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A 2024 Sales Kickoff Ferris Bueller Would LOVE

A 2024 Sales Kickoff Ferris Bueller Would LOVE

t’s that time of year again – time to plan your 2024 sales kickoff (SKO).

Sales kickoffs are tricky to plan, because everyone in the organization wants sales to do something. Product wants sales to pitch the latest and greatest features. Marketing wants sales to use the new materials. Enablement wants sales to employ best practices. Leadership wants sales to get excited for the upcoming year (and sell more).

Meanwhile, sales just wants to have a good time be more effective.

As you’re planning your 2024 SKO, let Ferris Bueller be your guide.


In one of the most famous comedic scenes in film history, Ben Stein, playing the role of an Economics Teacher at (the fictional, but based on Northbrook, IL) Shermer High School, attempts to teach a lesson on the Great Depression. He has good intentions (we presume), and tries to engage the class. It…does not go well.



“In 1930, the republican-controlled House of Representatives, in an effort to alleviate the effects of the…anyoneanyone…the Great Depression, passed the…anyoneanyone a tarrif bill…”

The boredom is palpable (well, to everyone but Stein). Don’t let that happen in your 2024 SKO!

Make your 2024 SKO engaging

When any sales team walks into a 2024 SKO, they’re expecting the common SKO playlist. Revenue updates. Product updates. Client success/renewal updates. Support updates. Maybe even contract and legal updates (for example, Maine’s new data privacy law is sure to impact marketing teams everywhere).

Your salespeople and sales support teams (presales, sales operations, inside sales/business development, client success) are craving a day that’s fun and informative. A day that delivers sessions that help them be the best version of themselves. They deserve their own day at the parade!

Here are 4 things you can do to ensure your 2024 SKO is (almost) as fun as Ferris Bueller’s day off (Fun fact – the filmmaker, John Hughes actually snuck Ferris’ float into an actual Chicago parade):

  • Telling stories > not telling stories
  • Team Events FTW (for the win)
  • Learn to Win with Executives
  • Give ‘Em What They Need

Telling stories > not telling stories

We’re big fans of storytelling here at 2Win – we believe there’s no better way to communicate your solution and value than by telling a story. And it so happens that this belief is backed by science.

According to Princeton University neuroscientist and researcher Dr. Uri Hasson, stories cause brainwaves to sync between storyteller and listener. Seriously! Dr. Hasson used fMRI to scan the brains of storytellers and listeners, and he saw their brains aligned in a process that he calls “neural entrainment” (Ed is totally calling his next band ”neural entrainment”). Writer Carmine Gallo met with Dr. Hasson and described it this way:

I begin talking, and as my story unfolds, Hasson sees movement in the scans—your brain waves and the waves of the others are going up and down in the brain region that processes sound, the auditory cortex. Suddenly, something amazing begins to happen. “The subjects lock to the story,” according to Hasson. In other words, your brain waves begin to move up and down together and blood flows to the same regions of your brain and the brains of the other participants. You are in sync with the other listeners and you are all in sync with me, the person telling the story…Stories trigger a release of neurochemicals that force us to pay attention to speakers, empathize with them, understand them, and get excited about their ideas.

Carmine Gallo, Quartz at Work

Just in case you’re thinking that it’s simply our brains being aware that someone is talking, Dr. Hasson repeated the experiment, but with someone telling a story in Russian to non-Russian speakers. He saw their auditory cortex light up as it was processing the sounds, but no brain alignment.

If you’re delivering a presentation during your 2024 SKO, consider telling stories as part of your talk. You’ll make more of an impact with your audience, and they’ll be more likely to respond to what you’re saying.

Your sales team is always looking for ways to improve their impact with clients and prospects. Consider making storytelling one of your floats in your 2024 SKO.

Team events FTW

One of the most common presentation crimes we see in a team selling environment is ”the power struggle,” and it happens because team members are fighting for control. Maybe the account executive wants to control the meeting, so they ask their sales engineer to show something that said sales engineer isn’t ready to show. Maybe the sales engineer wants to control the meeting, so they talk over the account executive. And when this power struggle plays out in front of an audience, the results are somewhere between ”uncomfortable” and ”dumpster fire.”

Here’s how to avoid power struggles: foster trust between team members. After all, the opposite of control is trust (credit to parenting expert Dr. Becky Kennedy for this insight).

If you want your teams to work better together, consider a team building float as part of your 2023 SKO parade. And by “team building” we don’t mean trust falls (unless that’s your thing, in which case, fall away). We’re also not talking about social events, as fun as those can be.

What we mean is, create a space for your sales team members to build trust. For example, run a session where they work on an opportunity together to create a plan that clearly defines the overall deal strategy, as well as individual team member roles and responsibilities. And then, have them role-play their presentation and/or demo, so they can identify where things are going well, and where things can be improved.

And of course, if you want help creating that space or running impactful role-plays, then we’d love to talk.

Learn to win with executives

Selling software to executives is very different than selling to users or department leaders. Executives are expecting to hear about how a solution will impact their overall strategic objectives, yet many sales teams take the approach of discussing features or showing a demo. Since the executive will (most likely) never use the software, leading with either feature-talk or a demo always fall flat. Sales teams need to know how to read an executive’s mindset (we call it their mode), ask the right questions during the meeting, and then have a discussion or, the right demo that aligns to that executive’s strategic goals.

Here’s a a simple exercise that you can run at your 2023 SKO to help your team become more effective with executives – identify an operational benefit, and then ask ”so you can” until you get to a strategic benefit. Here’s an example:

Our solution will help your users save time, so you can make your department more efficient, so you can reduce costs without adding headcount, so you can help meet the board’s objective of reducing expenses by 15% across the organization.

The more your team practices saying ”so you can,” the easier it will be to align benefits with an executive’s objectives.

Of course, there’s more to winning with executives than “so you can”. If your sales team has to rely on one of your executives to be present to ensure a successful client-executive encounter, go big at your SKO and get them what they need to navigate those crucial meetings.

Give ’em what they need

Your 2023 SKO is a great chance to do a bit of a reset for the upcoming year. To ask yourself what’s working for your team, and what isn’t. But don’t just ask yourself that question – ask your team. Your team knows what challenges they’re facing. They know what competitors they’re struggling with. They know at what stage their deals get stuck.

But what they often don’t know is why. For example, they may know that their meetings aren’t going well, but they might not know that it’s because of a power struggle. Or they might know that they aren’t able to close at the end of a cycle, but they might not know that it’s because they aren’t aligning their benefits with an executive’s strategic objectives.

As a leader, you can help them get to these answers – and then you can help them get better. So instead of looking at your 2023 SKO as a chance to tell your sales team stuff (technical term), use it as an opportunity to help them build the skills they’ll need to be effective through 2023 and beyond.

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