How to Find Customer Pain Points

Getting ready for a party in 1998, Sara Blakely couldn't get a smooth look under her white pants with the undergarments she had. According to Spanx's official history, she cut the feet off her control-top pantyhose.

That altered pair gives you two interview questions: what needed to change, and what did her workaround let her do? Try them with invented studio manager Dana and Thimbleledger, the expense tool you're writing for.

It's 4:40 on the last Thursday of the month. Dana has a client expense report open with one blank line on it: a train fare with no receipt. Billing closes at five.

A week later you interview her, and she says, "I hate chasing receipts." You could write "End receipt chaos forever" on the spot.

Before you draft, ask what the blank line changed for her. Her answer will tell you how much of a problem your copy can describe.

Start with an episode you can reconstruct

Ask about the last time it happened. "Walk me through the report you sent on Thursday" gets you a sequence of events. A general question about expenses tends to get you an opinion, which is useful background and hard to build a page on.

She tells you she spotted the gap at 4:40 and messaged the designer who took the train. Nothing came back, so she messaged again. At five to five she sent the report with the line still blank.

GOV.UK's interview guidance recommends asking about real, recent examples with open questions that don't steer. The voice-of-customer lesson goes into how to phrase them so you don't hand people the pain yourself.

Write down when it happens and to whom. The blank line exists for a manager who bills travel back to clients once a month. A freelancer with no reimbursable trips may never see it, and a headline about drowning in receipts would lose her in one line.

Follow the cost without putting a price on everything

Next, find out what the blank line changed. Ask what actually happened, and keep it apart from what Dana feared would happen. A fare billed a month late is a different fact from a worry that it might be.

You suspect a chain. The receipt is missing, so the report goes out incomplete, so the client pays for that fare a month later.

If the designer sent the receipt the next morning and it went on the same bill, the scarier version goes in the bin, however well it would read.

Dana's chain, one link at a time

1. The train receipt is missing at 4:40
2. Dana messages the designer twice
3. The report goes out with a blank line
4. The fare waits for next month's bill

The last link stays a guess until Dana confirms what happened to the fare.

Don't push her for a dollar figure she doesn't track. Ask how long the last one took, and note whether her answer is a guess.

If you work out an illustrative cost yourself, keep the sum in your notes with its assumptions. It isn't her quote, and it says nothing about what other studios would save.

Use categories to notice gaps

A few rough categories help you see what you haven't asked yet. Some pain sits in the work itself, or in money and when it lands. Some sits in how a person feels, or in how they look to the people around them.

Use the categories to spot a hole in your notes. Nobody has to fill every box.

The Christensen Institute's Jobs to Be Done theory looks at the progress someone is trying to make in a particular circumstance. It counts the emotional and social sides alongside the practical one.

Dana may want to walk into her client meeting sure of the numbers, but she has to say so before you write it down.

Ask who notices when the report is late, and she can answer however she likes. Ask whether it makes her look unprofessional, and you've handed her an embarrassing reason and waited for a nod.

Your notes from Dana's interview

What she told you happened

Dana sent the designer two messages before the cutoff.

The report went out at five to five with the fare line blank.

What you're still guessing

The fare will wait for next month's bill.

Dana fears colleagues think she's careless.

Every studio loses money because receipts go missing.

Move a line left only when Dana's own account supports it.

Two columns keep a guess from sliding across into a fact.

Look for pain in the workaround

Blakely's altered pantyhose show the fix she tried for the party, two years and many prototypes before Spanx launched. What does Dana's current receipt process let her do? Ask her to show you how it works before you decide where it fails.

She opens a spreadsheet tab called "waiting for receipt" and checks it before every invoice. Ask what it does for her and where it lets her down. Maybe it works fine and she has no reason to switch, which is worth knowing before you write a word.

Watch what the workaround does before you decide it fails.

The list might show the job, or it might already do it

A homemade fix shows you the job someone had to do and how well they managed it. Ask what the list catches and what slips past it. Ask how often she has to rebuild it.

Support threads and review-mining records can point you to episodes worth a closer look. Look for a customer who tried again, and follow what happened next.

Some tickets are questions about a new task, and others describe a mismatch no product could fix, so don't count every one as pain.

Separate the problem from a proposed feature

Then Dana says, "We need automatic reminders." That's her fix, and it's worth hearing. Ask what happens without reminders and what she hopes would change.

Underneath, you might find she can't see which receipts are missing. Or she might want to hand the chasing to someone else. Those lead to different pages.

For all you know, Thimbleledger already sends reminders and they land in an inbox the designer never opens. Ask Dana to show you where the last reminder arrived.

Keep the feature request beside that episode so you can check whether a reminder would reach the person who has the receipt.

A pain and a hesitation can sit side by side. Dana hates chasing receipts and also worries that a new tool will mean a month of chasing during setup. The customer-objections lesson covers the second worry.

Which pain points should you prioritize?

Give Dana's missing-receipt episode a source ID, D-01. Record the consequence you can trace: the report went out incomplete. Payment delay stays unconfirmed, and you still need to check whether Thimbleledger can show outstanding receipts under her billing setup.

Compare that card with your other accounts before deciding which problem leads the page. Consider the consequence and whether it affects the purchase, then check how often independent accounts describe it. One severe episode can earn a closer look without becoming the headline for everyone.

"Comes up a lot" needs a count and the source IDs behind it. Keep accounts where the current process works, too; they help you see who the proposed message would miss.

Before a pain point goes into the brief

• Can I name the recent moment and the person it happened to?
• Do my notes show a consequence, or only my reading of it?
• Did I keep the accounts where the current way works?
• Does it bear on the decision this page supports?
• Can the product help under the conditions she described?

Write the problem at its real size

Try a draft built on Dana's Thursday: "Still waiting on a receipt when the client report is due? See what's missing before you send the next reminder." It names a moment she'd recognize and offers one next step.

It also assumes Thimbleledger really shows missing receipts, so check that before it ships.

Now try "Missing receipts are destroying your business." Dana's account gives you no damage that supports that claim. Cross it out and underline the consequence you can trace: she sent an incomplete report.

Link the problem to something the product does, and then to a result Dana might want. "Keep every outstanding receipt on one list, so you can see what still needs chasing" promises visibility and stops there. "Get paid faster" would need evidence that the tool changes when money arrives.

For campaigns in the US, the FTC's substantiation policy expects evidence behind objective claims, implied ones included. Flag "Get paid faster" for your claims reviewer unless you have support for that payment-timing promise.

Reconstruct one difficult episode

Pick one interview or support thread that describes something that really happened. Write the customer's exact words in one column and your reading in the other. The Research collection can help you shape the follow-up interview.

Follow the obstacle to what it changed. Then draft the problem in a sentence and try two opening lines that use only product facts you can back up. Put a question mark beside every link you haven't confirmed.

Dana's card still has a question mark beside the fare on next month's bill. When she picks up the phone, ask her to open Thursday's report and tell you where that fare went.