I’ve often said that running a business is a lot like Monopoly. Except, of course, different people play the game differently. For example, I love to make up new rules and implement twists into the game, whereas my wife and kids are all about following the game’s original instructions to a T. While this might make for some heated moments during family game night, such varying approaches can actually work really well for a strong business partnership between a chief executive officer (CEO) and chief operating officer (COO). Here are some leadership tips based on my own relationship with my COO.

Decisive, Detailed & Goal-Oriented

There are a lot of things that a good COO should be, but a few matters more than the rest. If you’re wondering if someone would thrive in such a role, think about how they’d play Monopoly. My COO, Sarah Shepard, would keep her money in neat little rows (organized), convince me to play by the real rules (process-oriented), and be able to juggle all of the nuances of the game (able to consume information quickly and then act). All of this reflects Sarah’s strengths, which happen to be complementary to my own. This is essential in any good partnership. 

Additionally, a COO should be decisive, detailed, and goal-oriented. When Sarah started with StringCan, she was in an assistant role. Two years in, she asked me for a meeting, during which time she told me she wanted to be our COO within five years. She had an incredibly granular spreadsheet showing where she felt her contributions were at the moment, and how she planned to grow them over that time frame. 

From there, she followed through on her plans, documented everything, and created contingency plans for our business that I never would have thought of in a million years. When the five years were up, I knew she not only was ready to be COO but also that our business and I needed her to be in the role. 

You Must Be Challenged

One of the biggest mistakes I see other CEOs make when choosing a COO is going with someone who is essentially a “yes-person.” It makes sense at first glance to have someone aligned with your vision and plans, but you also need someone who will challenge you. 

As the visionary of StringCan, I’m constantly coming up with ideas I want to implement. But when I bring them to Sarah, she runs them through her own, very thoughtful filter and unique perspective. She considers whether my idea fits in with our quarterly goals, annual goals, our team’s capacity, and more. Oftentimes she pushed back – and I love it. If I’m being honest, though, there are times I get frustrated by this, too. But over time, I’ve come to be grateful that Sarah has spared us from making the wrong decision by challenging me. Every COO should do this. 

Invest In Time & Communication

One of the main focus areas for a COO are the people and Sarah has done an amazing job with focusing on each employee as a holistic human being. She obviously can’t handle everything so a few years ago she brought on an amazing consultant Jane Cebrynski who is our chief well-being officer. Jane meets with our team members to talk through their goals and concerns and to help them improve all areas of their life. We’ve invested heavily into this because we believe that our company can only thrive when our people do. 

Similarly, Sarah and I have established a relationship we invest our time and energy into. It’s the only way such a partnership can work, and it requires great vulnerability at times. For example, we meet every Friday to discuss everything – both business and personal – that is important to us. Sometimes, there are tears. Every time, there’s trust. This is when we work through problems, use one another as a sounding board, and get our strategy worked out. If you want a healthy business partnership, you have to make time and communication a priority. 

When all is said and done, Sarah and I have built trust, respect, and the ability for each of us to lead our company by staying in the lanes in which we’re individually strongest. The result is much more than one plus one. That’s what every CEO and COO relationship should yield, and it can – if you take the time to look for the right traits and choose the right person to be your counterpart.

Want to work with an agency that puts its people and relationships first? Let’s talk!