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Anatomy of a Leader: Dan Kelly, President and CEO, Canadian Federation of Independent Business (CFIB)

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As President and CEO of the Canadian Federation of Independent Business, Dan Kelly often finds himself in the media spotlight commenting on all sorts of issues relating to the small business community in the country.

He’s probably done 5,000 to 10,000 media interviews over the course of his 30-year career with the CFIB. During the pandemic alone, he was averaging about 2,000 interviews a year. 

“I recall those early days, even though I was working from home, I was probably doing interviews, back to back interviews, almost the entire day just trying to explain to the public just how serious the pandemic restrictions were imposing costs on small business,” said Kelly. 

Image: Dan Kelly

But being in the spotlight can be challenging.

“You do have to develop a thick skin. And I will say when I started this job I sure didn’t have one. I took it all very, very seriously. One of the things that helps though is I take my job seriously but don’t take myself seriously,” he said. “So if anyone looks at my Twitter or X feed, they will see just loads and loads of attacks, sometimes on small business, sometimes on CFIB and occasionally on me.

“I don’t take myself seriously and I think that helps. During the pandemic, I had lots of criticism on both sides of the equation . . . I had just some vicious, vicious comments and those ones I’ve got to admit I try to tune out. Luckily, my son who is now 15, he laughs them off whenever I get a death threat or anything else. That does happen . . . I had a couple of death threats myself and those don’t feel good.”

Kelly was born in Winnipeg and lived in Manitoba for the first 30 years of his life. He has a Bachelor of Commerce degree from the University of Manitoba.

“I had always hoped that I would have a career in the foreign service at one point or work internationally. Right after university I went and lived in Japan for a year teaching English, but with a goal of trying to get some international experience and that’s proven to be useful as I’ve been used by the Government of Canada a few times to promote the free trade agreements that we have with various countries. So I’ve often given speeches now over the last several years especially around the Canada/EU agreement. I was a fairly regular speaker overseas to promote the benefits of that both to business in general and to small and medium sized companies specifically,” he said.

Image: Dan Kelly

During university Kelly was heavily involved in politics which was right around the time of the free trade debate. After writing a couple of papers about free trade, he became a believer in the importance of Canada/U.S. free trade. It was a hot debate in the late 1980s with two very distinct sides on that. He got involved in supporting the agreement and the federal election campaign with the free trade debate at the centre.

“So I started to get involved in politics not because of a big desire to get involved in politics but because of a particular issue I felt quite passionate about,” said Kelly. 

After that election campaign, he became involved in a provincial election.

“It was really at that stage that my political views on the importance of business and having a greater voice really began,” said Kelly. “Right after our provincial election I was just finishing up university I was offered a job to go and work for the Premier of Manitoba (Gary Filmon). I thought that was a pretty cool opportunity, one that I shouldn’t pass up.”

Kelly worked as a policy analyst/advisor for about three years in the Premier’s office. At that stage, he began to see the inner workings of government but also the importance of connecting to the business community. At that time he had some meetings with the CFIB while he was working within the Premier’s office.

Image: Dan Kelly / CFIB

That connection eventually led to a job with the CFIB, starting in a junior position as a policy analyst in the Winnipeg office. He has been with the CFIB for the past 30 years. In 2012, after a variety of roles and experiences with the organization, he became its President. Today, the organization has close to 100,000 members across the country. The organization has 400 staff which makes it one of the largest not for profit advocacy groups in Canada.

“One of the reasons we have so many long serving staff at the Federation is because it is one of those jobs where you can go home every day feeling super proud of what you do, that you’re making a contribution, not just to the well being of the organization to which you work but in the betterment of society. And I truly believe that if we can help small and medium size businesses individually and collectively, making it a little bit easier, a little less complicated or a little bit less expensive in some way, we are not just adding value to that business but we’re adding value for employees and for society more broadly,” explained Kelly.

“Supporting small businesses is such a noble goal . . . That’s really been my life’s work and it’s work that I feel super passionate about, just as passionately about today. We’ve made a lot of positive strides but there still is so much heavy lifting left to do to help support and protect small and medium size businesses across the country.

“This is not the job for the faint of heart. You have to bite your tongue pretty hard. You also have to speak your mind fairly plainly. One of the things I think CFIB does very well is it speaks to power very sincerely. We don’t try to be antagonistic. We try to go into every relationship with every political party, every politician with fresh eyes. But at the same time we will be sharply critical. We will call a spade a spade and go after a minister, go after a party if they’re doing stupid things. But on the same day we can then be there working with a government or a party to support them on files which they’re making good progress.”

Politics has been part of Kelly’s life for a very long time. He enjoys working with politicians of different political stripes, finding it intellectually stimulating. But one of the things he doesn’t like is when politicians are so locked into their perspective that they reject even a discussion with someone who may not see it the same way as them.

To relax, Kelly spends a lot of time with his son and watching baseball. He enjoys spending time with his family and traveling as well. Kelly has a fairly big property despite the fact that he lives in a densely populated city like Toronto.

“I spend a lot of time in my backyard, tending to my garden, doing all the landscaping and work myself and that is a good stress reliever. In my job right now, there are very few things that I can actually accomplish and put away in a day or two. Whereas you go to work in the yard and you can actually on Saturday afternoon make some headway and actually see some progress in real time. That doesn’t happen in the lobbying world so I do find it satisfying to scratch another itch.”

Mario Toneguzzi
Mario Toneguzzi
Mario Toneguzzi, based in Calgary, has more than 40 years experience as a daily newspaper writer, columnist, and editor. He worked for 35 years at the Calgary Herald covering sports, crime, politics, health, faith, city and breaking news, and business. He is the Co-Editor-in-Chief with Retail Insider in addition to working as a freelance writer and consultant in communications and media relations/training. Mario was named as a RETHINK Retail Top Retail Expert in 2024.

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