Feb. 2, 2026
480: Before You Book Any Entertainment, Ask These Questions
Booking entertainment for a private club should not feel like a gamble. In this episode of Private Club Radio, Denny Corby breaks down the exact questions club leaders should ask before booking a band, DJ, comedian, magician, speaker, or specialty act, so your club events run smoothly, match the membership vibe, and feel worth the spend. You’ll learn how to vet for fit and professionalism, not just talent, how to build a clean run of show around food service and energy flow, and what to confi...
Booking entertainment for a private club should not feel like a gamble.
In this episode of Private Club Radio, Denny Corby breaks down the exact questions club leaders should ask before booking a band, DJ, comedian, magician, speaker, or specialty act, so your club events run smoothly, match the membership vibe, and feel worth the spend. You’ll learn how to vet for fit and professionalism, not just talent, how to build a clean run of show around food service and energy flow, and what to confirm ahead of time for sound, setup, stage, timing, and room logistics.
Denny also covers content boundaries, handling hecklers, what to ask for in references and video clips, and the must know basics around contracts, cancellations, insurance, and safety. The goal is simple, fewer surprises, less stress, and more events your members rave about.
Want help dialing in your entertainment plan, or need a trusted recommendation? Connect with Denny Corby, the club entertainment expert who has performed for 350 plus private clubs, at dennycorby.com or on LinkedIn.
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00:00 - Why Fit Beats Budget
02:26 - The Core Problem: Communication
03:00 - Question 1: Describe Your Show For Us
04:10 - Ideal Run Of Show And Room Needs
06:02 - Setup Explained In Plain English
06:42 - Great Performers Interview You Back
07:50 - Arrival Times And Stress-Free Setup
10:00 - Equipment, Backups, And Redundancy
10:46 - How Interactive Is The Show
13:10 - Do We Need A Host Intro
14:36 - What Not To Do Before Showtime
17:24 - Boundaries, Content, And Club Standards
19:12 - Off-Limits Topics And Redirection
20:50 - Handling Hecklers With Grace
21:42 - Relevant References And Real Clips
24:18 - Content Rights And Posting Policies
25:08 - Contracts, Insurance, And Safety
26:00 - The Ultimate Success Question
27:46 - From Gamble To System And Closing
WEBVTT
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Welcome to the Private Club Radio Show, the show where you get the scoop on life inside private golf and country clubs.
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I'm your host, Danny Corby, and each episode is a real conversation with club leaders, the pros, the people, and partners who help clubs thrive.
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We talk leadership, culture, food and beverage, member experiences, member engagement, marketing governance, and so much more.
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If you want practical ideas, better teams, and a club experience members actually feel and talk about, you're in the right place.
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Now, welcome to the show.
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So today, here are some questions that you can ask any performer, any outside vendor before they show up.
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Yes, this is more focused for the entertainment, but you can use this for anything.
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So, more particularly, uh, we're talking about magic, comedians, DJs, bands, speakers, specialty acts, all that.
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But you can use some of these questions for other people too.
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This is not the end all be all of all questions.
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I'm sure you have great questions you ask.
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I'm sure I miss some, but I think sometimes with these questions, we're not always going for perfect answers.
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Sometimes it's the value in how they respond.
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So it's not just interviewing talent, it's not just interviewing people, you're interviewing temperament, you're interviewing feel, and you're making sure we're creating that fit.
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Because sometimes clubs ask incredible questions.
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And sometimes they ask questions like, so you need a microphone?
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And sometimes the entertainer, like me, is the one asking the great questions, guiding the club, steering the ship, and saving the night before it even starts.
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Because most entertainment problems at a club are not talent problems.
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I would say they are fit and communication problems.
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And the good news is fit and communication can be handled way earlier and better by booking the right entertainment and asking the better and the best questions.
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And at the end of the episode, I will share with you my favorite question that I ask every show, every client, it's probably the best question ever.
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And I say this a lot, and I'm not going to stop, and that is stop hiring entertainment based only on budget.
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Start hiring based on fit, the fit for your club, the fit for your vibe, the fit for your membership, your room, your run of show, and the kind of night you are trying to create for your members, because you can book the most talented person in the world and still have a weird night if the fit is wrong or if the communication is sloppy.
