Coffee Conversations: Team


I am maniacal about talent. I know that the right team with a shared vision and a growth mindset can make all the difference. I also know a wrong hire can be devastating. That is why I spend so much of my time scouting talent and recruiting. In fact, if I count it all up, I spend anywhere from 10-30% of my time on talent each week. Sometimes this is hardcore-we have an open position in one of our portfolio companies and we are actively sourcing against a specific set of criteria. In these cases, I am helping to source, interview, negotiate and close. More often this falls into the realm of networking with individuals from different background and skill sets - understanding their roles as well as their unique strengths, challenges and personalities. Then, waiting for the timing to be right to make a match for one of our portfolio companies.

Recently, at least two of these coffee conversations led down an unexpected path. Both of these individuals are experience operators, one male and one female with an age range of 35-42. They both expressed the same desire. Their next role, they want to be a #2 in a growth company, where the CEO is exceptional and someone they can learn from. Neither candidate wanted their next role to be as a start-up or scale up CEO - although both have done this before and are capable of doing so again. They expressed a desire to have a mentor to learn from, someone experienced to help guide them through the next phase of their career.

This was such an unexpected answer that I began to get curious and went further into the “why”. Clearly there was something they felt they were missing. While the details need to remain confidential, I’ll just say the basic takeaway is this: there is a loneliness factor of being at the helm of a chaotic, hyper-scaling business. These experienced operators are expressing a need for an aligned, but objective thought partner to help develop a plan of action when things get rough. And, more than that both expressed a deep desire for learning and for a stronger sense of belonging.

My first level thinking on this was there are lots of ways to fill this gap. Building a good cohort of CEOs to meet and talk in real time about scaling challenges. Utilizing strong mentors and advisors. Finding a skilled performance coach. The trick to all of these is finding people that will challenge you in a meaningful and productive way.

I wonder though is that enough? None of those solutions create the sense of shared vision and collective results that a real team can instill. A team where every member is perfectly aligned and rowing in the same direction. A team that has productive conflict but that at the end of the day always has each other’s back. A team that shares the ups and the downs and ultimately achieves success or defeat together - without individual gravitas or finger pointing. A team that believes in having fun together but also in accountability and high standards. I believe my two coffee companions, were really saying it is hard to have that feeling when everyone is looking to you as the one with all the answers.

The answer, I think, is in sharing the burden.

I believe great leaders must communicate a compelling, confident vision but they must also share the burden of executing that vision. Share the burden of creating a strong, intentional culture. Share the burden of getting the right mix of team members. Share the burden of communicating the goals and objectives through the organization. Sharing the burden means everyone is individually and collectively accountable. Sharing these burdens also means sharing the joy and success of achievement.

So, for my two coffee companions, I have a challenge - don’t go looking for someone else to give you that sense of belonging. Find the next CEO opportunity and create it for yourself and your team.