Nicola’s mission: 

Iris is a freelance journalist and writer online. I want to make a product for online writers and I'm doing early generative research. My first step is to really understand my users: online writers. What are my assumptions about them, and am I correct?

Learning goals:

1. Understand context. Where, what, when, for whom, do writers write?

2. Understand tools. How do writers create their content? Dig into what tools are used, why, and what the biggest pains are there.

3. Find their pain points.

During the interview

With all those pieces in place, and maybe a colleague in the room to take notes, she dives into the interview. Here’s how she approached our call:

Warm up your subject. 

Nicola opened our interview with a bright “Hi!” and asked me about the time and weather in San Francisco. She also told me a little bit about her day. We bantered for a minute or two before diving in. It made me like Nicola, and it felt almost as if we were friends chatting. That’s the feeling you should aim for, Nicola says.

Share the agenda. 

Nicola uses this phrase in every single user interview she does: “The plan for today is we have about [X] minutes, right?” “It’s really important to give them context of what’s going on, and timeboxing so they know you won’t be chatting forever,” she says. Nicola explained that her team was building a product for writers and that their process included speaking to potential future users, then asked if I had any questions before we got started.

Lay the groundwork. 

Imagine a movie where the camera first pans over a city before zooming in on a house or person. Take the same approach to your interviews — create a foundational understanding of the person before honing in on specifics like pain points. Nicola kicked off with: “Maybe you can tell me a little bit about yourself. What do you do for work?” She followed that up with “How many writing projects do you have in the next week and a half?” She asked me to describe what I was working on currently. This, combined with Nicola’s friendly and curious attitude, slowly warmed me up to talking about myself and my work. Most people aren’t used to talking extensively about themselves with a total stranger, so be mindful of building the up, Nicola says.

Have people take you through their current process. 

Once you’ve laid the groundwork, here’s where you can start looking for pain points. Push them a bit on details, and don’t be afraid to ask follow-up questions, or even the same question worded differently. Nicola said, “Can you think of a recent project that you've done and just talk me through what does that actually look like? Take me step by step, even if they're really sort of little boring things.

Pivot if you’re barking up the wrong tree. 

Nicola wrote down and starred my comments when they struck her as interesting. As it turns out, her original thesis was wrong—which isn’t uncommon.  “It didn’t seem that marketing was a big pain for you,” she says. After asking me a few questions about marketing and listening to my answers, she changed course.

Wrap up using this phrase. 

“I did a lot of interviews before coming to this one specific phrase. I found that things could get kind of awkward at the end. How do you finish up? You’ve built up and built up, you’re having a really good conversation, people are really talking to you about themselves. Then time is up. Ok well, we’re done! It’s a bit awkward. So I say, ‘I just have one last question before we wrap up,’” Nicola says. “It’s really good because they know it’s about to be finished. You get them into that moment where the cameras stop rolling. Quite often, you close the book and stand up, then they stand up and turn to you and say, ‘Oh, also, gotta tell you that…’ Often what they say after the interview is over is really interesting.”

Nicola’s interview tips

For brusque interviewees, take an extra few minutes to build rapport. 

Nicola works to draw enthusiasm out from interviewees who are less than excited to be there. “The only other time people get interviewed is when they’re trying to get a job. Naturally people feel awkward. When this happens, I change track to get some measure of enthusiasm. Don’t go entirely off-topic — it creeps them out. But try questions like: ‘Tell me about your family. Who do you live with? What’s the last thing you watched on TV? What are your hobbies? What games do you play?’ Then pick up on whatever they say that they seem excited about, and chat about it for awhile,” Nicola says. “That’s a trick to help people open up a bit. And consider pulling back the curtain a little bit. I get vulnerable myself and tell them that we don’t know whether the work we’ve done is good enough.”

Never forget your goal. 

“I keep in mind the top three things I listed in my guide: understand a writer’s context, tools and pain points. It’s top of mind at all times, especially pain points,” Nicola says.

Parrot and mimic. 

Nicola used the phrase “So, to play it back to you…” a few times and would repeat what I’d just said. It helps confirm that you have the right understanding. To do this, make note of specific phrases the user is saying. “The notes are most important for me to look back on while I'm talking, to use the same phrases you used and ask relevant questions. I'll often jot down my next questions while the participant is talking,” Nicola says.

Use a friendly tone. 

Nicola kept her tone light and friendly throughout our call. She seemed genuinely interested and curious about my work, and soon, I found myself blathering away. Nicola didn’t interrupt me much if at all — and the more I talked, the more valuable takeaways Nicola got. “I love to get people to tell me stories,” she says. “A really big part of being a product designer is to really understand the person by talking to them, and that means speaking to them on your level.”

Results from our generative interview session

Even though the time was less than ideal at just 20 minutes, Nicola managed to get a ton of information out of me. After quickly learning that her original thesis around marketing pain points was wrong, she asked me, “What’s preventing you from being as successful as you want to be?” It was a pretty personal question, and wouldn’t have worked as well had she not built a rapport with me and built up to that moment by asking me about how I built my writing business and what tools I use to craft articles.

By the end of the interview, Nicola had struck gold. I told her it’d be nice to have an assistant to set up some of the raw material I use for writing — cleaning up interview notes, suggesting an outline, crafting summaries, transcribing audio or video.

“That’s what you really want to talk about as a product designer. You told me the exact work you don’t want to do, but have to do. All of those things sounded to me like they could be potentially provided by a service or product,” Nicola says.

From that 20 minutes, Nicola was able to glean enough for a product idea. “I have enough to create some sort of product, perhaps one that starts by machine learning to pull out interesting topics from automatically transcribed audio,” she says. “Hopefully at this point I’ve heard similar things from the handful of other writers I’ve interviewed.”

Nicola’s next steps would be to chat to four or five people total — other content creators, strategists and online writers, hopefully the same day or next day. “You want to create something quickly. By next week I’d want a mockup to show people, and it goes on from there. Keep iterating, 100% as quickly as possible. It’s so much better to create the quickest possible prototype. Super quick and dirty, draw it on paper if you have to,” Nicola says.

Just relax!

In conclusion, Nicola urges interviewers to consider users as if they are friends. “Try to think of each user as a new friend, and you want to learn about them. Don’t get nervous — relax! It’s just nice to create the sense that you’re having a conversation with someone. You’re listening to what they’re saying and flowing with what they say, not just reading a list of questions.”

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