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And before we get to the questions, which are in no particular order, if you are looking for some amazing entertainment and you want to have and ask some amazing questions and have an amazing bantery conversation about entertainment, check out dennycorby.com.
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There's excitement, there's mystery, also there's magic, mind reading, and comedy, a ton of laughs, gasps, and holy craps.
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And if you're looking for one of the most fun member event nights, from someone who's done well over 350 clubs to great success with great reviews, head on over to dannycorby.com.
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Question number one that you want to ask your potential entertainment is describe what you do for this exact audience, not your best audience.
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And we're asking this because relevance beats hype.
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We want to listen for if they tailor things, if they mention mixed age groups, dinner environment, right?
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You're just seeing how they respond and what they say.
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Are they saying more me, me, me?
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Is it more about you and the audience?
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And those are some of the things that you're looking for.
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Remember, not always the answer that you're looking for.
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You're looking for how they answer.
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Question number one is you want to ask them to describe what they do for their audiences and more specifically what they can do for your audience, for your club.
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And remember, we're not going for perfect answers.
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We're going for relevance.
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We're going for hearing how they respond.
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Relevance beats hype.
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So you want to listen for do they talk about tailoring?
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Do they mention just different aspects of their show?
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Is it more about me, me, me, or is it about we, we, we and us and how we work together to create a killer event?
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Because you want to hear also how they see themselves, how they envision themselves in your space, in your room, in your environment.
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Next great question you can ask is what does their ideal run of show look like and why?
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Now, I know I'm a very flexible entertainer and I saw and I like to partner with with my with my clubs, with my events and my clients.
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And, you know, I like to inhabit we can make it a little bit unique, makes it a little bit more fun for me.
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But also, you know, what does their ideal run of show look like and why?
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Because they might have or say something that clicks with you, or maybe they mention something that you may have not thought about, and not just for this event, but other events as well.
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So it's just always listening just to hear what their dream scenario looks like.
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Um, because a lot of pros know when they hit the hardest and a clear preference plus reasoning about attention, food service, detail, room energy, all that stuff can hit and make sense.
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And piggybacking off the last question, it's what do you need from the room to be at your best?
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So, kind of like the last question, which was, you know, what does your ideal run of show look like?
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The next part is what do you need from the room to be your best?
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And we're asking this because we may uncover just different things that they might need that we might not consider or think about, specific needs, mics, lighting, performance area, seating, distance, sound, stage, no stage, all that stuff.
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Just hearing what they like and ask them to be detailed if they can.
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Quick is fine, easy is fine, vague is not.
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And every good performer has their ideal scenario.
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They might not might not always get it, it might not always be able to happen, but every performer has their ideal scenario and knows their vibe of influence, but I don't even know where that line came from.
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But every performer has that ideal scenario and just hear what theirs is.
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Next is ask them what their setup is in plain English.
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If if they can't explain their setup clearly, be weary, surprises might be coming.
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That doesn't mean an organizer or anything, but you just want to see and hear what their setup needs, what their requirements need.
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And when in doubt, I always like to quote Michael Scott, which is explain this to me like I'm a five-year-old.
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So when in doubt, uh, when things might become a little difficult, always ask, explain this to me like I'm a five-year-old.
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Because as we know, sometimes at clubs, if depending on the entertainment, we might have our own internal sound system and internal stuff.
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And sometimes the person setting up the sound is also the person who's running bingo on bingo night for the club.
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So another great question is ask them what questions they have for you about the audience, about your members, about the room, about the flow.
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The best performers, the best people that you can bring in, interview you back.
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Just as you ask them great questions, you should also expect great questions back.
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We're when when we bring somebody into a club, I ideally, and sometimes it's not worth all of this, but you know, we're we're looking for curiosity, we're looking for smart, we're looking for practical questions, right?
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Not just where do I park?
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Do I have a special parking spot?
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Right.
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There, there's great questions that people can ask, which is, hey, what's the attire?
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Am I allowed to wear jeans to set up?
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Right.
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It's it's some of those things that when somebody asks those questions in your head, you go, you feel a little bit more at ease.
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And if they don't ask any questions at all, they're either unbelievably experienced or unbelievably overconfident.
