“You broke into Democratic National Committee headquarters? Tell me more about that.”

The Definitive Guide to Asking Follow-up Questions

Dan Brown
Dan Brown
Aug 3 · 8 min read

In a recent stakeholder interview I asked, “What do you think the main risk to this project is?”

He said, “I think the real bottleneck is with our Operations group.”

It was a good response and so it would have been easy for me to move onto the next question. But getting through my script isn’t my job. My job is to learn, surfacing obscure information and applying it to the design problem.

Give me deeper insights and buried connections: they add real value to the design process.

Being great at interviews — whether talking to project stakeholders or product users — means being able to ask good follow-up questions. Follow-up questions bring deeper insights and buried connections to the light of day.

“Stop asking me why why why why why.”

Five Whys and One Better Trick

Let me just get this out of the way. One trick interviewers use to dig under someone’s statements is to ask “why?” five times. While productive, you can’t really use it more than once or twice in a conversation, not without pissing off your subject. Rote patterns like this don’t show that you’re listening, that you’re incorporating what someone says into your preexisting knowledge. You’re just hitting the same note over and over again.

By the way, I recommend this technique in Practical Design Discovery, so I’m owning my contradiction here.

If you’re looking for a go-to technique, try saying, “Can you give me an[other] example of that?” Getting concrete examples gives you a clearer picture of what’s going on, and fodder you can use throughout the design process.

“Is now a good time for a follow-up?”

When To Ask a Follow-up

So, when must you ask a follow-up question? There are three cues I use:

Loaded Terms: When the participant uses a term that might have meaning beyond the dictionary definition — like “bottleneck,” in my example above. This also works for words that are meant to obscure or gloss over some interesting details, like “operations,” which might refer to a specific person.

Hesitation: When the participant stumbles out a response, I might sense that they’re still formulating their thoughts. By asking a follow-up, I give them another chance to provide a response, one that’s already been through a “first draft.”

Difficult Questions: When I know I’ve asked a hard question, I almost always restate the question from a different perspective. This flavor of follow-up is a prompt to get someone to keep talking, staying on the same topic and digging further.

“I have so many questions they’re coming out of my ears.”

Forming Follow-Up Questions

There are four flavors of follow-up:

  1. Ask for elaboration: You want them to provide further details on their initial idea.
  2. Ask in a different way: You want them to approach their idea from a different perspective.
  3. Ask about an orthogonal topic: You think there’s a connection to be made.
  4. Ask them to challenge assumptions: You want to surface what’s unsaid.

1. Ask for Elaboration

Never hesitate to get someone to elaborate. In all the interviews I’ve done, no one’s ever said to me, “You already asked me that.” So long as you ask respectfully and with genuine curiosity, people are happy to tell you more.

Tell me more about that. Easy and versatile. It’s especially useful if you don’t have a good concept or keyword to latch on to.

What do you mean by… Pick on a single keyword or idea, like when they’ve used loaded terms or jargon. But it works best when they use a common term where everyone assumes the meaning is well-understood. “And in this instance, what do you mean by ‘digital product?’”

Let me get this straight… Reflect their answer back at them. In addition to validating what they said, this generally prompts them to elaborate on the idea. “I want to make sure I understand what you said. You said you didn’t have much confidence in the product team. Did I get that right?”

How do you know? Used gently and respectfully asking about underlying knowledge can reveal how experts do their jobs. When they point out a bottleneck, you can say, “How do you know that’s the problem area?” and learn a great deal about what they look for.

“While I stare off into the middle distance, please elaborate.”

2. Ask in a Different Way

One way to follow-up is to re-state the initial question. So when I ask:

“What do you think the biggest risk to our project is?”

I could restate this question as one of these:

“What keeps you up at night?”
“What do you think the project manager worries about most?”
“Tell me about a time a similar project went wrong.”

I use a few techniques to generate these questions:

Use a synonym: People generally worry about risks, so when I ask about risks I can perhaps swap in asking about worries.

Inject a perspective: By suggesting that they put themselves in another person’s shoes I get new insights, and the added bonus of promoting the value of a perspective shift.

Point to a past experience: Putting the topic in the context of a specific event or incident can elicit more concrete insights and relatable stories.

“We are each going to ask the same question in a different way, but you’ll humor us because we work for the Washington Post.”

3. Ask about Something Orthogonal

Studying a domain means learning about aspects that are adjacent to each other. When I ask about what’s risky and I learn that the Operations group might be a bottleneck, I get the chance to learn about what the Operations group does. Or what other groups do.

