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How to Listen Like an Expert

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At Lexicon Strategies, a major component of most of our engagements involves developing and conducting structured listening sessions. Authentic qualitative research is so important to successful community and social impact work and, we believe, it’s what makes the solutions we deliver so much more effective. 

Listening to stakeholders is truly an art and a science. Words ARE data.

When we think about solutions or messaging, many people look to surveys or quantitative data. And, it’s always a mistake not to pair data with words. We live in a world driven by language and emotion, not numbers and percentages. The only way to capture actionable, successful insight is to listen to the people involved speaking directly to you.

Here’s some of the best ways we’ve found to make the most of the practice of structured listening:

11 is too many, 2 is too few

You’ll want to think carefully about how many people you want in each listening session. We find that group interviews are not only the most time-effective, they can yield more pathways to consensus than one-on-one sessions. That said, 10 people is really the max for a group interview, and you really want at least 3 or more in any session. And, for any group interviews you want to make sure you have at least two separate groups conducted on two different dates. Never mistake the thinking of just one group of people at one point in time as informative.

If you are listening to people within a singular organization, it’s crucial that you mix people at different levels and different regions, floors or functions. A room full of VPs may yield far less actionable insight than a room with the receptionist, a VP and some managers. And, of course, diversity in every form is important for authentic discovery: consider racial, gender, sexual orientation, socio-economic, age and ability perspectives.

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Build a rich, organized Interview Guide

Consistency of questions and process across groups is really the only way to capture meaningful qualitative data. You’ll want to write a detailed Interview Guide. Don’t overestimate how many questions you can cover in the time allotted. Write a time commitment for each question, and note which questions you’ll skip if time gets tight. 1.5 hours is the ideal length of any session; it’s long enough to cover 5-6 questions, short enough not to tire out the participants.

Don’t forget to open with a clear sense of confidentiality and the rules of the road for the discussion. And, if you are recording (which I highly recommend) you’ll want to explain why and the limits of the recording’s use.

Create moments for “Authentic Reactions” to visual material

Many people operate visually and it’s important to include visual elements, especially as we are conducting more of these sessions virtually. It’s very effective to read a statement for the group to react to and share a slide or poster with the statement typed out on it. Or, ask each participant to have a dark marker and plain paper on hand. Ask a question about “#1 reason” for something and have them hold up their handwritten answers at the same time. (This works well over Zoom. As people hold up their answers, take a screenshot of the group, and screen-share that image back.) Then, focus your discussion on those handwritten reactions for a bit.

There are also many, many Design Thinking techniques that can be used when we get back to “in-person” sessions. The concept was very buzzy for the last few years (thanks Harvard Business Review and others) but it’s a 50 year-old approach that will be valuable for 100 more years. I particularly recommend Alex West’s Visual Thinking Strategies (VTS) process if you’re wanting to really bring creativity and visual response to your qualitative inquiry.

Start things off with thinking and sharing

For introductions, which is a critical part of any listening session, be sure to include an intimate kick-off question. “Please tell us your name, where you work, what you do there and share one thing you are most nervous about for ‘X’ project.” This series of ice breaker questions is couched within some basic biography stuff most people are very comfortable sharing. It naturally lowers people’s nervousness or discomfort and will make for a much better discussion overall.

After this opening segment, it’s much better to ask singular questions but the series of perfunctory/easy questions and a thinking question combined just gets things settled and rolling very effectively.

Keep it wide open, especially as you close out

All of the questions in your Interview Guide should be truly open-ended. Really useful verbs are “describe,” “share,” and “tell.” DO NOT ask “yes or no” questions. Do not ask leading questions like “What do you dislike about ‘X’?” 

And, perhaps most importantly, at the end ask a truly open question, like “Did I forget to ask about something you expected?” or “Is there anything at all you’d like to mention as we wrap up?” 

Do not ask quantitative questions like “How many times a month do you ‘X’?” (you can ask people to fill out a survey before or after for these questions). Many times we actually pair a quantitative survey with listening sessions. The survey is sent ahead of preparing the discussion guide and the listening sessions are used to further understand and/or explore the results of the qualitative data.

And, perhaps most importantly, at the end ask a truly open question, like “Did I forget to ask about something you expected?” or “Is there anything at all you’d like to mention as we wrap up?” Often you’ll get another heightened emphasis on something you already asked, but occasionally you’ll get some really interesting new insight... maybe even a topic for a whole new round of interviews.


Lexicon Strategies Co-founder Brian Tolleson was previously CEO of the National Center for Civil and Human Rights, founder of renowned advertainment studio BARK BARK, and former Marketing and Creative executive at Viacom.

Brian has spent his career working at the intersection of human rights, media and social justice while managing billions in partnership marketing initiatives, multi-platform branding and content strategy for distributors like Sony, NBC Universal, and Google, as well as marketers such as P&G, Unilever, Clorox, Chase, Target, Microsoft, Starbucks, Mercedes Benz, Chevron and General Motors.