Finding the Right Second-in-Command Is the Biggest Decision An Entrepreneur Will Make

By Dave Maney, Founder and CEO of Deke Digital

The most important decision a chief executive makes is picking their second-in-command. And in a role often associated with outsized ego, the really great business leaders are the ones who take the bold decision of hiring someone who in many respects is better than they are.

Canadian entrepreneurs call their deputy 2iC, short for second-in-command. The term is British military shorthand for deputy commander of a unit, but in Canada it has become a business idiom.

The 2iC concept really captures the spirit of the position better that standard titles do. It has a simplicity and honesty that many titles are missing. Any rough-and-tumble founder knows grandiose C-level titles are hogwash. The nature of almost every startup is that we fight for our very survival daily for the first few years.

In those early years of a company, there’s not a lot of room for pomp and ceremony. We scrap because 95 percent of startups fail. C-Suite titles? Chief executive officer? President? Chief operating officer? Seriously? In the early-startup stages, we often sit at metal desks in a garage shivering from the cold or sweating from the heat. Fancy titles? Give me a break!

Your deputy might be someone who wants to avoid the spotlight — or perhaps someone willing to wait his or her turn in the top job. But what’s more important than the leadership structures taught in business school is to have a 2iC who is better and smarter than you are. In what ways? These, at least.

1. Braver than you

Great founders start things because they have to. They are so filled with conviction, or desperation or both that they have no choice to grind forward. It’s almost a biological imperative. Following a nut like you while you chase your vision, however, requires courage — and someone who believes in the cause. Think how Steve Ballmer supported Bill Gates at Microsoft, taking care of the nitty-gritty business of management, while the founder imagined new ideas.

2. Has a better command of details than you do

Founders tend to be dot-connectors and over-the-horizon thinkers. Great 2iCs are a walking database of practical resources — people, finances, timelines, objectives and tactics. And the real magic comes when they add structure around you without challenging your leadership. This person must fit hand-in-glove with you, and work that closely too.

That’s not going to happen if they’re just like you. Think Bill Clinton and Al Gore. Coming from Arkansas with no Washington experience, Clinton picked the consummate Beltway insider as his vice president. Gore was a policy wonk and the son of a politician who became a U.S. Senator too. Clinton had the charisma, Gore could muster the votes to turn ideas into laws.

3. Is more experienced than you

Your 2iC needs to know the terrain, the industry and the quirks of your business better than you do. Most importantly, a great 2iC is more battle grizzled than you. Think Dick Cheney. When George W. Bush sought the presidency, the Texas governor faced concerns about his experience. Enter Cheney, who served in the White House under Richard Nixon and Gerald Ford, becoming Chief of Staff, had served in the U.S. Congress and was Secretary of Defense. Together, with Cheney as vice president, experience was no longer a concern.

4. Is humbler than you

One of the things that made you a founder was your willingness — even your desire — to put your ideas and your reputation in the spotlight. Most founders are not shy and meek, so finding a 2iC who’s a little comfortable with a lower profile is likely a good thing. That might be someone who wants to be groomed for the spotlight, or someone happy to remain in your shadow. Berkshire Hathaway’s Warren Buffett gets the credit as the world’s best value investor, but behind him is Charlie Munger, who quietly beats the stock market year after year. Munger might have avoided the spotlight, but he has become a self-made billionaire.

Almost sounds like I’m saying you need to find a better version of you… than you. Doesn’t it?

Yes, that is what I am saying! You want a 2iC that makes everyone say, “Is it my imagination, or is your second-in-command smarter than you?” Or, “No offense, but I really prefer working with your 2iC. He / she is terrific.” Your team members should be comfortable turning to your 2iC with their questions and their problems. You want your board members to glance subtly at your 2iC when you tell them something, to visually gut-check that what you said is on-target.

It’s a tall order, of course, because you’re also seeking a second-in-command — not a leader. Many of the kinds of people who meet all the criteria I’ve laid out above are seeking the top slot, and frankly, the one you want is good enough to do it. That’s incredibly valuable, because when it comes time to sell your company, you will have a ready-groomed replacement for you.

In the end, a great deputy is a tool that will help you get the job done right. Archimedes may have preferred a lever in his quest to move the world, but I’ll take a phenomenal 2iC.

Dave Maney is the Founder and CEO of Deke Digital