Ryan Holmes has always had an entrepreneurial drive.
As a young kid, he washed windows to make money. By the time he was in high school, he saved up to buy used paintball equipment and convinced his parents to let him him start a paintball field on their farm in Canada.
Later he dropped out of the University of Victoria because he didn't want to wait any longer to start another business. He opened a pizza shop in 1998.
"I leased a space and bought equipment using a credit card with a $20,000 limit. I was a one-man show, responsible for ordering supplies, making the pizzas, manning the cash register, mopping the floors, marketing, you name it. It wasn't glamorous work — days were always long — but I was happy," Holmes says in a piece he penned for LinkedIn.
Itching to pursue more ambitious ventures, Holmes taught himself how to code and in 2000 launched a business building websites and digital services called Invoke.
It was during that time that Holmes noticed his customers trying to figure out how to leverage new platforms like Facebook and Twitter for professional purposes. So in December 2008, Holmes created a tool for that. It was so popular among his clients that a year later, he spun it into a separate company, which eventually became Hootsuite.
Today, Hootsuite is a social media management company that has more than 16 million users, including more than 80 percent of the Fortune 1000 companies. The company is currently valued at more than $1 billion.
As founder and CEO, Holmes is doing something right. But he says, as a leader, it's been an evolution for him, from pizza shop owner, to digital agency founder, to head of the corporate C-suite.
"You have to figure out how to be able to effectively communicate with all of those people and ensure alignment so that everybody is heading in the same direction," he tells CNBC Make It. "That has been one of the big learnings and things that I have been focused on."
It's particularly challenging now that Hootsuite has more than 1,000 employees.
"Every multiple of 10 employees you bring in, you are getting further and further away from communicating with people on a one-to-one basis. So your communication just has to get a lot crisper, clearer, in many ways simpler," says Holmes. Today, to reach the entire Hootsuite staff, Holmes has to communicate across geographic boundaries and languages.
Here are three specific strategies Holmes has learned to communicate more effectively — and to ensure his message is heard, comprehended and embraced.
When communicating a message, "In a lot of cases, I start really simply with 'why': 'Why are we doing this?'" explains Holmes. "'What is our purpose? Why are we showing up every day? Why are we doing this versus this?' "
"I think a lot of people jump into 'how' without really explaining the 'why," Holmes tells CNBC Make It. "In many ways, I think I used to jump into the 'how' a little too often, and now I let other people in the organization try to talk more about the how."
You can't expect your message to stay front-of-mind for others for too long.
"I communicate frequently," says Holmes. "As we have gotten bigger, I think more frequent check ins have been important for the team. I loop back to what are some achievements that we have had as an organization and how those achievements have happened, the good news — how does that contribute to the 'why?'" says Holmes.
"So I look for opportunities to try to loop back to our values, to our purpose, on a weekly basis."
"I often take it off of email," Holmes tells CNBC Make It.
"I think we have a lot of different messaging channels now. We have chat, we have social, we have email. People will write big missives in email or in these channels and that is great for crystallization of their own thinking. But if it is a large concept, just say to the other person, 'Great, well, let's get together and talk about this,'" Holmes says.
"The face-to-face nature provides a lot of velocity."
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