I had lunch with Brett Martin this week, an entrepreneur I’ve gotten to know a bit over the years. We were talking about a decision that I’m thinking through. I was kind of waffling.

He asked a really good question. “How will it feel when you have the right answer?”

This got me thinking in a completely different frame of mind. Usually, I think of decisions in terms of logical factors. Pro’s and con’s. Mental scoring across some set of attributes. Things like that.

“How you feel” is a bit different, and asked to answer how I would feel strangely put a lot of clarity around my thinking.

When I talk to some VC’s that are new to the role, we often talk about how one develops conviction around an investment opportunity. Again, we talk about factors one evaluates when looking at an investment opportunity. These are definitely important.

But I tend to also suggest something that is more akin to a feeling. I’m not sure where I heard it first. I definitely didn’t invent it. I think my old colleague Bijan has mentioned it in a blog, so maybe that’s where I first heard it. I encourage the investor to ask themselves “would I want to work for this company?” and “would I want to co-found a company with this founder?”  Often these feelings are completely supported by rational arguments or objective measures.  But framing it this way cuts through the clutter of uncertainty.

What are other feelings you want to have when you are making important decisions? Maybe for hiring decisions, or major strategy decisions? How will you feel when you come across the right choice?