How do you choose an event entertainment company without finding out on the night that you picked the wrong one? You ask better questions before you sign. Most bad bookings in Toronto don't fail because the performers can't perform. They fail on the boring stuff: a quote that left out sound, a band that has never loaded into your venue, or a sick lead singer and no plan B.
Below are the 12 questions we would ask if we were on your side of the table, what a good answer sounds like, and the red flags that should end the call. We run an and have produced 5,000+ events since 2008, so yes, we have a point of view. Hold us to the same list.
Should you book through an agency or hire performers directly?
Start here, because it changes which questions matter. You have three realistic options in the GTA: book a performer directly, book through an online marketplace, or work with an agency or production company that handles the act, the production and the coordination.
| Book the performer directly | Online marketplace | Entertainment agency | |
|---|---|---|---|
| Best for | One act you already know and trust | Small, simple, low-risk events | Corporate events, galas, multi-act nights |
| Who handles sound and lighting | Often you, or the act's own basic kit | Usually you | The agency, quoted up front |
| Backup if the act cancels | Your problem | Varies by platform | The agency's problem |
| Number of contracts | One per act | One per act | One for the whole program |
| Talks to your venue | Sometimes | Rarely | Yes, before the event |
| Price | Lowest headline fee | Low to mid | Higher headline fee, fewer surprise costs |
Booking direct can be the right call for a solo pianist at a 40-person dinner. Once you have a stage, a run of show, more than one act or a client in the room, the coordination work is the job, and that is what an agency is for. The questions below work for all three options.
What should you ask about the acts themselves?
1. Are these your performers, or are you booking someone else's?
Some companies run their own acts. Others are brokers who resell a third party's band with a markup and never see the show. Neither is automatically bad, but you deserve to know who actually shows up. Ask whether the act you see in the video is the act that will be on your stage, with the same core players.
In our case, uRequest Live is our own flagship band, where guests request songs from their phones, and we bring the full setup for our game shows like Majority Rules and Mega Golf. Ask us the same question about any act on our roster and we will give you a straight answer.
2. Can I see this exact act at a real event, not a promo reel?
Promo reels are edited to the best 90 seconds of a year. Ask for unedited footage from a live event, ideally one like yours: same room size, same type of crowd. A band that crushes a wedding can still struggle with 300 sales reps who don't know each other yet.
3. How do you adapt the show to our group?
A good company asks you questions before you ask it anything: who is in the room, what the event is for, what has flopped before. Listen for specifics. Will the band learn your must-play songs (most of ours can, with advance notice)? Will the game show use questions written from your company's material? If every answer is "our standard package," you are buying a standard night.
What should you ask about the quote?
4. What exactly is included in this price?
This is the question that saves the most money. A low quote often means sound, lighting, staging, setup time or travel got left out, and they show up later as add-ons or as a call to the venue's AV team at their rates. Ask for a line-by-line list:
- Performance time and number of sets
- Sound system, microphones and a sound technician
- Lighting and staging, if the room needs it
- Load-in, setup and teardown time
- Travel outside the GTA, parking and meals for performers
- Overtime rate if the speeches run long
Then confirm how tax is shown. Most services in Ontario carry 13% HST, according to the so a $10,000 quote is roughly $11,300 once tax is added.
5. What deposit do you need, and when is the balance due?
A deposit to hold the date is normal across the industry, and it is how we confirm bookings too. What you want in writing is the amount, the balance due date, and what happens to your money if you move the date or cancel. If a company wants the full fee up front months ahead with no cancellation terms, walk away.
6. What are typical prices for what we're asking for?
A good company will give you a realistic range on the first call instead of making you fill in three forms. For reference, here is what corporate entertainment in Toronto typically runs with us:
| What you book | Typical range (CAD, before HST) |
|---|---|
| Single performer or specialty act | $2,500 to $5,000 |
| Mid-sized event with several elements | $5,000 to $15,000 |
| Large custom production | $15,000+ |
| Interactive game shows | $2,500 to $10,000 |
| uRequest Live all-request band | From $8,500 |
| DJ | From $2,000 |
Prices move with location, duration, time of year, band size and production needs. December and summer cost more and book out first.
What should you ask about logistics and risk?
7. Have you worked in our venue, and will you talk to them before the event?
Every Toronto venue has its own rules: loading docks with time slots, freight elevators, noise limits, curfews and in-house AV contracts. A company that has never been in your room should at least call the venue's event manager and ask for a floor plan. Ours are planned around the room, down to power and setup space. For our game shows, for example, all we need is a space and power outlets, and setup takes 60 to 90 minutes, which you need to know before you lock the run of show.
8. Do you carry liability insurance, and can you send a certificate?
Most venues and municipalities in the GTA ask outside vendors for proof of commercial general liability coverage, and $2 million is a common baseline. The City of Mississauga's is set at $2 million, for example. Ask your venue what it needs, then ask the entertainment company to send the certificate, naming the venue if required. A pause on this question is a red flag.
9. What happens if a performer gets sick or cancels?
People get sick, especially in December. Ask what the backup plan is, in detail. An agency with a deep roster can swap in another player or a comparable act. A solo performer booked direct often has no answer at all. Get the replacement terms in the contract.
10. Who is my contact on the day, and will they be there?
You want one name and one phone number for event day, not a general inbox. Ask whether someone from the company will be on site or at least reachable during load-in and the show. For interactive experiences, find out who hosts: every one of ours runs with a professional host who keeps the room moving.
What should you ask that most people forget?
11. Who handles music licensing?
In Canada, live music at receptions, conventions and similar events falls under SOCAN Tariff 8, and the fee is usually charged per event based on room capacity. Venues often pass that royalty on to the client who rented the room, as this lays out. It is rarely a big number, but ask your venue and your entertainment company who is covering it so it doesn't land on your invoice as a surprise.
12. Can the show work for remote guests or a bigger room than planned?
Guest counts change and half the team might join from another office. Ask whether the act can stream, whether a game can be played on phones, and whether the band can scale up. uRequest Live runs from five to ten pieces, and Majority Rules is played on guests' phones, so the format holds when the list grows from 150 to 400.
What are the red flags when you hire event entertainment?
Any one of these is enough to keep looking:
- No unedited live footage.Only a polished promo reel and stock photos.
- A vague quote.One number, no list of what is included.
- No backup plan for illness or cancellation, or a shrug when you ask.
- No insurance certificate on request.
- No questions about you.They pitch a package before asking about your guests or goals.
- Pressure tactics."Three other clients want this date, sign today."
- No written contract,or a contract that leaves out times, deposit terms and cancellation.
If you are hiring a band specifically, our guide on goes deeper on repertoire, set lists and sound. For the rest of the planning, the puts entertainment in the right place on your timeline. And for the etiquette that rarely makes it into a contract, read .
How far ahead should you start asking these questions?
Earlier than you think. For events of 500+ guests, we recommend booking 6 to 12 months ahead. For 100 to 500 guests, plan on 3 to 6 months, and for under 100, 1 to 3 months. Peak dates in December and summer go first. Run through this list with two or three companies, compare the answers side by side, and the right one is usually obvious by the second call.
Want to test us on all 12? Ask our anything on this list. Tell us your date and guest count in the form below and we'll send options with a clear, line-by-line quote.