Most roadmaps are built from the loudest voices: a big client’s request, a competitor’s new feature, the founder’s instinct. Real users rarely get a seat at the table. You don’t need a lab or a large budget to change that. Five well-chosen conversations, each with a different kind of user, will tell you more about what to build next than any amount of internal debate.
Why five, and why these five
The point isn’t a magic number. It is that each of these interviews looks at your product from a different angle: someone who left, someone who loves it, someone who never started, someone brand new and someone who solves the problem without you. Together they reveal gaps a satisfaction survey will never surface. Run more of each type over time as patterns emerge.
Finding people is easier than most teams expect. Use your CRM, support tickets and sales notes to pick names, then send a short personal message by email or WhatsApp asking for thirty minutes. Be flexible about timing: across the region working weeks differ, many people prefer evenings, and during Ramadan, sessions often work better after iftar.
The five interviews to run
1. The customer who just left
Talk to someone who cancelled in the last month, while the reasons are still fresh. Ask them to walk you through the week they decided to leave and what they use instead. Churned users are often the most honest people you will speak to, because they have nothing left to protect. Their story usually points straight at your biggest leak.
2. Your most devoted power user
Find the person who uses your product more than anyone else and ask them to share their screen while they work. Watch for workarounds, spreadsheets on the side and features used in ways you never intended. Power users show you where the product is already valuable, and which small improvements would make it indispensable to more people like them.
3. The one who almost signed up
A lost sale or an abandoned trial is a gift if you ask about it. Ask what they were hoping to achieve, what made them hesitate and what they chose instead. In our experience across the Gulf, the answers are often surprisingly practical: missing Arabic support, no local payment option such as Tabby or Mada, or a sign-up form that asked for too much.
4. A brand-new user in week one
Sit with someone who signed up a few days ago and ask them to complete a real task while thinking aloud. Don’t help. You will see exactly where onboarding confuses people, which labels they misread and when they give up. These sessions are uncomfortable to watch, and they almost always produce your quickest wins.
If you can, run this one in person or on a video call with screen sharing, on the device they actually use. A user signing up on a mid-range Android phone over mobile data has a very different experience from your team on office Wi-Fi and the latest laptops.
5. Someone who solves it without you
Finally, find a person in your target market who handles the problem with WhatsApp groups, paper forms or Excel. Ask them to show you how. These conversations reveal what the job really involves, what good enough looks like and what would make switching worth the effort. They are where the biggest roadmap ideas tend to come from.
Users won’t tell you what to build. They’ll show you where it hurts.
How to run the interviews well
- Ask about the past, not the future — “tell me about the last time you…” beats “would you use…” every time.
- Keep it to 30–45 minutes and offer a small thank-you, such as an AED 100–200 voucher.
- Speak their language — run sessions in Arabic, Urdu or English as the user prefers.
- Bring a note-taker so the interviewer can listen properly, and record with permission.
- Stay quiet — pauses feel awkward, but the best insights usually come just after them.
Avoid leading questions such as “wouldn’t it be useful if…” and resist the urge to demo or defend your product. If a user criticises a feature you love, ask them to say more rather than explaining how it was meant to work. Video calls work well for most sessions, but for operational products, visiting a warehouse, clinic or shop floor shows context no call ever will.
Turning notes into roadmap decisions
Within a day of each interview, write down the three most important things you heard, using the user’s own words. After all five, group the notes by problem rather than by person, and look for the issues that appeared more than once. Those recurring problems, not individual feature requests, are what deserve a place on the roadmap.
Be careful not to over-read a single quote. One passionate user asking for a feature is a lead to follow, not a mandate. Check what you heard against your analytics and support data: if three interviewees struggled with the same step and the data shows a drop-off there too, you have found something worth prioritising.
Then be honest about what moves down the list. Share a one-page summary with your team, with quotes and short clips, and connect each roadmap item to a problem you heard. When the next big feature request arrives, you will have evidence to weigh it against, instead of opinions.
The bottom line
Five conversations take about a week to arrange and a few hours to run, yet they can save months of building the wrong thing. Start with these five types, ask about real past behaviour, and turn what you hear into clearly defined problems. Repeat the exercise every quarter, and your roadmap will steadily shift from guesswork towards evidence.
