My experience suggests that this dynamic often causes problems or leads investors to gloss over important issues. With friends, we too often pull our punches. As a board member, I take seriously the obligation to stay focused on what’s best for the company.
A little emotional separation from the falconer is good for the falcon.
Good coaches see your true potential
My best coaches knew better than I did what I was capable of, and pushed me to get there – including entering me in big races I thought I had no business racing. It made me nervous at the time but allowed me to run some of the best race times of my career.
As I coach founders, I try to take the same, deeply informed and supportive approach, even if it rankles. The more thoroughly I understand them and their management teams, the more effective I am at asking the right questions, understanding their priorities, and anticipating opportunities they might not yet see coming.
There is no shortcut, no Cliffs Notes for understanding the company or the exec team dynamic. There’s no substitute for showing up with high expectations for the athlete or founder who is counting on you, just as there’s no substitute for the athlete or founder logging the hours and pushing herself beyond what’s comfortable.
Until I participated in several portfolio companies’ International Women’s Day events, for example, I hadn’t realized how much progress a few executive teams and sub-teams had to make on their gender (im)balances. I recommended that each team begin tracking and reporting diversity metrics to the board.
Was this the first thing the exec teams wanted to prioritize? I assure you, it was not. Are the companies stronger and competitively better, now that their teams are more balanced? There is absolutely no question.
Different coaches for different needs
My most supportive coach was Pete, whom I met when I was a high school freshman. Understated and unassuming, he was then, and remains to this day, the school’s maintenance manager. He was the youngest coach at the school and had trained the fewest athletes of any of my three running coaches, but what mattered to me the most was that he deeply believed in me.
As a teenager, I needed a coach who supported me unconditionally and who had the time and patience to step me through crucial learnings.
Being coached on raw instinct by a gifted, big-hearted part-timer in high school was distinct from my college and post-collegiate experiences. Those coaches were textbook pros. I met my college coach, Peter, in his 26th collegiate season. At Nike, I helped my coach Frank Gagliano (we all called him “Gags”) – who has produced 140 All America athletes and 15 Olympians – celebrate his 75th birthday in the middle of track season.
As I grew into a top-tier athlete, these more experienced, premier-level coaches taught me precisely what I needed to learn at each stage, almost as if they had been orchestrated to come into my life at the right moments in my professional development.
Likewise, early-stage companies, still experimenting with their product, audience and eventual distribution, rightly partner with investors who believe – the ones who fit their needs. But as a company matures from startup to growth stage, the type of investor that can best help the founder(s) changes. No longer in need of unconditional support and encouragement, growth-stage founders are often best matched to an investor willing to push them – hard, sometimes – to give the company the best chance of achieving breakthrough success.
Don’t diss your competition
I was sometimes tempted to dismiss or demonize my competitors, to see them as the enemy and as not useful except as motivation. My coaches set me straight.
Track is all about running fast, and with the right competition or the right field of athletes, together we could unquestionably run even faster than any one of us could run alone. My coaches encouraged me to watch my rivals closely, learning what I could to beat them. And also to be gracious in victory – and defeat.
Coaching entrepreneurs, I’ve seen plenty dismiss their competitors’ strategies and emerging products in a misguided effort to defend their own approach. I advocate against this. Founders must learn as much as possible about their competitors, discerning their reasoning and strategy. Venture investors know it’s usually a good sign to see several companies attacking the same problem, because it demonstrates that the problem is important to solve. That competitive energy brings out everyone’s best work.
See farther, aim higher, win bigger
I was an athlete longer than I’ve been a coach, but I’ve been each long enough to appreciate that athletes and founders alike naturally get caught up in their own performances, focusing narrowly on only the next race, the next milestone.
Coaches lengthen the arc of athletes’ or founders’ performances and growth, broaden their vision and identify finish lines that are much farther out. Finishing the race – or hitting $50M in ARR – is important, yes, but better yet is winning a national or world championship – reaching $100M ARR, or an IPO.
Founders may be relieved to simply cross the finish line. The best coaches have already woven that achievement into the next phase of a bigger, more ambitious plan.