Questions to Ask Potential Customers
For founders and small-business owners talking to potential customers before a launch, or while selling, who want true answers instead of polite ones. The questions follow the order of a good conversation: the problem, what they do about it now, what they have tried and paid for, how a purchase gets decided, what would make them switch and at what price, and how to close. Where a question says 'this', name the task your product would help with; each has a note on what a promising or a worrying answer sounds like and what to do with it.
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The questions
Each question, and why to ask it
The problem
To start, what does a normal week look like for you, and where does this come into it?
Why ask it
An easy opener that also checks you are talking to the kind of customer you had in mind: the size of the business, their part in it, who they answer to. Listen for how much room the task takes up in their account. If they have to be reminded of it, that is your first reading of how much it matters.
What is the hardest part of this for you right now?
Why ask it
Name the task, never your product, and then stay quiet. A good answer comes fast and with some heat, and it may not be the part you planned to fix. If they have to think for a while, the problem may be more yours than theirs.
Can you tell me about the last time that happened?
Why ask it
A real story has a day, a place and a consequence in it. If they cannot recall one, the trouble is rarer or milder than they first made it sound. Write the details down, because most of the later questions can hang off this one event.
How often does this come up?
Why ask it
Daily and weekly problems tend to get paid for, and once-a-year ones tend to get put up with unless each occurrence is expensive. Check the number against the story you just heard: 'all the time' and 'last spring' do not go together.
What does it cost you when it goes wrong?
Why ask it
Let them choose the currency: hours, money, a lost client, an evening at home. A figure they can give without working it out means somebody has already counted, which is a strong sign. A shrug means the cost has never been high enough to measure.
What are you trying to get done this year that this gets in the way of?
Why ask it
A problem that stands between someone and a goal they already have, such as taking on more clients, is easier to sell against than an irritation. Their answer is the sentence your pitch should open with. If it blocks nothing, expect interest and no purchase.
If you listed the three things you most want fixed in your work, would this be on the list?
Why ask it
Ask it plainly and accept a no. A problem outside the top three rarely gets money or attention, however real it is. When the answer is no, ask what is on the list: you may be talking to the right person about the wrong problem.
Who else feels it when this goes wrong?
Why ask it
Trouble that lands on one person gets solved with that person's patience. Trouble that reaches a boss, a customer or a spouse tends to have a budget behind it. Note the names, since some of them turn up again when you ask who decides.
When did this start being a problem for you?
Why ask it
Often something changed: a new hire, a rule, a bigger customer, a tool that was retired. That change tells you who else is about to have the same trouble and where to find them. 'It has always been like this' is a harder sell, because they have learned to live with it.
Is it getting worse, staying the same or easing off?
Why ask it
Growing problems pull a purchase forward and shrinking ones cancel it. If it is easing, ask what made the difference, since whatever did that is your competition.
Which part of this do you honestly not mind?
Why ask it
Founders tend to rebuild the whole process when only one step hurts. Whatever they shrug at here is work you can leave out of a first version. It also gives them permission to say something is fine, which makes the complaints that follow easier to believe.
What they do now
How do you deal with it today?
Why ask it
The whole conversation turns on this, since what people do counts for more than what they say they want. A patched-together routine that takes effort shows the problem is real. 'We don't, really' usually means it is not painful enough to act on, so ask what happens when it is ignored.
Could you show me how you did it the last time, on the screen or on paper?
Why ask it
Seeing the screen, the form or the notebook beats any description, because people leave out steps they no longer notice. Watch for copying between two places, a printed sheet, or a pause to look something up. Ask before you take a photo, and expect a no where their own clients' details are on show.
Roughly how long did it take the last time?
Why ask it
Tie the estimate to one occasion, since averages get rounded down. Multiply it by the frequency they gave you earlier and say the total back to them. Their reaction to that number, surprise or indifference, is the finding.
What do you like about the way you do it now?
Why ask it
Whatever they praise is the bar you have to clear, and it is often something dull such as 'everyone here already knows how'. Familiarity is a real advantage of the old way. A long, fond answer means switching will be harder than the complaints suggested.
What annoys you about it?
Why ask it
Let the list run and ask 'what else?' until it stops. Then ask which single item they would remove if they could pick only one. A small irritation that comes up in several conversations is worth more than one dramatic complaint from one person.
What tools, apps or people do you rely on to get it done?
Why ask it
You are mapping what your product would have to sit beside or replace. A person in the answer, such as a bookkeeper or a cousin who is good with computers, is a competitor too, and one they have a relationship with. Ask which of these they would never give up.
