There are moments with founders that I need to let the silence speak.

Depending on the substance, topic, or dynamic in a conversation, there are times I need to understand what is really afoot.

Not, what I think or assume might be afoot. Rather, having complete clarity on it.

Now, it’s not necessarily that I am suspecting anything nefarious, through there are some times I’m not sure.

It’s often due to a softness of detail around a topic. A softness where I deem it important to brush aside and to expose the facts. In those situations, I’ve found that I need to:

Ask a short, direct question, and then sit in the silence. 

When you ask a direct, short question, you are trading cover for exposure.

What happens in the silence reveals something very important about the person - if they want to distance themself from the topic, or if they are secure about the topic.

What happens in the silence is what is not said - the non-verbals, the reaction, the facial expressions, what the eyes tell you. 

The sum of their answer is their words paired with what happens in the silence.

But here is the problem - we are not good at short questions.

This played out recently on the All In podcast, David Freidberg did a live interview Billy Evans, who is Elizabeth Holmes' partner. For additional context, see my article from last week. Clip is below:

The transcript is:

Friedberg: “I have to ask because I tried earlier but people will harp on it if I don’t ask. Why did she wear the black turtlenecks and speak in a deep voice? 

Bill Evans (repeating the question): “Why did she wear the black turtlenecks and speak in a deep voice?”

(Evans looks out. Eye movements convey an uneasiness and looking for an answer)

Friedberg: “I've met her.”

Billy Evans: “I mean she’s got a deep voice, but… (pauses)  

(repeats the question again) …Why did she wear the black turtlenecks?” 

Friedberg: “I mean, tell me about the experience you heard from her about being a young CEO and like, you know, is that where this is coming from? Where she was always telling her story and she felt like she had to play a role in storytelling? I'm not trying to put words in your mouth, but I'm just trying to understand the context.”

Notice what Evans did next when Friedberg asked him the initial question, Why did she wear the black turtlenecks and speak in a deep voice?

Evans looked out, tilted his head and scratched it, with eye movement conveying an uneasiness. He was searching for an answer.

The moment I first saw his reaction, I thought, “He doesn’t want to answer this question.” He wants to distance himself from this question.

Then Evans repeated the question again, elongating the moment in time, likely hoping that the hesitation would be a decoy.

Evan’s hesitation and silence makes Freidberg move the spotlight to something else. Another question, an easier question.

To which Evans responds with a cover line that he’s rehearsed a thousand times, “I’ll share a little bit but it’s really her story to tell.”

When I first saw this part of the interview, I was like, “Friedberg botched it.” He clouded the narrative. 

By coming in with that last caveat, Friedberg abandoned a very important question that he stated just 20 seconds before was a question that people would harp on if he didn’t ask. 

Instead of letting the silence speak, he gave other caveats or qualifications that changed the focus, allowing Evans to answer really any question he wanted.

Freidberg clouded the narrative. But you and I intuitively cloud the narrative too.

It is easy to analyze a conversation like this, but this is quite hard in normal conversation with someone that we don’t know well.

It’s because we find silence uncomfortable. 

We treat silence as a medium that needs to be filled.

But why?

Maybe one likely answer is that silence plays games on our social capital card.

We don’t want awkwardness. We want to be seen as coherant and dynamic conversationalists. So, we just keep talking.

But... why?

Furthermore…

When we ask questions, we tend to lay caveats or qualifications to the context, which subtracts from the intention of the question. 

In an exchange with someone that we don’t know as well, i.e. founders speaking with investors and visa versa, we tend to feel uncomfortable when they appear lost for words. 

If you give the respondent options, people will generally answer the question they want to answer. Or, they will try to find a way to deflect so that they end up answering the question they want to answer. 

Caveats and qualifications are like cover that the respondant could use in their reply.

There are moments that you need to get to the answer. You can’t have any cover in front of the answer. You need complete exposure of the fact.

When you ask a direct, short question, you are trading cover for exposure.

The respondant doesn’t have much to hide behind. That’s your complete intention.

This can take many forms, but here are only two examples of what I mean.

In one startup conversation, I was chatting with co-founder named Rachel. She happened to get on the topic about some of the relational challenges with her co-founder, Ryan. 

I needed to understand the state of affairs, without any fluff or caveating. I needed a direct question. 

I asked Rachel, “What’s your relationship with him now?” 

I got the answer. Rachel and Ryan don’t talk. 

I could have given Rachel options in my question such as, “Do you guys get along, where do you see eye to eye,” etc.

No. What’s your relationship with him asks for a short answer that gives no cover in a question that needed full exposure of the fact.

With another startup, I was talking with a founder who shared about their background and mentioned in passing that in their past, they had ”regulatory challenges.”

I made a mental note. In that moment, I continued with the conversation but needed to circle back.

Towards the end of the conversation, I said, “Let’s see, there was something at the beginning of our conversations about, I think it was regulatory challenges or something like that. Can you say more about that?”

The direct, short question of, “Can you say more about that” was just what needed to be asked. I then got the answer that I needed and was very grateful to have received. And it was an answer that the founding team, to their credit, did not hide from.

Now, I realized that major example in this article was from Billy Evans, who is married to Elizabeth Holmes and is also a pathological liar. Really, it’s just a convenient and entertaining dialogue to show an extreme example.

I want to be clear that letting the silence speak can and should be used with items in general where the details are soft. In some topics, soft details are acceptable. But there are other topics when soft details are actually a roadblock. In those situations, that need to be exposed and have total clarity about.

As I'm writing this as an investor, I also want to state that founders can also let the silence speak with investors. There are things that investors say where softness of detail may be inadequate.

Don't be afraid to let the silence speak. There are times when you need to welcome the silence and do not give caveats or qualifications to your question. Exchange cover for exposure.

What happens in the silence reveals something very important about the person - if they want to distance themself from the topic, or if they are secure about the topic.

The sum of their answer is their words paired with what happens in the silence.

You might be surprised what you hear… when the silence speaks.

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