What you ask before you sign a contract can make or break your event.

Too many organisers lock in entertainment based on a sizzle reel, a quick email and a price. Then on the night, the timing feels off, sound is patchy, or the performer’s style doesn’t quite match the crowd. All of those headaches could have been avoided with the right questions at the start.

We walk through what to ask your event entertainers before booking, with a detailed checklist and a thorough set of questions you can adapt for any type of performer – bands, soloists, DJs, roving acts, MCs, magicians, comedians and more. To find out exactly which questions you need to be asking for your next event, read on.

Why Your Pre-Booking Questions Matter

Entertainment is often the emotional core of an event. It controls energy, anchors key moments and will be one of the main things guests remember later. A strong act can elevate a simple venue. A poor fit can derail even the best styling and catering.

Careful questioning upfront helps you:

• Match the vibe of the act to your audience and event purpose
• Clarify who is responsible for tech, setup, pack-down and logistics
• Avoid hidden costs and last-minute “extras”
• Confirm professionalism, reliability and backup plans
• Align expectations about interaction, volume, content and timing

Think of it as due diligence for your program, not interrogation. Good entertainers want these conversations because it helps them do their best work.

Key Areas to Cover With Any Entertainer

Before we dive into the full checklist and question list, here are the big buckets you’ll want to cover for almost every event:

• Style, experience and fit for your audience
• Tech requirements (sound, lighting, power, stage)
• Performance format and run-sheet timing
• Set lists, content boundaries and requests
• Logistics: arrival, bump-in, pack-down, parking, access
• Contracts agreed: payment terms and cancellation policies
• Insurance, public liability and event safety compliance
• Backups and contingencies if something goes wrong

The more you clarify now, the calmer you’ll feel on the day.

Booking Checklist

This is our ultimate pre-booking checklist. Tick each row off once you’ve asked, agreed and documented the answers.

Detailed Questions to Ask Before You Book

Here’s a thorough list you can draw from. You will not need every question for every act, but having them in one place makes it easy to build a tailored script for phone calls or emails.

1. Background, Style and Experience

• How would you describe your performance style in three words?
• What types of events do you perform at most often?
• Have you worked with audiences similar to ours before (age range, industry, formality)?
• Can you share recent videos or references from similar events?
• How do you usually adapt your performance if the crowd is quieter or more reserved than expected?
• Do you prefer being a main feature act, background ambience, or a mix of both across the night?

2. Format and Run-Sheet

• How long is a standard booking for you, and how do you structure it (number of sets, length of each set)?
• What do you recommend for an event of our length and style?
• How much time do you need for sound check before guests arrive?
• Are you comfortable coordinating timing with our MC or event coordinator on the night?
• How flexible can you be with the schedule if we’re running behind or ahead?

3. Repertoire, Music and Content

(For bands, DJs, singers, musicians, variety acts)

• What genres and eras do you focus on?
• Can you adjust your music selection to match our theme or brand?
• Are you open to including a short list of “must-play” songs or segments?
• Is there a process for requesting specific songs in advance (e.g. first dance, entrance track, finale song)?
• What is your policy on guest song requests on the night?
• Are there any songs or themes you do not perform or prefer to avoid?
• How do you handle volume levels if guests feel the music is too loud or too soft?

(For comedians, magicians, MCs or speakers)

• What level of humour or content is standard in your set (family-friendly, corporate-clean, slightly edgy)?
• Are you comfortable avoiding certain topics or language if requested?
• How interactive is your show—do you call guests on stage or into the spotlight?
• How do you handle guests who are reluctant to participate?

4. Technical Requirements

• What equipment do you provide yourself (PA, microphones, stands, backline, lights)?
• What equipment do you expect the venue or organiser to provide?
• Do you require a stage of a particular size or will a flat area suffice?
• How many power outlets do you need, and at what load?
• Do you travel with your own sound engineer or rely on the venue’s technician?
• If the event is outdoors, what do you need to protect your gear (marquee, cover, flooring)?
• Do you need access to any venue equipment the day before (for large events)?