What happens just before this step, and just after it?
Why ask it
Work arrives from somewhere and is handed on to somewhere. If your product does not fit those two joins, people drift back to the old way. The answer also shows whether the pain starts in this step or only becomes visible here.
If you were away for a month, who would do this and how would they cope?
Why ask it
It reveals how much of the process lives in one head. Where the honest answer is 'badly', you have found a risk the owner already worries about, and that worry can be a better reason to buy than saved time.
Tried and paid
What have you tried so far to make this easier?
Why ask it
Each attempt is evidence of effort, and effort says more about a future purchase than any opinion does. Get the attempts in order and ask what each one cost. Someone who has tried nothing has told you where the problem ranks, whatever they said earlier.
Have you gone looking for a better way, and where did you look?
Why ask it
Looking is free, so someone who has never searched, asked a peer or read a review is unlikely to pay. For those who have, the places they name are where your own marketing belongs: a forum, a trade group, a supplier's counter, one trusted colleague.
What are you spending on this now, counting people's time as well as bills?
Why ask it
Money already leaving the account is the easiest money to win, since nobody has to find a new budget. Ask for the amount on the last invoice instead of a guess. If the only cost is their own time, find out whether they put a value on it, because many owners do not.
What was the last thing you bought to help with it?
Why ask it
Ask when, how much, and whether they would buy it again. A recent purchase means the wallet is open for this problem. Regret is useful too: the reason they regret it is a promise you will have to keep.
Is there anything you signed up for and then stopped using, and what went wrong?
Why ask it
Abandoned tools fail for ordinary reasons: setup ate a weekend, the team would not touch it, the price rose at renewal. Assume the same reason applies to you until you have shown otherwise. How long they lasted before quitting tells you how much patience a newcomer gets.
Is there anything your current tool or supplier promised that it has not delivered?
Why ask it
A broken promise from a current supplier is an opening, and the customer will describe it in more detail than any review does. Do not pile on: let them do the criticizing and write down their words. If nothing was oversold, the incumbent is doing a decent job and you need a different angle.
Have you made a workaround of your own, like a spreadsheet, a template or a checklist?
Why ask it
A homemade fix is about the strongest signal you can get. They cared enough to build something, and what they built is a rough specification of what they want. Ask to see it, and ask what it still cannot do.
Have you ever paid someone else to take this off your hands?
Why ask it
Outsourcing puts a price on the problem that you did not have to suggest. If they stopped, find out whether it was the cost, the quality or the bother of managing somebody. If they never considered it, the task may feel too small or too private to hand over, and both matter to you.
Deciding
Think of the last thing like this you bought. How did that decision go, from first hearing of it to paying?
Why ask it
A past purchase describes the real process, where a plan for a future one describes a tidier fiction. Listen for who raised it, who had to agree and what nearly stopped it. Your sale will follow that same sequence.
Who else would have a say before something like this was bought?
Why ask it
In a household it may be a partner. In a company it may be a manager, finance or whoever looks after the computers. If the person in front of you cannot name anyone, they have probably never bought anything like this, so ask who handled it last time.
When you are choosing between options for something like this, what do you look at first?
Why ask it
What gets looked at first is not always what settles it, so follow with what tipped their last choice. If price comes first, ask what would justify paying more: sometimes it means the options all look alike to them. Whatever they name is what your first page or first minute has to answer.
Who would use it day to day, and is that the person who pays?
Why ask it
When the user and the buyer are different people you need two conversations, because they tend to want different things: the user less hassle, the buyer a reason they can repeat to whoever asks about the spending. Ask to meet the one you are not talking to.
Is there money set aside for this already, or would it have to be found?
Why ask it
An existing line, such as software, training or a contractor's fee, is far easier than new spending, so ask which one it would come out of. With a consumer, ask what they would spend less on to afford it. 'I would have to see' is honest, and it means the money has no home yet.
How did you find the product or supplier you use now?
Why ask it
A recommendation, a search, a trade show, a cold call that happened to land: this is the route that worked on them once. If the same answer keeps coming up across conversations, start your selling there.
What would you want to see before you felt safe trying something new?
Why ask it
Some people need a free trial, some a name they recognize among your customers, some a word with an existing user. Whatever they ask for, note whether you could provide it this month. A demand you cannot meet yet is a reason to sell to a different kind of buyer first.
What has stopped a purchase like this in the past?
Why ask it
The usual culprits are a busy season, a colleague who objected, a contract with months to run, or a price that needed sign-off. You are collecting the objections you will meet, ahead of time, from someone with no reason to soften them.
