The Failure of Certainty

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Certainty is not an indication of truth.¹ In fact, the more certain you are, the less likely you’re right. 

About a year after I was promoted to Director of Sales, I had my first critical leadership crisis. We had finished the year with a great result and the team went home to celebrate Christmas, the new year, and their impressive success. 

They didn’t come back to work until March. They were in the office, they just didn’t do much.

I spent 90 days moving between frustration and anger, righteous contempt and momentary  empathy, but mostly, I was certain I was right. The sales reps weren’t putting in the effort.

Certainty is highly emotional. You’re ready to fight and bite to defend your idea and persuade others to join your side. 

That emotion is a tell-tale sign: you’ve been deceived. You’re not arguing for a truth, an unequivocal, objective truth. You’re arguing a point of view. Your truth in that moment.  

After a multi-week analysis, my boss flying into town, and a half-day meeting, the data bolstered my position: Our shameful performance was self-inflicted. 

The managers and I had already done everything we could to motivate the sales team. We publicly celebrated the few reps working late and putting in the extra effort. We doubled down on tracking metrics. I had difficult conversations with managers weekly. They did the same with reps in one-on-one and team meetings. 

The result? Nothing changed. No amount of carrots or sticks changed anything. 

By early April, I was a single sock that hadn’t seen its pair in years. In the office I felt lost, helpless, and alone. On January 1st, my team was a top-three global sales team. On April 1st, we were the worst sales team. In a moment of reflection, I asked myself a novel question: What if the low effort is not the problem, but a symptom of something else?

Without knowing it, I had given up on being right. Being right didn’t matter. It was time to get curious. We had implemented all the managerial frameworks and best practices, dotted all the ‘i’s and crossed all the ‘t’s, and the team was still floundering. “What else could be going on?” became my mantra. 

After a few weeks, the leadership team answered the question with Vision. The whole office, not just the sales team, did not understand where we were going and how they fit in. Their personal stories, ambitions, dreams, and families had become unmoored from the company’s vision.  The company and the personal stories had drifted too far apart. A darkness had snuck in right under everyone’s noses and like a past-its-prime avocado, we were rotting from the inside out. 

Unlike an avocado, we could fight and beat back the darkness. We became master storytellers that put our local employees at the center of the company mission. We tied their efforts to the success stories of our customers. We began to show how their work was creating more opportunities for everyone – our customers, our partners, the company, and most importantly, themselves. Overtime, a sense of abundance, opportunity, and hope swept back in. We finished the year strong and never looked back. A remarkable turnaround in hindsight. 

There are some moments in life that become your lifelong teacher, instilling you with new lessons throughout your life. Perhaps this crisis continues to teach me because I experienced such an array of emotions - surprise, anger, fear, despondency, hope, pride, and fulfillment.

I do not remember a specific moment of anger, but there were many. So many, that when I recall that period of my life, my memory has mashed all the moments into a well-mixed state of negative emotion. And that emotion is the signal amongst the noise. It does not hide. It will be in full force. And when you feel it – the heat, the anger, the intensity – remind yourself that perhaps you’re arguing just one point of view.  

We do not argue 1+1 = 2. It’s so obvious it doesn’t warrant a spirited thought. We only fight for our story when it is true to us, but not objectively true.


¹From Joseph Goldstein's "Clear Comprehension" discussion on meditation in Sam Harris's Waking Up app. 

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Dave Shepherd

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