This is a start to a rough travel week. I woke up, left for the airport at 4:10 AM, spent the day in our DC office which included a town hall and a ribbon cutting to celebrate our beautiful new space. Hopped in an Uber with two others and rushed to the airport to catch our flight. Delayed. Put on stand by for an earlier flight. Another delay. Then my exceptionally thoughtful CEO was the only person elected from the stand by list to board. He gave me his seat so I could get home to my kids. One and a half hours later, I’m still stuck on the tarmac and all routes to Boston are shut down because of weather. And I get to go to NYC this weekend, and London on Monday. Yup, business travel is not at all glamorous.
With every rainy cloud that prevented me from getting home at a reasonable hour, however, comes a silver lining. Tonight, my gratitude comes from a deep appreciation for the people I work with. Typically, it’s not lost on me how great they are, but tonight one simple observation turned my travel frown upside down.
First, let me explain our executive team. The average tenure of people on our executive team at Rapid7 is 5.6 years. (I removed our Co-Founder Tas Giakouminakis from this average, as he’s been here since the start, and he’d throw the numbers waaaayyyy off). Often asked why a self-proclaimed startup junkie would stay put for 8+ years, my response is simple. “The people.” Sure, I work with almost 1,400 smart, talented and committed people. However, at the gut level, I have two teams that keep me inspired; our incredible people strategy team whom I have the honor of leading, and our executive team who I share company leadership with. Tonight, I write about the latter.
The long tenure of this team, I believe, is a significant indicator of how committed to Rapid7 and each other we all are. Not just in a “please, take my stand by seat” way (which arguably is the kindest thing anyone has done for me in a long while) but in a more meaningful “Hey, we are on this journey together so let’s make the most of the ride” kind of way. With all that time spent together, we’ve supported career milestones and challenges. We’ve lived through each other’s increased responsibilities and scope, as well as stumbles and the inevitable missteps that come with our rapid growth. And because we spend so much time together, we’ve also seen each other through divorces and health scares, as well as the more joyous victories of our children’s accomplishments and the purchase of that car we had dreamed about and worked our butts off to finally earn.
In other words, these are my people. We have a shorthand with each other, and even though we are all different in significant ways, they are just as much family to me as my own blood. When I have a bold idea, they are the people who jump in and help me advance it further rather than roll their eyes at me. When I am struggling with a problem, they are my trusted advisors who I look to for their sound counsel. When I have a win, they are the first to cheer me on. As we each take turns on the high wire, the rest form the safety net below. I am unabashedly my true self with them, without reservation.
Any person would be lucky to work on a team that brings out the best in each other. The fact that this crew forms our company’s leadership team is even more significant to me, however. Of course, we aren’t perfect, and sometimes we drive each other crazy. More often than not, though, we can be found pushing each other to our best work. For every high five that comes with a win, we will also take the time to share constructive feedback to aid each other along. Rather than watch our backs in fear that someone is about to backstab us, we actively seek out each other’s opinions because we know it will result in a better outcome. This mode of operating is deeply rooted in trust, and a whole lot of time spent building something we all care passionately about. And because we all behave this way, we model it for the rest of our company. The bar is set for what healthy teaming looks like, and not surprisingly, we hold each other and our teams accountable for that as well.
Tonight, I sat at an airport restaurant table with two of these cherished colleagues/brothers/friends waiting to learn the fate of our flight home. As we ordered dinner and shared ideas, we mindlessly munched on a communal bowl of chips and salsa. We were in the middle of a conversation about how insecurity leads to risk avoidance, and how detrimental those traits can be in leaders of growing companies. Then Corey looks down, and says, “That’s the mark of a good team…”. Lee and I likely looked at him like dogs with their heads cocked to the side, trying to figure out what he was talking about. “Look at the chip bowl,” he explained. “This is why we are a good team. All that’s left in the bowl are a bunch of broken chip pieces and one good last whole chip. We are all nibbling on the crumbs, and we all avoided that last chip, rather than take it for ourselves.” With all the work I’ve done studying teams and leadership, that last chip observation kind of summed up this team perfectly. It’s about "the we", not "the me".
As I sit on the tarmac tonight, eager to get home and sleep in my own bed, I reflected on just how fortunate I am to work with such an incredible team. We all have strengths, as well as flaws, but somehow, we just seem to bring out the best in each other. THAT is a huge reason why I’ve stayed at Rapid7 for eight years. That, and the fact that when we all got up to head to the gate, the single remaining chip was still in the bowl.