Is there a date by which you need this fixed, and what happens if it passes?
Why ask it
A date with a consequence attached, such as a renewal, an inspection or the start of a busy season, is real urgency. 'Sooner is better' is not. Without a date, expect the decision to slide behind whatever does have one.
If you went looking for a new option tomorrow, which names would you check first?
Why ask it
These are your competitors as the customer sees them, which is often not the list you drew up. If they name nobody, the category may not exist in their mind yet and you will have to explain the problem before the product. Ask what they have heard about each one.
Switch and price
What would have to be true for you to change from what you do now?
Why ask it
Listen for conditions, not enthusiasm: 'it would have to take in my old records', 'my staff would have to pick it up in a day'. Each condition is a requirement with a customer attached. If the answer is 'nothing, really', believe it and thank them.
What would make switching a headache?
Why ask it
Years of records, an agreement with time left on it, staff habits, a process their own customers see. Ask how their current contract works instead of assuming what they can leave and when. The length of this list is the amount of help you will have to offer with moving over.
If you replaced what you use now, what is the one thing the new option would have to keep?
Why ask it
One feature of the old way is usually non-negotiable, and it is rarely the one a newcomer copies first. Finding it now is cheaper than finding it in a cancellation email. Ask what happened the last time they had to go without it.
What would make you rule something out straight away?
Why ask it
Dealbreakers come in a few kinds: a missing feature, a pricing model they dislike, a supplier too new to trust, where their data is kept. Do not argue with any of them in the meeting. Count how often each one recurs before deciding which to fix.
If you could wave a wand and change one thing about how this works, what would it be?
Why ask it
A popular question that needs care. The wish is a clue to the pain, not a specification, so follow it with 'what would that let you do?' People tend to describe their trouble well and design the cure badly, and the second answer is the one to build from.
Six months after buying, what would need to be different for you to call it money well spent?
Why ask it
Their answer is the result you are really selling, and it is usually plainer than your feature list: fewer late nights, no more chasing, one less person to hire. Borrow their wording for your sales page. If they cannot picture a difference, the value is not yet clear to them.
How do you pay for what you use now: monthly, yearly, per person or per job?
Why ask it
People have habits about how they pay as well as how much. A buyer used to a one-time fee may balk at a subscription even when it works out cheaper. Match the familiar model where you can, or be ready to explain why yours differs.
What would you expect something like this to cost, and what are you comparing it with?
Why ask it
The comparison matters more than the figure. Someone anchoring on a free app and someone anchoring on a part-time assistant will name very different prices for the same thing. Do not offer your own number first, or you will only hear it repeated back.
At what price would you start to doubt the quality, and at what price would you stop considering it?
Why ask it
Two numbers give you a range, which is more honest than one. Treat both as rough, because a price named for a hypothetical is not a price paid. Asking for a deposit or a trial sign-up afterwards is what tests it.
What is something you paid more for than you expected and still thought was worth it?
Why ask it
The story shows what this person rewards: speed, reliability, somebody answering the phone. It is a truer guide to their ceiling than a number given for a product that does not exist yet.
Closing
Out of everything we have covered, what would you fix first?
Why ask it
After half an hour of prompts, this lets them rank things in their own order. Compare it with the hardest part they named at the start. When the two match you can trust it. When they differ, ask what shifted as you talked.
What did I not ask about that matters here?
Why ask it
The person who lives with the problem knows which part you walked past. Wait through the silence: the first reply is usually 'no, I think that covers it' and the useful one comes a few seconds later.
Now that you have heard what I am working on, what makes you hesitate?
Why ask it
Save this until the listening is done and you have described the idea in two sentences. Then ask for doubts by name, since politeness will otherwise hide them. Thank them for each one and do not defend against it.
If it did what we have discussed, would you put down a deposit or sign up for a trial today?
Why ask it
Praise costs nothing, so ask for something that does: money, a signature, an hour of their time next week. A yes outweighs every compliment that came before it. If they hesitate, ask what is behind it, and find out how deposits and pre-orders have to be handled where you trade before you take one.
Would you try an early version and tell me what is wrong with it?
Why ask it
Asking for faults makes yes easier to say and sets the right expectation for a rough first release. Agree on an approximate date. Those who accept are your testers, and the ones who then open it without being reminded are likely to be your first buyers.
Who else do you know who deals with this, and would you introduce me?
Why ask it
An introduction is a small commitment, and whether they make it shows how real the problem felt to them. It also keeps your next conversations inside the same kind of customer. Offer to write a two-line message they can forward.
May I come back to you when I have something to show, and what is the best way to reach you?
