why it worked.

1. No one judged

Okay, okay. Who knows, there might have been someone. But I watched the hush come over the crowd like a wave at a large stadium. I’d be willing to bet my next keynote fee that 98% were in his court. I’d venture to guess there were at least 100 prayers lifted up in his direction. There was no scolding. No, “We trusted you with a coveted spot” speeches. No, “Don’t ever do that again pep talks.” Or stories of “a long recovery.” It was more of “Well, that happened. It sucked. Let’s figure out how to move on.”

2. They let him try again.

Risky. If he had blown it again, it would have been a nightmare for him, and sent questions about the certification process. The meeting planners knew the risk. They went there anyway.

3. He was willing to.

It would have been easier to have a few drinks, call his wife, and obsess over this for the next two decades. He took the risk of getting back on the stage, and trying again.

4. He worked hard.

I don’t know how many times he practiced, but I’d be willing to bet my NEXT keynote fee, that he left nothing to chance. A humbling experience makes us stronger.

5. They acknowledged success.

A standing ovation.

What could have devastated his confidence, became a career highlight. I’ll bet somehow the moment of 1700 peers saying “I understand” will be in his “best of” highlights reel.

Failure feels like an island.  Can you imagine what would happen if we started with finding opportunities for redemption?

There’s awesome power in winning well.

Let it be so. #winningwell

How Not to Screw Up When You've Been Screwed Over

When I heard his story, I wanted to scream with him and for him. But screaming at water under the bridge just brings more rapids. I paused for what was an uncomfortably long time. Then, I whispered, “I know this hurts. But you have to stop. Kick and scream and get it all out, and then take a deep breath and take off on the high road.”

It’s true that John didn’t deserve this. Passionately devoted to the company mission, he’d invested years of hard work and extra hours. His team teased that he bled the company colors. There’s no other way to say this. He’d been screwed. The details don’t matter. You can fill them in with your own history or imagination.  What matters now is what he does next.

5 Ways to Respond When You’ve Been Screwed Over

The truth is everyone is watching your reaction. Chances are most folks know that what just happened wasn’t fair.  Handling this disappointment elegantly will foster deep respect.

1. Stop Talking

Not to everybody–but chose your words and your audiences carefully. Your angry words will travel faster and farther than you ever thought possible.

2. Don’t Be a Blamer

Accusations make terrible leadership apparel.

3. Don’t Give Up

If you fold your tent, the bad guys really win. Stay committed to the cause and to your career.

4.  Channel Your Energy to Create Something Extraordinary

You’re fired up. Use that powerful emotional energy to fuel your creativity and your next stand-out move.

5. Let Your Anger Inform Your Leadership

When the time is right, step back and assess what really happened here. Make a vow to yourself to never screw over anyone in the way you’ve been screwed.

This is more than lemons and lemonade. Your team is watching. Your brand is at stake. Respond as the leader you are.

How Not to Screw Up When You’ve Been Screwed Over

When I heard his story, I wanted to scream with him and for him. But screaming at water under the bridge just brings more rapids. I paused for what was an uncomfortably long time. Then, I whispered, “I know this hurts. But you have to stop. Kick and scream and get it all out, and then take a deep breath and take off on the high road.”

It’s true that John didn’t deserve this. Passionately devoted to the company mission, he’d invested years of hard work and extra hours. His team teased that he bled the company colors. There’s no other way to say this. He’d been screwed. The details don’t matter. You can fill them in with your own history or imagination.  What matters now is what he does next.

5 Ways to Respond When You’ve Been Screwed Over

The truth is everyone is watching your reaction. Chances are most folks know that what just happened wasn’t fair.  Handling this disappointment elegantly will foster deep respect.

1. Stop Talking

Not to everybody–but chose your words and your audiences carefully. Your angry words will travel faster and farther than you ever thought possible.

2. Don’t Be a Blamer

Accusations make terrible leadership apparel.

3. Don’t Give Up

If you fold your tent, the bad guys really win. Stay committed to the cause and to your career.

4.  Channel Your Energy to Create Something Extraordinary

You’re fired up. Use that powerful emotional energy to fuel your creativity and your next stand-out move.

5. Let Your Anger Inform Your Leadership

When the time is right, step back and assess what really happened here. Make a vow to yourself to never screw over anyone in the way you’ve been screwed.

This is more than lemons and lemonade. Your team is watching. Your brand is at stake. Respond as the leader you are.