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How to talk so people will talk: encouraging them on

Deploy Empathy
Deploy Empathy
This was written as part of the rough draft for Deploy Empathy, a practical guide to interviewing customers.
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I got my start doing proper customer interviews in the personal finance space. It’s an extremely delicate topic, and I’m so grateful I learned in that environment because I really had to learn how to handle an interview and get someone to open up.
It’s like a gymnast on a balance beam who could fall to the floor with the slightest wobble. People keep personal finance decisions close to their chest, and conducting the interview right takes practice and focus.
The wonderful thing about interviewing people in a B2B context, by contrast, is that the information isn’t as sensitive. Plus, people have likely never talked to anyone else about these work-related tasks they do daily, weekly, or monthly.
Maybe they work with a co-worker on them, or gripe to a coworker, but they’ve probably never sat down and had someone genuinely ask them what they think about creating SLA reports or following up on invoices. Never really talked through where they spend a lot of time, the tools they use, and so forth.
I find that once you build the trust with someone and show them that you are willing to listen, they will talk, because no one has ever cared about that part of their daily life before.
Interviewing someone is a delicate dance. I like to say that it’s somewhere between improv and acting, rather than a conversation. (I talked a little about that at MicroConf in 2019.) A conversation implies exchange of ideas, but in a customer interview you’re trying to just focus on the person you’re interviewing and get them to open up.
There are several keys to helping an interview flow, all of which work together to make the person you’re talking to comfortable talking to you and willing to open up. I’m going to dive more into each one of these elements in future issues, but the overview is:
  • Not interrupting the person
  • Not explaining anything when they point out something wrong
  • Not negating them in any way
  • Leaving pauses for them to fill
  • Encouraging them on
  • Asking for clarification
The bullet points above each deserve their own newsletter. Books about user interviewing tend to mention these behaviors and maybe give a 1-2 sentence description, but I find that to just not be enough to take someone from “scared to talk to people and unsure where to start” to “ready and confident.”
Today we’re going to talk about Encouraging Them On, and my goal here is to be super nitty-gritty in the kinds of things you might say in an interview to keep someone talking.
There are specific phrases you want to use to show someone that you’re interested in what someone is saying. Psychologists and therapists often describe them as “validating statements.”
People tend to stress about what they would say in an interview, but most of what you say during an interview isn’t questions at all. It’s these sort of validating statements that show someone you’re open to what they’re saying and are listening. Your goal is for them to talk as much as possible, and you as little.
(If you’re a ratios sort of person, the share of talking should be 90-95% the interviewee.)
In a customer interview, you will use validation even when you don’t necessarily agree with what the person or said, or what they have said sounds absurd to you. You cannot break the window of trust, ever, even when something wacky happens.
(Which it will. In a memorable interview years ago, the interviewee suddenly said “Sorry, I’m eating a quesadilla right now” about 45 minutes in to a phone call, after previously having made no mentions or given signs of eating. My research partner, the unflappable Dr. Helen Fake, just rolled with it and said “oh you’re fine!”)
BUT – you do not want to say that you agree with them, or congratulate them, or do anything that implies that you have an opinion, even if it is a positive opinion. They may ask you if you agree, and you need to purposefully find a way to make that question go away (“I can see where you’re coming from.” rather than “Yeah I agree.”) Agreeing or disagreeing will remind them that you’re a human being with opinions and judgements, and the trust will start to melt away.
For example, when I was interviewing people about their finances, they would admit to doing things that a financial planner or portfolio manager would never endorse. Even though we knew that, we couldn’t “correct” them. But we also couldn’t want to agree with them, either. What we were searching for was their internal logic and thought processes, and if we were to introduce outside information or agree or disagree with them, they would have shifted into trying to impress us and holding back information.
I think you get it.
