If you run a small business, talking to customers is part of the job. You answer calls, emails, and texts on a daily basis. You listen to questions, requests, and concerns. You communicate changes and adjustments to reassure people and meet expectations.
These conversations are necessary and are usually task-oriented. They focus on execution: what needs to happen today, tomorrow, next week.
What they don’t reliably do is generate insights.
In talking with business owners, a common pattern shows up: there’s no shortage of customer conversations, but very few of them are designed to surface why someone reached out in the first place, what was happening before they did, or what alternatives they were weighing at the time.
That difference matters.
This post focuses on how to talk to customers with the intention to surface insights. Doing so helps you recognize patterns. Those patterns lead to clearer positioning, more relevant content, and better decisions about where to focus. These kinds of conversations don’t happen by accident, and they also don’t require hours of research or formal interviews. A few simple adjustments to ordinary conversations can have a disproportionate impact on what you learn from customers and what you do with those insights as a business.
By the end of this post, you’ll learn:
- How to ask questions that invite stories and context instead of surface answers
- How to listen for the signals that actually drive decisions
- How to turn everyday conversations into a simple log that reveals patterns over time
The bottleneck isn’t collecting more data. It’s learning how to ask better questions and capturing what you hear in a way that reveals patterns.
If this way of thinking about customer insight resonates, I share short updates like this as I develop the rest of the series—focused on clarity, follow-through, and sustainable growth.
Insight starts with asking better questions
When customer conversations don’t turn into insights, it’s rarely because people are unwilling to share. More often, it’s because the questions don’t give them room to share.
Most of us default to questions that are efficient and direct. These questions can usually be answered with “yes,” “no,” or a single sentence, and often signal what you’re hoping to confirm. These questions work when you’re trying to complete a task or narrow on a known outcome. But when you’re trying to understand why a decision happened, direct and efficient questions fall short.
Getting at “why” requires a different approach, namely, asking questions that invite stories, contexts, and sequences. These questions aren’t clever or provocative. They’re curious. Open-ended curious questions leave room for someone to tell you about their experience rather than confirm your preexisting interpretation or beliefs.
You’re not trying to get better answers; you’re trying to get better stories.
This idea is central to The Mom Test by Rob Fitzpatrick. The book argues that most bad interviews fail not because people lie, but because the questions make it easy to give polite, shallow answers. The goal isn’t to corner someone into a truth; it’s to ask in a way that makes it easier for them to talk about what actually happened.
For example, you might ask a customer, “What are you looking for today?” and get a short response: “I’m looking for X.” That tells you what they want, but not why they want it, or what led them to that conclusion.
A different question that often works better is, “What happened that led you to reach out?”
Instead of asking what they reached out for or whether something was a priority, ask them to walk you through what was going on when the problem first came up, what changed that made it feel urgent, or how they ended up talking to you. Questions like these anchor the conversation in time and circumstance, which helps people recall real events rather than tidy, after-the-fact explanations.
Slow down, follow-up, and take a backseat
One of the easiest ways to cut off revealing moments is to move on too quickly. When someone answers a question, pause. Let the silence sit. Often the most useful information comes after the first response: when someone corrects themselves or adds, “Actually, the bigger issue was…”
Follow-up questions should go deeper, not wider. You’re not trying to cover more ground; you’re trying to understand cause and effect. When something stands out, stay with it. Ask them to say more, explain why it felt frustrating or risky, or describe what happened next.
Finally, avoid leading the witness. Questions that hint at an expected answer — about time, cost, or confusion — make it easy to agree and hard to learn. Neutral questions keep the framing in the customer’s words, which is exactly what you want to capture.
Curious questions start from not knowing and invite someone to fill in the gaps. With that approach in place, the next step is understanding what you’re listening for in those stories and how to make sense of them. This isn’t about doing more; it’s about listening differently.
What you’re really listening for (Jobs to Be Done, simply)
Once you start asking better questions, you’ll hear something different. People don’t talk in terms of features or categories or offerings. They talk about situations, pressures, and what wasn’t working.
A useful way to make sense of these stories is a framework called Jobs to Be Done, developed and popularized by Clayton Christensen and colleagues in Competing Against Luck: The Story of Innovation and Customer Choice.
At its core, Jobs to Be Done is based on a simple idea: people don’t choose products or services just because they exist. They choose them because they’re trying to make progress in a specific moment. The “job” isn’t the work you perform; it’s the outcome they’re trying to achieve in their life or business.
When someone reaches out to you, something changed in their life. A problem escalated, a deadline moved up, or an alternative stopped working. Other options were considered and rejected.
Jobs to Be Done helps you listen for that context. When you listen closely, most conversations contain a small set of underlying stories:
- What was happening before they started looking for help
- What changed that made this feel urgent or necessary
- What they considered or tried instead, including doing nothing
- What progress they were hoping to make by taking action
- What felt risky or uncertain about the decision
These stories explain why a decision happened when it did.
