Interviewing Techniques to Extract Deeper Insights

how to interview better

For marketers, interviews form the basis of many important activities:

Doing research to inform user personas
Getting a better understanding of customers
Garnering insights for longform content
Creating customer case studies
Publishing the Q&A as a blog post

Interviews are also important for other roles: notably, product management and sales. Hiring managers, too!

Recently, we had a design thinking workshop at DNN. During the workshop, we learned how to garner deep insights from interviews. I now apply these techniques when performing interviews for my marketing efforts.

An Interview Counter-Example

First, let’s consider a counter-example.

When an interview question generates a one-word answer, you fail to uncover meaningful insights. Consider this conversation with my child and her school friends:

Me: “How was school today?”

Them: “Good.”

Me: “Without saying the word ‘good,’ tell me about your school day in a complete sentence?”

Them: “It was OK.”

To get more meaningful answers, I now try questions like these:

“Tell me about the best thing that happened during school today?”
“Tell me about something at school that bothered you?”

Now that you know what not to do, let’s consider more effective techniques.

1) Don’t interrupt.

The only thing worse than a one-word answer is closing off a story before it surfaces. Only interrupt if you need to get the conversation back on track.


Me: “Tell me about a time you used a similar product that gave you a positive ROI?”

Them: “Did I mention I ran five ultramarathons? I ran one on five different continents. Boy, I can remember the pain I felt after each one.” (You may be inclined to interrupt right here.)

Resist the urge and give it some time. The interviewee may continue for a little while on ultramarathons, but the punchline might be a fabulous analogy that connects to driving ROI.

2) Strategically phrase questions to draw deeper insights.

Just as I discovered with my child’s school friends, use open-ended questions that encourage deeper insights. Draw out the interesting stories and insights. One-sentence answers are an adversary; one-word answers are your enemy. Use a timer and see if interviewees can spend more than a minute on each answer.

Instead of starting questions with these phrases:

Can you
Would you
Do you see yourself

Try these instead:

Tell me about
Describe a time when
In what scenarios would you (and why)

Asking “Would you use” results in a one-word answer: yes or no. “Yes” is an easy answer, so people will answer affirmatively even when the answer is no. Instead, if you ask “in what scenarios would you use,” then the “yes” is implied, but you also uncover the requirements and conditions for the “yes” to occur.

3) Follow answers with a series of why’s.

As a parent, you may recognize this conversation:

Child: “Why is the sky blue?”

You: (Quote a few sentences from Wikipedia)

Child: “Why?”

You: (Quote a few more sentences from Wikipedia)

Child: “Why?”

Without you realizing it, your child is exhibiting effective interviewing techniques. It would seem awkward if you took this approach with your interviews. However, find the right phrasing in order to follow up an answer with a “why question.” You’ll uncover some amazing insights.

Try this exercise out at work:

Sit down with a colleague
Have them empty the contents of their wallet or pocketbook
Ask them a “why question” about any single item
Ask them another “why question” based on their answer
Continue for another 3-4 cycles of “why questions”

We did this exercise in our IDEO workshop and I learned fascinating things about a colleague.

4) Invoke emotion.

We experience life via emotions. From graduation to wedding to first day on the job, we experience emotions in everything we do. When you understand and capture people’s emotions, you add captivating elements to your story.

Be sure to explicitly tap into your interviewee’s emotions and feelings. Ways to start your questions:

How did it make you feel when
Describe your feelings when the new product launched?
Tell me five adjectives that describe your feelings about X?

Note: bonus points if you follow these questions with a few why’s.

5) Go for the extremes.

Common scenarios are boring. Boundary cases are interesting. When I’m feeling bored, the circumstances surrounding that feeling aren’t likely to interest you. However, when I describe “the time I felt the most bored, ever,” there’s probably a good story there.

Ask interviewees to describe the circumstances around extreme conditions:

Tell me about the last time you were overcome with joy?
Tell me about a time you were the most frustrated?
Describe the most memorable event from your childhood?
Think about the time you were the happiest in life. What was happening then?

Put yourself in the shoes of the interviewee. Isn’t the story more compelling when you describe the time you were “most frustrated” versus just “frustrated”?

6) Don’t ask leading questions.

Remove declarative statements from your questions. In a conversation, we can suggest an answer to a question without even realizing it. So narrow the question down to its simplest form.

An example of how easy it can be to cloud the conversation:

Me: “Tell me about your roles and responsibilities.”

Customer: “I run Public Relations, but am also responsible for a small web development team.”

Me: “I never heard of that combination. How did a PR person get assigned web developers?”

Based on how I phrased my follow-up question, the customer may be slightly offended, and may answer in a defensive way. I’ve managed to bottle up the answer by inserting judgment. Don’t judge.

A better way to ask the follow-up question:

Me: “Interesting! Tell me what was happening within the organization when you were assigned this additional role?”

Try it Out

Try some of these tactics during your next interview. I’d love to hear how it goes! While I’ve incorporated this approach in my interviews, I still have a lot of room for improvement. By the way: how did this post make you feel?

Note: Photo credit:

Note: I originally published this post on LinkedIn.

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