Three leadership lessons from Slack’s Stewart Butterfield

Photo credit: Scott Schiller (Slack)

Last week, I had the pleasure of sitting down for an intimate fireside chat with Slack’s Stewart Butterfield as he was honoured with C100’s Icon of Canadian Entrepreneurship (ICE) award. This award is presented yearly to a Canadian who has played a historic role in technology and innovation, as well as demonstrated a commitment to giving back to Canadian entrepreneurship. Past recipients include Tobi Lütke, CEO and Founder of Shopify, and Patrick Pichette, former CFO of Google.

What Stewart has built with Slack is nothing short of amazing. In only five short years, the product has redefined enterprise communication with tens of millions of active users and a business that is now valued at more than $7 billion.

While many people have contributed to Slack’s success, it’s the leader at the top who makes it happen – and Stewart is one of the best. We can all learn from what he has done and what he’s doing, and here are the top three leadership lessons that stood out for me during our chat:

 #1: Repeat the company vision ad nauseam

The most important thing a leader can do is to make sure that the whole organization understands the company’s vision, priorities, and goals. Yes, this is widely accepted advice that often shows up in leadership articles. However, most CEOs underestimate just how often the vision needs to be repeated so everybody is truly on board. In Stewart’s words: “Repeat the message until you are sick of hearing yourself talking about it.”

#2: Invest in your own growth

Most people are not natural managers, but everybody can improve their management skills. And if the company scales as quickly as Slack scaled, its leaders need to scale equally fast. Such growth is only possible if you are self-aware about your strengths and weaknesses.

Stewart is not only incredibly self-aware, but he also actively seeks continuous feedback on how he can further improve himself. Informal and formal mentors, coaches, 360° feedback from direct reports, and aggregated feedback from the whole company are all tools to help him grow.

#3: Surround yourself with the best team

Great CEOs hire a great team and Stewart is no exception to that rule – it also helps that he is a very good recruiter. Slack made a very interesting decision early on that they wanted to have one of the most diverse workplaces. This was long before diversity was on the radar for most tech companies. They have been doing such an excellent job in cultivating diversity that they have increased their talent pool by many times and have built a team that most companies could only dream about.

Congratulations to Stewart on this prestigious honor. We are all looking forward to seeing what you’ll do with the next five years.

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