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Sales Training Games

  • Writer: Terry Withers
    Terry Withers
  • Aug 26, 2025
  • 9 min read

Updated: Sep 4, 2025

I recently had two new clients reach out about improv workshops designed to hone sales skills. What follows is a quick rundown of what the two clients were looking for, which was quite different structural reasons but not at all that different in terms of desired outcomes. I’ll go through the asks from both and include a sample curriculum for each client, stopping to examine specific sales training games I haven’t written about before.


(I thought about naming this blog post, A Tale of Two Improv Workshops for Sales Development, but who am I, Dickens? For those of you keeping track at home, that’s one Dickens joke.)


The first inquiry was pretty much a standard one: the client had about 14 sales professionals early in their careers looking for a workshop offsite, but close to their offices in NYC. The client had specific goals that were mostly variations on agility, things like “staying in the moment,” “active listening,” “responding to client needs,” etc. Oh and I asked them the thing I always ask when pitching a sales workshop (“Could your team use a fun exercise to address objection handling?”) and their eyes lit up.


This Sales Person Has Been Trained By Improvisers. You Can Just Tell.
This Sales Person Has Been Trained By Improvisers. You Can Just Tell.

The first big challenge was finding a spot, which in NYC can be tough and expensive. I always offer clients the option to have RA find an offsite location for their workshop at no additional charge, but I don’t recommend it. Teams seem to perform better in their offices, I suspect because they feel more comfortable there, less surrounded by the unknown and therefore more willing to take risks. 


In any case, it just didn’t matter in this instance as the client didn’t have a suitable meeting space for improv in their offices. Most good rehearsal studios in NYC are Midtown and really not that far away from this company’s Chelsea offices. But this seemed too far to the client, who wanted the location to be a quick walk to and from her offices in Chelsea.


Fortunately Cre8ive NYC, a new rehearsal studio facility in the heart of Chelsea was available, a fact I discovered to my delight thanks to a tip from the workshop’s excellent instructor, Molly Thomas. Cre8ive used to be Simple Studios and IMO was the best improv rehearsal facility in the city pre Covid, but closed during the pandemic. 


It boasts spacious rooms that are well lit and kept clean by the staff. Big windows, great chairs, shiny floors that aren’t slippery. When it opened as Simple Studios it was the brain child of storied improviser Ali Farahnakian, so it is no wonder the space is so friendly to improv and that I like it so much.






Sample photo of Cre8ive studio arranged for an improv workshop.
Sample photo of Cre8ive studio arranged for an improv workshop.

Anyway, the client actually texted me 10 minutes into the workshop with a very excited and grateful text. What was the subject? How nice the room I had provided for the workshop was!


That made me laugh because they were with a master improviser who is a delight to work with, but they were focused on the room they were in! Maybe their offices are similar to the ones that appear in Bleak House? 


(Dickens joke number two!)


The other inquiry was for an event happening across the continent in LA. There 80 insurance sales reps would be gathering for a weekend summit, too many for just one excellent instructor. They wanted mostly the same sort of agility workshop my other client did, with one wrinkle.


They wanted to address hitting specific points in presentations. 


That’s a tough one for improv, an artform all about being in the moment and making real time decisions based on the specific circumstances you find yourself in. Frankly it is a tough one for sales too, a profession that might be described the same way. Still there are a few exercises that fit that bill and one in particular which asks participants to follow a set sequence while remaining in the moment and aware of what is going on around them.


You can go two ways when looking for an improv event for 80 people. You can go the cost effective route by having a solo instructor lead everyone in exercises en masse. This works well for events with tighter budgets or limited space.


Because it is such a different experience RA has labelled such events not as workshops, but instead as interactive lectures.


Or you can go for the top shelf option: concurrent workshops taught by multiple instructors, typically pairing one instructor with no more than 20 students. This gives everyone an improv workshop experience, allowing participants to have moments in which they shine and allowing for a lot of direct interaction with their instructor. It is more expensive, but this was the option the client selected.


The event was being held at The Omni in downtown LA, so securing space for breakout rooms was no problem. I designed the curriculum to start and reconvene with everyone in a large conference room. This way you can have that breakout room experience without losing a communal sense among all participants that they are engaged in an activity together.


Good for team building.


I normally will have a lead instructor for events with concurrent workshops, someone who will take point communicating with the client and corralling the other instructors. I was lucky to get Ari Voukydis for this event, a true applied improvisation legend, having started UCB’s initial program over 20 years ago and having been instrumental in its growth.






Photographic proof that the improv workshops at The Omni happened!
Photographic proof that the improv workshops at The Omni happened!

Typically events with concurrent workshops will reconvene in the main space at the end for a final exercise that often feels both performative and cumulative, but Ari surprised me by suggesting we also start with a short exercise. I normally just plan an intro (often a retelling of the origin of improv and Viola Spolin’s work at Hull House as an explanation for why the event is happening at work) but have wanted to start with a group exercise for everyone before the breakout sessions begin. I just hadn’t been able to put my finger on a good option.


So Ari suggested a quick version of Yes And Conversations. His plan was to do it en masse in just about 5 minutes. Perfect idea, because the format of that exercise makes it easy for everyone to do it simultaneously, plus it is easy for people to grasp as a first exercise.  


Also the concept of Yes And has broken out into the zeitgeist at this point. While the exercise can still be impactful for those having their first experience with improv, the exercise often doesn’t pack the punch it did 20 years ago. Taking 5 minutes to play around with the concept, have some fun and get ready for the larger workshop was just what was needed.


