How to find a second-in-command you can rely on

Face it: you need help, but you can’t entrust your business to just anyone. Here’s how to find a trusted deputy

Two people working on the floor gesturing at sketches

(Alys Tomlinson/Cultura/Getty)

It’s good to be different

“My company, Achievers, would never have become the company it is today without a strong number two. You tend to want to hire people in your own image—people who are strong at what you’re strong at, who get you. But when it comes to a number two, that’s completely the wrong strategy. Your partner has to believe in the mission and share a set of values but needs a completely different skill set. I’m really passionate about the customer-centric side. My number two is really passionate about growing companies, but he doesn’t want to be the face of the company.”

Razor Suleman, chairman and chief evangelist, Achievers, Toronto

Be realistic about your abilities

“The business here is a partnership, so we had a number one and a number two to begin with. But as we grew, it was clear that even between me and my business partner, there was only so much we could handle. Delegation is the one thing entrepreneurs fight as long as we can. Eventually you realize that unless you’re willing to work 24 hours a day, seven days a week, it is inevitable. You need to come up with an effective way to delegate tasks—and not just menial ones, but important tasks—to people who are qualified to execute them on your behalf.”

Keith Carter, CEO, StoneShare, Gatineau, Que.

Lead, don’t manage

“I went into business to build something from nothing; I didn’t go into business to become a manager. Management is a totally different function from entrepreneurship. My last company, the branding agency Espresso, grew very quickly. It was a service-based business, so we had to hire quickly, train quickly and try to get people into the culture quickly. It would have been amazing to have a great number two when that challenge started coming up. There’s so much effort required in just running a business that it becomes a distraction from selling. It’s important for an entrepreneur to have a strong, people-centric number two who is able to oversee these operational factors so the entrepreneur can focus on what he or she is best at.”

Jacquelyn Cyr, co-founder, R3VOLVED, Toronto

Trust your team

“Stop looking at it as giving up power to another individual. The reality is that the CEO is still responsible for the whole organization. If you have a strong, cohesive vision of where you’re trying to go and a team that understands and buys into that vision, the fact that day-to-day operational decisions are being made without you is actually a blessing. Of course, you put checks and balances in place to ensure decisions percolate up to you regardless of whether or not you have a COO in place. In general, you need to know the people you work with and have a common purpose and a set of values you’re operating under. Trust flows from those things.”

Leon Salvail, president and CEO, Gevity Consulting Inc., Vancouver

Wait until you know the business

“Familiarizing myself with all facets of the business really helped me get up and running, and made the company more efficient in the long run. I had to be the marketing department, the payroll department and the HR department for a long time. When it came time to fill a position, I knew what it entailed because I had been doing those jobs for years. Once people did come on board, I could train them and knew what they were talking about. Now I’ve got lots of different departments with department heads, but they all still report to me. I like being involved at every level, big and small, and being in the loop that way.”

Roy Almog, founder andbroker, 2% Realty Inc., Calgary

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