Sometimes, Skip the Question

I am quite comfortable asking questions in public, and usually they seem to land pretty well. I know that mostly because people often come up afterward to tell me they appreciated the question or were wondering the same thing.

Recently, I had the opposite experience. It was unusual enough that I found myself thinking about what I could have done differently, and it reminded me of two things about asking questions in public.

The first is simple: read the room. Sometimes it’s better to just skip the question. In this case, after being selected, I naively forgot that was an option!

I was at an event where the person who asked a question before me managed to irritate pretty much everyone. He was ostensibly asking a question, but was also promoting his services, telling a sophisticated audience things they already knew, and questioning the honesty of people on the panel. Not surprisingly, the response from the panel was hostile.

Then I was next.

In retrospect, I should have just passed.

It didn’t really matter that my question was completely unrelated. I was still the next person asking a question after an uncomfortable exchange. The room had changed. The panel’s mood had changed. And I hadn’t had enough time to reconsider whether the question I had prepared was the right one for that moment.

There’s a useful lesson in that. You don’t have to ask the question just because you were planning to. Sometimes the person before you changes the conditions enough that the best decision is to bow out.

The second lesson was about the question itself.

I’ve been thinking a lot about how much more expensive the world seems to be getting. Not just ordinary inflation, but the cost of technology, infrastructure, tariffs, supply chains, and all the inputs that go into building ambitious companies. At the same time, there’s enormous geopolitical uncertainty and a tremendous amount of capital and expectation wrapped up in AI.

I was genuinely curious about what all of that means for an investor who wants to have a positive impact by backing companies that can become force multipliers.

But the question I asked leaned too heavily into the downside scenario: What if geopolitical conflicts get much worse? What if the AI boom is a bubble? What happens to your investment thesis then?

Those are things I’m interested in, but on reflection, they weren’t the question.

The question underneath them was more constructive: As the world becomes more expensive and uncertain, how does that change the way you maximize your impact as an investor? Does it change the kinds of companies you back, how many investments you make, how much you invest in each one, or the guidance you give founders?

The darker scenarios are useful stress tests of that question but they don’t need to be the framing of it.

I’m not convinced that phrasing it this way would necessarily have changed how the response I got went. Context matters, and following an unpleasant interaction probably wasn’t the best moment to ask a complicated question about an uncertain future.

But that may be the more useful takeaway.

Sometimes you need to phrase the question better.

And sometimes you need to recognize that this isn’t the moment to ask it at all.