Why You Need a Strong Second-in-Command

This is the second post in our ongoing series on leadership, inspired by Ryan Pinney’s recent LinkedIn articles.

No time to read? Watch our video overview:

Today’s business culture celebrates the strong leader: the entrepreneur who built a billion-dollar company from nothing, or rescued an existing company from debt and obscurity.

From Steve Jobs to Jeff Bezos, Mark Zuckerberg, and Elon Musk, we’re obsessed with the idea of a visionary who single-handedly changed an industry. Of course, Apple, Amazon, and Tesla aren’t one-man shows…and that’s the point.

Somewhere along the way, we forgot that none of the “great men” of history got there alone. Headlines get more clicks when we turn a business’s story into a hero’s journey. It makes the story more dramatic and relatable – we, the audience, can each imagine ourselves in that hero’s corner office. It’s much less glamorous to imagine ourselves in Zoom meetings.

But there’s tremendous value in having a strong second-in-command (2iC). Real leaders not only understand this, but depend on it – and actively seek out people with strengths that complement their weaknesses.

The best executive is the one who has sense enough to pick good men to do what he wants done, and self-restraint to keep from meddling while they do it.

If you’re a one-man shop, you might be tempted to skip this post. But in our business, there’s always someone behind the scenes. It might be carrier representatives, the technology vendors who provide you with online tools, or a BGA (that's us!). These folks are your 2iC, running things in the background so you can grow your business. With that in mind, you can apply the criteria below to your current partners and vendors to make sure they’re focused on helping you grow.

Because as we’re about to find out, the people you surround yourself with are the key to your success.

4 Ways a Strong Second-in-Command Makes You a Better Leader

  • They give you confidence. When you know your 2iC can deliver, you’re more likely to seek out partnerships and opportunities. It’s also good to know they have your back whether a project succeeds or fails. As our Candi Brundage says, “I admire those who can continue to push forward even if they have many failures. I think when they finally achieve their success, it’s all the more meaningful.” That’s the kind of attitude and support you want.
  • They let you focus on the big picture. Imagine how little time you’d have for long-range planning if you had to train new employees. And sign off on timecards. And write all the company disaster and evacuation plans. A good second-in-command can do (or further delegate) all this for you.
  • They give you the time and space to dream…or refocus. You can’t be “on” all the time. You have to be able to retreat and unplug to keep your physical and mental health in top shape. A strong #2 lets you do this without worrying about the business (which would destroy the whole point of downtime).
  • They give you a sounding board for ideas – and often sharpen or deepen your own. Here at Pinney, Ryan depends on Katie Cumalat and Tracy Meier to help sift the good ideas from the bad, make the good ideas better, and bring different perspectives to the table: “When the three of us discuss issues, we often look at many more factors then just the bottom line or a particular employee. We’re all trying to come up with the best decision and outcome for all involved.”
If you want to do a few small things right, do them yourself. If you want to do great things and make a big impact, learn to delegate.

4 Real-World Examples

Now let’s look at a few real-world examples that show how much more you can get done with a strong 2iC.

  • Pershing and Patton. In Ryan’s favorite example, we see how having a great #2 keeps you humble and focused on the big picture. General John “Black Jack” Pershing chose George Patton as his personal aide because he saw Patton’s potential. His instincts were right – Patton became one of the best generals in modern history. Patton later acknowledged how important diverse points of view are to leadership: “If everybody is thinking alike, then somebody isn’t thinking.” Sometimes leadership means putting the right person in the job, even if it’s not you.
  • Catherine the Great and Grigori Potemkin. Under Catherine’s rule, Russia expanded…a lot. Rather than try to personally govern it all herself, she delegated authority in newly annexed territories to her lover (and likely secret husband), Potemkin. While he did things like build cities, roads, and military outposts, Catherine focused on foreign policy.
  • Ronald Reagan and George H.W. Bush. Prior to the 1980 election, some thought Reagan should pick former president Gerald Ford as his running mate. But when Ford told the press he preferred “something like a co-presidency,” Reagan looked elsewhere. (Source: CNN) He chose Bush, who did the grunt work of chairing task forces and working to improve America’s standing in Europe, Asia, and the Soviet Union.
  • Steve Jobs and Steve Wozniak. These two high-school friends both loved tech, but whereas Wozniak was a great inventor, Jobs had the business sense, drive, and ambition that made Apple what it is today. Steve Wozniak said of Steve Jobs “He always wanted to be one of the important people and had a focus that there are very few people that drive the world forward.” (Source: Washington Post)
Surround yourself with the best people you can find, delegate authority, and don’t interfere as long as the policy you’ve decided upon is being carried out.

