You know your products, services and your business. You’ve put a lot of yourself into it, and you probably have a pretty good idea of what makes it worth choosing. But when was the last time you interviewed a customer to find out whether their experience matches what you think you’re delivering?
For example, earlier in my career, I had the privilege of revisiting our ideal customer profile, or ICP. Who were we best suited to help, and what were those customers actually struggling with? We had a lot of that information already. It was sitting in our internal documents.
We had a private, secured company license that enabled us to work with documents in our internal SharePoint, including our statements of work, or SOWs. Those documents captured the problems customers had approached us to solve and the work we’d agreed to do after winning their business. Using Copilot, I was able to pull out those pain points, look for common themes, and consolidate them into a more cohesive picture of our ideal customer, grounded in the work we’d actually won.
Now, that’s a luxury a lot of small businesses don’t have. This was a complex B2B environment, and we could do that work because we’d captured so much of the information in the first place. If you’re running a small business, you may not have a SharePoint full of detailed project documents to work through. Some of what you know about your customers might still be in your head, or scattered across emails.
But you can go back and gather it. Interviewing customers gives you a way to revisit what brought them to you and understand where the experience could have been better. Then you can put a simple process in place to keep capturing that feedback as you go, without making it another chore for your customers. You don’t need the setup we had to start building a clearer picture of the people you serve.
I use the word “interviewed” intentionally. You might talk to customers every day, whether you’re checking on an order or working through the details of a project. Those conversations matter, but how often do you get to step back and ask why they chose you in the first place? Or what almost stopped them?
That’s a different conversation. And it’s one I think more small business owners should make room for.
My background in journalism helped me develop an ability to identify storylines and ask thoughtful questions, something I’ve carried through more than 15 years in marketing. What interests me is what happens after the first answer, when you ask a follow-up and begin to understand what someone actually means.
A customer tells you the project went well. Great. But what made it go well? Was there a moment when they felt confident they’d chosen the right company? Was there something they had to figure out themselves that you could have made easier?
That’s where the conversation starts to become useful. Customer interviews for small businesses don’t have to be elaborate, but they do deserve more intention than a quick “Everything good?” on your way to the next thing.
You’re close to the business. Your customer sees it differently.
When you’re too close to the fire, some things are apparent while others lurk in shadows. I think running a business can feel that way. You’re close enough to see details nobody else sees, but that doesn’t mean you can see the whole experience from where you’re standing.
You know why a service costs what it does, why certain products take time, or what happens after someone submits a form. You might assume a customer understands those things, too, because they’re so familiar to you.
Meanwhile, that customer could be sitting on the other side wondering what’s taking so long.
Or the opposite might be happening. Something you consider a normal part of doing business could be the very reason people choose you. You take the time to advise them through a decision, and to you, that’s just doing your job. To them, it might be the thing they couldn’t find anywhere else.
If that never comes up in conversation, you might keep burying the good stuff at the back of the store or the bottom of your website when it deserves a much bigger role.
In marketing, this is part of the overall voice of the customer (VoC). The term can sound more complicated than the idea behind it: understanding how people experience your business, in their own words, and using what you learn to make better decisions.
Start with one conversation
I know. You’re running a business, so finding time for coffee with a customer might rank somewhere below answering the emails you’ve already ignored twice and the thousand other tasks that you swear provide more value.
I’m not suggesting you interview every customer or put the business on hold while you conduct a research project. Start with one person and ask for 15 minutes. Choose someone who recently bought from you or worked with you, while the details are still fresh enough to talk about. Or, make it a point to try to document those golden nuggets you hear as you go about your day.
A customer you know well can be a comfortable place to start. Just don’t stop there. Eventually, you’ll want to hear from someone who didn’t buy or hasn’t come back. The people who already love you can tell you something valuable, but they won’t tell you everything you need to hear.
Make the invitation personal. You could say:
“I’m taking a closer look at what it’s like to work with us, and I’d really value your perspective. Would you have 15 minutes to talk about your recent project? I’d like to hear what worked and anything we could have made easier. No sales pitch. I’m hoping to learn something.”
Then give them room to say no, or to offer feedback by email if that’s easier.
With an existing customer, I’d start with a sincere request and respect for their time. Buy the coffee or lunch if you’re meeting in person. If you’re asking for a longer conversation or interviewing people who don’t know you, compensating them for their time may make sense.
And if you promised it wouldn’t be a sales pitch, keep your word and don’t kill the vibe. Nobody wants to be pitch slapped.
Give yourself room to listen
If you’re trying to write down every word, it’s hard to pay attention to where the conversation is going. Recording can help, as long as the customer is comfortable with it and you’ve asked first.
Keep the request straightforward:
“Would you mind if I recorded this? I’d like to focus on our conversation instead of trying to take notes the whole time. I’d use it to go back through your feedback afterward. If you’d rather I just take notes, that’s completely fine.”
If you’re using an AI transcription service, explain that, too. Be clear about what you’ll do with the recording. Agreeing to share feedback doesn’t mean someone has agreed to appear in your next testimonial.
If they’d prefer not to be recorded, take notes. You’re there to understand their experience, and you can still do that without a transcript.
Ask a question, then follow the answer
I’d build the conversation around an actual buying experience. “What do you think of our company?” leaves someone with a lot of ground to cover. Asking what was happening when they first started looking gives them a specific place to begin.
Here are some questions I’d keep in your arsenal:
“What was happening that made you start looking?”
