Question: What are you wearing?
Why: Turns out, every vendor has a different idea of what is appropriate for a wedding. We have run into situations where a vendor shows up in an outfit that doesn't match the vibe of the event being serviced. To avoid embarrassment on all fronts, just ask ahead of time.
Question: How many people are you bringing?
Why: This factors in to how many people you'll need to feed on your wedding day. Vendor meals can be a significant unexpected cost, especially when dealing with large groups of vendors like a 7 piece band. Most venues charge about half of your per-person cost for a vendor meal, so that can add a major chunk to your budget really fast.
Question: Does this price include travel fees/delivery/set up/additional fees?
Why: Sometimes they do, and sometimes they don't. Sometimes vendors don't ask about specifics until later, and that can mean extra fees take you by surprise. If you don't have specifics set yet, just make sure to set aside a certain amount for potential surprise costs.
Question: What time are you leaving?
Why: When you're signing your vendors, you're very likely not thinking about your day-of timeline and itinerary yet. As a result you may end up having vendors leave before major moments like the cake cutting, or in the case of a wedding I worked a few years ago, having the waitstaff leave before dessert was served. Talk about a logistical issue. Luckily we handled it all, but if this situation was planned properly, we would have been sure to have the waitstaff stick around to bus tables and breakdown for strike.
By asking these questions early on in the planning process, you'll avoid confusion and create clarity and open lines of communication. Happy Planning!