Steve Portigal is a consultant who helps organizations build more mature user research practices. He’s the author of Interviewing Users: How to Uncover Compelling Insights and Doorbells, Danger, and Dead Batteries: User Research War Stories. He’s also the host of the Dollar to Donuts podcast about research leadership. In this conversation, we discuss the skills required for conducting successful interviews with users.

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Jorge: Steve, welcome to the show.

Steve: All right! Thank you.

Jorge: You and I have been friends for a long time, and I’ve long wanted to have a conversation with you on the show. Some folks who are listening in might not be as familiar with you as I am. How do you go about introducing yourself to people you haven’t met before?

About Steve

Steve: Well, I might say, “Hi, I’m Steve.” I mean, in the context of professional networking, as opposed to just the real world, you know, I might tell someone that I’m a consultant. I mean, anybody that works for themselves or anybody that has a non “normal” occupation, probably like many people who are listening, has to figure out… right? How do you explain to somebody what you do? And I guess I’m always trying to gauge how much they’re interested and not… we talk about elevator pitches? I could give the elevator pitch right now if I was any good at it.

But I’m trying to stick to the spirit of your question, or at least maybe not the spirit of your question, the words of your question. I might tell somebody I’m a consultant. I might tell somebody I work in UX because people have heard of UX, and they kind of think it’s something. If we get a little bit further, I might say I’m a user researcher. And then, assuming somebody asks what that is or doesn’t change the topic or something, I might tell them that I help companies learn things about their customers to help them make decisions about their products.

And, outside of our collective fields, that’s usually when the subject gets changed, or they might ask for a specific example. My elevator pitch is more about where’s my focus as a user researcher, and that is around the… to be buzzword-y, the maturity of user research practices.

Jorge: And what is your background? Where are you coming from to research?

Steve: I mean, at this point that we’re having this conversation, it’s really about 25 years of experience. You know, the further away you get from your academic background… well, I guess from me, the less specific relevance it has. So, yeah, I studied human-computer interaction and have a graduate degree in computer science. And that was before the web, so we didn’t have the phrase “UX.” We didn’t have very much design — however you want to kind of construct that — in the world of software. So, I came from a previous era of professions and practices and, you know, through a number of… I don’t know, coincidences? Opportunities? Left turns? Persistence? Found myself just… sort of discovering that user research was a thing and that, at least, I had an attraction to it.

Of course, I didn’t know that I would’ve had a talent for it at the outset, but I thought this was really, really interesting and pulled together a lot of strands of things that I had been playing with in terms of what could my “value-add” be. But, I think as a practitioner, I am self-taught. I didn’t come out of social science. I didn’t come out of design school. You know, there was sort of the practitioners, self-taught path, I guess, is the one that I followed. Yeah.

And we’re going back, a long period of time, and I think the opportunity in that era was to reflect as well as… because we don’t really know what we’re doing and there’s not really… we don’t know what sources? You know, myself and my peers, my colleagues, we don’t know where we would learn this from. We had very little… there was an internet, but there was no social media; there were no communities of practice. There were, I think, a lot of opportunities to reflect and even document and say, “well, here’s what we think.” Here’s how we think this should be to onboard new employees to the agency that I was working on and say like, “here’s how we work,” to explain to clients, and so on.

So, it’s a big mix of things that kind of started me off, and then just, yeah, years of experience and being now a part of a community and learning from other people and teaching other people and learning from them and learning from doing that. Yeah, that brings me up to today.

Jorge: I think that you and I might be part of a similar cohort that came into this at the origins of the field. All of this that you’re saying about having to find your own way resonates with me in that there wasn’t really a school of UX when I got into this, so we’ve had to find our way. Now you touched on… I think you said that at some point, you discovered that you had a talent for this particular part of it, for research. What do you think is a talent for research? Like, what makes a good researcher?

What makes a good researcher

Steve: I’ll answer for sort of a little bit about how that went for me, which maybe is an oblique answer, but I was basically an apprentice. And maybe there was even some reluctance to let me be an apprentice. I think I was looking for a home inside a small team. And so, being an apprentice meant: well, what task will we let Steve do? I could review videos from interviews, or I could sit in synthesis meetings.

When I say synthesis, from that era, it was really like a lot of talking. Not any kind of formal analysis or anything, but discussion and trying to find connections. I might review some videos and say, “Hey, here’s what I saw.” So, I was kind of a backstage researcher, like making sense of data was where I started. And then I was allowed to hold the camera. Like, there’d be two people out in the field. One would be running the interview; I’d be allowed to hold the camera. Then I could ask one question. And then I could co-lead. So, there was just this slow kind of onboarding over many, many projects to take on, like the range of tasks that we think a researcher should be able to do.

