Stewart Butterfield (co-founder and chief executive of Slack) in “The Corner Office”

12-CORNER-blog427Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Stewart Butterfield, co-founder and chief executive of Slack, a communication service for businesses. He observes, “If you have no ability to empathize, then it’s difficult to give people feedback, and it’s difficult to help people improve. Everything becomes harder.” To read the complete interview, check out other articles, and obtain subscription information, please click here.

Photo credit: Earl Wilson/The New York Times

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What were some early influences for you?

I was born in a little town called Lund, in British Columbia. It’s like a fishing village. My parents were hippies. They tried to live off the land, so I grew up in a log cabin, and we didn’t get running water until I was 4. The next year, we got electricity. Then we moved to the city, Victoria, British Columbia, so I could go to school.

I was pretty entrepreneurial as a kid. I had a lemonade stand. When I was 12, I arbitraged the price of 7-Eleven hot dogs; I’d buy the ones that are pre-wrapped with the bun and then sell them on the beach. When I was 14, my dad and two of his friends bought an art-house cinema. I worked the concession and figured out that it was better to take people’s orders while they were standing in line before the movie. Plus I got tips.

Did you always want to be an entrepreneur?

I don’t think it ever occurred to me that I wouldn’t be an entrepreneur. My dad became a real estate developer, and that work is usually project-based. You attract investors for a project with a certain life cycle, and then you move on to the next thing. It’s almost like being a serial entrepreneur, so I had that as an example.

What are some leadership lessons you’ve learned?

I can tell people a story that they believe in and get behind. So I’m good at the leadership part. But I’ve always said that I’m a terrible manager. I’m not good at giving feedback. People are like horses — they can smell fear. If you have a lot of apprehension going into a difficult conversation, they’ll pick up on that. And that’s going to make them nervous, and then the whole conversation is more difficult.

If you go into those conversations with no apprehension of any kind, that just makes people feel at ease. I’ve tried to absorb that lesson. I’m not able to practice it 100 percent of the time, but it’s definitely something I’ve learned.

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To read the complete interview as well as Bryant’s interviews of other executives, please click here.

Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times’ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.com that he started in March 2009. In his book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews of hundreds of business leaders. To read an excerpt, please click here. To contact him, please click here.

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