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

Canadian military leaders need what they call their 2iC, or deputy, to be a better version of themselves. So do you.

learn more about Dave Maney

By Dave Maney

Anthony Bolante | Reuters
Microsoft chairman Bill Gates (L) speaks while Microsoft President Steve Ballmer listens during the Fourth Annual CEO Summit at the software giant's headquarters in Redmond, Washington, May 24. More than 160 CEOs from the world's top 1,000 companies are m

Opinions expressed by Entrepreneur contributors are their own.

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.

Related: How to Add Senior Management to Your Startup Without Losing Your First Team

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.

Related: 6 Traits of Exceptional Military Leaders That Apply in the Business World

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.

Related: 3 Life Lessons From Steve Ballmer's Rousing Graduation Speech

Dave Maney

Founder and CEO of Deke Digital

Dave Maney is a national economic and financial writer and commentator and founder and CEO of Deke Digital, a content-based digital media and marketing services company. He writes about the economic future for the Daily Beast and appears weekly with Neil Cavuto on the Fox News and Fox Business News networks. He is a three-time entrepreneur, having successfully founded and led a broadband technology services company, a middle-market merchant bank and now Deke Digital.

Related Topics

Editor's Pick

Everyone Wants to Get Close to Their Favorite Artist. Here's the Technology Making It a Reality — But Better.
The Highest-Paid, Highest-Profile People in Every Field Know This Communication Strategy
After Early Rejection From Publishers, This Author Self-Published Her Book and Sold More Than 500,000 Copies. Here's How She Did It.
Having Trouble Speaking Up in Meetings? Try This Strategy.
He Names Brands for Amazon, Meta and Forever 21, and Says This Is the Big Blank Space in the Naming Game

How to Detect a Liar in Seconds Using Nonverbal Communication

There are many ways to understand if someone is not honest with you. The following signs do not even require words and are all nonverbal queues.

Business News

American Airlines Sued After Teen Dies of Heart Attack Onboard Flight to Miami

Kevin Greenridge was traveling from Honduras to Miami on June 4, 2022, on AA Flight 614 when he went into cardiac arrest and became unconscious mid-flight.

Business News

Jake Paul and Lindsay Lohan Fined $400,000 for 'Illegally Touting' Crypto

The SEC just disclosed that eight celebrities agreed to a massive settlement without admitting guilt.


After Early Rejection From Publishers, This Author Self-Published Her Book and Sold More Than 500,000 Copies. Here's How She Did It.

Author Karen Inglis breaks down the strategies and tactics you need to generate awareness and sales for your self-published book.

Business News

Would You Buy Maggie Murdaugh's Monogrammed Snake Print Pillows? Items From the Murdaugh Family Home Are Going Up for Auction

The sale comes just weeks after Alex Murdaugh was sentenced to two consecutive life terms for the June 2021 murders of his wife, Maggie Murdaugh, and son Paul Murdaugh.