Most founders ship a link to ten users and check back a week later wondering why nobody signed up. They quietly bounced. They got stuck on a button. They couldn't find the core feature. They didn't tell you because telling you felt rude.
You only get one first session per user. Make it the most observed hour of your week.
Half live, half async. Both formats teach you different things.
| Format | Tool | What you learn |
|---|
| Video call (5 users) | Cal.com | Real-time hesitation, follow-up questions, emotion |
| Loom recording (5 users) | Loom | Natural behaviour without your hand-holding |
For the live calls, share your screen if you must demo a step, but mostly stay silent. Watch their cursor. Note where they pause. The goal is not to teach them — it's to watch where the product fails to teach itself.
For the Loom users, give them one prompt: "Record yourself trying to do [the core task]. Talk out loud while you do it." Ten minutes of someone narrating their confusion is worth more than any survey.
Log everything in a single Notion doc. One row per blocker. Columns: user, where they got stuck, severity, fix.
After the ten sessions, count the blockers. Don't fix all of them. Fix the top three that hit multiple users.
Bad: "Three people couldn't find the export button — I'll add a tooltip later this month."
Good: "Three people couldn't find the export button — I moved it to the top toolbar this afternoon and re-tested with two of them."
If three users miss the signup button, it's not their fault. It's yours. If nobody can find the core feature, the name is wrong or the placement is wrong. These notes are your roadmap for the next two weeks.
- Treating silence as success. Stuck users leave quietly and never tell you.
- Fixing every single blocker at once. Pick the top three by frequency, ship those, then move on.
- Defending the design while you watch. Bite your tongue. The user is the data.
- Skipping the live calls because they feel awkward. Awkward is where the truth lives.
Schedule 5 live onboarding calls and request 5 Loom recordings. Watch every one. Log blockers in Notion. Ship the top 3 fixes before the week ends.
Ten completed first sessions documented in one Notion log, with every blocker recorded and the top three already fixed in the product.
Most founders ship a link to ten users and check back a week later wondering why nobody signed up. They quietly bounced. They got stuck on a button. They couldn't find the core feature. They didn't tell you because telling you felt rude.
You only get one first session per user. Make it the most observed hour of your week.
Half live, half async. Both formats teach you different things.
| Format | Tool | What you learn |
|---|
| Video call (5 users) | Cal.com | Real-time hesitation, follow-up questions, emotion |
| Loom recording (5 users) | Loom | Natural behaviour without your hand-holding |
For the live calls, share your screen if you must demo a step, but mostly stay silent. Watch their cursor. Note where they pause. The goal is not to teach them — it's to watch where the product fails to teach itself.
For the Loom users, give them one prompt: "Record yourself trying to do [the core task]. Talk out loud while you do it." Ten minutes of someone narrating their confusion is worth more than any survey.
Log everything in a single Notion doc. One row per blocker. Columns: user, where they got stuck, severity, fix.
After the ten sessions, count the blockers. Don't fix all of them. Fix the top three that hit multiple users.
Bad: "Three people couldn't find the export button — I'll add a tooltip later this month."
Good: "Three people couldn't find the export button — I moved it to the top toolbar this afternoon and re-tested with two of them."
If three users miss the signup button, it's not their fault. It's yours. If nobody can find the core feature, the name is wrong or the placement is wrong. These notes are your roadmap for the next two weeks.
- Treating silence as success. Stuck users leave quietly and never tell you.
- Fixing every single blocker at once. Pick the top three by frequency, ship those, then move on.
- Defending the design while you watch. Bite your tongue. The user is the data.
- Skipping the live calls because they feel awkward. Awkward is where the truth lives.
Schedule 5 live onboarding calls and request 5 Loom recordings. Watch every one. Log blockers in Notion. Ship the top 3 fixes before the week ends.
Ten completed first sessions documented in one Notion log, with every blocker recorded and the top three already fixed in the product.