How do you find where new users get stuck during onboarding?

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A signup tells us someone was interested, but it doesn't tell us whether they reached the part of the product that helps them. A user might leave because they got confused, or simply because the product wasn't right for them.

I think a short conversation with someone who didn't finish onboarding could reveal more than a funnel number alone. But it can be hard to get a reply from someone who has already left.

How have you found the point where new users get stuck? What did you change after finding it?

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The drop-off happens right after the agent prints a green checkmark saying the migration was complete. The schema had not changed. A loud crash gives the user an error trace to inspect. Getting told everything is fine while staring at a dead state leaves them with no next action, so they close the tab.

 That false success message would be frustrating. Checking the actual schema before showing the green check could make the next step clearer. How did you catch that the migration hadn't happened?

 Checking the database logs against the session replays showed the runner hit a permissions error, swallowed it, and returned exit code zero without touching any tables.

If people who left won't reply, I'd watch a new user try one real task without coaching. Ask what they expect before the next click, then compare that with what happens. That helps separate a confusing step from a task they never needed in the first place.

 I like asking what they expect before the click. It shows where the product breaks their mental model, without leading them to an answer. Do you test this with a specific task or let them choose one?

I'd ask what they came to do, then give them a concrete task that matches it without naming the steps. Keep that task consistent when comparing users. Let them choose the route, and note if the task itself feels irrelevant.