episode 5:
How to ask “hard” questions in customer interviews


Hey friends and fam, this is Hannah and this is another episode of better customer interviews, the kind of interviews or conversations you should be having with your customers to really research and understand them from their perspective so you can write better copy, better marketing that gets clicks, gets even more customers.

The idea for today’s episode came out of a conversation I had with a client. She asked me this, how do I ask the really tough or tricky or uncomfortable questions in an interview?

I love that question because it’s super relatable, right? If you’ve done interviews, even a small handful of customer interviews yourself, you’re probably well acquainted with the emotional roller coaster of running an interview. The stress of planning of booking, the anxiety of meeting a stranger, wanting to build the right amount of report so they’re comfortable and they open up.

All of which is amplified, like, tenfold when you’re interviewing a tight lipped customer or a Rambler, you know those quote unquote, bad customers.

So, okay, how do you ask the really tough or tricky or uncomfortable questions in an interview?

First, as with anything in life, really, and my podcast in particular, there is no formula here. So turn off that part of your brain.

And full disclaimer. My answer is rather hokey. It’s one most marketers and copywriters would probably consider pretty will maybe it is will I don’t know. But it is a very real part of interviewing customers, especially for those of us who want to get really good and become masterful engineers.

Ready? Okay.

The way to ask really tough, tricky or uncomfortable questions is to get over the idea that you need to be or feel comfortable in order to ask those questions.

You don’t. They are tricky and uncomfortable or challenging questions for a reason. Because they are, in fact tricky and uncomfortable or challenging to ask. And if you feel that dis-ease, it’s totally okay. And it’s totally normal.

The point is, don’t expect or wait for that feeling to go away before you ask the hard questions.

Your job is to learn to ask those questions anyway and not wait until you feel comfortable about asking to ask them.

Because the more you ask them and dare to feel the discomfort of asking them, the more comfortable you will feel asking them. Yeah, it’s the old annoying practice of learning by doing.

But also, what is it about the question that feels hard or risky to ask? Take a second to think about that. Because usually the question is hard because of two things: Either asks for detail that feels a bit intimate or private. And you don’t necessarily want to invade the customers privacy or overstep. Or, you want to ask about something you think you should know the answer to. Maybe the customer said a name or a place, or an expression that you don’t fully understand. But you’re embarrassed to ask about it and reveal that you don’t know.

In either case, the answer is meaningful. It will either point you to an inside that is, in fact private and something your customer wouldn’t normally share, which is great. Or, it puts you in the know about something common or obvious to your customer, which is also great.

That level of insight or both of those levels of insight are a huge win. And they’re likely going to be really helpful in crafting those sticky marketing messages.

In fact, in my experience, it’s those kinds of questions, the hard ones, the ones that feel uncomfortable to ask that really differentiate customer in interviews from, say, Amazon review mining or surveys. So, you definitely want to ask them.

And to make that happen, you need to know that when you want to do something out of your comfort zone, your ego will start shouting. Literally shouting at you.

For me when I say my ego shout, it means it comes up with really crafty, logical, convincing, super compelling arguments in my head about why I really need to do the thing that scares me. Basically, my ego talks me out of it.

So, expect that expect your ego to flare up in some way, shape or form to make you want to back away from asking the hard question. And have a script or prompts ready to combat that.

This is the exact reason I handed out scripts and problems in my last workshop. And why I’ll do the same in my next workshop. The value of scripts or prompts isn’t necessarily for you to have something to read off of – you actually want to step further and further away from reading them verbatim. But it’s to have something to practice with, and to help you prep for the interview. And especially for the times when you blank out mid interview, forget the next question, don’t know how to respond to an answer the customers giving you, all of the above. Okay?

So, what now? Now, grab a practice partner, hop on a zoom, call and practice with them. Practice your way through the discomfort of asking hard questions in customer interviews.

I’ve done this exact exercise with clients in the past. We hopped on a call for an hour and it is so fun, and really quite powerful. Because, see, when it comes to writing, copy or learning marketing, there’s a lot less emphasis on application and implementation of those skills. It’s more about theory and frameworks.

But in customer interviews, it’s a little – or a lot – different. You can know all the things about good and effective questions to ask, but they don’t mean a thing if you can’t implement smoothly, effectively and consistently. Skilled conversation is an actual skill.

So don’t wait until you’re in front of a customer to test that skill. Find a friend and practice or get on my email list and book yourself into my calendar.

And, we’ll work on your trouble spots and put together. And rehearse crisp, clean responses, and phrasing that can actually help you tackle those sticky customer interview situations.

The goal is to find an approach that’s custom to you, that sounds objectively comfortable and confident to your customer. Because it’s custom, it matches where you’re at and your comfort level with these interviews.

Now, if the practice makes perfect advice is annoying to hear. I totally get it. And, I’d actually say that that’s maybe your first stumbling block. Or, if I’m being really cheeky, it’s maybe your ego talking? Perhaps? In which case, thank you, ego. And decide to practice anyway.

Alright, that’s enough from me. That’s enough on your ego. Thanks for tuning in.

And if you have an opinion about this podcast, I want to hear it, hop on over to my iTunes. If you Google “iTunes better customer interviews”, my podcast will be top of the list. Click on over. Give me a review. Your thoughts, your commentary. Good, bad, in-between, whatever it is, I want to hear from you.

And, I’ll catch you next time in better customer interviews. This is Hannah. I’m out, bye.