100% agree the first step is discovering what exists. Our goal is to make that discovery less intimidating by automating as much discovery as possible.
When a user connects their email address we automatically search for 70 categories of critical documents & bills (ex: property tax, homeowners insurance, life insurance, etc...) so all they have to do is click yes to confirm instead of trying to remember what's important and where it's stored.
The next step is series of simple yes/no questions to help folks remember what critical documents/contacts exist.
If you have other suggestions to make the process less stressful, we definitely want to hear them.