Open Ambition

Here’s a news flash: You can learn a lot about someone by asking a question and seeing how they answer it.

That’s so obvious, and we’ve all heard it a million times. I spend a lot of time listening to pitches from startup company CEOs, as well as spend a lot of time with the CEOs of my companies, and in both cases, end up asking a lot of questions.

The questions, that’s where the really hard part of making productive use of time is. Anyone who has the ambition and the drive to start a company is generally smart, and has spent so much time on their business that they’re awash in information about it. Anyone who is CEO of a startup is the same way, except they’re not pitching a vision to you, they’re living and managing it. In either case, it’s their job/role to have anticipated the key questions, and have the answers to them.

So, it’s hard to ask questions that dig below the surface, that reveal something that hasn’t already been thought of. If you’re lucky enough to have thought of one, it can accelerate everyone’s understanding of the business and the people running it. Conversely if you’re the CEO, when those questions are asked, it will put you in a potentially awkward position. Do you have an answer, and should you have had an answer.

This is true about life in general, so while what follows is specific to my job, I find it’s the same calculus with friends, spouses, children, parents….

I love it when we get to that juncture and the CEO says “I don’t know the answer”. It’s even better if they then say “there are a number of ways to try and answer it, let’s start….”. Now you’re about to take a trip to a very rich landscape indeed. A landscape where you’ll find out something potentially valuable about the company, about the CEO, and about your ability to work together to solve problems.

But there’s another direction that frequently gets taken. When the CEO produces an answer. I choose that verb deliberately. The answer is produced right there, like a big patch applied over a void. The void is hidden, not explored. This is where ego and insecurity hijack intellectual curiosity and drive it right past a tremendous source of opportunity.

It’s where the person being questioned feels the need to have an answer for every question, that somehow exposing that they don’t know is bad or weak.

Once you become familiar with the “answer for every question” mentality, it becomes a warning sign of significance. I hate it. It spoils all the fun. Worse, it destroys credibility at an alarming pace, but in a very quiet and nuanced way – because you can’t possibly have all the answers in a company that’s still more vision than substance.

And it turns out, the people who most often fall into this trap are the folks who have left the large technology companies to start up a company. It reveals the culture they had to navigate through to succeed in the “big company” world. The problems generally were so well understood you could have and were expected to have all the answers. And if you didn’t, you could “patch and pivot”, loop back, and get the answer – accountability was so diffuse, and decision cycles so long.

But what gets missed here is that the answer isn’t important, at all. It’s seeing that juncture where you don’t know the answer – that’s the super valuable piece of information. That may tell you about a core set of assumptions that are off, or an area of opportunity that’s been missed or overstated.

I love the landscape that is revealed in not knowing the answer. I love working with people comfortable with traversing it. I love it when a CEO sits me down to talk through a tough problem, and will state the truth: “I know I’m missing something here, help me figure it out”. When I hear that, I know the fun is about to begin.

Tags: answers, humility, Intellectual curiosity, not knowing, start-ups

This entry was posted on November 27, 2008 at 2:18 pm and is filed under Business planning, Intellectual curiosity, Self-knowledge, Values, Venture capital. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.