Interview questions
👋 Hi, below is a list of questions that, in my opinion, are worth asking business owners.
Goal: Find out how the business actually works today: which processes, which tools, what is done by hand. Based on this we will decide which features to build.
☝️ Interview rules
It may seem like there are a lot of questions and a call with a participant could go on forever, but that’s not quite true. I think at an active pace each call can realistically be finished in 40-60 minutes.
I would like you to follow a few recommendations while running the interview to make it as effective as possible.
- It would be great to record interviews with customers in Google Meet, Zoom, or other services (before starting, ask whether the participant agrees to being recorded). If you record the interview, you won’t need to take many notes, and we can rewatch the recording later and work through it.
- Questions marked [Must] are the most important ones, so try to always ask them and not skip them. Under each question there are also notes “What you can learn”. These notes will help you understand what the answer will tell us, that is, why we ask this question at all.
- Ask only about the past and present. Don’t ask about the future, because people are bad at predicting what they would do, but good at describing what has already happened.
- Let participants talk more and show more.
- Don’t discuss our product and future features. In the introduction we say we are building an app for businesses like theirs, and that is where the topic of the product ends. Don’t explain how it works, don’t discuss future or possible features, and don’t ask whether they would use it. If the participant starts saying what they would like to have or which features would be useful, don’t spend time on it and don’t ask follow-up questions. Thank them and gently steer the conversation back to how they work now or worked recently: the real insights are in their current and recent work, while wishes about the future say little about real behavior. If they ask directly what we are building, answer in one or two sentences and return to the specific case.
- You don’t have to follow the order of the questions. If you think you should ask something of your own, that is absolutely fine.
Questions
Introduction (worth saying out loud to set the general context)
Hi, we are at an early stage of building an app that owners of delivery and service businesses like yours will be able to use. I own a carpet cleaning service myself, so I know a lot from the inside. But every business is set up differently, so it’s important for me to hear how it works for you, in your own words.
The conversation will take about 50 minutes. I’ll mostly ask about specific recent cases, such as your latest order, and sometimes I’ll ask you to show a notebook, chat, or spreadsheet that you use. Everything you show will stay within our team. Some questions will seem simple. That’s intentional.
🔴 Is it okay if I record our conversation?
Part 1. About the business (6 min)
| № | Question |
|---|---|
| 1 | [Must] Who works for you now and what does each person do? (Checklist, don’t read it out: owner, dispatcher or office, couriers or drivers, cleaners or workshop staff, others.) What you can learn: The team structure and whether there is a dispatcher role, which shows who our real users will be. |
| 2 | [Must] Think of your last five new customers. How did each of them find you? (Hint for the interviewer, don’t read it out right away: first let the owner recall on their own. If they can’t remember, help with questions: “Was it a call? Instagram? Telegram or Viber? A website, Google, a referral, an ad?”) What you can learn: Which acquisition channels really work and where new orders first enter the business. |
| 3 | What do you want to achieve with the business this year and what is getting in the way? What you can learn: Their real priorities and whether a tool like ours would help with what they want. |
| 4 | Walk me through yesterday: what did you personally do for the business, from the first task to the last? What you can learn: What the owner really spends the day on and how much of it is operational work that could be automated. |
Part 2. Walk me through an order (15 min)
Ask the owner to walk through the most recent real order, not a typical one, from start to finish. Don’t accept the answer “it depends”. Ask for one specific case. When possible, ask them to show the notebook, chat, spreadsheet, or app where it is stored.
