Ben Chestnut will never forget the day he learned he was a bad leader. The Co-founder and CEO of Mailchimp, the popular email marketing service, had just wrapped up an all-hands meeting that, he says, went about as poorly as it could go. A last minute change to the meeting's location, and a request for employees to turn off their emails, had many staff thinking they were about to be fired. When Chestnut was asked about the company's long-term strategy, he said he didn't have one. "That generated looks of horror," he said during a recent interview at the Inc. 5000 conference in San Antonio, Texas. 

The most startling encounter he had, though, was when a recently hired employee came up to him and told him that he might want to consider speaker and leadership training. "It was courageous for her to walk into my office and say that, but I took it hard. I was in a funk for at least six months," he says. "My wife thought I was angry with her and said she could move out with the kids. That was a rude awakening for me." 

Chestnut soon enrolled in a leadership class and it helped to completely transform his leadership style. The biggest difference? He's no longer a know-it-all, he says. He also learned three important things about becoming a better leader--and difference maker. 

1. More We, Less Me

One of the more important lessons Chestnut learned was there's more to the company than just him. While he's the one who needs to promote MailChimp's culture and purpose, he doesn't have to do everything himself. "I learned to take a step back and let others lead," he says. "That was a big mindset shift." 

2. Share Your Feelings

Many CEOs, Chestnut included, feel as if they can't let on that they're overwhelmed. He was told to open up to his wife and talk about the stress he was experiencing. "This was news to me because I felt it was my job to be the smartest person, and I had to look like I was in control of the business," he says. Opening up did make a difference. "I told my wife that I have no clue what I'm doing and that this was really scary," he says. "Don't bottle it up, let it out."

3. Listen Harder

For years, Chestnut's leadership style was "me, me, me," and he would talk more than he listened. At leadership school, though, he learned that listening makes a difference. He had to stop focusing exclusively on himself and pay closer attention to the people around him. While that can still be hard at times, he's trying to be more attentive. "I'm never a good enough listener, but I try and listen a little harder every day," he says. 

By listening more, acknowledging his feelings and letting others take control, Chestnut has not only made a difference in his own life, but in the 17-year-old company's, too. Mailchimp, which was Inc.'s company of the year in 2017, now has 700 members on staff, more than 16 million customers, and exceeds $500 million in revenue every year. "Every time there's new strategy you have to get rid of old dogma," he told Inc. last year. "I go around and I tell people, 'Remember what I said? I was wrong. It's time to change.'"

Published on: Dec 12, 2018