In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that
have shaped their business philosophy.



CEO, Salesforce.org


Background:  

Salesforce.org is the philanthropic arm of the cloud computing company Salesforce. Based in San Francisco, Salesforce.org seeks to improve communities through technology, people and resources. Salesforce originated the 1-1-1 Model, which dedicates 1 percent of Salesforce’s equity, 1 percent of its products and 1 percent of its employees’ time to giving back to communities.

The Mistake:

When I was in high school, I was one of the best runners in the state. I put a tremendous amount of pressure on myself to win. I was so afraid of losing, I’d stay up at night because my adrenaline was going.

This one race wasn’t that important. I probably had half a mile left in a three-mile race. I was in the top six, but I was so afraid of losing or disappointing my coach. I felt like I was losing steam—that happens in and out of a race.

I literally fake rolled my ankle, so I’d have an excuse to not lose.

My coach came over and said, “It looks OK to me.”

There was such a fear of losing and letting people down. When I look back, I take that back with me. I take it back to the office and I talk to my kids about it.

I was afraid of not winning, so I finished in last place. The irony of that is profound, once I pulled back. It’s so ironic. I was so afraid of not winning the race, that I actually did exactly that. I didn’t even finish the race.

I was afraid of not winning, so I finished in last place. 

The Lesson

In the business world, when I’m talking to my team … they’re under incredible amounts of stress. They’re asked to produce an output in a short timeframe. The way to get them to do their best is to take that focus off of being wrong or failing.

Just do your absolute best, and you can sleep at night. Even if you’re 80 percent right, that’s better than panic and failure. Literally, the whole team calms down and relaxes. It’s like, “I’m doing my best, doing 80 to 90 percent right. That’s the best I can do in the time constraint.”

I had two keynotes (at Dreamforce, the annual conference put on by Salesforce) with new messaging about what we’re doing, in front of an audience that’s critical. … You have to have a thick skin. People are going to criticize those who put your hat in the ring.

I think a lot of people allow their anxieties to overwhelm them or put pressure on themselves. So they don’t get in the ring at all. They’re afraid of not succeeding. Then by definition, you’ve set yourself to do what you feared.

Follow Rob Acker on Twitter at @Rob_M_Acker

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