| № | Question |
|---|---|
| 5 | [Must] Take your last order. How did it start: who contacted whom, through which channel, and when? (Then ask them to show that chat or call log.) What you can learn: Which channels orders really come through and who handles the first contact, as well as which messengers they use with customers. |
| 6 | [Must] Show me where this order is recorded. What did you have to find out from the customer and what did you have to ask twice? (Checklist: address, phone, size or volume, time, payment, notes.) What you can learn: Where order data lives, what is missing from it, and what workaround (notebook, chat, Excel) they use. |
| 7 | [Must] Who decided when the order would be completed and who exactly would do it? What information did that person use to decide? What you can learn: Who the dispatcher really is and what they look at when deciding, that is, what data the planning feature needs. |
| 8 | [Must] How did the courier or driver find out about this order? What exactly did you send or tell them, and how? Can you show me? (Then ask: what does the courier have at hand while working: their own phone, a paper list, a messenger, an app? When did you last give couriers a new tool or way of working and how did it go?) What you can learn: How work is passed to couriers, how reliable that handoff is, what gets lost along the way, what couriers really use today, and how likely they are to adopt an app. |
| 9 | [Must] When was the last time the customer wasn’t home, the address was wrong, or the time changed? What happened and how much did it cost you? What you can learn: How often exceptions happen and how much a failed trip costs, which sets the value of handling such cases better. |
| 10 | How did the customer pay for this order? How did you find out the money had arrived? When was the last time the numbers didn’t add up? What you can learn: Which payment methods are used, where the cash risk is, and how reconciliation works. |
| 11 | What happened after the courier left? When did you consider the order complete and where did you mark it? (Don’t suggest receipts or reviews. Ask about them later.) What you can learn: How orders really get closed and whether steps like confirmation, a receipt, or a review get skipped. |
| 12 | [Must] Tell me about the last order that went wrong. What happened, how much did it cost (time, money, customer), and what did you change afterward? What you can learn: The most painful failure in the process, its real cost, and whether it was ever fixed. |
| 13 | Which step in this last order took the most time from you or your team? What you can learn: The biggest time sink within a single order, that is, the strongest candidate for automation. |
Extra questions: carpet cleaning
| № | Question |
|---|---|
| 14 | How did you set the price for this carpet? Who measured it and when did the customer first hear the price? When did you last get a price wrong? What you can learn: How pricing really works and where pricing errors happen, which shows whether a price calculator is needed. |
| 15 | [Must] Where is the last carpet you accepted right now, and how would you find that out? Show me. Which stages has it gone through? What you can learn: Whether they can find an item in the process at all, which shows the need for stage tracking. |
| 16 | [Must] Tell me about the last time a customer said you damaged a carpet, or you almost mixed up carpets. What did you do at pickup (notes, photos) and what happened? What you can learn: How serious the risk of damage or mix-ups is and whether condition records at pickup would be useful. |
Extra questions: water delivery
| № | Question |
|---|---|
| 17 | [Must] Tell me about the last time a customer didn’t return the bottles. What happened to the deposit? How many bottles do you think are with customers now and how do you know? What you can learn: The scale of bottle and deposit losses and whether they track returnable containers at all. |
| 18 | At the end of yesterday, how did you find out what each courier delivered, what they collected, and what was left in the vehicle? When did it last not add up? What you can learn: Whether an evening reconciliation of stock and deliveries exists and where it breaks down. |
Part 3. Dispatching and couriers (7 min)
| № | Question |
|---|---|
| 19 | [Must] Who planned yesterday’s trips to customers: what to bring to whom and what to collect from whom? How long did it take? (Then ask: what did this person base the plan on, and what had to change during the day?) What you can learn: Daily time spent on planning, who will be our dispatcher user, and how often the plan breaks during the day. |
| 20 | [Must] How did you find out yesterday where your couriers were and when a delivery was done? When did you last have to call a courier just to find that out? What you can learn: The visibility gap: how couriers are tracked today and how much effort goes into checking status. |
| 21 | [Must] When was the last time a customer asked “where is my order?” How did they ask, who answered, and how did that person find the answer? Roughly how many such calls or messages were there last week? What you can learn: How many “where is my order?” requests come in, which shows the value of tracking for customers. |
| 22 | Tell me about the last urgent or last-minute order in the middle of the day. What happened, who was notified, and what had to be pushed back? What you can learn: How well the process copes with changes and how much late orders cost. |
