1.6 The 5 Questions Framework

Most founders go into customer research asking “do you like this idea?” That’s not research. That’s validation-seeking. The five questions below are designed to extract buying behavior, not opinions. Work through all five before you write a single line of copy or build a single feature.

The 5 Questions

Question 1: What have they already tried and failed with?

This is the most important question you’ll ever ask a potential customer. It tells you the exact solutions they considered credible enough to try, and why those solutions fell short. David Park was stuck at $2K MRR with Jenni until he stopped asking customers what they liked and started asking what wasn’t working. That pivot in questioning took him from $2K MRR to $3 million ARR.

Question 2: Where do they complain about this problem publicly?

You need to know where your customer vents. Reddit threads, niche Facebook groups, Slack communities, X replies, YouTube comment sections. This isn’t just research, it’s your acquisition channel. The language people use when they’re frustrated is the exact language your landing page should speak back to them.

Question 3: What triggers the search for a solution?

There’s a specific moment when someone stops tolerating a problem and starts looking for a fix. For Vikash’s Bulk Mockup customers, that trigger was getting a job order for 1,800 mockups and realizing that doing it manually in Photoshop at 30-40 minutes per 50 mockups was going to take days. The trigger is not the chronic pain. It’s the acute moment that breaks the tolerance. Find that moment and market directly to it.

Question 4: What does winning look like for them in 90 days?

Not in a year. Not in their career. In 90 days. This grounds their success metric in something concrete enough to sell against. Thomas built Packager to $60K MRR in part because the 90-day win for an IT admin was simple: stop spending an hour per application on Microsoft Intune packaging and cut that down to minutes. He could promise that outcome clearly because he’d lived the pain himself.

Question 5: What are they already paying for that partially solves this?

If they’re paying for something that half-solves the problem, you have proof the problem is worth money. Demetri validated Screenshot One by checking how many customers competitors had before building anything. Existing spend is the clearest signal that a market exists. If your target customer isn’t paying for anything in this category, you might be solving a vitamin, not a painkiller.

Worked B2B Example: Packager

Thomas’s customer is an IT administrator managing Microsoft Intune deployments. What had they already tried? Manual application packaging, following Microsoft documentation, cobbling together scripts. Where do they complain? IT admin forums, Reddit’s sysadmin communities, Microsoft Tech Community boards. What triggers the search? A new fleet of devices to onboard, or a deadline from a manager to roll out a new application by end of week. What does winning look like in 90 days? Every application in the deployment queue packaged and verified without burning half a workday per app. What are they already paying for? Microsoft Intune itself, plus whatever hours they’re billing to packaging work. That’s a customer with budget, a clear trigger, and a measurable outcome.

Worked B2C Example: Push School

Alejandro and Mario’s customer is someone doom-scrolling Instagram for two hours every morning. What have they tried? Screen time limits that they disable when inconvenient, willpower, deleting apps and reinstalling them a week later. Where do they complain? Reddit’s r/nosurf, r/digitalminimalism, X threads about phone addiction. What triggers the search? A moment of genuine disgust, usually realizing they’ve been in bed for 90 minutes and accomplished nothing. What does winning look like in 90 days? Opening their phone less and building a consistent workout habit. What are they already paying for? Probably a gym membership they’re not using. Push School, which requires a set of push-ups before unlocking social media, sits directly on top of two existing spending categories: fitness and the phone itself.

Run these five questions on your own target customer today. Write out the answers in full sentences. If you can’t answer all five, you don’t know your customer well enough to sell to them yet.