The CEO of a $2.8 Billion Startup Explains Why He's a 'Terrible Manager'

WebVisions 2005 - Stewart Butterfield
Kris Krug/Flickr
By Jacquelyn Smith

Nobody's perfect. Even super-successful people like Stewart Butterfield, the cofounder of Flickr and chief executive of Slack, have weaknesses.

The 42-year-old Canadian-born entrepreneur recently told Adam Bryant of The New York Times what he's not good at when it comes to being a boss."I can tell people a story that they believe in and get behind. So I'm good at the leadership part," Butterfield said. "But I've always said that I'm a terrible manager. I'm not good at giving feedback."

He continued: "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."

But, he said, if you go into those conversations without any apprehension, people feel at ease. "I've tried to absorb that lesson. I'm not able to practice it 100% of the time, but it's definitely something I've learned," he told Bryant.

He may have things to work on — but for the most part, Butterfield seems to be getting things right.

Slack is one of the fastest-growing business apps of all time, now worth an estimated $2.8 billion — and Butterfield recently graced the cover of Forbes magazine.

Click here to read the full New York Times interview.
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