On Asking Great Questions
What connects Gorbachev, a small cup of ice-cream, and a conversation between two Dutchmen?
Cal Fussman is a journalist who asked Gorbachev a seemingly simple question about a childhood memory. He chose to ask this question in an interview about nuclear disarmament. But asking this one question turned a ten minute interview into a two hour-long conversation.
Clarence Seedorf was a very, very good footballer, and is now a journalist. He was able to get the coach of the Liverpool Football Club to admit something that he would much rather have never spoken about at all in the first place.
And what connects the two of them? Both of them strike me as great examples of how to get the kind of conversation you want to have going.
Cal Fussman
Here’s Cal Fussman, narrating the most wonderful story involving himself and Mikhail Gorbachev, on Tim Ferriss’ podcast1. For context, a one hour interview slot had been whittled down to just ten minutes, and he had just the one shot at a question that needed to work a miracle:
“And so the publicist leads me into the room, and at this point I’m thinking okay, if it’s two and a half minutes, just do your best. I look up and there he is, Gorby. And he’s a little older than I remember; he’s about 77 at the time. He was in town to speak about nuclear weapons and why they should be abolished. And we sit down, and I’m looking at him and I just know, just know he’s expecting my first question to be about nuclear arms, world politics, Paris troika, Ronald Reagan. He’s just ready.
So I looked at him and I said: what’s the best lesson your father ever taught you? And he is surprised, pleasantly surprised. He looks up and he doesn’t answer. He’s like thinking about this. It’s as if, after a little while, he’s seeing on the ceiling this movie of his past. And he starts to tell me this story. And it’s a story about the day his dad was called to go fight in World War II. See, Gorbachev lived on a farm and it was a long distance between this farm and the town where Gorbachev’s dad had to join the other men to go off to war.
And so the whole family took this trip with the dad to this town to wish him well as he went off. And Gorbachev is talking about this trip and he’s providing these intricate details, and I’m transfixed but I’m saying oh, my God, I asked the worst possible question. This interview is going to be over and he’s not even got to telling it.
Finally they do get to town, and Gorbachev’s dad takes the family into this little shop and he gets ice cream for everybody. And Gorbachev starts describing this ice cream and the cup that it was in, this aluminum cup. And as he’s telling me, it’s almost like he’s got his hand out in front of him and the cup’s in it. It’s that vivid to him. And it’s as if in this moment, we both have this same realization: that cup of ice cream is the reason that he was able to make peace with Ronald Reagan and end the Cold War.
Because that cup of ice cream, just the memory of it, is the memory of what it felt like for his dad to go off to war, for him to see his dad going off to war. That cup of ice cream in the memory was the dread that he knew of the possibility of never seeing his father again.”
It’s a great story, right?
And you might think that the lesson to be drawn from this is that you should figure out “the killer question” to ask, and that too on the spot, and that’s what makes you a truly great interviewer. But that is the wrong lesson to draw from this story, and that is both good news and bad news.
The good news is that no, you don’t have to be that one in a million conversationalist, with an uncanny and seemingly god-given knack of asking just the right question at just the right time to just the right person. Such things are all but impossible probabilistically speaking, which implies there must be an explanatory factor.
That factor being, in this case, Fussman just is that kind of person. It is who he is: a person who is intensely curious about what makes people who they are. Read the rest of the interview with Tim Ferriss to understand why I say this, it’s a great conversation. But I’ll give you just one example here to explain where I’m coming from. Tim describes to Cal a trip to Iceland that he took his mother on. This, mind you, while Cal is telling Tim some entirely different story about Iceland.
Cal is perfectly happy to meander away from his own story about Iceland, and ask Tim about his trip to the country. Tim talks about the reason for the trip, which is his mother’s long running wish to see the aurora borealis. And this was Cal’s next question:
“What did your mom’s face look like when she got the view that she wanted to have?”
My point is that Cal Fussman didn’t dream up that question to Gorbachev on the spot. That’s not what makes him awesome.
