Hootsuite’s Ryan Holmes shares the two incompatible skills leaders need to get right


I started my first digital agency out of my apartment — building web and marketing tools for other companies. Initially, I was the only employee. I rolled out of bed each morning and started building. Over the years, we slowly grew to more than a dozen employees, before coming up with a tool to monitor multiple social media accounts, all from one dashboard. It became known as Hootsuite, and I spun it off into a separate company.

In some respects, everything has changed from those days. Hootsuite now has more than a dozen offices around the world. We’re an industry leader in the social enterprise market and work with 800 of the Fortune 1,000 companies. I have a whole team of brilliant senior executives to advise me.

Experiencing both sides of the coin — as a solo entrepreneur and as head of a big company — has been a unique education on the skills needed to be an effective leader. The interesting part to me is that two of these skills — at least, on the surface — are almost completely incompatible. But finding a way to make them work together turns out to be super important. For other leaders out there, here’s a few thoughts on this supremely important balancing act.

Jack of all trades, master of some

The most critical lesson that I carry with me is the importance of being a jack of all trades and master of some. As the CEO of a tiny company, this is a matter of necessity. To get off the ground, I had to learn — largely on the fly — about nearly every facet of running a business: product and engineering, sales and marketing, accounting and finance, customer service and client relations, human resources and more. The process of building a business from the ground up truly represented a mini MBA for me. In hindsight, this was actually a luxury that a lot of my peers — who dove right into leading fast-growth, venture-backed companies — never had.

I’m not saying I was an expert coder or sales guru. But I learned enough to be dangerous. I understood enough product development to vet the developers I was hiring. I had learned enough about sales to hop on calls with key customers and drive a deal home. I learned how to make a compelling pitch to investors. Really, I had no choice. Either I gained a basic competency in these areas or the company died on the vine.

In the end, these oppositional skills — knowing enough to be dangerous but knowing when to delegate — continue to serve me as a leader today.

Early on at Hootsuite, for example, we didn’t have an advertising budget to promote our social media management platform … and I had no training in rolling out a global marketing plan. But we noticed that an unusually high percentage of our users were from Japan. So I got on a plane for a guerilla media tour — speaking at conferences, chatting with reporters, even talking my way into a meeting with one of the country’s biggest phone makers. By the end of it, we had cemented our place in the Japanese market, which remains one of our key customer bases. I learned on the fly, mainly because I had to!

To this day, it’s invaluable for me to be able to engage with my product team, sales leadership and marketing squad in a knowledgeable way — understanding their challenges and limits from the inside and being able to lend insight.

The humility to know when to delegate

Eventually, though, I also learned an equally important lesson and paradoxical lesson. As you move beyond the early startup stages, the quickest (really, the only) way to accelerate growth is to aggressively delegate and not try to do everything yourself. As soon as you’re able, in other words, hire people who can do specific jobs better than you can.

As Hootsuite grew, and we suddenly had millions of users around the world, I had to learn to let go — to focus on my strengths and find capable people to do the things I wasn’t good at. I like sales, but don’t want to live on an airplane, so I hired someone to head up that group. We still had a fledgling sales org when I brought in a CRO to help us handle financing and operations as we scaled globally. With plenty of past experience building global teams at major companies, Steve Johnson quickly grew our squad and set us on course to target huge businesses.

I was still able to focus on my core competencies — product and marketing — but bringing capable people into the picture early on enabled us to grow exponentially, far outstripping anything I could have done alone.

In the end, these oppositional skills — knowing enough to be dangerous but knowing when to delegate — continue to serve me as a leader today. It’s about having the confidence to roll up your sleeves and tackle any job yourself, but also having the wisdom to see the talents of the people around you and recognize that together you’ll go farther. The blend of general competence and humility isn’t always easy to get right. But I think that knowing when to lean in, as well as knowing when to back off, is a tension all good leaders have to learn to acknowledge and successfully wrestle with.

Syndicated with permission from Ryan Holmes’ Medium account.

Ryan Holmes

Ryan Holmes

CEO @hootsuite, Founder @invoke. I like social, startups, grownups, cycling, am learning to walk on hands and addicted to yoga.

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