In this tutorial, you’ll learn how we conduct interviews at Draft.

There have been multiple books written about this topic. If you’re interested in a deep dive, go pick one of them up.

The Outcomes

First, let’s talk about what interviews should do. They should:

  • Teach you about the customer. Who are they? What do they care about? What demographics do they represent? What are their motivations? Do they represent a “typical” use case, or do they represent an outlier?
  • Teach you about how people make a purchasing decision. When do they begin thinking about it? When do they consider alternatives? Where do they go to research the product? How much does word-of-mouth play into the decision?
  • Teach you about real-world use. How are people onboarding to the product? Are there transition costs from a competitor? Do people stop using the product after a while? What motivates them to stop? What motivates them to restart?
  • Teach you about the competition. Is the market crowded? Is it easy to make a purchasing decision? How is competition vetted? What do people look for when weighing one business’s product against another?

Taken in aggregate, interviews should offer a more complete portrait of who uses the product, how they find out about your business, how they make a purchasing decision, the lifecycle of their use, and any special “outlier” cases that might result in outsize purchasing volume or special considerations for new products.


Let’s talk about the rigors of your interview setup first. Tactically, you should:

  • Prepare the participant. Good interviews go both ways. You should anticipate issues before they happen – by ensuring the participant has a good connection, clear sound quality, directions to the site, a confirmed time slot, and clear expectations of what will happen during the interview.
  • Pad your interview. You absolutely need air space of at least a half-hour before, and an hour after, each interview you conduct. Why? First, interviews involve a tremendous amount of emotional labor, and you will be wiped after conducting one. But you will also be awash in new ideas, and you will want to take as many notes about the interview as possible when they’re fresh in your mind. Finally, you’re going to want to prepare for an interview in the half-hour beforehand – no matter how many you’ve given, every participant is unique, and you always learn how to do better from the previous interview. It’s a grievous rookie mistake to think you can run interviews back-to-back. You can’t. Because you’re human.
  • Record the interview. I use Audio Hijack to record my interviews. If over the phone, I run the call through FaceTime on my Mac. If on a computer, I use my podcasting rig to make the call – closed-air headphones, a supercardioid mic, and an XLR mic preamp – so I can sound as good as possible to the participant. If in person, I use Voice Memos on my iPhone, connected to a nicer microphone.
  • Remember that if you have a portable device of any kind – laptop, iPhone, iPad – always connect it to a power source during the interview. You want to think about as few things as possible as an interview happens – and your battery life is one of them.
  • A nice-to-have, but not always realistic: use a wireline for your interview. The absolute last thing you want is for an interview to go south because your connection keeps dropping. Apple has a perfect solution for this..
  • Have a second person on hand to take notes. That way, you can focus on what the participant has to say – and you can always be thinking of the next question to ask them. Are you a lone wolf like me? Know who’s great for your recorder? College students who want to get a background in real, research-driven UX design. Here’s a terrific guide for hiring part-time employees, which I used to hire my own assistant.

The Anatomy

Interviews have a basic anatomy:

  1. The softball questions. These are super basic questions that get people warmed up and used to answering questions. Who are you? What do you do for a living? Education level? Marital status? Got kids?

  2. Baseline questions. These are a few questions that you ask people in order to get some baseline insights from them. They include consumer insights like:

    • Do you use our product right now?

    • How many times have you purchased our product?

    • What model(s) of our product do you own?

    • When did you purchase it?

    • How do you use it?

    • And other questions about the search:
    • How did you find out about us?

    • Did you make a purchase right away?

    • How long have you been seeking out this sort of product?

  3. The actual interview questions. We’ll get into what these are in a minute.

  4. Turn the table. Now you’re wrapping up. Ask if they have any questions for you.

  5. Explain the project. You owe it to your customers to be honest and forthright about what kind of work you’re performing. Tell them what you’re working on, and ask if they have any questions about the work.

  6. Compensate them for their time, thank them profusely, and send them on their way.

The Interview Itself: One Example

Go back to the first section of this tutorial, where I discuss the outcomes of the interview. Good questions will address these considerations head-on. The specific questions you ask will depend heavily on the participant and the business’s needs. There’s no way I can provide “one weird trick” for creating interview questions – but I can show my process for creating interview questions.

Let’s say you work for the division of Amazon that makes Kindles. You want to improve reading time on Kindles – because that sells more books that are made for Kindle. Here are some questions I would ask (which are based, in part, on some questions found in Steve Portigal’s aforelinked Interviewing Users):

  • Tell us more about yourself: what are your hobbies, other interests, etc?
  • Why do you read?
  • What is your current reading habit like?
  • Where do you read?
  • What kind of books do you read?
  • What motivates you to find new books in [topic]?
  • How do you find out about new books?
  • Is your current reading typical? In what ways does it differ?

Now, let’s assume you work for a domain registrar. Here are a few questions I’d ask of a customer:

  • How many domains do you own?
  • Are they all at our registrar? If not, where are they spread among?
  • What motivates you to buy domains?
  • Is the number of domains you currently own typical?
  • Do you let domains lapse? How do you feel about that?
  • Have you ever let a domain lapse accidentally?
  • On what devices do you buy domains?
  • Who do you buy domains for? Yourself? Friends?
  • Have you ever switched registrars?

You should type up all of your questions, so you can refer to it during the interview itself. Nothing sucks more than realizing you missed an important question right after the participant leaves.

