- Where is the site hosted?
- What languages/stack does the site currently use?
- Where is important data stored and how is it accessed? (site content, tickets, memberships, payments, reporting)
- What kinds of services are either integrated with the site or does the site link out to? (analytics, customer tracking, payments, fundraising platform, email verification, chat, sending email, ticketing, memberships, CMS, admin)
- What kinds of services are used to support the site itself? (version control, monitoring, tests, etc.)
- How is maintenance handled?
- How are new features handled?
- How is content managed?
- How is data managed?
- Who gets called if something goes wrong or the site is down?
- Who are the internal users of website? (admins, content managers, analysts, developers)
- How do they feel about working with it?
- Are there parts of the website that operate independently?
- Are there parts of the site that everyone loves?
- Are there parts of the website that sometimes don't work?