Before I introduce the phrases: when you’re using these statements, you’ll want to say them in your gentlest voice possible. “Why would you do it that way!” said in a normal-volume voice with emphasis on certain words could make it sound accusatory and put them on the defense, versus “Can you tell me more about why you do it like that?” in a gentle, unassuming, curious voice will help them open up. (In general, a customer interview should be conducted in the most harmless voice you can possibly muster.)
Here are some of the phrases you’ll want to use:
  • That makes sense.
  • I can see why you’d do it that way.
  • I’m interested to hear more about how you came to doing that way.
  • Would you be able to walk me through the context behind that?
  • I can see what you’re saying.
  • It sounds like that’s frustrating/time consuming/challenging.
  • It sounds like you think that could be improved.
  • Can you help me understand what you were thinking when [x]?
  • Can you tell me more about [x]?
  • It makes sense that you think that.
  • It makes sense that you do it that way.
  • It sounds like there are several steps involved. I’m curious, can you walk me through them?
  • It sounds a lot goes into that.
When I’m using these phrases, I purposefully use the word “think” instead of “feel.” Some people, I’ve noticed, will find it insulting to say that they feel a certain way, but think is interpreted as more neutral. For example:
  • It sounds like you feel the process is complicated. vs
  • It sounds like you think the process is complicated.
And remember: most people like to think their job is challenging. Let me tell you a story I read years ago on Twitter but cannot, for the life of me, seem to locate. Someone who had recently moved to LA with their spouse and was not part of the entertainment industry, and kept finding themselves struggling to make conversation at cocktail parties. Things shifted when whenever someone said what they did, they replied “That must be challenging,” even if it sounded easy or boring to the person asking. And that would open people up because it felt like a compliment, and it would lead to an interesting conversation about the things that person did at work.
A promise and a word of caution
I suggest you start practicing this on friends and family before moving to customers or potential customers.
But I want you to make me a promise: you’ll only use this for good, not to be manipulative, and you won’t use what people say against them. Anonymously using their phrasing in marketing copy is fair game, but remember that someone’s confidence is a sacred gift, and should be handled gently and respectfully.
I also encourage you to practice on friends and family… but not too much.
I didn’t realize just how much these techniques had woven themselves into my normal conversation habits until I was at the grocery store a few years ago. I was in line with a dozen items and noticed that the cashier hugged the woman in front of me (oh, pre-Covid days). I don’t know if I’d just gotten off of an interview or what, but I found myself asking the cashier about it.
Me, with a smile: Oh, I notice you hugged her, is that your sister?
Cashier: No, she’s just a long-time customer. I’ve worked here for a long time.
Me: Oh, how long?
Cashier: Almost 20 years. I’m due to retire soon. Company’s changed a lot in that time.
Me: Oh, has it?
Cashier: [proceeds to tell me about how the store chain was bought out by another chain 10 years ago, how they changed the retirement plan, and how she’s worried about having enough income from Social Security, her 401k, and her old pension in retirement, and how she’s making extra 401k contributions]
This was all in the span of less than five minutes, ringing up the dozen or so items I had in my basket.
I went home, and told a former coworker about it, and joked “do I have ‘Tell me about your retirement finances?’ written on my forehead?” I was amazed that a stranger had told me that kind of information in such a short amount of time.
It reminded me how we need to be careful with these skills, and to know when to hit the brakes. It’s people’s decision what to reveal, but I always keep that story in mind, and remind myself to back off or shift topics when it seems like someone is on the verge of sharing too much. It’s possible to make someone too comfortable. It’s always okay to say “Thank you for telling me that. I was wondering if we could go back to something you said earlier. I’m curious about… [some other topic]”
But it also reminded me of how so many people don’t have people in their lives who will just listen to them, especially about things that are processes or tasks they complete daily or goals that are top-of-mind. Just being a presence who is willing to listen is more powerful than people realize. It’ll take you some time, and some practice, but I think you’ll notice a difference even in your personal life by using these sorts of phrases.

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Deploy Empathy
Deploy Empathy @mjwhansen

A practical guide to interviewing customers

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