How to Choose a Strong Second-in-Command

So how do you go about picking a 2iC?

Here are some qualities to look for:

  • Comfortable in the background. Not all personality types make a good 2iC. Can you imagine any of the Kardashians in the #2 spot? As another example, Vice President Aaron Burr refused to support President Thomas Jefferson after the House of Representatives chose Jefferson in their election tie-breaker. Ask your 2iC candidates how they handled a tough loss, and look for signs they moved on without any bitterness.
  • Practical problem solver. As the leader, your job is to think big. But as the 2iC, their job is to implement your vision. They need to sweat the small stuff without letting the small stuff derail your bigger plan.
  • Honest and tactful. You’re relying on this person to tell you the truth. They may also be privy to information you don’t want everyone in the company knowing. Your 2iC needs to be discreet, handle awkward conversations smoothly, and most of all, give it to you straight. A little role-playing might help you suss out whether someone is up to the task: would they tell you if you have spinach or lipstick on your teeth?
  • Calm demeanor. This doesn’t mean they’re a pushover or too scared to smack you upside the head with an unpleasant truth. It means their demeanor helps you stay calm and focused. They show up and do what's needed, and they do it without tantrums, complaints, or excuses. Bonus points if they do it cheerfully, like Dopinder the cabbie in the Deadpool movies or Ned in Spider-Man: Homecoming.
  • High emotional intelligence (EI). Your 2iC has to be able to read a room and pick the right moment to offer opinions, fact checks, or reprimands. They also have to be able to watch your team members and sense the mood to be able to report back to you later.
  • Real-world experience. In our office, the feedback Tracy and Katie give Ryan comes from experience. They’ve sold insurance, so they know exactly what the process entails. They train and review employees, so they see what parts of our process work and which parts need help. So they’re able to give great feedback on prioritizing projects, bumping up the ones that help team members and our partner agents most, even if those projects aren’t the sexiest.
Hire people who are better than you are, then leave them to get on with it . . . Look for people who will aim for the remarkable, who will not settle for the routine.

Ready to Build Your Team?

If you already have a team, start looking for potential #2s. Not planning on expanding or promoting anyone right now? That's okay. You have plenty of time to watch and make character assessments before the time comes to make that choice.

Ryan suggests looking for people who aren’t just your Mini-Me. “I see the personal benefits of this,” he said, “with Tracy and Katie both bringing skills and abilities I don't have to the table.”

As we look ahead into the next century, leaders will be those who empower others.

If you’re a lone wolf who loves the limelight, think about what you could achieve with help. Could you spend more time on sales if someone took care of admin and marketing? Could you sell other products if you had more time to get familiar with them?

Asking for help can buy you that time.

Is the idea of sharing your ideas and responsibility still scary? You don’t have to do it all at once. One of Tracy’s favorite leaders, business coach Rachel Hollis, explained how hiring help as an investment in the business took that business to the next level: “I challenge you to weigh it [the expense of hiring help] against the level of content we’ve been able to push out into the world in the last five years. I wouldn’t have been able to do a tenth of this work if I hadn’t had help.” (RISE podcast, episode 96)

That’s how a lone wolf grows into a true leader.

Leadership is the art of getting someone else to do something you want done because he wants to do it.

That's our quick look at why you need a strong second-in-command!

Do you have a second-in-command...or two or three? How did you know they were the right people for the job? Tell us in the comments!