Why ask it
Get the channel they answer, which may not be the one you used to arrange the call. Send a short thank-you the same day with one thing you learned from them. Keep their details for the purpose you stated, and ask before adding anyone to a mailing list.
How to get honest answers from potential customers
Practical guidance for the conversation itself
Before you talk to anyone
Write down what you need to learn
Before each round of conversations, note the two or three things you least know: whether the problem is common, what people do about it now, who pays. Choose questions that answer those and leave the rest. A conversation with a purpose stays shorter and friendlier than a march through a list.
Find people who have the problem, not people who like you
Friends and family will be kind about anything you make. Look for strangers who do the task: in a trade group, a local business association, an online community, the line at a supplier. A plain request works: 'I am trying to understand how people handle this before I build anything. Could I have twenty minutes?' Only say you have nothing to sell if that is true for the whole conversation.
Keep the idea out of the invitation
Once someone knows what you plan to build, they answer about your idea when you wanted to hear about their week. Say which task you are studying and stop there. The groups on this page are in that order on purpose: The problem, What they do now, Tried and paid and Deciding all come before you describe anything, and the two questions that need your idea on the table are held back until Closing.
Choose about ten
Half an hour holds roughly ten questions with room for follow-ups. For a first conversation, take most of them from The problem and What they do now and one or two from Tried and paid. Leave Switch and price for a second conversation, or for the people whose answers showed the problem is real for them.
Put the task where the page says 'this'
The questions say 'this' so they fit any business. In the room, name the job: 'getting invoices paid', 'planning the week's meals', 'booking the vans'. Use the customer's own word for it once you have heard it, and never put your product's name in that slot.
During the conversation
Ask about the past, not the future
'Would you use an app for this?' gets a guess, and guesses are generous. 'What did you do the last time?' gets a fact. Most questions here are worded about what has already happened for that reason. When one of your own starts with 'would you', try to turn it around before asking.
Follow one answer further
The first reply is a summary. 'What happened then?', 'why was that a nuisance?' and 'what did you do about it?' reach the part with detail in it. Two follow-ups on a good answer are worth more than two new questions.
Do not suggest the answer
'Is that frustrating?' and 'so you would want it to be faster?' hand people a line and most will take it. Ask the open version, then wait. If you hear yourself offering options, stop at the question mark.
Talk less than they do
A pause feels longer to the asker than to the person thinking. Let it run. If you are explaining your idea before the last ten minutes, you have switched from learning to selling, and the answers after that point will be kinder and less true.
Take notes in their words
Write the phrases people use for the problem, exactly as said. They become your headline and your search terms later. If you would like to record, ask first and take no for an answer; the rules on recording a conversation differ from place to place, so check how it works where you and they are.
Reading the answers
Compliments are not evidence
'That sounds great' and 'I would definitely buy that' feel like progress and commit the speaker to nothing. Thank them and go back to what they do today. The notes worth keeping are complaints, figures and stories.
Count what people have done
Money spent, hours lost, a workaround built, a search made, an introduction offered, a deposit paid. Each is an action with a cost to the person. Rank your conversations by how many of these turned up, not by how warm the meeting felt.
Look across conversations, not inside one
Write each one up the same day while the wording is fresh. After a handful, lay them side by side and look for the same story told by people who do not know each other. No fixed number of conversations is the right one. Keep going until new ones stop surprising you.
Notice who cared and who was polite
People with a real problem lean in, correct you and ask when it will be ready. People without one agree with everything. If the keen ones share a trade, a company size or a stage of life, that group is where to start.
Treat a clear no as a result
Hearing 'we are fine as we are' from most of a group is cheaper than learning it after launch. Change one thing, the customer or the problem, and run the conversations again.
When you are already selling
Use the same order on a sales call
A prospect who came to you already knows what you offer, so the risk moves from leading them to rushing them. Spend the first part on The problem and What they do now anyway. What you hear there tells you which two features to talk about and which ten to leave out.
Skip what they have already told you
If an inquiry form, an email or an earlier call covered something, build on it instead of asking again: 'You mentioned the old system was slow at month end. What did that hold up?' It shows you read what they sent.
Bring up price and the decision before the end
Questions from Deciding and Switch and price feel awkward in the last two minutes and natural in the middle. Asking who else is involved and how they pay today is ordinary business, and it spares both sides a proposal that was never going to fit.
End with a next step that costs something
A trial start date, a meeting with the other decision-maker, a list of records to bring over. 'I will think about it' with nothing attached usually means no, and it is kinder to both of you to ask what would need to change.