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This is one of the most important leadership lessons according to Keith Tanaka.

One lesson every leader should learn

Do you know what famous quote I really don’t like? 

“To do or not, there is no try.” -Yoda

It’s not true. It’s outdated. Trying and failing, and learning to do so with grace and resilience is genuinely a life-long pursuit. 

As a sales leader who came up through the ranks as an individual contributor,
I’m no stranger to disappointment. Being a father to young boys, I fail hard and often as I learn to parent each child according to their own sensitivities and strengths. And of course, anyone who’s married knows that at times, it’s an almost comical practice of trial and error. 

My point is that so often, in both my career and personal life, I’ve found myself having to reckon with the reality of where I am versus where I think I should be, and it hurts like hell. 

This summer, amidst the raging pandemic, I turned on my TV, and CNN’s Anderson Cooper happened to be interviewing Stephen Colbert. (Don’t worry―what I’m about to say has nothing to do with politics!).

In the interview, Colbert told Cooper about how at the age of 10, his two older brothers and father were all killed in a devastating plane crash. 

Colbert then went on to say something that will stay with me forever. He said that since the day he lost his brothers and dad, that he’s strived to learn to, “Love the thing I MOST wish had not happened.”

He then goes on to quote the great author, J.R.R. Tolkien who wrote, “What punishments…are not gifts?” 

It took me a while to digest what Colbert had said. I think so many of us, including myself, could name several disappointments, failures, and events that we’d have an incredibly difficult time reframing so positively that we’d deign to call them “gifts!”

But I digress. Sure, I’ve had my share of triumphs but in equal measure, I think what Colbert said in that interview is the single most important key to success―it’s also the most difficult ongoing lesson of my life. But through the ups and downs, I’ve adopted a few tricks to help me keep my focus, keep moving forward, and as Colbert said, “love the things I wish I most had not happened.” Throughout the coming months in this column, I’ll share a few of the things that have helped me cope and even embrace disappointment and failure along the way. The first one being the gift of curiosity, learning, and time. Let me explain…

The great American artist, Georgia O’Keeffe said, “Whether you succeed or not is irrelevant, there is no such thing. Making your unknown, known, is the important thing.” 

It’s worthwhile and essential to have goals. As a sales leader, I’d be remiss if I didn’t believe that to my core, but it’s just as important to have perspective. 

After a recent disappointment in my personal life, I asked one of my mentors if I could take him to lunch. I needed his advice to help lift me out of my funk and self-loathing. 

Over sushi, I gave him the rundown on my situation, why I thought it was unfair, and how upset and disappointed I felt. He put down his chopsticks and looked me in the eye and said, “Keith. You’re lucky.”

I was expecting a pep-talk or an ego-boost, but his response definitely wasn’t that. 

He said, “You’re not ready. And if this would have happened as you wanted it to, you’d have gone in blind. Consider this an opportunity to have more time to learn and to discover what you don’t yet know so that when you DO get there, you’ll be fully equipped.” 

He helped me change my mindset from “I’m not good enough,” to a mindset of deep gratitude that I have more time to get more reps in, gather more experience, more knowledge, and reevaluate and discover areas where I can grow, improve, and learn from others who have done it before. The perspective and curiosity my mentor encouraged me to embrace in light of my situation replaced my pain with gratitude and respect for the journey. 

Another way I’m learning to embrace curiosity is when it comes to people. There is power in deep connections built with your team. During the pandemic, I made it a personal goal to meet with every single rep in the sales org, one on one, before the end of the year. 

This experience changed the way I lead and interact with my team. Because of it, I’ve now implemented “snack breaks,” a program where our reps are randomly matched with other reps throughout the org, and they meet via Zoom to share a virtual snack and shoot the breeze. Oftentimes, these reps have never met prior―either because they’re on different teams, or because we’re working remotely at the moment. 

I can feel the change already. We are stronger. We are sharing stories, tips, and getting to know each other. People are feeling more and more like they belong, which I believe, is the most crucial aspect to a person’s happiness in the workplace. The camaraderie, in that they feel they can call each other with questions, advice, or to share successes and failures, is priceless. 

Curiosity for our own strengths and weaknesses, getting to know others, and for what life has to offer are my secret weapons, and they’ve been one of the most, if not THE most important keys in my life when it comes to learning to “love the thing I MOST wish had not happened.” It’s the starting point for personal and professional growth, and even for growth and strength as an organization. I believe to my bones that it’s the secret to greatness. The rest? As in, the job titles, the recognition, the money―whatever your goals may be―they will follow. 

“I have no special talents. I am only passionately curious.”

Albert Einstein

Keith Tanaka grew up in Hawaii and now calls Utah home. He’s spent his career in software sales, helping companies of all sizes scale. Keith loves family, food, and fun, especially when it involves surfing and snowboarding. Keith is currently the SVP of Sales at Lucid.

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