Why Every Business Needs a Listening Tour
Most of us can picture our ideal customer. What's harder is knowing whether we truly understand her problem, or just our solution to it.
Recently, I got some telling feedback from an unexpected comment. One woman founder who was congratulating me on starting up The Venture Together Collective said, "I'm probably not your client, since I've been in business for 10 years." I paused and thought back to the messaging I was putting out. Odd. I hadn't said anywhere on my website that I only worked with new startups. In fact, I thought I'd explicitly stated that I work with entrepreneurs at any stage of their business. Even more puzzling, the feedback was in direct response to a program designed for five- and six-figure companies ready to scale to the next level.
So I mentally noted that comment and began listening for other signals from other prospects. Much to my surprise, a variation of that same feedback kept surfacing. And this, as brand strategist and founder of Storybook Road Creative Agency Kristin Archambault would say, is a clarity problem, not a marketing problem.
I had fallen into the same trap I had advised other companies against: I was talking so broadly as not to exclude anyone. Unfortunately, this is not how marketing strategy works. In fact, it has the opposite effect. In my recent interview with Kristin, she shared:
"Often, companies are trying to speak to too many people, which makes their messaging feel generic and diluted. As a result, their audience can't clearly tell who they're for or what they do differently."
Yep. This was me. I knew better. I did it anyway. Fortunately, due to a background in market research, I knew my solution lay in listening to my consumer.
Many of you have heard me share that I've been learning a lot from Running Lean by Ash Maurya lately, and one concept keeps coming back to me: "fall in love with the problem, not the solution." When I sat with that for a little while, I realized I had launched VTC 100% in love with my solution. I saw the community I wanted to build, the women I wanted to bring together, the conversations I knew we needed to have, and I built toward that vision. But as I dig deeper into messaging and product and who I'm really here to serve, I keep running into the same gap: I understand my solution really well, and I'm not confident I understand my customer's problem at the depth I need to.
Here's what happens when we build from the solution side: we attract interest, but it's fuzzy. People are excited, but not quite the right people. The messaging resonates with some, but it's not specific enough to pull in the ones who are exactly right. And when you try to tighten it, you're guessing, because you're working from your own experience of the problem, not theirs.
My favorite way to fix this is the same place I start anytime I see a client struggling to take hold in a market: go back to the customer. The age-old advice is to listen before you build, and keep listening as you evolve. So that's what I'm doing: I'm kicking off a listening tour.
Case Study
Before we get into the framework, here's what this actually looks like when it plays out.
Prior to VTC, I spent several years at an education nonprofit. We were three or four people, and what we were producing was genuinely good work. The organization was making a real impact in the education space, and people who knew us were impressed by how much we accomplished with such a small team. But even with strong results at a small scale, we were struggling to grow. We couldn't bring in the bigger funders we needed, and although people were impressed with our day-to-day work, the larger vision, the bigger "why" behind all of it, wasn't coming through the way it needed to. We weren't sure whether that was a messaging problem, a positioning problem, or something more fundamental. We just knew something wasn't connecting.
Then we got two pieces of feedback that really opened our eyes. One of our board members told us she would not introduce us to a potential funder until we "upscaled our image and marketing." And then a potential funder told us directly that he didn't understand what we were ultimately trying to accomplish. That one was hard to hear, because we thought we'd been saying it clearly for years. But clearly (pun intended), we hadn't. Two people who already believed in what we were doing couldn't make the case for us. That was the signal we needed.
Our first instinct was probably the same one you'd have: go straight to the visuals. Bring in a designer, update the look, create a sexy pitch deck. But we didn't start there, and I'm so glad we didn't. Kristin was right. We had a clarity problem, and you cannot design your way to clarity.
So instead of hiring a designer, we went back to the basics. For me, that always means one thing: go talk to the people who matter most.
We sat down with our board, our educators, and our funders. With the board, we asked about our strengths, the opportunities they saw in the field, and where they envisioned the organization going over the next five to ten years. With our educators, we asked them to dream with no ceiling: if there were no constraints, no budget limits, what would the future of chemistry education look like? What was working in their experience, and what had held them back? With our funders, we asked what they were personally trying to accomplish, what a real win looked like for them, and where the gaps were between what they hoped to support and what they were actually seeing.
We came back from those conversations with something we hadn't had before: real clarity. We could finally articulate what made us different in a way that was easy to say out loud. And we were able to communicate a plan that people could see themselves in, and in some cases because they had helped build it with us. Our funders, our educators, our board members all knew we were talking about a future they were invested in, and they could clearly see their place in it.
Then the real test: we started changing our messaging. And it worked. Funders who had been giving us a few dollars each year increased their contributions to support substantial scale. Our focus on a specific target user excited them, and they committed large sums over multiple years. After that, we secured additional funders, all supporting the initiatives we had built from the results of our listening tour. We grew from a U.S.-focused organization to one with global reach. We tripled our funding and our impact, brought on multi-year commitments (which, if you've ever worked in the nonprofit world, you know changes everything about how you can actually plan), hired brilliant staff, and built something we never could have built without first sitting down and listening.
So you might be wondering: if I'm so committed to talking to potential customers and have learned this lesson firsthand, why didn't I start there?
Well. Technically I did. Before I officially launched The Venture Together Collective, I went out to talk to potential customers with every intention of really listening. I wanted to understand the journey these women were on, the real challenges, what wasn't working, what they were piecing together to get by. But something kept happening: the conversation would start to open up, and then it would circle back to VTC. They'd get curious about what I was building, ask a question, and suddenly we were spending the hour talking about my solution instead of their problem. And people were genuinely excited, which made it easy to walk away feeling like I'd learned something. But when I actually looked at my notes, what I had was mostly enthusiasm and almost nothing about what was really going on for them.
