Hiring a planner is the one wedding or event decision that shapes all the others. Yet most people choose on portfolio and personality alone — both of which are curated. Here are the ten questions we'd ask any planner, including us. The answers reveal what a portfolio can't: what happens at 6:47pm when the band's van breaks down.
The ten questions
- "Walk me through the last thing that went wrong at an event." A planner who claims nothing ever goes wrong has either planned very few events or is lying. You want a specific story with a specific fix — told calmly.
- "Who exactly will be at my event?" Some firms sell you the founder and send a subcontractor. Get the name of your lead and the size of the on-site team, in writing.
- "How do you charge, and what's not included?" Flat fee, percentage, or hourly — all can be fair. What's not fair is discovering the exclusions in month eight. Ask for a sample itemized proposal.
- "Do you take vendor commissions?" Some planners collect referral fees from vendors, which quietly shapes their recommendations. Whatever the answer, you deserve to know whose interests are in the room.
- "Can I see a real run-of-show from a past event?" The document tells you everything: a planner with minute-by-minute cues, vendor contacts, and contingencies operates differently from one with a one-page schedule.
- "What's your weather plan process?" For any outdoor element, listen for: a written plan B, a decision deadline, and who makes the call. Vague reassurance is a red flag with a forecast attached.
- "How many events do you take per weekend?" There's no universally right answer, but there is a wrong one: more events than they have senior staff to lead.
- "Which venues and vendors do you work with most?" Deep local relationships get you dates, favors, and rescues that outsiders can't. In Connecticut, ask specifically about your shortlisted venues.
- "What happens if we go over budget?" Good planners track spending in real time and flag drift early — not at the final invoice. Ask to see the tracking format.
- "Can I speak with two past clients?" Not testimonials — conversations. Two phone calls will tell you more than two hundred five-star reviews.
The red flags, compressed
- Pricing that can't be put in writing
- No answer to "what went wrong" — or blame-heavy answers
- Pressure to sign before you've met your actual lead planner
- A portfolio without a single event resembling yours in size or culture
- Slow replies during courtship — it only gets slower after the retainer
Hire the planner whose calm you'd want in the room when the lights go out. Everything else is decoration.
We're glad to answer all ten of these about ourselves — several are already answered on our FAQ page, and the rest are yours at a complimentary consultation.