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Thoughtful Listening Leads to Wise Decisionmaking

OVP Staff
March 28, 2016

I took a course in law school on medical ethics, mostly because it was taught by Dr. Jay Katz, a Harvard trained physician, medical ethicist (he had participated in the Federal inquiry into the Tuskegee Syphilis Study), Freudian analyst (in his spare time, I suppose) and campus wise man.

One day in class he told a brief, self-revealing anecdote.  When he first started seeing patients in analysis – and this was the four day a week, on the couch, Woody Allen variety of treatment – he was terrified of making a mistake, so he listened very closely but said almost nothing.  After a few years, he gained a great deal of confidence in the power of his insights, so he shared them with his patients, often and at length.  Then, in what we might call the third phase of his career as an analyst, he recognized how his strong views were not as helpful as he had thought and settled back into thoughtful listening, occasional guidance and trust in the power of the analytic process.  His patients, he came to realize, largely improved through self-discovery.

This memory came back to me (I suppose I free-associated to it) in thinking about a recent CEO retreat we held at Osage Venture Partners.  Fifteen of our CEO’s attended a two day session of intensive and structured conversation.  Although OVP is an early stage fund, our CEOs range broadly in experience, from the very new to some who have led multiple companies.  They are a talented group, and gathering them together is one of the highlights of our year.

This year our retreat featured a panel of four regional CEOs who had led their companies to hugely successful outcomes.  They were, given their success, surprisingly modest in affect and advice.  Rather than say, “You should do this or that,” they said “This or that worked for us, and it may work for you.”  Rather than trumpet their success, they talked about luck, timing and perseverance.  And rather than ascribe their success to their own talent, they emphasized the importance of having a great partner in their enterprises and, of course, in hiring A Players.  All four of these highly successful CEO’s had great confidence, although they spoke of fear and paranoia as an important motivator.  Their confidence did not come from a belief that they were a walking encyclopedia of best practices that guaranteed the next Unicorn.  Their confidence was rooted in their belief that they had learned a process, that through careful listening to highly- talented people they and their teams would self-discover what was best for the company at that moment in time.  Their confidence was not so much knowledge based as process based, that they had learned how to combine humility with decisiveness.

When we gather our CEOs, all focused on B2B software but each with a unique strategy and organization, and augment them with four seasoned and successful CEOs, it becomes obvious that there is no single path to success.  Since most of our CEOs are in the portfolio for several years, we have the benefit of hearing their voices change over time.  The trend is fairly consistent; no matter your starting point, running a start-up is a lesson in humility, and the faster and deeper you learn the lesson, the more likely you are to make winning decisions.

OVP Staff