One of my first learnings as an investor was to focus not on what you can or would do with the company, but what the founder will do.
It’s a continual work in progress to take this viewpoint because, when you’re excited about the promise of an idea, your natural reaction is to think of all that you could and would want to do with it.
However, if you decide to invest, you often soon discover that the founder takes the company in a different direction than what you imagined.
If you formed your view of the company’s future without carefully listening to the founder before investing, this direction can be radically different.
If you listened well, although there will still be surprises due to the experimental nature of startups, hopefully these changes will be for the better and the general direction of the company will remain as you envisioned.
I recently listened to an excellent TED talk by Celeste Headlee on how to have better conversations.
Conversational ability has always been an important skill, and it is becoming even more important as technology further increases the frequency and pace with which we communicate both verbally and in writing.
Here are the 3 strategies which most resonated with me:
1. Listen to understand, not reply
2. Don’t equate your experiences with their’s
3. Stay out of the weeds
You can listen to the 12 minute talk below.
The most important determinant of an investor’s success is their investment decisions.
And making good investment decisions requires really understanding what a founder is thinking, their values, and their likely actions following an investment.
And in order to really understand a founder, you have to really listen to them.
This goes well beyond just listening to them talk about their background and their plans for the company.
For example, it requires analyzing the structure in which they think to determine the extent to which they leverage facts and assumptions to justify their decisions. It also requires monitoring their body language to gain insights into their true feelings about specific issues. Finally, it requires observing their interactions with others to determine whether they’d be a leader who earns the respect of their followers. These are just some examples.
There’s no single recipe to really understand a founder. It’s one of those things where you need to continually ask probing questions, to the founder and to yourself, and to dig deeper in a specific direction when an answer tells you to do so.
And this requires really listening.