So, what makes a good researcher? There are so many facets to it, and it’s great if anyone can do all of them, but wherever you are in your path, you know we have this idea now that we have this profession of research operations. I know some people in operations that have gone on to be a “researcher.” I don’t know that that’s the objective or the skillset, but research does really well when things are well organized. Everyone knows where they need to be. They have the documents; they have directions; there’s technical infrastructure in place. Non-disclosures are signed that need to be signed. All the pieces to make research go really, really well.

If you don’t do that, you cannot have a good interview because now you’re on the back foot saying, “oh, did you not get this?” “Did you not sign this?” “Oh, I thought we were meeting tomorrow!” “Oh, you’re on Zoom! We needed to be on Teams. Are you on the computer, or are you on your mobile device?” All those sorts of logistics things are essential. That’s not my core strength, so I didn’t start there. I had to learn a good enough kind of logistics infrastructure because you see the pain if you don’t do it. But that’s an essential skill.

And so, either to be organized and have the details and all the players aligned or collaborate with someone that can do that? At a gross level, I described making sense of data and gathering data like doing research are big parts of it. Communicating, activating… we use this awful phrase, socializing. You know, trying to figure out how to have influence, how to have impact. How to create those learning-ready moments? How to facilitate that is another really important skill. Yeah, let me stop there. That’s plenty! There are many, many more, but let’s… that’s a good start, I think.

Jorge: research is an area that has many different practices, and I get the sense — and maybe this is from your books — but I get the sense that the area that you’re focused on has to do with qualitative research. I.e., sitting down with users and interviewing them. Is that right?

Steve: I mean, I think as a researcher, yeah. Like, the kind of practice I want to have in doing research, because of course our practices include lots of related activities. But the practice that I can bring the most to, and that I personally get the most out of, and then I think my clients get the most out of, is, yes, sitting down with somebody and asking them questions; learning from them, trying to connect their view of the world with some problem or challenge or curiosity that I’ve started with with my clients.

Jorge: Does that entail a particular way of being? Like, I can’t imagine doing that if you’re not like a people person, right?

Being intentional with your energy

Steve: I don’t know if I’m a people person. There are ways of being that are our defaults. And there are ways of being that we can… you know, put on, like a suit or a dress or something. I mean, and I think an analogy is: doing conference presentations or leading workshops. Being on a podcast! Those are all… I mean, people assume that I would be an extrovert, for example. Which I think is sort of the broad brush that we characterize those behaviors with.

But introverts are… I feel like most researchers are introverts, and one thing that introverts are good at is playing a role, and that might make people uncomfortable because it sounds like I’m talking about being inauthentic. But it’s a choice. It’s like, I’m going to be a people person. I’m going to be engaged. I’m going to be curious. I’m going to give energy to this interaction. And knowing what the role is, if you know, being a workshop leader at an event or being on a podcast. These are all kinds of intentional ways of being as opposed to the one that you leap out of bed with in the morning.

So, being able to summon up different kinds of energies, different kinds of mindsets as you go from situation to situation. And I actually think that makes for a better researcher because no two situations that you find yourself in are the same. The energy and the mood that the person you’re talking to is going to be different, so being able to adjust your energy and mood and approach and tactics and tone and all those things in order to respond to that situation is… I mean, I can’t say it’s easier for introverts than extroverts because I’ve never been an extrovert, but if we are putting on clothing and kind of adjusting it based on situations like playing a role, I think that potentially can be more dynamic and more responsive to the context.

Jorge: Yeah. And I think that my question about being a people person… I can see how that might be interpreted as asking whether you’re extroverted or not. But I think that what you mentioned about being attuned to people’s energy and mood might be a better way of thinking about it. I think that if you are… and this is my assumption, but I would expect that if you are unable to get in tune with another person’s vibe, it would be very difficult to do effective interview research work. Is that fair?

Steve: It’s going to be different, right? I think there are people that have just enormous amounts of charm, like a superpower of charm and energy. And I think they can make things happen in their interpersonal interactions in interviews that I can’t. And I love seeing that because there are just so many different ways to go about this. It’s not, “I can’t do that.” It’s easy for me to say, “that’s not the right way to do it. You have to let go of yourself and surrender your personality and objectives,” and so on, and be responsive and be attuned. But there are different approaches.

