How to Pick Entertainment for a Company Event When You've Never Done It Before

I've been performing at corporate events for a long time. And somewhere along the way I started paying attention to the people booking them, not just the people attending them. Event planners carry a lot of weight. They're in charge of finding the venue, the catering, fine tuning the timeline, sifting through the guest list, and many other things before people walk through the door. Entertainment is usually one of the last things that gets sorted out, and by then there's not much runway left to think carefully about it.

So I wanted to share a few things I've noticed from where I stand, which is usually somewhere in the middle of the room, watching how it all comes together.

This is probably the thing I think about most when I'm talking to a new client. Not "what do I do" but "who's going to be in that room." A financial services firm at a year-end dinner feels completely different from a tech company at an offsite. Same headcount, totally different energy.

I don't think there's a wrong answer when it comes to what kind of entertainment you book. I just think it helps to start with the room and work backwards from there. Who are these people? What do they care about? What would actually surprise them?

Those questions do most of the filtering on their own.

Magic entertainment usually comes in two formats for corporate events: strolling and stage. They serve completely different purposes, and the best events often use both. Strolling entertainment is where the performer moves through the room during cocktail hour or dinner and is perfect for breaking the ice. Guests don't have to do anything. The entertainment comes to them, engages with them, and suddenly two people from different departments who've never spoken are laughing together over the same impossible moment they just shared.

Stage shows work best when you want a communal shared moment. Something the whole room experiences together. It can become the anchor of the evening, the thing people reference on the way home. Knowing which one you need, or whether you need both, comes down to your event structure and what you want people to feel.

If you're putting together a corporate event and want to talk through what would actually work for your specific crowd, I'm happy to have that conversation. No pressure, no pitch. Just an honest look at whether we'd be a good fit.