Planning a company holiday party in Boston: the entertainment decision

Field Notes · August 2026 · Corporate

Most company holiday parties are planned backward. The venue gets booked in September, the caterer or food option in October, and then sometime in the second week of November someone looks at the run of show and finds a gap in the middle of the evening where something is supposed to happen.

Those are the emails I get. They are polite, slightly apologetic, and they more often than not contain the sentence “we are not really sure what we want.” Which isn’t the worst case scenario (because the actual bad decisions haven’t been made!).

I have spent more than twenty years building shows for spaces like these, in hotel ballrooms, restaurant function rooms, and a few spaces that were never meant to hold two hundred people. Some of that work has been on television, on Penn & Teller: Fool Us, or in extravagant theaters around the country. But most of it has been in rooms exactly like the one you are booking. Here is how I would think about the entertainment decision if I were the one planning it:

The room you are actually planning for

A company holiday party is not always a party among friends. It is a room of people who mostly see each other in meetings, plus a layer of spouses and partners who know no one, plus an open bar.

The failure case (or sometimes the awkward case) is not boredom. It is fragmentation. Finance ends up at one table, sales teams at another, the newer hires near the door with their coats still in hand, and the evening never becomes a single event. People leave having talked to the same eight colleagues they talk to every Monday morning.

A holiday party works when people who do not work together end up in the same conversation. Most of the rest is food!

That is the actual brief for entertainment. Not filling time. Giving the room a reason to mix, and giving everyone a shared thing to have been in the room for.

Two formats, and what each one asks

Close-up magic, performed table to table or through a cocktail hour, manufactures small groups. Six people who were not talking are suddenly watching the same thing at the same distance, and when it ends they have something to say to each other. It needs no stage, no microphone, no AV line item, and it works while the room stays loud. The best walkaround magicians understand how to approach individuals and join together audiences out of different small groups.

A seated set is a different situation. Thirty to Forty-five minutes, sightlines, a microphone, and a room that agrees to become an audience. It can ask a lot of an audience to hand over that much attention for that much time. But it also gives everyone a communal experience to share.

Rooms with columns, low ceilings, and hard surfaces – which describes a good number of Boston function rooms – tilt the decision toward the strolling format. Ask your venue for a floor plan with the tables actually in it rather than the empty photograph on the website. And the performers you want to trust with your room are the ones that know to ask about these type of logistics).

The hour that decides it

Timing matters more than format. We need to look at your event and understand where entertainment fits best. Often, with walkaround magic, the cocktail hour is the natural fit. But when exactly to start it and how long to run it for based on your group are important follow up questions.

A stand up show is a different animal. A dinner show needs wildly different material and preparation than an after dinner performance. A set between courses needs a tight run of show to keep things moving at pace and a professional performer who comes in at the right amount of time.  There are as many possible choices as there are events because tailoring the performance to the situation is its own art form.

Booking it in Boston, in December

The first two Thursdays and Fridays of December are often the most contested nights of the year in this city. Venues, caterers, and performers all go first on those dates, in that order, and they go earlier than most people expect. If your party is on one of them, September is not early planning.

The practical sequence is date, then venue, then the evening itself. Most of the holiday party entertainment I take on in Boston is booked six to ten weeks out, and the conversations that go best are the ones where the planner tells me what the room is like before telling me what they want me to do in it. But always reach out and even if I’m booked I can point you to a reliable local performer!

What it costs

Holiday work is priced the way the rest of my corporate calendar is priced, by room size, format, and how much of the evening it has to carry. December is the one month where the date itself carries weight, because the calendar is finite and the best nights go early. I wrote the unhedged version of that conversation, including where the money actually goes, in what corporate magic costs.

When not to hire anyone

If the party is twenty colleague/friends around one long restaurant table, entertainment can be an interruption. There are exceptions, but some small companies are friends who simply want to chat. Buy the better wine.

If the company is having a difficult or busy time of year, some companies have been moving celebrations to calmer January times to spice up a slower quarter.

And if what you actually need is someone to hold the room together through an awards segment, that is a host, not a magician. Different job, but let me know and we can make that work.

The short version

Book the date before anything else. Choose the format that fits the room you have rather than the room in the brochure.

— E. N.