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Stewart Butterfield on leadership: I am a terrible manager

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August 4
3:27 AM 2015

In an interview, the CEO of $2.4B worth Slack app and Flickr co-founder, Stewart Butterfield, admitted he is a 'terrible manager'.

"I can tell people a story that they believe in and get behind. So I'm good at the leadership part," Butterfield told The New York Times earlier this July. "But I've always said that I'm a terrible manager. I'm not good at giving feedback," the CEO of Slack confessed.

He resembled people to horses as both people and horses can sense fear. "The conversation will be more complicated if you will talk to them with anxiety; they will sense it and it will make them nervous", Butterfield explained.

"However, if you take conversations lightly and make them feel comfortable, they will feel the same. Though he's not applying it all the time, he said he's trying to learn it."

Stewart Butterfield is a Canadian businessman. He is named among Time 100's list of "The People Who Shape Our World". He's included in the Forbes annual's "Eight Masters Of Information" and Fortune Magazine's Best Beard in Silicon Valley.

He has investments in other startups such as Etsy, Summify, Rouxbe, 99designs, Flowgram, Thingtonand Bloom Studio.

But before he became a Slack CEO, he co-founded Flickr, an image and video hosting services in 2004. It has an online community and is widely used by photographers and bloggers to share images. Flickr was bought by Yahoo a year after for approximately $30M. Butterfield still is one of the board members as the Director of Product Management.

He built up the $2.4B worth Slack in 2013 in California. Slack is a free group communication app that offers instant messaging and document archives. It includes groups restricted only to members, chat rooms sorted out by topics and private messaging. Slack has tied up with other services like GitHub, Zendesk, Heroku, Dropbox and Google Docs.

Butterfield looked back on his younger years. He would buy the pre-wrapped hot dogs with the bun in 7-Eleven when he was 12 years old and sells them at the beach. When his dad co-owned a movie house, he would take customer's orders and have tips.

His dad became a project-based real estate developer, a job that requires every aspect of the business for only a span of time. After a project was done, he will move again to the other. Although at first, he doesn't have a full grasp of what he wanted to become, he grew up in an entrepreneurial setting.

Butterfield highlights an important point about leadership. He stressed out that initially, you have to learn how to empathize with the people around your workplace. If you do not learn how to do it, it would be hard for you to assess and help them improve.

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