Interviewing Techniques to Extract Deeper Insights

July 25, 2016

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.

Design Thinking for Meetings and Events

February 11, 2013

David Kelley speaks about design thinking on 60 Minutes


Recently, I watched a 60 Minutes episode featuring David Kelley. Mr. Kelley is the founder and chairman of the global design consultancy IDEO and professor (and founder) of Stanford’s

Kelley is a leading thinker on “design thinking,” a methodology for designing products and procedures via empathy, diversity, collaboration and iteration. The program highlights many of Kelley’s (and his firm’s) great product achievements, including the design of the first mouse for Steve Jobs at Apple.

Design Thinking for Events

In a Harvard Business Review piece on design thinking, IDEO’s CEO (Tim Brown) writes:

“As more of our basic needs are met, we increasingly expect sophisticated experiences that are emotionally satisfying and meaningful … design thinking is the tool for imagining these experiences as well as giving them a desirable form.”

I suppose this blog posting was foretold by Mr. Brown: let’s use design thinking to create “sophisticated experiences that are emotionally satisfying and meaningful”!

Apparently, I wasn’t the only one thinking about design thinking for events:

Overview: Design Thinking

Design thinking components

Image source: SAP

The design thinking process can be broken down into three components: inspiration, ideation and implementation. To quote a design thinking article co-authored by Mr. Brown:

  1. Inspiration: “Think of inspiration as the problem or opportunity that motivates the search for solutions.”
  2. Ideation: “Ideation as the process of generating, developing, and testing ideas.”
  3. Implementation: “Implementation as the path that leads from the project stage into people’s lives.”

Here are some useful resources that provide overviews on the design thinking methodology:

  1. Stanford’s crash course on design thinking
  2. An Introduction to Design Thinking from SAP
  3. From the Emergent By Design blog: What Is Design Thinking, Really?

Incorporating Design Thinking into Meetings and Events

I’ve taken a look at the tenets and methodologies of design thinking and considered how they could be applied to meetings and events. Let’s consider some.

Attend Your Own Event (Empathy)

Meeting and event planners should take off their “planning hats” and attend one of their events solely with their “attendee hats” on. After all, you can only have true empathy for your attendee if you put yourself squarely in their shoes.

And that means that you can have no part in planning the event. Go through the entire cycle of registration, travel, sessions, workshops, social events, etc. Practice further empathy by understanding how fellow attendees are experiencing the event.

Deepen (and Broaden) Your Team Roster

Design thinking introduces the notion of “multidisciplinary teams,” in which people of assorted backgrounds (and schools of thought) ideate, iterate and collaborate.

Consider it a blender, where what comes out is a fascinatingly tasty beverage. You need a group that creates divergent thinking, which, according to Mr. Brown of IDEO, “is the route, not the obstacle, to innovation.”

Mr. Brown suggests “architects who have studied psychology, artists with MBAs, or engineers with marketing experience.” While this may be a stretch for the typical event planner, I’d recommend adding folks from Finance, HR and Engineering.

They don’t have to be core members of the event planning team; however, their perspectives can be more valuable that you’d think.

Where No Idea is a Bad Idea

The scientist Linus Pauling once said, “To have a good idea you must first have lots of ideas.” (quote source: an SSI article co-authored by Mr. Brown). Design thinking teaches you that no idea is a bad idea. If you make an early judgment on the quality of an idea, you may have just squashed a “germ” that would develop into a breakthrough.

The ideation process is critical in creating the next breakthrough event.

Instead, design thinking teaches you to build upon each other’s ideas, sort of like the “yes, and..” methodology in improvisational theater. As a meeting planner, then, your role is to encourage ideation and “shepherd” the process so that no idea is left abandoned (too quickly). And to the earlier point, here’s where multidisciplinary teams can be a goldmine.

Meeting and Event Prototypes

Recall that part of the ideation phase is “testing ideas.” It’s an iterative process in which you deploy a prototype, collect “real user feedback,” determine what you learned, then ideate on product refinements (repeating the cycle all over again).

Let’s say you’re planning next year’s 5,000 person sales kick-off meeting and you have innovative new ideas for it. Create a prototype using 50 sales people and actually implement those ideas in a “real prototype” (event). Determine what worked, make adjustments, then plan another prototype. When the “real thing” comes around, you’ll have a much better “product.”

Potential Barriers to Adoption

Seasoned event and meeting planners (who’ve gotten this far in my post) may be calling me crazy. And I can understand that. What I’ve proposed (in concept) must be balanced against the realities of a meeting planner’s job. And the following barriers could come into play.

Budget, Timeline and ROI

Simply put, design thinking methodologies could add significantly to meeting and event costs, while extending the timeline to deliver them. The ideation phase of design thinking is intentionally non-sequential. Meeting planners are highly organized creatures who thrive on delivering against a sequential timeline. Additionally, meeting and event management may not be comfortable spending more without knowing the precise ROI on it.

Risk Mitigation

The meeting planner is like an NFL coach: every season (i.e. every event), your job can be on the line. In his article, Mr. Brown wrote, “One of the biggest impediments to adopting design thinking is simply fear of failure.” The natural tendency of the meeting and event planner is to be risk averse, which is very much the opposite approach of design thinking.


Design thinking is surely not applicable to all meetings and events. And as I’ve outlined, meeting and event planners will likely shudder at the very concept. What I hope to accomplish with this post, however, is to introduce its concept to meetings and events. It’s my belief that true breakthrough events and experiences can result from it.

Note: This post was originally published on the eVenues blog. Here’s a link to the original piece.

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