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Both are exciting.
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Just only one is helpful.
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Another great question is what is your arrival time and how much setup do you need?
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Uh, because rushed setups usually equals stress performances and just stress for everybody.
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So we're listening for real times with buffers built in.
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Great question to ask is what is their arrival time and how much time do they realistically need to set up?
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Because we don't want anything rushed.
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Rushed setups and rushed things equals stressed performances, equals stressed performers, equals a stressed staff.
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And we just don't need that for our members, for our clubs, for our events.
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Clubs are adult playgrounds.
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We're supposed to be there to having fun, especially with our events.
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So to keep it as less stressful as possible.
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Um, like I just know, for example, for me, by the way when the members show up.
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So from the time members show up, I want to be there.
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I like to be there at least two hours prior.
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I am paranoid on show days, sometimes even even more.
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I'd rather be sitting there twiddling my thumbs than waiting in traffic or rushing.
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I just get super paranoid.
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I usually fly in the day prior just because of like flight.
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I just get paranoid.
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So I usually show up about two hours before the audience does because that gives me time to chat with the chat with the staff.
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It gives me a little bit of time to maybe chat with some members or just slowly say, I don't like to be rushed either.
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So I know that's how I like to work.
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And if their setup starts as guests are walking in, that is not setting up properly and they are performing a live stress documentary.
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That is just crazy.
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Um plus, I don't know, it thinks like a weird thing of like setting up in front of members.
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I I don't know, or just like people and shows in general, random tangent.
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Another great question, depending on the type of act and entertainment and vendor that you're bringing in, is what equipment do you need?
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And what equipment do you bring?
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What do you need us to provide?
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What do you provide?
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And that's also because a lot of last-minute disasters are just missing one stupid little cable, or it's because of one little thing that people forgot about.
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We're looking for a clean list that's cleanly described mic, speaker, music playback, power needs, table, chairs, stage, a dad, whatever.
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Put it all on there.
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You can also do a backup question to this is hey, do you travel with any backups?
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And we ask because backups are professional.
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And when someone says, Oh, yeah, I have a backup, this, this, and this, puts you just more at ease.
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I'd say with this question, you're looking for redundancy.
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And if their backup plan is hope, that is not a plan, that's a hallmark rom-com.
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I'd say a question I get asked a lot, and if I don't get asked, I usually bring this up in conversation.
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Uh, that's just because it just relates to my show, and that is how interactive is the show?
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How interactive are you with the members?
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Because interaction without priming sometimes can become awkward.
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So it's about knowing what the members are signing up for.
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So you as the host, you as the club, you as the pros can properly describe the evening, the event, whatever's coming to the members.
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So you want to ask, how interactive is it?
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Clear expectations.
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Uh, usually, you know, it's always good if the host, the GM, somebody does a nice intro for the show.
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Uh, for me, I'd say it's about 50-50.
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Sometimes the club pros uh do, sometimes they don't.
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I also don't mind just starting my show cold.
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I shouldn't say cold because I'm usually working the room prior, doing some close-up stuff, um, you know, just mixing, mingling, saying hello, getting the vibe, getting the energy going.
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So by the time I hit it come up on stage and I make custom videos for the clubs as well, promoting the show.
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Um they kind of know who I am.
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They understand the energy, the vibe.
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So I like kind of going up and doing my own intro anyway.
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But uh, I know with some people, it's very important for the host to do a proper intro.
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Next question is, and this is important.
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I think it's a very important question.
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If I don't get asked it, I usually bring it up in conversation because I know it's probably gonna come.
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But that is, you want to ask, how interactive is the show?
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And that could be for anything from DJs, bands, comedians, especially, magicians, everybody.
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How interactive are they?
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And do you want them to be interactive?
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For me, interactive is my main thing.
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Interaction, banter, crowd work, back and forth, using people from the seats up on stage.
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I love that back and forth.
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That is where I get my juice.
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That is one of my, that is my happy place.
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Um, but I also know that there are some situations, some clubs, some events, they don't maybe want that.
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So at the at the end of the day, these questions are helping us figure out are the people we are bringing in, is the entertainment we are bringing in the best fit and best, best vibe for our members.
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So a great question is how interactive is it?
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Another one is do you need the host to say something up front?
