5 Mistakes to Avoid When Booking Corporate Entertainment For Company Events

Planning a corporate event is no small task—especially when it comes to entertainment. Whether you’re organizing a holiday party, company retreat, conference, or client appreciation event, the entertainment you choose can make or break the experience.

Unfortunately, many planners fall into the same traps when booking corporate entertainment. As a professional corporate entertainer with years of experience, I’ve seen it all. Here are five common mistakes to avoid—and how to ensure your event goes off without a hitch.

1. 

Waiting Until the Last Minute to Book Talent

The best corporate entertainers book up quickly—especially around peak seasons like the holidays. Waiting too long can mean you’re stuck with limited options or rushed logistics.

Tip: Begin researching and contacting performers at least 3–6 months in advance, especially if your event falls between October and December.

2. 

Not Matching the Entertainer to the Audience

One of the biggest mistakes is booking entertainment that doesn’t align with your audience’s demographics, company culture, or the event’s tone. A high-energy, comedy-driven illusionist might be a hit at a holiday party but feel out of place at a formal awards dinner—unless it’s tailored appropriately.

Tip: Choose an entertainer who customizes their performance to fit the audience—like Robby Bennett, who adjusts his show for everything from black-tie galas to startup retreats.

3. 

Forgetting to Consider the Technical Requirements

Many corporate event planners overlook the technical needs of performers—lighting, sound, stage size, etc.—until it’s too late. This can result in a poor audience experience or even a canceled performance.

Tip: Ask the entertainer for a technical rider early in the process, and make sure your venue can accommodate their needs.

4. 

Booking Based on Price Alone

While it’s tempting to go with the lowest quote, cheap entertainment often means cutting corners—outdated acts, poor audience engagement, or a lack of professionalism. Your entertainment reflects your company’s brand, so quality matters.

Tip: Look at experience, reviews, video footage, and referrals before making a decision. The right entertainer offers value far beyond the price tag.

5. 

Not Communicating the Event Vision Clearly

The best performances are a collaboration between the planner and the entertainer. If you don’t clearly communicate your event’s theme, goals, or potential sensitivities, the performance might fall flat—or worse, backfire.

Tip: Share your event objectives, company culture, audience makeup, and desired tone in advance so the performer can deliver a tailored experience.

Bonus Tip: Choose a Corporate Entertainer Who Makes Your Job Easier

An experienced performer doesn’t just show up and do tricks—they partner with you to make your event a success. Robby Bennett brings decades of experience delivering high-impact, customizable shows for Fortune 500 companies, small businesses, and everything in between. With professionalism, reliability, and jaw-dropping entertainment, Robby is the smart choice for your next event.

Ready to Book a Corporate Entertainer Who Delivers Every Time?

Avoid the stress, mistakes, and uncertainty. Contact Robby Bennett today to learn how to elevate your next corporate event with world-class entertainment that amazes and engages.