Someone might tell you they were looking for shrubs, but a follow-up reveals they wanted more privacy from the neighboring yard. They weren’t sure what would grow in that spot or how much space they’d need to leave. Now you understand more about what brought them in. They needed help figuring out what would work in their garden before they felt comfortable buying anything.
“What other options did you consider?”
Leave room for an answer you weren’t expecting. Your competition might have been another nursery or a big-box retailer, but it could also have been leaving that problem alone for another season. Ask what made moving forward worthwhile.
“Was there anything that made you hesitate or nearly walk away?”
This one can be uncomfortable, especially when you’ve put so much work into the business. Give them time to answer. If you immediately explain why something happened, you may never hear the rest of what they were going to say. You can investigate the reason afterward. For now, understand what it felt like from their side.
“What ultimately made you choose us?”
You may think you know the answer. Ask anyway. If they say “service,” don’t leave it there. What did someone do that gave them confidence? The specific example is much more useful than the general compliment.
“After you decided to buy, what could we have made easier?”
The experience doesn’t end when the sale closes. Maybe the buying process was great, but they had to chase an update afterward. Maybe they weren’t sure who to contact. These are the details you can miss when you only ask whether someone is satisfied overall.
“What would you tell someone who’s considering working with us?”
Listen to the language they use. How do they explain what you helped them with? What do they mention first? Their description may be clearer than the one you’ve spent hours trying to write yourself.
You don’t need to get through every question. If an answer opens up something worth exploring, follow it. “Can you give me an example?” is one of my favorites and is sometimes better than the next question your had queued up.
Before you wrap up, tell them what you think you heard and ask whether you’ve understood correctly. It gives them a chance to clarify, and gives you a chance to catch an assumption before it becomes an action item.
Do something with what you hear
Here’s a hypothetical garden nursery example. A customer says, “I liked the shrub, but I wasn’t sure it would work in my garden.”
You could hear that as a request for a better plant label. But spend a little more time with it. Were they unsure how much sun that spot received? Did they understand how big the shrub would get? While walking around the nursery, could they find someone to ask, or did they leave with the question still in their head?
Those answers point to different improvements. Clearer signs might help someone narrow down their choices. You might need to make it easier to find staff, or let customers know they can bring a photo of their garden for advice, if that’s help you offer. Rewriting the website won’t help much if someone still walks around the nursery unsure who to ask.
Now imagine another customer says, “You took the time to help me choose something that would actually grow in my garden.” To you, that might just be part of running a nursery. To them, it might be why they chose you over the garden center down the road. If that’s support you consistently provide, are you making it visible on your website and when people arrive?
This is the part that interests me as a marketer. A conversation can uncover language for your website, but it can also reveal something about how the business operates. I wouldn’t want to reduce all that to a better headline and call it done.
Keep the customer’s words in the picture
Bring your notes into one working document. Keep the customer’s actual words alongside your interpretation so you can go back and check what was said. A spreadsheet is enough to start, with room to record a possible improvement and who’s going to follow up.
As you have more conversations, look for themes. If several people describe the same confusion, that’s something to investigate. If one person makes an unexpected observation, keep it visible without assuming it represents every customer you serve.
An AI tool can help organize de-identified feedback, but I’d still go back to the original comments. A tidy summary can lose the detail that made an answer useful in the first place.
You can also keep listening between interviews. Add a question to a follow-up email: “What could we have made easier?” If you have employees who work with customers, give them somewhere to capture what they’re hearing. Set aside time each month to review it and decide what deserves attention.
Then close the loop when you make a change. “You mentioned it was hard to find someone to ask about plants. Here’s what we’ve changed.” That’s a much more meaningful response than letting someone’s feedback disappear into a document nobody opens again.
Free tools to help you get started
Start with what you already have. You don’t need another subscription before you can ask a useful question
- iPhone Voice Memos: An option for recording in-person conversations with permission. Transcription depends on device and language support. Apple’s transcription guidance.
- Otter.ai: A recording and transcription option for interviews. Check the current plan limits, especially recording length and file imports. Otter plans.
- Your meeting platform: Check whether your Zoom, Teams, or Google Meet account offers saved transcription. Availability depends on the service, subscription, and settings. Test before the interview; live captions alone don’t establish that you’ll receive a saved transcript.
- Google Forms or Microsoft Forms: Useful for short written surveys. Responses can be collected in or exported to a spreadsheet. Google Forms / Microsoft Forms.
- Airtable: Another form-building option. It has a free tier option for small businesses.
- Google Sheets or Excel: Keep the customer’s words alongside the issue, proposed action, person responsible, and follow-up date.
Let what you learn inform where you go next
Over time, these conversations can help shape how you describe your business and what you choose to emphasize. They can also inform a brand manifesto, giving you a way to compare what you say you stand for with what customers actually experience.
That doesn’t mean changing direction every time someone has an opinion. Your values are still your values. But it’s worth being open to the possibility that customers see a strength you’ve overlooked, or that something you intended to deliver isn’t coming through the way you hoped.
That’s why I see this as an ongoing part of running a business. What mattered to customers when you started may still matter today, but their circumstances can change. Continuing to have these conversations gives you a way to understand those changes instead of guessing at them.
Start with one customer this month. Give yourself time to hear the answer, especially if it’s different from the one you expected. Then decide what you’re going to do with it.
If you’d like someone to help conduct those interviews and work through what they mean for your business, that’s something I can support through RoeMark. I work with small businesses in the Portland area and throughout the Pacific Northwest, bringing my journalism background and marketing experience to that conversation.