So, I think the bulk of what I see is what you’re describing. People who have that skill and that ability to kind of put their needs from an interaction, their needs to kind of put themselves out in a certain way… they can lower the need to do that. I think that’s a pretty effective technique that most people can lean on, but there are always these interesting exceptions with people that can bring that to it. And I guess in no way am I encouraging anyone to think that they are that person and put that on because there’s the recipe for failure when you think that you are more charming or more kind of impactful as a person than you actually are.

Jorge: When you talked about charisma in that way and having a researcher who is somehow charming and energizing in that way, the question that came to mind is: is that even desirable? Because the person that is being interviewed would somehow get them out of their normal state of being and into some kind of elated state that somehow skews the interview.

Steve: The interview is skewed anyway. There’s no naturalistic interview that’s like… you’re not a fly on the wall. Any of us doing whatever our level of charisma is, we’re there to interrupt the process and distort it and talk about it. Because it’s not normal to be interviewed, so yeah, who’s to say that that distortion… like I’m thinking about, a woman I worked with who… I mean, she was really great in workshop settings, which is not naturalistic anyway. But she would look people in the eye and say their names, and even in interviews, she’d ask people to draw things, and she’d say things like, “okay, Jorge, I’m going to hand you this marker here. Do you want the green one to the red one?” And like, “I’m going to hand it to you, and I’d love you to draw…” And so, just the level of kind of direction and overt facilitation, like you’re now doing her thing. But the thing that she would ask you to do is emergent from the context of the interview.

And so, if we’re going to make kind of caricatures on a continuum, you’ve got her one end, like just being very like… what I imagine sort of Dale Carnegie tells you to do. Like, just really be in that person’s face in a kind way. And you’ve got maybe someone like me. I might be leaning back and nodding and just waiting and leaving silences. And yeah, that’s what I’m good at. I’m very good at that. And I can make all kinds of things happen and come in at the right moment and really look for these things that need to be… you know, grabbed and highlighted and reflected back to dig a level deeper.

But my old colleague could also get there. So, yeah, I guess I want to hold onto that as an effective technique for someone that is really, really good at it. That’s the exception, right? I think more people would look like me if we were to take this continuum and kind of put dots where all the researchers are. They’re going to be down at the like… much more of us are down at the wait and watch and listen kind of approach.

Improv and interviewing

Jorge: How did improv help you conduct better interviews?

Steve: I mean, improv, I think, gave me some confidence that some of the things… there’s a lot of times doing research — perhaps all of it — like, in the moment of an interview, or the many moments that make up an interview, where you feel lost. Like, this isn’t going where it’s supposed to go. We’re going to run out of time. I don’t know if any of this is useful. I don’t just mean the self-doubt mind that maybe we carry around all the time, but like really responsive to what’s going on and being uncertain and not knowing what your next technique is. And if you do research enough, you just… I guess I want to say you get over that feeling. I think you just learn to sit with that feeling.

And improv… and there are many kinds of improv, but thinking about doing small sketches where you’re given a problem to solve. Here’s a constraint in how you’re going to talk, here’s how you’re going to use the space that you’re in, here’s what the topic of the scene is, and it’s all emergent. You can see pretty quickly with improv — even poorly performed improv — and I’m not talking about watching it; I’m talking about doing it. You can see the thing that you’re trying to make. It gets made. Like, it works. If you follow these constraints, things emerge that you could not have planned for that are good based on some definition of good. Sometimes they’re funny. Sometimes they’re interesting. And improv only works if you let go of trying to control what the endpoint is going to be.

And in improv, you may find yourself with someone who is incredibly charming and who is incredibly present, and naturally funny. And if you’re not that person, you can still work the system. Work these rules and these constraints with all this unknown on top of it, and make something else happen that you could not have got to if you said, “here’s the outcome I want to get to,” and then try to grind it out to get there. You couldn’t have done it.

So, improv and interviews are kind of analogous to each other. Practicing something else that kind of teaches you those principles and gives you some confidence in a process that is always going to challenge your confidence. I think that is nice… it’s a skill transfer for sure. And you just got things like not knowing what I’m going to say next. And sometimes, in improv, you start the sentence… in response to something that someone else has said, you start the sentence, and you don’t know where you’re going to go with it.

