You need to, at a regular cadence, walk through the entire user journey of signing up for your product and setting it up for the first time.
You’ll be shocked to learn how quickly things get out of date:
If you don’t proactively make time to do this, you’ll go months and months and months without experiencing your new user onboarding flow. Why would you? Your own use of your product / your demo accounts never return to those early stages.
I recommend once each month. If nothing else, it will serve as a constant reminder of where your onboarding can be better. It’s easy to prioritize the next new feature (over making your most important user flow an A+ experience) if you’re never personally going through a sub-par onboarding experience.
The best way to do this is to have dummy data for fake company on hand. You should as closely as possible recreate the experience that your customers go through when setting up your product.
If your product is generally adopted by a team, you’ll want to pull other team members into the exercise to recreate this experience as well.
After going through onboarding, actually use the product a few times over the coming days. Put time on your calendar to fully exercise the primary flows that make up the core of your product.
Make note of where the experience is lacking!