This is the final post (18) of the Techstars Mentor Manifesto. As with item 17, Jay Batson, a long-time Techstars Boston mentor, nudged me several times to finish this up and wrote a draft from his perspective. Following is item #18 of the Techstars Mentor Manifesto, in Jay’s words.
During one of the Techstars Boston cohorts where I’ve been Mentor-in-Residence, I worked with a 20-something CEO founder (code named Mary) who, shortly after raising a seed round of several million dollars, hired a high-powered exec, granting a significant equity option. This new hire was a commercial hustler (code named Scott), moving quickly and broadly to try to secure customers and partners, including some of the tech industry’s largest companies.
Mary had never managed somebody a decade senior to her and was struggling to manage Scott. Further, Scott tended to work autonomously, sometimes doing things outside his remit that was not well-communicated to Mary. As a result, Mary was worried about how this looked to her board. A massive sense of imposter syndrome started creeping in, especially since Mary felt investors had bet on her, yet Scott was having a notable impact, for better and worse, on the strategy and success of the business.
Mary was concerned that the investors thought she wasn’t being effective. A fear was brewing in the pit of her stomach and she worried that everything was going to come apart.
Pause for a moment. Recall the last time you had a consuming passion. Remember how it felt. Think about that incredibly exciting idea that grabbed you and took over your mind, time, priorities, and emotions. Remember how excited you were as you imagined all the threads of what could be, and how your heart beat faster and your adrenaline surged.
And then … you had an existential crisis. A moment when you feared that this awesome future might come crashing down because of a particular situation or the actions of one person. Your heart beat faster again, but this time out of worry, anxiety, and fear.
I want you to replay your joy and fears again for a moment. Having empathy requires you to feel what the other person is going through. To put yourselves in their shoes and feel their fear. And to not immediately try to fix it. Remembering your own hopes and fears will help you have empathy. And this is critical as a mentor because startups are extremely hard.
In the situation above, I could relate to Mary feeling imposter syndrome. My first venture-backed company was not a big exit, and neither I nor my investors fared well. So I felt some imposter syndrome when founding my second venture-backed company (which, happily, has done well.)
So what Mary needed from me as a mentor was to talk to a neutral third-party who understood how technology companies worked and who had felt the expectations placed on a founding CEO. She needed to talk openly about how she was feeling to someone not on her board or exec team, and to whom she could be fully and safely transparent.
Doing that first allowed us to get around to eventually discussing ways to handle the situation. I reminded Mary that first and foremost, Techstars mentors are here to coach her on how to manage athletes like Scott, so she should relax and look for help. She had time to handle the situation if Scott was indeed a problem, as his option grants had a one-year cliff and he was only a couple of months in. So, instead of feeling anxious and pressured into reacting, I encouraged Mary to focus on helping Scott be successful and assess things again in a quarter.
Several years later, after the company, led by Mary, was acquired and had a very successful outcome, she told me that the most memorable and important thing I did for her at that moment was to simply sit, listen, and relate to the feeling she was having. I hadn’t immediately replied with a solution to her problem. Instead, I started with empathy.
As a mentor, be aware when to suspend, or defer, your advice or judgment. The entrepreneur you are mentoring may not be in a head space to hear your solution. Mentoring is often an emotional rather than a functional or intellectual role. Take a breath and be empathetic, instead than jumping in to solve the problem. And never forget that startups are hard.
Jay Batson has been the founder of four companies, including two venture-backed startups, with some big success and disappointing failure. His biggest success is as founding CEO of Acquia, now an 800+ person company with offices around the globe. In 2012, Jay invented the “Mentor-in-Residence” role at Techstars. MIR’s spend near-full-time at Techstars during each cohort to help as extensively as possible with companies and help other Mentors be good at it. Jay has embraced this responsibility for every Boston cohort since then. He’s an LP in several Techstars funds and a direct investor in a selection of Techstars companies.
Also published on Medium.