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Do they need to do an intro?
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And do they need to say how interactive it's going to be?
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Um, because interaction without priming could become awkward, especially in a comedy-style show.
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So to kind of back up the last question, it's do you need the host to do an intro, which I always think a host should do an intro.
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Um weird, shameless, you know, side bit.
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I don't uh I some I do in I do my intro about half the time.
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Um, just because sometimes I've already worked the room, I've already met people, they already kind of know who I am.
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So I don't mind just kind of going up there cold and you know, starting the show, even though it's not really cold because it's already started, because they're warm because they know who I am.
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But uh a good event is also somebody, the GM, the AGM, could it be the food and beverage manager, it just or could be just somebody who just needs some good stage time, right?
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I also think using situations like this, um, to having somebody else on your team who might need a little bit of public skills or public speaking skills, right?
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They might need a little bit of juice.
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So this is a great opportunity too to help other club staff get better on the mic, get better on stage, get better speaking in front of people.
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Another great question to ask your entertainment that you're bringing in is what should we never do right before you start?
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And we're doing this to prevent accidental sabotage.
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Um I know check drops aren't an an issue for things of of this nature uh for shows at clubs, but you want to, because every entertainer, every entertainment, everything is a little bit different.
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So we want to make sure we're not doing anything right before the show starts.
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Fantastic question to ask, entertainment is what should we, as the club, never do right before you start?
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That can be very important depending on the act, the entertainment.
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Some people might care, but other, you know, other times I think people sometimes just don't always think and they're trying to rush or get something in.
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And this happens more on the corporate side when I do things less the club side, even though it has happened on both, um, not often, but still happens, even though you tell people and they understand.
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But it's happened a few times where before I get up on stage, before you know they they do the show, the owner, the GM, somebody gets up and goes, Oh, thanks all for being here.
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Bling, bling, bling, you know, and then it'll be something like, now, unfortunately, you know, Bob couldn't be here.
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Bob was with us for 25 years.
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His this was his favorite night of the year was comedy night or magic night or the annual meeting.
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But uh, as you all know, he passed last month.
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So let's take a moment of silence for Bob.
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All right, let's get to the entertainment.
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Let's bring on Denny Corby.
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And you're like, what in the world?
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And the audience is like, you know, it's just a weird thing.
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So it's very important you should ask, what can we do, what shouldn't we do before you start?
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And there's some things that you should just know you don't do before you start.
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But different acts, different people might have different things that they just like doing.
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No speeches, no service clatter, no music, no surprise sponsor moment, right?
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Everyone has different things.
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So that's just another great question is what should we never do before and as the show starts?
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I think at a minimum, just if you're going through this, you know, if you're gonna clear plates and you're gonna do some service work, do it right before or wait until after.
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So I think for me at this point with a lot of clubs, they'll it gets to where they will clear most of the tables.
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So if they have dessert, they'll put the dessert on the table.
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I'll usually start right as dessert's ending.
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And sometimes the clubs will say, Hey, we'll clear, uh, we'll clear all the stuff off the tables, or others will just wait until the show's done.
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Um, some clubs can get away with silently taking stuff off the table.
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Some, it's a, it's a, it's, it's that's a whole episode in its start in itself, the art of clearing a table quietly.
00:16:32.000 --> 00:16:38.080
Um, but I think that's, you know, it's just more importantly, ask the person, ask the act, and they will give you the proper answer.
00:16:38.240 --> 00:16:47.279
This one's less of a question and more just a conversation between both parties, which are what are your boundaries content-wise for the performer and the club?
00:16:47.440 --> 00:16:52.080
Because this is about protecting relationships, protecting the club, protecting the vibe.
00:16:52.240 --> 00:16:54.559
And we're listening for standards.
00:16:54.720 --> 00:17:00.159
We're listening for you as the club standards, as well as the standards of the entertainer.
00:17:00.320 --> 00:17:04.000
Now, this being said, this is a weird kind of little side quest.
00:17:04.160 --> 00:17:15.200
And I've I've talked about this before when it comes to comedy, and in a private club, there can be R-rated comedy nights.
00:17:15.279 --> 00:17:20.480
There could be dirty comedy nights, there could be political comedians who come in.
