Anna Kowalski

Four of five people said it was fine. All four paused first.

That's the pattern I'd expect from these interviews if we ask them the usual way, so this guide avoids asking for opinions about the app and asks about their real weeks instead.

BEFORE YOU START

• 45 minutes. Record with permission.
• Say: "There are no wrong answers. I didn't build the app, so you won't hurt my feelings."
• Count pauses. Write down the word they say right after one.

WARM-UP

1. Tell me about the properties you manage. How did you end up as a landlord?

THEIR REAL WORK

1. Walk me through the last time a tenant had a problem. What happened, from the first text to when it was fixed?
2. How do you keep track of rent payments today? Show me, if you can.
3. What's the part of being a landlord you put off the longest?

THE APP, BY WAY OF THEIR STORY

1. Think back to the week you signed up. What was going on that made you look for something?
2. What did you try to do first in the app? What happened?
3. Tell me about the last time you opened it. What were you trying to do?
4. When you stopped opening it, what did you do instead?

CLOSING

1. If a friend who just bought a rental asked how to manage it, what would you tell them?
2. Is there anything I should have asked and didn't?

QUESTIONS I LEFT OUT ON PURPOSE

• "Would you use this feature?" People say yes to be kind, then don't.
• "What do you like about the app?" It invites politeness, not truth.
• "Why did you stop?" Too direct. Questions 7 and 8 get there without making them defend themselves.

AFTER EACH INTERVIEW

Write three exact quotes within the hour, while you still remember the tone.

Their words, not mine. — Anna

Four of five people said it was fine. All four paused first.

In a booking flow, that pause is usually where people give up at home. This plan is built to find those pauses before launch.

WHAT WE'RE TRYING TO LEARN

1. Can pet owners book the right appointment type without calling?
2. Where do they hesitate or go back?
3. Do they understand what happens after they book?

WHO

5 pet owners: 3 current clients and 2 people who've never been to the clinic. At least 2 over 60. At least 3 on a phone, since that's where most bookings will happen.

HOW

• 30 minutes each, in person or on a video call with screen share.
• One person runs the session; one takes notes.
• Use the test version of the booking site, not the real one.

THE TASKS

Read each task out loud. Don't explain the screen.

1. "Your dog Max is due for his yearly checkup. Book an appointment for next week."
2. "Your cat has been throwing up since yesterday. Book the soonest visit you can."
3. "You need to move Max's appointment to a different day."
4. "Find out what to bring to the appointment."

WHAT TO WRITE DOWN

WHAT NOT TO DO

• Don't help. If they're stuck for 2 minutes, say "What would you do at home?" and then move on.
• Don't ask "Was that easy?" Watch instead.

AFTER ALL 5

I'll list every problem with how many of the 5 people hit it, and the quotes that go with it.

I noticed task 2 is the riskiest: a worried owner may pick "checkup" just because it's the first option. Worth watching closely.

Their words, not mine. — Anna

Four of five people said it was fine. All four paused first.

That was their answer to "How do you feel about invoicing?" Then they told me, in different words, that they dread it.

WHAT I DID

Read all 5 transcripts twice. Pulled every exact quote about invoicing. Grouped them only after that. Counted how many people said each thing.

FINDING 1: THEY DON'T FORGET. THEY AVOID. (5 OF 5)

• "I know exactly when it's due. I just don't want to be the person asking for money." (Person 2)
• "Invoicing feels like asking for a favor." (Person 4)
• "I'll redo the logo for the fifth time before I'll send the bill." (Person 1)

I noticed all five described invoicing as a social act, not a paperwork task.

FINDING 2: THE AWKWARD PART IS THE FIRST INVOICE TO A NEW CLIENT. (4 OF 5)

• "After the first one, it's fine. It's the first one where I don't know how they'll react." (Person 3)
• "With old clients I just send it." (Person 5)

FINDING 3: THEY UNDERCHARGE WHEN THEY INVOICE LATE. (3 OF 5)

• "By the time I send it, I feel guilty, so I knock some hours off." (Person 1)
• "I rounded down because it was so late." (Person 4)

FINDING 4: REMINDERS DON'T HELP. (3 OF 5)

• "My calendar reminds me. I snooze it." (Person 2)

WHAT THIS SUGGESTS (MY READ, NOT THEIRS)

1. More reminders won't fix it; they'd be snoozed.
2. The first invoice to a new client is the moment to help. For example, agree on invoicing terms at the start of the project, so the first bill isn't a surprise.
3. Late invoices cost them money, not just time. That's worth saying in your marketing, in their words.

WHAT I'M LESS SURE OF

Only 5 designers, all solo, all under 8 years in. Agencies or developers may be different.

Their words, not mine. — Anna