How to Be Really Good at Losing

Selling UX

A unique perspective on service UX

A column by Baruch Sachs
September 20, 2021

One program I helped develop and now lead at my company is an innovative, deep-level customer-engagement program that combines design thinking, business-value analysis, and enterprise architecture to help potential clients look at their business challenges in a different way. Rather than focus on features, functions, or even software in general, we focus on helping clients to better understand their business needs and frame them in a way that prevents their seeming insurmountable or like something they could fix only through a massive investment in the wrong technologies.

Overall, this is a highly successful program that has really unlocked benefits for our clients, as well as our own company. In general, our win rate is rather high when we get involved, so many clients want to engage with us—and not just one time but for a longer-term, strategic level of engagement. While that is an achievement for which we are striving, nothing is perfect. So, even when we get involved, we don’t always win. When we don’t win, we often become discouraged and beat ourselves up about what we could have done differently to prevent our losing.

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Although it is important to ensure that we understand the process we followed and, as best we can, why we might have lost, it is also sometimes necessary to understand that we perhaps did not lose as much as we thought we had. In fact, we needed to start reorienting ourselves to focus on what we gained through the engagement.

I get asked, by people across our organization, about what we can do when our engagement does not lead to a win. Some want to know why we engaged, but did not win. Sometimes it’s hard to avoid focusing on the elements that got in our way or to identify situations in which we could have done things differently. In short, it’s hard not to immediately go on the defensive. However, defending a loss is almost never as effective for growth as looking at the lessons you’ve learned from a loss. In fact, losing and losing well is probably the best vehicle for growth, enabling you to win in the future.

Even When You Win, You May Still Lose

I am going to make a bold statement, but one I think will resonate: Winning has never made anyone a better person. Winning certainly helps us see the results of our dedication and hard work, but it rarely provides learning opportunities. Losing, on the other hand, should inspire self-reflection, so we can figure out what we could be doing better. Losing—if we think of it in the right way and internalize the experience productively—should result in a surge in self-improvement.

A couple of years ago, I took up squash. My son had played the sport a little and wanted to play with me. Having never played any sort of racquet sport, the idea was a bit daunting. Being a tall, broad person, I had always played sports that were more suitable for my body type. After watching a few videos of professional squash players, I realized immediately that my body type was not really compatible with playing squash. However, a father’s desire to play with his son overcame my hesitancy, and I decided to take a lesson. In just 45 minutes, I felt crushed. I had never had to move that way. Everything was completely new. I was a complete and utter loser at playing this game. As I drove home, I thought about what I had learned. It turned out that my size gave me a few advantages that I could use against my opponent—if I could just learn how to control the space and the ball. So I kept at it. Two years later, I am a reasonable player, but always looking to improve. What’s more important is that I actually enjoy playing the game quite a bit.

I’m telling you this story because playing squash made me face my demons. I had never felt that I was built for that kind of sport so I had avoided racquet sports my whole life. In a way, I was always winning—simply by never playing the game. Once I started taking an active role in overcoming my lack of knowledge and skill, it became apparent that I could actually succeed. That first step is always the hardest. To take it, we need to become way more comfortable with losing.

Losing, but Still Winning

Innovation involves a lot of losing. I know that completely turns the common view of innovation on its head, but it’s none the less true. I have written before about how the majority of innovation does not involve coming up with new things, but reimagining things that already exist and connecting them in new ways to accomplish something that had previously failed or had never even been thought of. What most people rarely talk about is that a successful innovation typically happens down a road that is literally paved with loss. Even if they do talk about losses, the one piece that needs more discussion is how losing teaches us to deal with the emotional aspects of losing. Losing is a terrible feeling, and it does not get any better no matter how many times it happens. Sometimes that emotion involves realizing you were not as good as you thought you were, so it’s a humbling experience that can be hard to digest.

Sometimes that emotion is all about realizing your ego and arrogance far outstrip the skillset you thought you had. When we believe that we have seen and done things long enough to have risen above the little things that are often necessary for success, we put ourselves at a major competitive disadvantage that permeates throughout everything we do.

To become good at coping with loss, we must first deal with these emotions, which can actually take some time to process. Instead of doing the common post mortems that happen when you lose a project or a customer, spend some time processing the actual emotions that you are feeling. We often tend to skip over that crucial step to learning. I know I sometimes do this still, and it remains the hardest part of recovery.

In general, it is good business practice to learn from losing and to be good at learning from losing. On a global scale, human society is relatively uneasy with failure. Even the word I just used—failure—may have made many of you who are reading this column feel a bit uneasy. However, we should not sugarcoat that word. Instead, we should draw strength from it. I have failed many times and at many things that I have tried to do. Losing has always been and still is tremendously difficult to deal with. I know I do not always handle loss in the way I should. However, as part of the innovation process, we know that learning from loss keeps us agile and enables us to deal with challenges in the future.

Uninterrupted winning is not only a fantasy but one that prevents our being able to manage change. What’s worse, it’s a barrier to our being able to adapt and figure out new approaches that would work.

Learning from loss—and taking inspiration and insights from others who have lost as well—gives us the ability to recover our losses and also embodies within ourselves a tremendously powerful tool. Failure, in the end, creates an exceptional environment for our improvement and ultimate success in life—both personally and professionally. 

Vice President, Client Innovation, at Pegasystems

Cambridge, Massachusetts, USA

Baruch SachsAt Pegasystems, Baruch helps global clients develop new ways of streamlining their operations, improving their customer experience, and creating real transformations—digital or otherwise. Previously, during his 12 years at Pegasystems, Baruch led their global User Experience team and served as the principal end-user advocate for the Pegasystems Services organization in their delivery of user-interface design and user experience to customers and partners. He has led and participated in successful efforts to improve user experience across various industries. Baruch earned his Bachelor of Arts in Professional and Technical Writing and Philosophy at the University of Hartford and his Master’s of Science in Human Factors in Information Design from Bentley University’s McCallum Graduate School of Business.  Read More

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