00:17:20.640 --> 00:17:21.519
There can be.
00:17:21.759 --> 00:17:24.720
It all boils down to expectations.
00:17:25.039 --> 00:17:34.720
Expectations of the members, expectations of the club, expectations of the entertainer, but expectations of the members coming to that comedy night.
00:17:34.880 --> 00:17:42.640
Meaning, if you're gonna have a comedian and you want to have an R-rated dirty show, or like a comedian who pushes, pushes that that way.
00:17:43.119 --> 00:17:48.160
There is nothing wrong with that as long as that is how the night is booked.
00:17:48.240 --> 00:17:58.000
I've seen killer comedians who are raunchy and dirty kill it at clubs when it is booked and promoted properly, right?
00:17:58.160 --> 00:18:02.799
It's when you see the list come up and you see Gertrude is on there and her husband.
00:18:03.039 --> 00:18:05.599
You go, hey, listen, we know you guys.
00:18:05.920 --> 00:18:14.000
And we, we, I don't know if you saw the flyer, but the flyer says R might be dirty, whatever you're gonna put on there, just so you know, he he might get raunchy.
00:18:14.240 --> 00:18:18.640
And I think having those conversations is important and having different types of entertainment.
00:18:18.720 --> 00:18:22.319
You can play comedy night safe, and that's a great way to do it.
00:18:22.400 --> 00:18:23.599
I think that's the best way to do it.
00:18:23.680 --> 00:18:33.839
But also there is a way to do dirty comedians and having, you know, I just in dirty comedians is wrong, but like just more of an edgier, we should say, edgier acts.
00:18:34.000 --> 00:18:42.240
And to me, I think a really good entertainer, really good comedian or whoever you're bringing in knows that room.
00:18:42.480 --> 00:18:47.440
They know the club, they know the line, they know how to go right to the line without going over.
00:18:47.519 --> 00:18:57.759
They know the different, they have their own bits and things that they sprinkle out there that lets them know where the audience is at and they know how to get to the line and they know where to find the line.
00:18:57.920 --> 00:19:04.559
Um, so really it's you know, you want to know the boundaries of yourself and the boundaries of your performer.
00:19:04.720 --> 00:19:07.279
It's not about being sensitive, it's about being smart.
00:19:07.440 --> 00:19:11.920
And kind of picking off piggybacking off the last question, which is boundaries.
00:19:12.000 --> 00:19:16.960
This is what topics do you avoid, even if someone in the room steers you there?
00:19:17.119 --> 00:19:19.519
And I think that's another question for both sides.
00:19:19.680 --> 00:19:23.359
And a question I always ask is because uh you know, I travel a lot.
00:19:23.440 --> 00:19:26.880
I go to some weird, weird, I go to weird cities, go to weird places all the time.
00:19:27.039 --> 00:19:31.839
No, but uh, I go to different different states, different cities, different pockets of the world.
00:19:32.000 --> 00:19:40.480
And I always ask, hey, and this is more of a question like once I'm there, is there is there anything, any weird topics I should be aware of?
00:19:40.720 --> 00:19:47.920
And and and I'll say, usually besides politics, the usual religion, all that, any weird things to stay away from?
00:19:48.079 --> 00:19:55.680
And that could be, you know, pineapples, because maybe there was a big pineapple fiasco two weeks ago and everybody got food poisoning.
00:19:55.759 --> 00:19:56.319
I don't know.
00:19:56.480 --> 00:20:02.720
But you know, that that just might be something that, you know, heaven forbid I might just say pineapple and everyone's like, oh my goodness, and the room changes.
00:20:02.799 --> 00:20:06.720
But those are just little things that I like to know before a show.
00:20:06.799 --> 00:20:12.000
And that's just also part of the conversation um that that that you have.
00:20:12.319 --> 00:20:19.119
Um, and also, you know, it's it's you're also trying to figure out because sometimes members test the performers, right?
00:20:19.200 --> 00:20:24.480
So you all you always want to kind of give a little a little bit of a heads up.
00:20:30.720 --> 00:20:32.480
So what topics do you avoid?
00:20:32.640 --> 00:20:37.200
Asking the entertainment, what topics do you avoid if someone in the room tries to steer you there?
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