Keep in mind that the interview should wander. You need to be listening for interesting details that the participant would be able to expand on. “You mentioned [THING] before. Can you tell me a little more about that?” and “You told me about [THING]. Has this changed over time?” are two excellent questions that you can use to get real motivations out of participants. You should be using them multiple times in every interview you conduct.

And just as the interview should wander, you shouldn’t be afraid to pull the conversation back to the topic at hand. Always keep the interview focused on the business needs – even as you show an interest in the participant. This is a very fine balance to strike, and you’re going to suck at it first.

The Approach

There are many things that make or break interviews – and all of them depend on you, not the participant.

This sounds weird, right? But you screen the participants. You confirm times with them. You ask the questions. You’re the one with the business needs. Interviews are yours to lose.

Good interviews are all about being positive, staying as open-ended as possible, and carrying yourself in a way that makes the person feel welcomed.

Check Your Worldview

First, you need to check your own worldview at the door. Interviews are all about understanding how other people operate. The more you assume about that, the less likely an interview will go well – both in terms of gathering data and in terms of that data being high-quality enough to guide a successful project.

Ask Open-Ended Questions

Leading questions assume something of your audience. Let’s assume you’re observing somebody working with a site and they furrow their brow at one step. A leading question would be to ask “Frustrating, right?” A better way to ask this would be to say “Tell me what you’re thinking right now.”

Open-ended questions allow the participant to fill the gaps with what they think is the right answer. And that’s what’s important: giving them space to be themselves.

Act Naïvely

People avoid asking questions to which they already know the answer. But you should err on the side of asking “dumb”, naïve questions – because you might end up gaining crucial insights

Here’s an example, again from Interviewing Users. Let’s say you’re working for TurboTax on a new product, and you’re interviewing people about their taxes.

  • Question: When are your taxes due?
  • The answer (which you probably already know, if you live in the US): April 15
  • The response you fear: Why are you asking me this stuff? Everyone knows that it’s April 15. Get out of my house, jerkface!
  • The type of answer you are just as likely to get if you swallow your discomfort and ask the question anyway: I always complete everything by March 1. I think it’s April 15 this year, but I never really pay attention to that.

That last answer could provide a really interesting insight for this project – and it all came from your not assuming anything and asking the question anyway. And to be clear, I get these sorts of answers all the time in interviews.

Shut Up & Listen

Never interrupt someone unless they’re totally flying off-topic. You would be shocked what happens if you stay silent after they appear to have finished responding; they might be encouraged to keep talking, and you’re liable to get a more honest response at that point.

It is tempting to fill a vacuum in conversation: we instinctually try to. But all world-class interviewers withhold further comment and tease more out of the participant – and you, as a viewer of the interview, barely notice.

Course-Correcting an Interview

All people are weird. You learn this after interviewing enough of them. Weirdness is fine. It’s part of the process. But once every year or so, we run an interview that just turns out to be an unusable disaster. The participant digresses, or they turn out to be such an edge case that they don’t represent real-world use of the product.

This isn’t what we’re talking about here. What we want to discuss is the sort of interview that slowly digresses. You need to get it back on track to get the sort of insights that your business needs. First, though, you need to get a feel for the different ways that an interview can go amiss.

The different forms of interview weirdness

The feedback session. Interviews are not appropriate avenues for negative feedback about your product – yet many participants think that they’re being called to grouse.

How to address it: Tell them that you’ll bring up their issues with support, and that you want to change the topic to discuss their experience with your product. If the issue is that they haven’t received your product yet, or it didn’t work to specification, note what happened and end the interview.

The autobiography. We all want to feel heard & seen. You do. I do. And so do your participants. The problem is when your participants use your interview session as an opportunity to talk about every detail of their lives.

How to address it: Reflect back what they’re saying, and start providing firmer boundaries on the conversation. Say you want to shift gears and talk specifically about you product. Retreat to more binary yes/no questions. Avoid cutting someone off if you can, as the broader goal is to make them feel heard.

The boiling frog. This is by far the most common. The participant says or does something that seems innocently weird, and then they keep doing it. As with the boiling frog that doesn’t know it’s in danger until it’s too late, the interviewer can realize that they’ve digressed too far from what they wanted, or that the interviewer has their own agenda for how it should proceed.

How to address it: It’s hard to discover that you’re stuck in this situation until far along in the interview. If you have more than 15 minutes left in the interview, you might want to alert the person to an upcoming topic change and set a light boundary around how they’re engaging. Suggest alternatives to how they’re communicating if at all possible.

Knowing when to cut loose

Sometimes, you just need to end an interview – or let it play out, knowing that you’ll throw away the results.

You should still compensate the participant, since they showed up and provided you with their time and attention. Plus, that compensation matters way more to the participant than it does to your business.

Then, book another interview with another participant. Dust yourself off. Know that no participant will ever meet the other participants, and they have no idea what kind of experience you’ve had with your interviews. Tomorrow’s another day.

Interviews are a Practice

You’ll get better with practice. Interviewing is a game of a thousand small techniques. And I hope this gives you enough to go out and interview people today. Ideally, you have some people scheduled. Next up, build an example set of questions – which acts as a field guide to performing the interview. Once that’s done, write up a set of expected outcomes that the interview should accomplish for your business – and take a look back through your questions to ensure that they fulfill your business’s needs.

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