10 Leadership Lessons from Life’s Most Embarrassing Moments

by Alli Polin on February 14, 2017

Everyone has an embarrassing story or two or three. Some people let those flashes of embarrassment turn into horrifying moments locked away never to see the light of day again. Others, once the sting has passed, are embraced.


Over the years, many things embarrassed me, but none stick out in my memory more than a dinner I shared with my smart and insightful friend Blair.
Blair flew across the ocean to visit me, and we met up in Sydney Australia. As a part of our time together, we booked a fancy dinner at one of Sydney’s top restaurants. We spent time at the hotel before dinner getting ready and I chose to wear a simple black dress with a big cut out that exposed my back. It was one of my favorite dresses that I only had an opportunity to wear less than a handfull of times.
Early in our meal, we were already slightly tipsy. We raised our arms and toasted our adventure when suddenly I felt a breeze. My zipper had failed and popped open at the seam. From my armpit to my hip, I was exposed. I quickly wrapped my shawl around myself, but it wasn’t a workable solution. The other diners were going to have a dinner to remember since they were going to see me naked. Crap.
Blair and I strategized and decided to tell our waitress what happened and ask if she could find any safety pins. Five minutes later the maitre d’ came to our table with a small dish of pins for my, uh, little problem.
We headed to the restroom and Blair pinned me as best she could. Luckily it was enough to finish our meal without flashing the other tables. Whew! Not only was it an eventful meal for the two of us, but also for the restaurant staff who all were in on my problem and solution. Thank goodness for discretion (and a good bottle of wine).
It’s easy for an embarrassing moment to become utter humiliation. Trust me, I felt a flash or two when my dress was hanging open. However, the biggest lessons come not by pretending it never happened but instead mindfully embracing your story.
I’ll guess that you have your own embarrassing moments that you’ve managed to endure. The great news is that experience has made you a better leader. No, really.

10 Ways Your Most Embarrassing Moments Boost Your Leadership

You are a survivor.

In the moment, it can feel like the world is spinning. Embarrassment is a powerful emotion, and it can throw you. Instead, when the embarrassment has passed, remind yourself that you got through it. Now you know that you are a survivor and you’ll get through the next challenge too.

You have a great story to share.

We connect to others through our stories. Sharing lessoned learned with your team without a story is, well, not very powerful. Leaders share their stories, even their most embarrassing ones. Show your team you’re human, like them, and make a connection.

You had a memorable moment. Too many days simply pass us by.

As crazy as it sounds, celebrate it. Most of us have lives where one day blends into the next. We’re expert at running on our hamster wheels while our neighbors appear to be doing the same thing. There are too few experiences in life that stick with us, don’t be ashamed of yours.

Your stories hold no power over you.

The stories you tell yourself can keep you deeply stuck. When you cling to your darkest, most embarrassing moments, and replay the horror over and over, you leave no room for growth. As you change your life, you change the story. It’s in your power. Not only can you transform a moment of embarrassment but also any story that’s taking over you life and leadership.

You know the worst most unexpected event won’t throw you off course.

This is a big deal. Many people go through life fearing the unexpected, and you lived through it. As a leader, you’re always dealing with the unexpected and thrown into ambiguous situations. You now have a gift from your embarrassing moments, the gift of knowing the pain is temporary and you can and will keep going.

You laughed at yourself.

The best way to get over yourself and help others move on too is to laugh at yourself. It’s easy to laugh at others, right? With practice, you’ll learn that laughing at yourself is a key leadership skill whether you’re running a business, leading a team, or responsible for your family. It breaks the tension and builds connection.

You let it go.

Replaying crazy events in your mind doesn’t change them. An essential leadership lesson from those embarrassing moments is to let it go. You either learn to let it go or those incidents will eventually define you, and the shame will become a part of who you are.

You learned something about yourself and others.

When my dress was blowing in the wind, I learned a ton about myself, about my friend Blair and about the willingness of others to help. Look for the lessons in even the worst situations and a small part of you might even be glad it happened… eventually.

You don’t live in fear of being embarrassed.

Embarrassing moments suck, but they are unpredictable and unavoidable. You can either live life in a bubble or full-on. Living and leading as your best self means you can’t worry about the potential for embarrassment. Yup, it might happen but truly, who cares? Not you.

You bring compassion for others embarrassing moments.

This is huge. You know the feeling of intense embarrassment and don’t mock others who are going through it. The best leaders bring compassion because they’ve lived through their own less-than-ideal situations too. It’s the marriage between self-awareness and other-awareness that brings out the compassionate leader within you.
Willing to share an embarrassing moment of your own or what you learned from living through it?



{ 17 comments… read them below or add one }

Kate Nasser, The People Skills Coach™ February 14, 2017 at 6:04 am

This post is full of emotional intelligence and truth. I especially like you point about our own embarrassments helping us to develop & share compassion with others.

Embarrassment can be a connector when everyone sees it respectfully. It can show our inner strength to be able to handle it with grace and dignity.

Valuable post with great insight. Thank you!!


Alli Polin February 14, 2017 at 10:39 pm

Thanks, Kate. Leadership without compassion is cruel. Too often we’re cruel to ourselves and others when there is a better choice. Embarrassment is an opportunity, not a blemish on an otherwise perfect record.




Jon Mertz February 14, 2017 at 8:18 am


We learn a lot in life’s funnier moments! It builds our self-awareness and, as you point out, our compassion.

Enjoy life, learn from life!



Alli Polin February 14, 2017 at 10:40 pm

If we don’t allow ourselves to enjoy life, but instead beat ourselves up for every misstep… that would be a sad life indeed.

Thanks, Jon!



