The one question to ask before you book
Most of the questions couples ask wedding entertainment companies have rehearsed answers. Do you have backup equipment, yes. Are you insured, yes. Can you emcee, yes. Every company says the same thing, and every company is mostly telling the truth.
Here is the question that does not have a rehearsed answer.
"Walk me through the last wedding you worked. Not the highlight. The whole thing."
Ask it and then stop talking.
What you are listening for. Specifics. What time they arrived and why. What the room was like before guests came in. What the timeline said and what actually happened. Where it nearly went wrong. What they changed on the spot.
Someone who has genuinely produced weddings will tell you a story with texture in it, because that is what the job is made of. Someone who has not will give you a version of their sales page, because that is all they have.
What it reveals. Whether they think about the whole event or only their four hours. Whether they notice what other vendors are doing. Whether they have opinions about pacing, or just about music. Whether anything is ever their fault. And whether they find this work interesting, which matters more than it sounds, because interested people notice things.
Why it works. Every other question invites a claim. This one invites evidence, and evidence cannot be prepared for a question nobody expects.
Ask it on the call. Ask it of everyone you are considering. The answers will not be close.