1. Inquiries and the calendar

Can you see every open inquiry, who owns it and what happens next? Does a held date show on the calendar so you never double-book?

2. Contracts and money

Can clients sign agreements online? Are deposits, payment schedules and balances tracked on the booking? If you also cater, can one booking carry venue and catering amounts separately?

3. The client side

Couples have a lot of details to give you: guest counts, timelines, vendors, menu choices. A client link where they fill those in saves dozens of emails per wedding.

4. The day itself

Look for event timelines, prep tasks and a table layout planner. Your team needs a run sheet, not a CRM record.

5. Team access

Owners, coordinators and day-of staff need different access. Check that roles control who sees money and who can edit bookings.

6. Switching and your data

Ask how you import existing bookings, and how you export them if you leave. WIBookAI imports CSV exports from HoneyBook, The Knot / WeddingWire, Dubsado, QuickBooks, Aisle Planner and Planning Pod.

7. Price and contract

Many tools in this category, including Tripleseat and WIBookAI, quote prices on request. Ask for the full cost: setup, seats, payment processing and contract length.