| 23 | [Must] Tell me how you last calculated courier pay: what scheme they are paid by, where you got the data on their work from, and how long it took. What you can learn: How complex the pay model is, how long the calculation takes, and how often disputes arise. |
| 24 | [Must] Tell me about the last time a courier caused a problem (lateness, wrong address, lost cash, damaged goods, a dispute about what was done). What happened and how much did it cost you? What you can learn: Losses caused by couriers and trust issues, which point to the need for delivery confirmation and cash control. |
Part 4. Tools and systems today (8 min)
| № | Question |
|---|---|
| 25 | [Must] What did you use yesterday to run the business: to write things down, calculate, and communicate with customers and couriers? Please show me. (Hint for the interviewer, don’t read it out right away: let the owner answer on their own first. If they named only one or two and went quiet, help with questions: “What about paper or a notebook? Excel? Phone notes? Messengers?”) What you can learn: The full set of tools, which shows integration candidates and what we would replace. |
| 26 | [Must] Think of the last time you needed a customer’s previous orders. Where did you look and how long did it take? Show me. What you can learn: How easy it is to find customer history, which shows whether a real customer base exists. |
| 27 | (Only if there is a website or online form.) Where did the last order from the website go and what did you do with it next? What you can learn: Whether online orders get into their system automatically or are retyped by hand. |
| 28 | [Must] When did you last do bookkeeping, invoices, taxes, or cash counting: which tools did you use, who did it, and how long did it take? (Follow-up: 1C, Excel, Checkbox, banking apps.) What you can learn: Which accounting tools are used and whether we need to integrate with them or support export. |
| 29 | When did you last copy data by hand from one place to another? What was it and how often does that happen? What you can learn: Duplicate data entry, which is the most obvious automation opportunity. |
| 30 | What was the last business tool or app you paid for? How did you choose it and who decided? (Then ask: roughly how much do all your tools cost per month together? Have you tried any CRM, delivery, or dispatching software? Why did you start, why did you stop or why do you still use it? What annoyed you most?) What you can learn: What and how they buy: budget, willingness to pay, who makes the decision, and what past experience with software taught them (why it didn’t stick or did), that is, adoption risks for us. |
Part 5. Manual work and pain points (8 min)
| № | Question |
|---|---|
| 31 | [Must] What took the most of your time or your employees’ time last week? Roughly how many hours did you personally spend organizing the work (calls, planning, checks, paperwork)? What you can learn: How many hours are lost to administrative work and the biggest pain by their own ranking. |
| 32 | [Must] What have you already tried to make this easier? How did it go? What you can learn: Whether the pain is serious enough that they have already tried to solve it, and what we will be competing with. |
| 33 | [Must] Besides the order that went wrong that you told me about earlier, what other mistakes happen regularly (wrong address, forgotten order, double booking, wrong price, lost money)? How often, and what was the worst in the last six months? What you can learn: How often each type of mistake happens, which is the core of the business case. |
| 34 | [Must] Tell me about the last customer you lost or order you missed (slow reply, missed call, late delivery). How did you find out? What you can learn: Revenue lost to slow responses and whether they measure it at all. |
| 35 | [Must] When did you last notice that a regular customer stopped ordering? How did you notice and what did you do? Who are your best customers and how do you know? What you can learn: Whether they track customer retention and how well they know their customer base. |
| 36 | [Must] How many of last week’s orders came from regular customers? How do you know who is due to order again? Show me. (Then ask: when did you last remind a customer about a regular order or send a seasonal offer, such as “time to clean your carpet” or “your water is running out”? How did you do it, how long did it take, and what came of it? If never: why?) What you can learn: The share of recurring revenue, how repeat orders are tracked and triggered, and whether reminders and seasonal offers happen at all, which shows the need for subscriptions and a repeat-order feature. |
| 37 | [Must] When did you last look at how the business is doing (revenue, number of orders, cost per delivery, courier performance)? What did you look at, where did you get the numbers, and how long did it take? What you can learn: Whether they have visibility into key numbers and how much effort it takes to get them. |
Part 6. Wrap-up (3 min)
| № | Question |
|---|---|
| 38 | [Must] Imagine you have a magic wand and can instantly fix one thing in your work. What would it be? (Then be sure to ask: why that one? When did it last let you down? What did you do to work around it?) What you can learn: What the owner themselves considers their main problem and whether it is backed by the real cases they described earlier. This is a hypothesis, not a feature requirement. |