5. Logistics, Travel and Timing

• What time will you arrive on site, and how long does setup usually take?
• How close can you get your vehicle to the performance area?
• Do you have any specific access requirements (loading bay height, lifts, ramps)?
• Are you comfortable working around other suppliers setting up at the same time?
• Do you require a green room or private area to get ready and store cases?
• Will you need meal breaks, and how long should those be?
• Is there a maximum finish time you will work to, and what happens if we’d like to extend on the night?

6. Fees, Inclusions and Contracts

• What is your total fee for this event, and what does that include?
• Does your price include travel, accommodation (if needed), parking and all equipment?
• Are there any potential extra costs we should be aware of (e.g. late finish, additional setups, extra sound systems for bands in multiple rooms)?
• How much deposit do you require to secure the date, and when is the balance due?
• What is your cancellation or postponement policy?
• Do you have a formal contract or performance agreement, and can we review it before committing?

7. Insurance, Licences and Safety

• Do you hold current public liability insurance? Can you provide a certificate for our venue?
• Are all members of your team covered under that policy?
• If your act involves high-risk elements (fire, aerials, stunts), what extra safety measures do you have in place?
• Have you performed this specific routine before in similar environments (indoors/outdoors, on temporary staging, near public walkways)?
• Are there any venue requirements (ceiling height, clearance, exclusion zones) that must be met for the act to be safe?

8. Audience Interaction and Crowd Management

• How interactive is your standard performance?
• Do you involve the audience in games, call-outs, or on-stage participation?
• Are you comfortable adjusting interaction levels if we have a reserved or conservative crowd?
• How do you handle guests who have had too much to drink or become disruptive?
• Are you happy to work with our security or event team if we need to manage behaviour?
• Are there any types of humour, banter or audience participation you will not do?

9. Brand, Theme and Dress Code Alignment

• Can you tailor your clothing to match our dress code (black tie, cocktail, smart casual, themed)?
• Are you willing to incorporate our brand colours or subtle branding items (e.g. lanyard, pin, backdrop logo)?
• Are you comfortable with being introduced in a specific way or including short brand messages in your MC work?
• Do you have any restrictions on logo placement in photos or video?

10. Photography, Video and Social Media

• Are you happy for us and our guests to film and photograph your performance?
• Are there any restrictions on what we can post on social media?
• Can you share any professional photos or clips after the event for our own recap content?
• Would you like to be tagged or credited in our posts, and if so, what handles or website should we use?

11. Backups and What-If Scenarios

• What happens if a performer falls ill or can’t attend? Do you have a backup within your team or network?
• If extreme weather impacts an outdoor event, can your performance adapt to an indoor backup area or covered space?
• Do you carry backup equipment (spare microphone, cables, laptop) in case something fails?
• If there is a temporary power outage, how do you handle the situation on stage to keep guests calm and informed?

How an Entertainment Partner Can Help

All of this can feel like a lot to manage, especially if you’re coordinating multiple acts across different stages or event zones. Working with a specialist entertainment provider means much of this questioning and vetting is handled on your behalf.

A good partner will:

• Pre-qualify acts for professionalism, reliability and technical standards
• Match performers to your brief, audience profile and budget
• Liaise with your venue and AV suppliers about technical needs
• Coordinate run-sheets and ensure entertainers understand timings and tone
• Provide backup options and support if something changes

That way, you can focus on the bigger picture: your guests, your message and the atmosphere you want to create.

Turning Questions Into Confidence

The right questions upfront turn entertainment from a gamble into a solid, dependable pillar of your event. Instead of hoping an act will “just get it,” you walk into event day knowing they understand your crowd, your tone, your timing and your non-negotiables.

Careful questioning is not about being difficult; it’s about protecting the guest experience and giving entertainers everything they need to succeed. When both sides are clear, performers can relax into their craft, and guests enjoy those effortless moments of connection that live entertainment does best.

If you’d like support choosing and briefing performers, or want a curated shortlist of acts already vetted for professionalism and crowd appeal, Onstage can help coordinate entertainment, production and planning so your next event feels as good behind the scenes as it looks on the night. Reach out to us today.