And if you can decouple or unlink that scripting part of your brain and get the mouth to move without that part of the brain happening, interesting things happen. And that’s hard to do in a professional situation. We are under a lot of pressure. We’re being recorded. We’ve paid a participant to do this. Our colleagues are going to watch it. We’ve only got x days until the report is due. It’s hard to limber up and practice how to decouple from that and just start talking without knowing where you’re going to go… and feel like that’s a good thing, not a bad thing. I mean, when I say that sentence, it sounds like a bad thing. You should know what you’re going to say before you say it, but it’s a flow state when it happens. I think in interviews, at improv. So, having some other venue where you can practice some of that hard stuff, I think is… can really be effective as a sandbox or a place to keep working it out.

Jorge: Well, what you’re speaking to is having a degree of self-confidence that allows you to both be in the moment — present in the interview — but also keeping an eye out for the outcome, and you talked about these constraints. In the case of a conversation like the one you and I are having now, there are many ways this conversation could go, right? And we both have in mind the fact that we are recording a podcast that will hopefully have some value for listeners. Like, if we start rambling and just taking this anywhere, the conversation will somehow be less valuable. And I’m wondering if that confidence to be in the moment and responsive to what you’re hearing is something that comes with experience and time or if it’s something that is innate to people. Like, you come fresh into the role of user research interviewer — the first time doing it — and you’re able to do that. Versus someone like you or I who’ve been doing this sort of thing for many years, and we now at this… I’ll speak for myself, at this stage in my career, I feel like I can sit down with someone and take things in different directions without losing the plot. But it’s taking me a long time to get there. That doesn’t come naturally to me. So, is it a matter of having it grow over time, or is it a matter that some people are born with it?

Innate and learned skills

Steve: I love that you frame it around self-confidence, and I just want to poke at some nuance there. Because that’s a loaded term, right? Self-confidence sometimes implies cockiness or arrogance or entitlement, or you know, what’s the… Dunning–Kruger, is that the effect? You know, the effect on our skills?

Jorge: Dunning–Kruger?

Steve: Yeah. I think that’s what that word sometimes affords. And, I guess the phenomenon for me is often feeling uncertain and just scared or a sense of doom or impending failure or whatever. Just all the senses of things not going well. And so, the confidence is like… it’s like comfort with discomfort, you know? Being able to sit with that and accept that and trust the process a little bit. Because I think… so that is a form of confidence, but it’s not… it’s also confidence about what you don’t know and not being certain how things are going to succeed.

To your actual question, though, is this innate? Does it come with experience? I’m sure everybody arrives at adulthood with different amounts of all these ingredients that we need, whether it’s charm or self-confidence or the ability to sit with discomfort. But what I have found, because I do a lot of teaching teams to do research… and often that involves sending them out to do something and then having them come back and talk about what happened and, you know, they’re in front of their colleagues, they’re in front of this external instructor, me, that they’ve hired. And so, I think there can be some intimidation to it.

And I have found, over the last few years, that in addition to providing tactics and kind of mindsets and sort of, “here’s what I advise and recommend for you to be successful in doing this work.” In these interactions that we have in kind of these feedback sessions, the role that I’m often playing is in giving people confidence and being able to say, “oh, the thing that you are describing is very common.” Because I think people have some experience, it feels weird, and they’re like, “well, I’ve screwed this up.” And so I’m working hard to give people confidence and say… to affirm their experience, to validate the uncertainty and struggle they felt in it. And then maybe say, “yeah, here’s a thing that you can try,” or, “ you know, there are tactics to kind of address this.”

But they need the confidence as much as they need the tactics. Because they might get to those tactics on their own, but if they feel like, “this is not the right way to do it, I’m screwing this up,” because it is a weird thing, because you may find yourself feeling like you’re screwing up when you actually are succeeding, because you’re dealing with the absolute uncertainty of another person who you don’t know, who you’re spending time trying to get to know a little bit… it’s entirely unpredictable and uncontrollable. And so, all the ways that we expect ourselves to be successful is to be controlling for all that uncertainty, but it’s inherently uncontrollable to some extent.

So yeah, the more you do it, the more you either make mistakes or feel uncertain about an experience that you’re having and reflect on it, whether it’s through listening to a podcast where people are talking about this or reading a book, or, working with someone who’s more experienced, who can reflect back to you. Those are all ways that we do become more confident with these sort of… surprising or unexpected aspects of what the nature of the work is.

Jorge: Hearing you talk about it makes me think that these are skills that apply not just to interviewing users for user experience research. These are key skills to human interactions, right? The ability to listen, the ability to tune in to the other person’s state. We didn’t talk about this, but being keyed into the context and the influence that that has. I’m wondering the degree to which doing this work has influenced other aspects of your life beyond your work?

