Choosing the Right Performer: 5 Questions to Ask Before You Book
Last summer, I got a call from a woman in Hartford who'd just fired her entertainment three hours before her husband's 50th birthday party. The "magician" she'd booked showed up in a wrinkled tux, reeking of cigarettes, and asked if he could "warm up" with a few drinks before performing. She found me through a frantic Google search, and I managed to save the evening. But here's the thing—this disaster was completely preventable with five simple questions.
After 15 years performing at private parties across Connecticut and New Hampshire, I've seen the good, the bad, and the "please never let this happen at my event." Whether you're planning an intimate gathering in Portsmouth or a backyard celebration in Stamford, these questions will help you separate the professionals from the people who bought a magic kit last Tuesday.
Question 1: "Can You Share Videos from Similar Events?"
Here's what most people don't realize: performing at a corporate boardroom requires completely different skills than entertaining at a backyard birthday party. When I perform at New Hampshire private parties, the energy, pacing, and material all shift from what I'd do at a Boston gala.
Ask for videos from events similar to yours—not just their highlight reel. A performer who crushes it at kids' parties might freeze up at your sophisticated cocktail party. I once watched a balloon artist try to entertain a group of Connecticut hedge fund managers. Let's just say the giraffe balloons didn't land quite as well as they did at the preschool.
What to look for:
Natural interaction with guests (not just staged performances)
Audio quality that lets you hear audience reactions
Similar venue types and crowd sizes
Comfort level matching your event's formality
Question 2: "What's Your Backup Plan When Things Go Wrong?"
I learned this lesson the hard way during a New Hampshire wedding where the power went out mid-performance. No microphone, no sound system, no spotlight—just me and 200 guests in near darkness. Luckily, I had battery-powered LED accessories and material that works acoustically. The show went on, and it actually became one of the most memorable performances of my career.
Professional entertainers don't just have a Plan B; they have Plans C through Z. Ask them directly: What happens if you're sick? Traffic disaster on I-95? Equipment failure? Their answer tells you everything about their professionalism.
Red flags to watch for:
"That's never happened to me" (it will)
No backup performer network
No equipment redundancy
Vague reassurances without specifics
Question 3: "How Do You Handle Different Personality Types?"
At a recent Connecticut party magician gig in Greenwich, I had three distinct groups: teenagers glued to their phones, middle-aged professionals comparing stock portfolios, and seniors who'd "seen it all." A good performer reads the room and adapts. A great performer makes all three groups feel equally engaged.
Some entertainers have one speed—loud and center stage. That works great for some events, but what if your gathering is more wine-and-conversation than dance-and-shout? I've developed different approaches for introverts who prefer one-on-one amazement versus extroverts who want to be part of the show.
Follow-up questions to ask:
How do you engage shy guests?
What if someone's has had too much to drink?
Can you work with guests who don't speak English?
Question 4: "What Do You Need from Me as the Host?"
The best New Hampshire private party entertainment happens when there's clear communication beforehand. Professional performers will give you a specific list—not demanding, just organized. When I perform, I typically need: arrival time for setup, a designated performance space (doesn't have to be huge), and a brief rundown of any VIP moments or special circumstances.
Beware the performer who says "I don't need anything." They absolutely do, they just haven't thought it through. Also concerning: the one with a three-page rider demanding specific brands of bottled water. You're booking entertainment, not adopting a diva.
Essential logistics to discuss:
Setup and breakdown time
Parking and load-in access
Performance space requirements
Guest count and age ranges
Any sensitive topics to avoid
Question 5: "Why Should I Choose You Over the Other Three Quotes I Have?"
This isn't about being confrontational—it's about understanding their value proposition. When people book me for Connecticut or New Hampshire private events, it's rarely because I'm the cheapest option. It's because I guarantee their guests will remember this party five years from now.
Listen for specifics, not generalities. "I'm really good" means nothing. "I invented an original trick that's been viewed 14 million times on YouTube and fooled Penn & Teller" means something. Everyone claims to be professional, experienced, and engaging. Ask for proof.
What you want to hear:
Specific differentiators
References from similar events
Understanding of your event goals
Genuine enthusiasm for your specific party
Clear articulation of their unique approach
The Bottom Line: Your Gut Matters
Here's something I tell every potential client: if something feels off during our conversation, it'll feel worse at your event. That performer who took three days to return your email? They'll be just as responsive when you need them day-of. The one who seemed pushy about their most expensive package? They'll upsell your guests too.
Your private party—whether it's in a Connecticut mansion or a New Hampshire backyard—deserves entertainment that enhances the celebration, not complicates it. These five questions won't guarantee perfection (nothing can), but they'll dramatically increase your odds of hiring someone who'll make your event memorable for all the right reasons.
Planning a private party in Connecticut or New Hampshire? I'd love to discuss how interactive entertainment can transform your celebration from good to unforgettable. Let's chat about making your event the one people actually remember.