Okay so here are outlines of the curriculums with links to facilitator guides and light thoughts on why the exercises are included. Following that I’ll be exploring two exercises in depth as I think they have unique application to sales workshops in general and these events in particular


CURRICULUM FOR LA EVENT:


CONFERENCE ROOM INTRO

Intro Exercise / Get To Breakout Session Rooms - 10 Minutes

(Led by lead instructor.)


Yes And Conversations - 5 Minutes - Quickly run through the three conversations in this exercise, asking participants to partner with whoever is closest to them in the room. To speed things up, don’t have participants switch partners between conversations. Overall goal is to underline the power of using Yes And as a governing principle when working with others, even potential clients!


BREAKOUT ROOMS - MAIN SESSION


Pass The Face - 5-10 Minutes for nonverbal listening and confidence. This is essentially a warm up and meant to get everyone laughing


Yes And Point - 10-15 Minutes for staying in the moment even while maintaining a sequence. (More on this below.)


Pass The Clap - 15 Minutes - Really like this one for sales communication. I’ve written about it before. Sales people can often fall into the habit of judging potential clients. "They're dumb," or "They don't like to listen." But sales is not a profession of identifying people you think are dumb. It is about communicating value propositions in a way customers can understand. That’s a sink or swim collaboration. Just like the act of clapping simultaneously either sees two players succeed or fail together, communication in sales sees sales professionals and customers either communicate successfully together or fail to communicate together, always. 


Made Up Story Hotspot - 20 Minutes - Great for agility. 


Repeat, Reword, Say Why - 15 Minutes - Great for listening, especially in sales.


World's Best Coach - 20 Minutes - Address objection handling here. (More on this later.)


CONFERENCE ROOM OUTRO

Final Exercise - 20 Minutes

(Led by lead instructor)


Guest Panel is the final exercise. Only 8-16 people (or so) will get a chance to participate, but everyone else will have a great time in the audience. This exercise weaves lessons from the entire workshop into a final culminating performance that will leave everyone feeling like they had a shared experience. 


NOTE: You’ll want at least two wireless mics to run Guest Panel if you are working with over 80 people.


DOUBLE NOTE: It often makes sense to build a little time at the end of the breakout session for Guest Panel to be practised there, that way everyone gets to experience it and will appreciate the final exercise a little bit more. 



CURRICULUM FOR NY EVENT:


CONFERENCE ROOM INTRO


Introduction - 5 Minutes


WarmUps


Pass The Face - 10 Minutes for nonverbal listening and agility. 


One Word Story - 10 minutes for listening and staying in the moment (people often plan what their word will be, but to play this exercise successfully you really need to wait until it is your turn to select your word).


Main Workshop


Yes And Point  - 15 Minutes (see below)


Pass The Clap - 15 Minutes - Focused on teamwork and successful communication


Yes And Conversations - 15 Minutes - Focus on listening and agility.


Made Up Story Hotspot - 20 Minutes - Agility / Staying In the moment. 


Environment Charades - 15 Minutes - Nonverbal Listening / Staying in the moment


Repeat, Reword, Say Why - 15 Minutes - Great for sales listening. (Skip this one for time if running slow)


World's Best Coach - 20 Minutes - Address objection handling here. (See below).


YES AND POINT

(Please read through the facilitator guide before continuing, so you understand the exercise we’re discussing.)


Yes And Point is often used in beginner improv classes as a way to get people used to saying “Yes” and staying in the moment. I remember the first time I used it in a corporate workshop for a sales team in the larger DC area. Something strange happened:


People couldn’t do it. 


They understood the exercise, how could they not when it is so simple? But they were unable to wait until they heard “Yes” before moving. They would point and move immediately or sometimes even say “Yes” to themselves while moving.


I would stop the exercise, explain it again, everyone would understand, and then they would mess up. The best they could do was start to move and then pull themselves back. The difficulty they had floored me.


I came to realize that the nature of sales makes this exercise more difficult. Sales people are confident and assumptive. Sometimes they even use sports psychology tricks, like visualizing success.


Honestly they are just too optimistic, like Mr. Micawber in David Copperfield. (BANG! That’s a third Dickens joke. I know you were waiting for it.)


Problem there is, if you are fantasizing about what will happen will you notice what actually does happen during important meetings and presentations. If you can’t be in the moment for something as unimportant as Yes And Point, what hope do you have of being in the moment when closing your largest client’s annual order?


It also happens to be a perfect exercise to work on hitting specific points in a presentation while staying in the moment. Only a few things can happen in Yes And Point and you have to do them. The trick is, can you do them at the right moments, not before.


WORLD’S BEST COACH

(Please read through the facilitator guide before continuing, so you understand the exercise we’re discussing.)


I love this exercise for sales workshops. One of the most dreaded skillsets to work on, both for sales managers and professionals, is objection handling. Roleplaying objection is painfully boring and repetitive and often fails to capture the very real surprises that interrupt otherwise successful sales.


World’s Best Coach allows players to practice listening, acknowledging objections and then overcoming them by working through them. It perfectly captures the surprising feeling of real world objections and allows participants to practice the agility they need to creatively overcome them.


Plus it is fun! I highly recommend giving it a shot with your sales team today!


There you have it, a thorough review of two curriculums built to deliver top notch improv for sales workshops. If you are a sales pro and have thoughts, I’d love to hear them!



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