Gary Gruber February 14, 2017 at 8:19 am

One reason you are so good at what you do is your honesty, your candor and your ability to use your experiences to teach and coach others. I’ve had so many embarrassing moments over the years that it’s hard to pick just one but here’s one from just a few years ago. I was giving a TedEx talk in Redmond, Washington, and forgot an important slide and it threw me off what I was saying. I blanked for a moment and wondered how to recover and go on. I just stopped, took a deep breath, backed up, regained my balance and continued. I asked a few people later if it was noticeable and they said yes but they liked how I dealt with it. I wasn’t sure if they were just being kind or whether they were being honest because honestly, I felt that I had screwed up. I think what we have to do is acknowledge the situation and find the resources to deal with it best we can. That’s what you did and that’s the best that each of us can do.


Alli Polin February 15, 2017 at 9:08 am

First of all, very cool that you got to share your expertise in a TedEx talk. Would love to hear more.

Your story reminds me of when I used to act when I was in college. If I messed up at all, even the smallest thing, I felt as if a spotlight was on that moment. Most people never even noticed. In your case, they did notice but that wasn’t necessarily a bad thing. When I see someone mess up, have an embarrassing moment, and get through it with grace, I’m inspired. It sounds like you did just that.

Many thanks to you for sharing your story. You’re right – the key is acknowledging the situation and coping. Collapse isn’t a choice.



John Bennett February 14, 2017 at 11:22 am

Great post! Important to Consider as always. I presume you are familiar with Dr. William Glasser and his “Choice Theory.” It’s been quite a while since I read and Considered it; but Choice Theory goes something like thus… We live our lives aligned with the pictures in our mind / head. The key is to consciously make choices of which pictures we have.

Consistent with this post, (1) it’s important to truly make the choices – what’s my response picture to embarrassing situations, my own and those of others; and (2) from any one specific situation, what other pictures get stored as a result. If that were my trousers, I would have pictures of (a) addressing the situation rather than ignoring; (b) always having an ‘OK’ solution; and (c) always having others who can and will help if asked – to list three.


Alli Polin February 15, 2017 at 9:12 am


You always add depth with your comments and I greatly appreciate it. Yes, our response is always within our control even when the event is not. Understanding that we’re always a moment of choice is essential. Life doesn’t simply happen to us.

Fascinated by your example of choice theory. Have read through it a few times and am now hitting google for more. Thanks so much!



John Thurlbeck February 14, 2017 at 5:43 pm

Hi, Alli

Great post, great tools, great practice!

I loved your story and your post. The message is powerful, and that is how I live my life and have done for many years. Once I discovered how to laugh at myself, the rest was relatively straightforward.

You have, however, to strip back the pretensions we all build around ourselves and open yourself up, though not always so physically as you did, my friend!

Love your style, and delighted Blair was there to support you so fulsomely!




Alli Polin February 15, 2017 at 9:14 am

I’m delighted that Blair was there too! Makes it even more fun to think about knowing that she had a view of my face when it happened. Must have been total and complete shock (because that’s what I was feeling.)

You truly have such a beautiful way of embracing your life. Every time we connect I leave our time together with the passion that you have not only for what you do for a living but for the life you choose to live. Yes, laughing at ourselves lightens the load, doesn’t it?

Appreciate you!



Terri Klass February 15, 2017 at 9:15 am

Wonderful post Alli! It is true that embarrassing moments can first throw us for a loop until we regain our footing.
During one of my recent programs I mixed up the names of two of the participants who I really knew but for the moment forgot. I felt so embarrassed and concerned how they would feel. But I just had fun with it and put everyone at ease. Sometimes we just have to roll with our imperfections and mistakes. And this is not the only time this has happened.
Thanks Alli and will definitely share!


Alli Polin February 15, 2017 at 9:20 am


You’re right! Sometimes the best way forward isn’t to hide it but to have fun with what happened. To acknowledge the moment without getting bogged down in it. Bringing it forward and laughing about it showed your participants that you’re fallible, like them, and that’s okay.

You’re awesome by the way. 🙂



Chery Gegelman February 15, 2017 at 12:35 pm


I love imagining you and Blair bonding at an even higher level over this!

I was on a business trip to DC with a woman I had known for only a short time. On our last day in town we were walking and talking and I was so intent on the conversation that I walked into a small revolving door with her. (So small that it was intended for one person at a time!) We got stuck!!! …And have laughed about it for years!


Alli Polin February 17, 2017 at 3:01 am

Oh my gosh, Chery! What a story! I can only imagine how shocked the two of you must have been. Laughing at it definitely takes the weight of the moment away. I’m so glad that you shared this here. I’m smiling just picturing you. You rock.



LaRae Quy February 15, 2017 at 1:20 pm

What a great story! And to your point, stories always get us hooked, right from the beginning! You had the self-awareness to deal with the problem in the right way…essential for good leaders!


Alli Polin February 17, 2017 at 3:03 am

My only real choices were to leave, be distracted for the entire meal by the breeze despite my shawl 😉 or ask for help.

Stories aren’t something we should be ashamed of – we’re all living real, messy, silly, serious, complex lives. It breaks down walls quickly when someone is able to share something beyond the surface shine.

Thanks, LaRae!



Angela Lin February 20, 2017 at 4:49 am

One hundred times yes to this blog post. Embarrassing moments are the source of growth and self-learning. I love your anecdote because even though it truly seems like an embarrassing moment, in the end, it wasn’t that much of a big deal. The staff members handled the situation calmly and the other customers didn’t really make a huge fuss – no one really remembers these situations except yourself.
Another interesting thing I read somewhere – people are naturally drawn to people who have embarrassed themselves. This is because embarrassment is a universal emotion, which mean they automatically relate to that person – one more reason why embarrassing moments may not be as bad as you may think!


Leave a Comment

{ 1 trackback }