He genuinely wants to know the soul affirming stories of the people he is speaking with. That’s what makes him awesome.
Why do I call this bad news? Because if you’re training to be a good interviewer, or a good conversationalist, your job just got a lot harder. Learning to ask the right question at the right time is tricky. Learning to be the kind of person you need to be to ask that kind of question you’d like to ask is all but impossible.
Invert this process. Learn to ask the best kind of question you can, given the kind of person you are.
That comes naturally to you by definition, and that’s therefore the kind of interview/conversation you do best.2
Clarence Seedorf
The context in this case is that Clarence Seedorf happens to be one of the best footballers to have ever played the game. He is now a pundit with Amazon Prime UK. Now, offering your opinion as an ex-player is one thing.
It doesn’t necessarily follow, however, that you will also make for a great interviewer. In Clarence Seedorf’s case though, it definitely does follow. He conducted an interview that was so good that it became the subject of an entire article in The Athletic.
An important distinction needs to be made clear. What Cal Fussman got going, both with Gorbachev and with Ferriss, was a conversation. What Seedorf was conducting here (and the verb matters as much as the noun) was an interview. Fussman wanted to explore. Seedorf wanted to grill. Both obviously asked questions suited to their objectives, and both were therefore of a very different nature.
Watch from around the 3:20 mark for the interview between Seedorf and Slot - the background is that Slot is coach of the Liverpool Football Club. A key player (a guy called Salah) from that club gave an explosive interview some days before, all but saying that he was done with the club, on account of having been dropped from the starting line-up for three games straight. This has created major controversy, and all the conversation around the club is about that interview, and not about on-field performances. It is Slot’s job in this interview to deflect questions about Salah, and to focus on what happened in the match.
Why was this a great interview? Because Slot made the mistake of publicly announcing that he was declining to speak first.
The power dynamics matter here. As Nick Miller puts it:
This was a Dutchman who had a limited playing career, talking to a Dutchman who had one of the great playing careers of all time. Slot and Seedorf are around the same age, but it’s inevitable a guy who was a journeyman midfielder for a series of middling Eredivisie clubs would be just a little bit starstruck by a guy from the same country who won Champions Leagues with three different teams
The point here is not that Seedorf took this into account and used his position to get Slot to open up more than he would have otherwise, and therefore this was a great interview. It’s the same point as in Fussman’s case: this was a great interview because of two reasons. One, talking like this comes naturally to Clarence Seedorf. Two, Seedorf is one of the very few people who commands the respect one needs to be able to ask questions such as these. No journalist is going to begin an interview by saying to the coach of a football club “I don’t agree with you”, for example.
Slot was cornered into having to answer the questions that he did about Salah both because of the way they were put, and because of the stature of the person asking them.
Because you and I both know that if we were the ones to ask those exact same questions in Clarence Seedorf’s place, we wouldn’t have gotten the time of the day out of Slot. It wasn’t that the questions were all that great, nor was it just the personality of the interviewer.
In this specific case, it was a combination of the two.
We should all aspire to be better conversationalists. And the way to do it is not by understanding what makes other folks great at asking questions. It is by having the kind of conversations you wish to have.
As simple, and as difficult, as that.
Who is a great conversationalist himself!
There is, and this should go without saying, a lot more to it than that! But authenticity is a necessary condition, for sure. What is equally for sure is that it alone is not sufficient.
Interesting ideas, as always! Agree with what you say on asking great questions. But when it comes to making a conversation truly engaging, do you think one person asking the right questions is enough to make it great? Or could that also mean it's a great "interview"? I have experienced that even if you ask thought out questions and create space for the other person to open up, it doesn’t mean that they will also reciprocate and involve you equally. For a conversation to really flow, perhaps both sides need to follow this framework? Or is one side enough? Or is it an indicator that the questions still aren't good enough? ;)
Perhaps it depends on what you want from the exchange. But you've given a lot to think about, thanks for that!
Very interesting piece!