Here’s how I take a left turn during an interview:

When they mention a person or group, I ask “who else?” Since understanding connections are important, I can use the mention of one group to trigger a conversation about additional groups. When they mention a group like Operations, I can ask “Who do the Operations people interact with regularly?”

When they mention a process or action, I ask “what else do they do?” Verbs offer great hooks to explore the range of actions or behaviors. When they say that the Editorial group reviews all the materials, I can ask, “You said they review the materials. What else do they do with them?”

When they mention a state or condition, I ask “how else might it be?” Descriptors in the real world–like “first draft” or “final”–reveal that something can be appear in other states. So when someone says, “It comes to me as a draft,” I can ask, “Is there also a final state or approved state?”

When they mention a timeframe, I ask “when else?” Words like “sometimes” or “frequently” establish a timeline. Besides asking follow-ups like “how frequently,” I can ask about those areas not covered by the stated time frame. When they say, “always,” I can ask, “But when is it not?”

“Ask about orthogonal topics, but only one at a time.”

4. Ask Them to Challenge Assumptions

When people make generalizations, they’re usually saying more about their feelings or impressions of the thing than about the thing itself. Generalized statements like “Operations never completes their tasks for the publishing process on time” gives you a chance to dig into these impressions.

Get them to quantify. Asking them to put their observations in real terms validates their impression and offers more insights. “You say ‘never’ but I’d like to understand that better. How late are they with their deliverables?”

Get them to compare. Like quantification, comparisons validate the impressions and offer more insights. “OK, how does that compare to other groups involved in the publishing process?”

Get them to slow down. Making a generalization covers a lot of ground. By asking them to slow down, you’re asking them to build to their conclusion, so you understand how they got there. “OK, let’s take a step back. Walk me through the process so I can see their part in it.”

“Follow-up question: Does Deep Throat own a McDonald’s franchise?”

Getting Out of Your Own Way

When I neglect follow-up questions, I almost always regret it, and it’s usually because of one of these things:

The Pressure of the Script

When I’m nervous or anxious about an interview, I rely too heavily on the script. The script is, in this instance, an enabler of my anxiety. It lets me neglect my duty by turning the work into a checklist. When I see my work in this way, I don’t give myself permission to have a conversation with my subject.

My scripts are categorized by topic. I often highlight the most important question in each category. This takes the pressure off hitting every question and instead drives me to ensure I’ve covered the topic thoroughly.

Cognitive Load

In the moment of the interview, your attention is on the cognitively labor-intensive activity of listening and capturing. It can be difficult to devote the mental resources to thinking of the next question.

Whenever possible, I defer capturing the conversation to the recording or to a note-taker, so I can free up my brain. This isn’t always possible, which is another reason I memorize the patterns described above, to minimize the effort in formulating these questions.

Propriety and Etiquette

It’s weird to ask people the same question for a second or third time. It’s weird to pry into minute details. As much as we’re striving for a conversational tone, these kinds of questions aren’t conversational at all.

I use phrases to make these a little less awkward, like “I may have already asked you this” or “I want to ask this a different way.” These phrases create the space to ask follow-up questions.

This is what it looks like when you’re too confident about asking follow-up questions.

Perfecting the Art of the Follow-up

One final piece of advice: Listen to great journalists conduct an interview. Whatever you might think of modern journalism, there are still many who ask great follow-up questions. My favorite is Michael Barbaro on The Daily, the New York Times podcast. When conducting an interview, I sometimes ask myself, “What would Michael ask next?” And I catch myself using his phrasing, like, “let’s slow this down a bit” or “so what you’re saying is…”

I’ve stopped thinking that a good UX interview should mimic a natural conversation. While the relaxed, informal nature seems ideal because it means our research subjects are at ease, there are other ways to build trust. Follow-up questions, well-positioned and well-crafted, transform an interview from a scripted set of questions to a genuine research instrument. They produce more insightful information and deeper connections. And don’t worry about building trust: good follow-up questions show you’re listening and you’re genuinely curious. Nothing builds trust faster than heartfelt interest in what another person is saying.

Getting ready to make changes to an existing product? EightShapes works closely with organizations to facilitate design processes and drive product discovery. Get in touch, and let’s talk about what you’re working on!


A collection of stories, studies, and deep thinking from EightShapes

Dan Brown

Written by

Dan Brown

Designer • Co-founder of @eightshapes • Author of 3 books on UX • http://bit.ly/danbooks • Board gamer • Family cook


A collection of stories, studies, and deep thinking from EightShapes

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