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.

5 Ways To Build Career Resiliency

Bad things happen to good people. Karma doesn’t always show up in time. Even good people may find that the knife in their back sports their own fingerprints. Even the most well-intentioned leaders do stupid stunts from time to time. My time in HR gave me a front row seat to such tragedies. It’s not a matter of if you’ll need career resiliency. It’s when.

Sometimes I could help. Many times, even the most energetic HR fairy dust couldn’t save them. The best I could offer suffering souls during these times was resiliency support.

If all’s well in your world, amen. Please contribute to this community by sharing your own lessons and stories. Brilliant recovery stories strengthen anguished adversity.

5 Ways to Build Career Resiliency

Resiliency is hardly ever about “returning to the original form after being bent, compressed, or stretched.” Chances are that original form had something to do with current predicament. It’s about gathering up the lessons and energy from the potentially crippling scene, and emerging stronger, wiser… knowing you have the fortitude to recover the next time. There’s always a next time.


Your career is a story. Tragic events by nature scream “ending.” Rewrite them as the critical turning point… just before everything got better. Become the author of your own story. _________ happened. That sucked. But then _________. If _______ hadn’t happened I would never have ___________. Spend time considering the possibilities for the next chapter.


Okay, allow yourself to grieve, throw things, and yell at your mirror for a few minutes. Then work on interpretation. Why did this happen? Grab the lessons with eager fists. Hit yourself in the head with them if that feels better. Then try alternative views… “On the other hand, this is great news because____________. Generate as many answers to that question as you can. Put an asterisks next to the ones you most believe.


When the wind is at your back, there’s little need or energy to adjust the compass. Don’t waste this scarce opportunity to let the sails flap for a while and consider your best direction.


The natural scramble is to look for more of the same: a similar role, or industry. Consider all your gifts. Diversity builds future resiliency. Look for opportunities to pivot toward a role that will strengthen and stretch.


Assume you’ll land on your feet and get ready for next time. You’ll face tricky situations again. Take some time to write down your key learnings. Build your network (by giving first). Save some money once you’re able.  Having some cash in the bank is the best way to reduce frenetic grasping and slow down for better options.

Your turn.  Share your ideas, advice and stories on resiliency.