Part of it was just the natural energy of those conversations. When someone is building something they believe in, people want to talk about it. But a bigger part of it was me. I had already fallen in love with my solution, and even when I thought I was asking open questions, I was quietly steering toward confirmation. And then, because I love data, I did what any market researcher would naturally do next: I wrote a survey. I gave people categories to rank: Leadership, Marketing, Boundaries, and asked them to rate their interest. Almost 30 women responded. And when I looked at the results, I expected something I could actually act on. What I found instead was interesting in a vague way, but not useful at all.
"The problem was that I went in with a solution already in mind and designed the research to confirm it rather than discover something new."
The categories I gave people were so broad they were almost meaningless. When I say "leadership," I might be thinking about managing a growing team, but a solo founder at the launch stage might hear "managing my own fear on a hard day." Not the same thing. I had almost no open-ended questions, which meant I had no way to understand the context behind anyone's answers, no way to hear the story underneath the number. Surveys are useful tools, but they're best for quantifying and validating insights you've already gathered through real conversations. What I realized I still needed was more information to generate entirely new insights. That's not what surveys do.
I'm a case study of what not to do according to Running Lean. The way I'd been collecting information was solution-forward all along, even in the survey. I was getting glimpses of the real problems, but I was biasing every response by leading with my solution. What I needed, and what I'm doing now, is something different: conversations designed to surface the problem, not validate my answer to it.
Ash writes that the goal of a discovery conversation isn't to validate problems but to discover them, and you don't do that by asking people directly about their problems. You do it by asking how they're currently solving them and listening for where that process breaks down.
"Finding points of friction in their stories or gaps between their desired and actual outcomes," he writes, "is how you uncover problems worth solving." (Running Lean, p. 171)
These are exactly the types of questions we used in our listening sessions at my last organization, and they got us the results we needed. The difference was that I really didn't know the solution then, so I was on a genuine quest to find it. If I had approached VTC that way from the start, I would have gotten much closer to the answers I needed.
One of the reasons I keep returning to Running Lean is that it gives you practical, accurate, and actionable tools. The discovery framework offers open-ended questions designed to invite people into their personal stories rather than lead them toward a predetermined answer. Here's what I'm using as my guide:
To open: Tell me about where you are in your business right now. What are you most focused on over the next few months?
To understand how they currently operate: When you hit a challenge you can't quite solve, what do you usually do first? What resources or support are you currently relying on? Walk me through the last time you felt genuinely stuck. What happened?
To find the friction: What part of that process felt like the most effort? What keeps coming up that you haven't been able to resolve? If you had to name the one thing that slows you down the most right now, what would it be?
To understand the stakes: What does it cost you, in time, money, energy, or confidence, when that problem doesn't get solved? Have you tried other approaches? What happened?
To get to the ideal: In a perfect world, what would it feel like to have this handled?
Our job in these conversations is to really listen. And I mean record-it-so-you-don't-miss-anything listen. Pay attention to the specific words people use, because those words become your messaging. Notice where their energy shifts: where they lean in, where there's a sigh of relief, where you can hear the frustration underneath what they're saying. We're not just trying to understand a problem intellectually. We sell an emotional state, and the emotions in these conversations are the data.
One practical note, and I'm saying it again so you don't skip it: record everything, and build in time to debrief right after each interview while it's still fresh. Running Lean has debrief templates for this that are actually useful. Capture everything in one dedicated folder, organized by interview. And here's where it gets interesting: once you have 10 to 20 conversations, bring them to AI and ask it to find the patterns. The words that come up most often, the emotions that keep surfacing, the friction points that repeat across different women at different stages. AI gives you a read on the data without your personal bias filtering it, and sometimes it surfaces a pattern or a solution angle you hadn't even considered. This gives you the kind of customer insight that can actually shape, or re-shape, your offer.
Here's something I want to say before I wrap this up: listening to your target market isn't just a launch activity. Listening to your consumer is for businesses AT ALL STAGES of growth (yes, I'm shouting this on purpose).
My last organization did a listening tour when it wanted to grow from six figures to seven figures. My 300-year-old church did a listening tour before it kicked off a new planning cycle. I'm doing it now as I'm evolving my pilot offers at VTC. Companies evolve the way people do. Your offers change, your audience shifts, the environment changes, your positioning moves. And sometimes your brand stays in one place while your business has quietly become something different, and you find yourself wondering why things that used to work aren't working anymore. Customer feedback should be baked into everything you do so you can continue to evolve with your customer.
Kristin at Storybook Road has some great techniques for incorporating powerful feedback forms into your website to get a continuous stream of feedback and testimonials that convert future buyers. She also has other tried-and-true methods for listening to customers, understanding their needs, and refining your value proposition.
On May 14th, she'll be sharing these tips and tools with us at a hands-on interactive workshop. We'll be learning the basics of brand strategy while digging into the work side by side. If my story resonates with you, or if you've been feeling like your ideal client is scrolling (or strolling) past you, join us on May 14th at 1pm ET to see what tweaks you can make to clarify your messaging.
I'm kicking off my discovery sprint this week, with a goal of 20 conversations over the next three to four weeks with women at every stage of entrepreneurship. I want to understand what's actually hard, how women are currently solving their biggest challenges, and where the gaps are between what exists and what's genuinely needed.
If you're a woman entrepreneur anywhere on her journey (I need ALL the perspectives), I'd love to hear your story.
Shoot me an email and we'll get a call on the calendar.
Venture Together Collective is a community for women entrepreneurs built on real strategy, genuine connection, and the kind of support that actually moves your business forward. venturetogethercollective.com