What listening really means

Steve: I’m going to offer a humble brag. I met with some folks a couple of years ago. I was visiting their team and doing some work with them, and a few of us went out to lunch, and one of the guys was just a really, really nice guy said to me how much he’d gotten out of one of my books and how much he’d learned. And then he pauses. He said, “it really helped me in my relationship with my wife as well,” which was obviously a very gratifying thing to hear.

Any time anyone tells you that they got value as something that you put out in the world, it’s great. That is obviously not anything I know anything about or anything that I wrote about. It’s a side effect that he pulled from this. He made the connection. He said, “this idea of what listening really means and being there to understand the other person’s point of view and having patience for that…” Yeah! So, that was an amazing compliment to me. Again, it reflects on him that he could, you know, make those kinds of connections. I mean, it’s nice to have that.

Back to what I was saying about kind of introverts being able to put on different modes in different situations, it’s nice to have that mode to be able to go into in situations that I’m unprepared for or in situations that maybe are socially uncomfortable for me, being able to ask questions of somebody is a way to, you know… if two people meet and it just is awkward. Like, being able to ask questions and actually not… for me to take my own focus out of how this moment feels and ask more about the story. It’s a way to put somebody else at ease and a way to make my own awkwardness or discomfort or uncertainty about how to handle something.

That is not in no way am I trying to imply I’m Mr. Suave-socializer, and I’m always defaulting to that mode. I’m always asking questions. Because I also may be incredibly quiet, and I may be quiet and listening, or I may be quiet and like just retreating because I can’t… there’s too much going on, and I can’t focus. So, I think having many modes to cope with different kinds of ways that we find ourselves in situations with new people or familiar people — it’s good to have that. And certainly, years of doing interviews have strengthened a number of those modes to go into.

How to ask better questions

Jorge: What would you advise to folks who want to be able to ask better questions?

Steve: Questions or follow-on questions? I mean, we use the word “question,” and when people prepare for interviews, hopefully, they’re writing up the questions they want to ask, but we’ve probably all seen people — or done this ourselves, even — ask the list of questions that we’ve written.

But it goes back to you bringing up improv. You should definitely write up a bunch of questions to ask because that’s a pre-vis activity that really helps you at least generate some default context, so you have something to fall back on. But the best questions are the ones that emerge from the conversation. And that you could probably break that down into a couple of levels. There are very basic follow-up questions, and that could be, “how so?” Or, “hmm?” Or, “why?” Or, “was that after the first time that you tried that?” Like, they’re just very, very simple questions, but they keep that conversation going and keep that answer going. And I think some of the best interviews can be just that.

But follow-on questions can also be emergent, fully emergent. Like, “this is not a thing that I knew I wanted to ask about.” And I don’t know where your questions are coming from in this interview, but some of them are responsive to something that I have said. And I’m going to guess that some portion of this conversation is stuff that you have realized from what I’ve said, that maybe I didn’t literally bring up something, but it connected some dots in your head, and it made you reach outside what you had intended to talk about to bring something else into this. And so, if you just talk about the topics that you have already decided you want to talk about, you could just as easily do a survey.

It’s the stuff that you didn’t know that you didn’t know about that is super important. So that is very improv-y. So I think that first piece of asking just basic follow-ups is really about… like you see stand-up comics do this. You’re really milking the joke, right? It goes on and on, and on you take that bit, and you let it really… you just give it so much space to bloom.

So that’s follow-on questions, and then a thing that you start to discover that you want to create some space for in the interview is another kind of follow-on question. So a) prepare, b) ask those kinds of micro follow-ups, and c) find something new to talk about that’s emergent in the interview. I think those are my three.

Jorge: Those are great prompts. I’m going to end with a prepared question. Where can folks follow up with you?


Steve: I’m on LinkedIn. So under my name, Steve Portigal. I probably post work-ish stuff there most often. My website is It’s certainly fairly static, as I think maybe a lot of websites are, but you can find information there about my books, podcasts that I’ve been on or hosted, conference talks, those kinds of things. The work that I do a little bit more about that is there as well. So, and LinkedIn are probably where I would direct people to.

Jorge: Fantastic. Steve, it’s been a pleasure having you on the show.

Steve: It’s great to chat with you. Thanks for all the great questions and good discussion.

Jorge: Thank you for being here.