When I started Community Connect Inc., I was 23 years old and my only job after graduating college was working at Merrill Lynch as an Investment Banking Analyst for 2 years. I had never managed someone yet in my career and therefore never learned how to hire well. I was recently reading the annual shareholders’ letters by Jeff Bezos and in the letter reviewing 1998 he writes the following:
During our hiring meetings, we ask people to consider three questions before making a decision:
• Will you admire this person? If you think about the people you’ve admired in your life, they are probably people you’ve been able to learn from or take an example from. For myself, I’ve always tried hard to work only with people I admire, and I encourage folks here to be just as demanding. Life is definitely too short to do otherwise.
• Will this person raise the average level of effectiveness of the group they’re entering? We want to fight entropy. The bar has to continuously go up. I ask people to visualize the company 5 years from now. At that point, each of us should look around and say, “The standards are so high now — boy, I’m glad I got in when I did!”
• Along what dimension might this person be a superstar? Many people have unique skills, interests, and perspectives that enrich the work environment for all of us. It’s often something that’s not even related to their jobs. One person here is a National Spelling Bee champion (1978, I believe). I suspect it doesn’t help her in her everyday work, but it does make working here more fun if you can occasionally snag her in the hall with a quick challenge: “onomatopoeia!”
When I reflect on how I hired, I focused much more on the question “Can this person do this job well?”. However, I tended to hire people that didn’t intimidate me. Meaning I avoided hiring people that were so smart, talented and knowledgeable that there was not much I can do to teach or instruct them on. As a first time CEO and manager for that matter, I avoided those type of hires because I wanted to feel like I had full control. It was like being a first time pro basketball head coach and then having Michael Jordan on your team. Do you think being a first time head coach and coaching Michael Jordan would be a bit uncomfortable? Definitely. This insecurity pushes us to hire comfortably instead of what would be truly best for you as a manager or for the company.
The first time I hired uncomfortably was when I hired Court Cunningham as COO of Community Connect. Court had more experience than me and is both an amazing strategic thinker and operator. Court later went on to run Yodle which has been a very successful local marketing services company based here in NY. Having Court around elevated my game because he pushed me in ways that I had not been pushed in the 8 years prior running the business. I learned a valuable lesson at that point. If you are not hiring uncomfortably, you are probably not hiring well.
I have a friend that was recently promoted to manage a team at a large media company. She recently hired someone senior at her team and she said that she was intimidated by him because she said “he can probably do the job better than me”. I told her hiring uncomfortably was a demonstration that she was hiring well which is one of the most important attributes in being a great manager. As an investor, I see this hesitancy happen all the time with first time entrepreneurs. To be a great entrepreneur, you need to embrace hiring uncomfortably and push your managers to do the same. By doing so, you will constantly raise the bar and create an environment of excellence.