The following is an exercise we use at our Annual Sales Kickoff Event. It requires a lot of planning. That’s the bad news. The good news? When done right, this exercise can be super effective. It will solidify your team and teach them the skills they need to succeed in the year ahead.
That’s because play — which comes in the form of simulated games at the workplace — is the best way to build, and reinforce, a positive and collaborative community.
And when it comes to a big event like your Annual Sales Kickoff? One where the stakes are high and everyone’s a little nervous about the challenges they’ll face this year; there’s no better way to break that tension and teach your teams what they need to know to succeed.
So, we’re going to tell you about an exercise we run here at Cirrus Insight for our Annual Sales Kickoff Event, and we encourage you to give it a try at your next kickoff.
Sometimes, It IS All Fun and Games …
This year, we’re training our team on how to sell our new Email Blast functionality:
In the video above, you can see Kendall explain what Email Blast is, what it does, and why you should use it. Which, we totally think you should. So, if you haven’t yet, you can give it a spin here.
Now, the goal of the exercise is to help every member of our team (not just sales, everyone) learn how to explain Email Blast in such a way that it gets customers excited to try it.
Here’s How The Exercise Works:
Step 1
We’ve already completed this step, which is to explain: What the product is. What it does. And why someone would want it.
But we think it’s important to stress that the actual amount of yaking (or to put more professionally, lecture time) be kept to a minimum. You don’t want to be lecturing to your team, and really the company. You want the team(s) to be able to explain the what, the why, and the how in their own words and using their own methods.
So, if you can put the time in before your kickoff event and record a video like Kendall did? Great. If not, that’s ok too. But the important thing is to be comprehensive but brief. Give your teams all the information they need, but don’t bore them to death with details.
We think a video or slide deck that could be viewed asynchronously via Slack could also do the trick prior to the event itself. Although there’s always a couple of jokers in the bunch, so it's good to show the video and quickly go over what’s in the slide deck at the event as well. Just to make sure everyone has heard the same information at least once.
Step 2
The Management Team running the Annual Sales Kickoff Event should rank their sales reps based on their ability. Think of this like the NCAA bracket, complete with the usual subjectivity found within those rankings. This, to be clear, won’t be an exact science. 
Someone ranked 10th doesn’t mean that they suck. And someone ranked 1st doesn’t always mean they are the best. Please treat this exercise with some seriousness, but not enough where you’re letting your personal biases guide your decisions.
If anyone asks about the seedings, and why they were ranked where they were, explain your rationale plainly. This is a team building exercise, and you can’t have that without trust. So be clear and transparent, but also stress that this is a game and not some final, all consuming judgment on that person’s career.
Step 3
Now, there are a couple of ways you can slice this turkey. This will depend on the size of the team, how much time you’ll have with them, and who you have to serve as possible audience members or referees.
You could run this game exactly like the NCAA tournament, where the winner of each match up advances to the next round. Or, perhaps more collaborative and in the spirit of what we’re trying to teach you here about team building exercises: You can pair up your top seed with your bottom seed and have them take on teams featuring the next highest seed paired with the next lowest seed. So, a team featuring your #1 and #8 seeds would play a team featuring your #2 and #7 seeds, and so on.
The idea is that the top performer can teach the lower performer through collaboration. This is the single best way to transfer knowledge and skills among your team, making everyone better in the process. The choice is yours on how you want to do this.. But this is the fun part. And we want to stress that word: FUN. Play builds trust, trust builds collaboration, and collaboration builds strong company cultures that perform well and meet their targets.
Step 4
No matter how you choose to seed and sort your sales team — as well as other divisions within the company, all are welcome and invited to participate in some capacity — referees are then selected to pick and choose who had the best presentation.
The presentation is scored on clarity, simplicity, understanding, and entertainment value. 
That doesn’t mean every presentation should morph into a stand-up comedy routine. Your mileage may vary on how well that works within your organization and with your prospects, but you don’t want any of these presentations to be so dull that everyone starts looking at their phone either.
The important thing to grade on here is whether or not the product being positioned for sale is easy to understand in terms of what it is, how it works, and why someone would want to use it. Clarity. Simplicity. And understanding.
The winner of each matchup is then selected by the referee(s) and proceeds to the next round.
The teams that don’t advance have an opportunity to watch the rest of the tournament and take notes on what they could change or improve.
There are NO losers here, and we also want to stress that. If you don’t advance, that’s alright, as long as you’re learning and looking to improve.
Also, how you do the scoring is totally up to you. There’s no hard or fast way to do this. We prefer having an audience watch each of the matchups and let the audience decide who should advance. There are pros and cons to this as well. You want to look out for popularity contests, but having an audience (consisting of other employees and teams in the company) also presents a great opportunity for the rest of the company to learn about the latest product. This is so important to the company’s overall success because they will learn how they can help support the sales team through watching the presentations.
Step 5
Finally, a winner is selected. Hopefully everyone had a lot of fun, and now the company knows a great way (or three) to position their new product. This is great because even though there may be only one tournament winner, everyone in the organization wins. This is because they’ve collaborated and learned new skills and new products in such a way that they’ll remember.
Really, the trick to do this exercise successfully is in the pre-planning of it. You’ll want to know the product you want the sales team to learn inside and out. You’ll need to know what the strengths and weaknesses are of each team member (depending on how you want to sort them or team them up), and you’ll want to know who you can arrange from the company to have as the audience.
You’ll also want to discuss with the management team what skills you’re looking to emphasize, and teach your sales team those skills within the exercise. For example, if you want your team to say or do a certain thing, you’ll need to make sure to clearly highlight what that thing is. why it’s important, and then let them know you’ll be looking for that exact thing within each round of the tournament.
This exercise has MANY variations and is incredibly flexible in how you want to run it. In today’s article, we’ve demonstrated just one of those ways, and we hope it’ll give you something to work with for your own upcoming events.