Why You Need a Strong Second-in-Command

My last few posts have focused on what you need to be a leader. This time, I want to talk about someone else – the person who just might be the most important aspect of your success. 

In today’s business culture, we tend to focus on the success of a single individual: the solopreneur, the visionary, or the iconoclast. It’s inspiring, but also misleading. Because whether we’re talking about Elon Musk or Jeff Bezos, we all know they didn’t get where they are without help. I’m not talking about mentors, coaches, or teachers, either – I’m talking about the person who takes their ideas and makes sure they happen. 

"No person will make a great business who wants to do it all himself or get all the credit." - Andrew Carnegie

Being second-in-command isn’t a sexy job title, but it’s more important than we give it credit for. Let me give you a few examples to show you how important a second-in-command can be: 

• Genghis Khan may have created history’s largest contiguous empire, but his general and strategist, Subutai, conquered most of the territory that put him in the record books. 
• Inspector Gadget had go-go gadget arms, but Penny was the one who did the legwork to solve their cases. 
• Mark Zuckerberg may have invented Facebook, but Sheryl Sandberg made it profitable. According to her Forbes profile, during her tenure as COO, she took the company from a $56 million loss in 2008 to $18.5 billion in profits in 2019. Whatever you think about how she did it, it’s hard to ignore those results. 

This is a totally different dynamic than you’d have with a partner. A second-in-command works for you, but you’re depending on them to be as invested – or more invested – than a partner would be. That’s what makes this relationship so complex and important. 

My Real-World Example: Pinney Insurance 

I see the personal benefits of having a strong second-in-command every single day. In our office, I turn to our VP of Sales, Katie Cumalat, and VP of Operations, Tracy Meier. These ladies bring skills and abilities I don’t have to the table.  

You might be thinking those skills and abilities probably include softness or empathy – something to balance out my practical side and military background. But that’s not the case at all.  

In fact, what I appreciate so much about Katie is her ability to be a shrewd and calculating businesswoman. And when I say that, I’m not necessarily talking about money. Whenever we discuss a project, Katie’s analytical mind automatically takes both big-picture and detail-oriented factors into consideration.  

Katie has internalized these considerations so effectively that she can point out issues or points of view I’m overlooking. Where I tend to push for go-big-or-go-home projects, Katie is more likely to recommend I tackle something less glamorous…but that would better serve our partners or agents right now.  

"Don't tell people how to do things, tell them what to do and let them surprise you with their results." - George Patton

As for Tracy, if you know her, you know why our team loves her. She’s incredibly patient – more so than I am. She’s also incredibly compassionate, but at the same time, she doesn’t allow anyone to take advantage of her or the business. She never tolerates sloth, laziness, or someone who can’t get the job done.  

I depend on Tracy to have an accurate gauge of how people in the company are feeling, when and how they need help, and what we need to do to create a happy, healthy place to work. She has a knack for getting to the root of a problem and fixing the underlying cause rather than the problem’s symptoms. 

Both Tracy and Katie can make hard decisions. They don’t let “false empathy” or those trying to elicit sympathy from their situation stop them from making those decisions. They also have no trouble disagreeing with me (trust me on this one).  

In short, they make me a better leader – and give our company a much better and more successful team.

5 Qualities of a Strong Second-in-Command 

A lot of advice out there suggests you pick someone who has strengths you lack. But it’s not as simple as picking someone who’s introverted if you’re extroverted, or insanely focused if you have ADHD. Those traits might be helpful, but you need a base skillset that goes much deeper. 

Here are some traits to look for: 

• Someone who’s been in the trenches. You want someone who’s experienced what your team members will experience – or who’s willing to do that now in order to get the necessary perspective. Take David Bronczek, for example – he’s the former president and COO of FedEx, who served under chairman and CEO Frederick W. Smith. He started as an hourly employee in 1976, then moved into operations and management and, finally, the C-suite.  
• Someone who’s organized. The buck is going to stop with them on a lot of issues, and you have to trust that they’ve got things under control when you’re out of pocket. 
• Someone who’s calm. We all get upset, but you need someone who can keep anger and frustration under wraps in front of the team. They also need to deal with stress in a healthy way. Look for someone who has interests and hobbies outside the office to help counter-balance work stress.  
• Someone who can solve problems creatively. If your agency’s goal is to sell 100 policies by the end of the month, the obvious way to do that is to hit the phones hard. But what about offering a bounty on up-sells that bring in additional premium? What about reaching out to lapsed policyowners and asking them to re-up? What about having a contest to reward your top sellers? What about having a goal (like a party, in non-pandemic times) everyone can work toward? A good second-in-command will use creative solutions – not just brute force – to get you where you need to be. 
• Someone who’s honest. The hardest part of being second-in-command is giving honest advice. It takes strength of character to tell the truth, even when doing so is going to cause trouble. It’s not easy to tell someone they’re wrong, or to stand your ground when challenged. A good second-in-command knows when to do both of those things…and when to compromise.

"Delegating means letting others become the experts and hence the best." - Timothy Firnstahl

 There’s another quality that’s hard to define but equally important: is this a person you enjoy spending time with? Imagine all the hours you’ll spend in meetings, on phone calls, or at conferences together, talking about the business and your industry at large.  

You want to be able to connect over these things, like Elon Musk and former Tesla CTO JB Straubel did during a 2003 lunch. When they realized they were both interested in finding a way to use lithium-ion batteries in transportation, they found a way to make it happen – and made history. 

No Man (or Woman) Is an Island 

If you work alone – and you’re still reading this – you might be thinking none of the above applies to you. 

But is that really true? 

Think about your carrier reps. Think about your BGA, if you have one. They don’t work for you per se, but they’re a vital part of your business. They make things happen on your behalf. While the relationship isn’t as close as a second-in-command, it’s still a relationship – or at least it should be. 

Whether you have a COO or work alone, take a look at who fills the role of a second-in-command for your business. If they’re killing it, let them know. If they’re not, create a plan to build the skills they’re missing, or consider finding someone better suited to the role. This step is worth your time, because as I’ve learned, the people who support you are often the most important factor in your success. 

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Ryan J. Pinney, LACP is a twelve-year MDRT member with twelve Top of the Table qualifications. Recognized for using innovative technologies to drive insurance sales, streamline the application process, and speed up underwriting, Ryan has been honored by AdvisorToday as a “4 under 40” Financial Advisor, by LifeHealthPro Magazine as one of the “24 Most Creative People in Insurance,” and as a National Association of Independent Life Brokerage Agencies (NAILBA) ID Twenty award recipient. Utilizing a wide array of digital marketing tools and home-grown technology, his agency sold thousands of policies direct-to-consumer over the internet last year. Ryan is also active in the industry, where he has served as National Trustee for the National Association of Insurance and Financial Advisors (NAIFA) and Divisional Vice President of the Million Dollar Round Table (MDRT).