If you’re asking curious, story-based questions, these signals are usually already present in the conversation. Jobs to Be Done doesn’t change how you ask — it gives you a way to organize what you’re hearing so the patterns become clearer.
From curious questions to real insight
The difference isn’t the wording, but intent. Curious questions that invite stories make it easier for people to describe what actually happened, not just what they decided. Below are some concrete examples. These are not meant to be magic bullets, but instead illustrate the difference in approach and outcome.
| If you ask… | You’ll usually get… | Try asking… | You’re more likely to hear… |
| “What are you looking for?” | A short, task-focused answer | “What was going on when this first came up?” | The situation that triggered the search |
| “Was this a priority?” | A yes/no answer | “What changed that made this feel important now?” | Why the timing mattered |
| “Why did you choose us?” | A polite, surface-level reason | “What other options did you consider?” | How they evaluated alternatives |
| “What problem are you trying to solve?” | A compressed summary | “Can you walk me through what wasn’t working?” | Context, constraints, and tradeoffs |
| “What’s your budget?” | A number (or deflection) | “What felt risky or uncertain about deciding?” | The real hesitation behind the decision |
Turning conversations into a usable customer log
Good conversations are helpful in-the-moment. Insight shows up when you can look across conversations over time.
To turn isolated conversations into patterns, I suggest a simple customer log, a lightweight place to capture what mattered in recent conversations so patterns can emerge later. (Don’t worry this isn’t a CRM or database.)
A customer log is as simple as this: After a conversation, note what triggered it, what progress the person wanted to make, what alternatives came up, and what hesitation mattered most. Bullet points are enough. Shorthand is fine. What matters is capturing the context while it’s still fresh and in a place you can review later alongside other conversational notes.
You don’t need special interviews to do this. Sales calls, onboarding conversations, support threads, and informal check-ins all count. If someone is explaining their situation or decision to you, it’s log-worthy.
Steal this: If you want a simple way to try this without overthinking it, grab the customer log here.
Three contexts where the same questions matter
The questions don’t change much. What changes is who you’re asking them to, and what their decision reveals.
When someone chooses you, they’re evidence that, in a specific moment, your work felt like the right decision.
Example 1: the customer who chooses you
For example, a customer hires a lawn service. In conversation, you learn they used to handle it themselves, but work got busier and weekends started feeling spoken for. They didn’t hire a lawn service because they suddenly cared more about lawns. They hired one because maintaining it stopped fitting into their life. Customers like this help you understand when you’re a strong fit.
Example 2: the customer who chooses someone else
Non-customers are just as useful. A homeowner reaches out to a general contractor for a remodel. Your quote is actually cheaper than another contractor’s, but that contractor responds faster and provides a clear ballpark estimate immediately. The homeowner goes with them. Cost wasn’t the issue — clarity and speed were. These conversations highlight friction in how decisions get made.
Example 3: the customer who might choose you later
Then there are people who might choose you later. A small business considers working with a web agency but decides to stick with social media for now. A website feels expensive, ongoing maintenance feels intimidating, and the real need for a site isn’t clear yet. They don’t say no; they say “not now.” These conversations often reveal future demand and opportunities to adjust how you frame or package what you offer.
Insight comes from patterns, not individual answers
One conversation is anecdotal. Insight shows up when the same themes repeat across outcomes.
Repeated language, similar triggers, recurring hesitations, and the same alternatives appearing again and again are all signals. Insight doesn’t come from tallying answers; it comes from comparing situations.
These patterns help explain past decisions as well as help you shape future ones. They help you decide what to clarify, what to emphasize, and what to do next. in how you talk about your work, what content you create, or how you structure future conversations.
Keeping it lightweight (and actually doable)
Identifying patterns doesn’t need to take all day. A simple rhythm is enough. Log conversations as they happen. Review once a week. Look at your log for things that repeat or surprise you. Maybe customers mention a particular competitor you never heard of. Maybe people misunderstand the same language on your website. Maybe people are looking for reassurance more than cheaper rates.
If the process feels rigid, you won’t use it. If it feels forgiving, it will stick.
What comes next
Once you understand why people reach out, what slows decisions down, and what alternatives feel “good enough,” you’re ready to zoom out.
The next post in this series looks at market and competitive awareness, grounded not in abstract positioning exercises, but in how real people make tradeoffs.
Cheat Sheet: Turning Conversations into Insights
| Area | What to Focus On | Why It Matters |
| Question intents | What changed before they reached out, what progress they wanted to make, what alternatives they considered, and what felt risky or uncertain | These intents surface why a decision happened, not just what decision was made |
| Question-asking techniques | Ask for stories instead of summaries, anchor questions in time, leave silence, and follow interesting threads | These techniques invite context and sequence, producing insight rather than polite answers |
| Types of customers to document | People who chose you, didn’t choose you, and might choose you later | Comparing across outcomes reveals patterns you’ll miss if you only look at customers |
| Signals and patterns to look for | Repeated triggers, recurring hesitations, common alternatives, and consistent language | Insight emerges from repetition and contrast, not from individual conversations |