6 min read

The 4 types of speakers you don’t want at your 2024 sales kickoff

The 4 types of speakers you don’t want at your 2024 SKO is part of our series on 2024 SKO planning. Book a 2Win SKO Speaker here!


I’ve seen a lot of SKO programming, and there are a few that stand out as particularly cringe-worthy.

There was the time that the head of sales challenged the head of marketing to a push up contest. To paraphrase a line from my favorite TV show (Arrested Development), he made a huge mistake. She was a fitness junkie, and he…was not. It didn’t go well for him.

There was the time that the company rented out a club in Las Vegas for all of the employees, and the executives spent the entire night in a VIP area that literally looked down on everyone else.

But the one that stands out is the new General Manager’s presentation that was, if I’m being generous, tone-deaf. Here’s what happened:

The out-of-touch SKO speaker

The SKO presentation was for a business unit that focused on marketing and customer experience technology, and this general manager was speaking to the sales organization for the first time. The theme of the presentation was “the ideal customer experience,” and the presenter decided to talk about their Porsche.

The presenter went on for quite some time about how much they loved their car. They loved the experience of driving it. They loved the sound it made (this section had sound effects). They loved it so much that, even though their spouse thought it was a ridiculous purchase (their words), they didn’t care because it was so great.

That presentation would have been cringe-worthy enough on its own, but there’s some context that made it even worse: layoffs were coming. Everyone knew layoffs were coming. The GM definitely knew that layoffs were coming. And yet, they got in front of the entire sales organization and talked ad nauseam about their six-figure car.

This is just one example of an SKO speech gone awry. We call this character “The Out of Touch”. Here are 4 types of speakers that you definitely don’t want at your 2024 SKO:

  • The Yeller
  • The Inspired
  • The Comedian
  • The D-List Celebrity

The Yeller

Ever see former Microsoft executive and current NBA team owner Steve Ballmer give a presentation? He was known for being…intense. Here’s an example of what has become known as his “monkey boy dance.”

Ballmer could (mostly) pull this off because it was his “thing.” He did this pretty much every time he was in front of an audience. But there’s only one Steve Ballmer, and unless you’re him (in which case, thanks for reading this blog, Steve!), you can’t pull this off.

Why you don’t want The Yeller speaking at your 2024 SKO

The yeller is a bad SKO speaker because it comes off as disingenuous. Your SKO isn’t a high school pep rally. Your team can see right through a “rah rah” speech. So instead of running around the stage yelling or having a speaker that opens with “How’s everyone doing this morning?…I said… HOW’S EVERYONE DOING THIS MORNING?!!!”, give them reasons to be excited.

Honor and highlight the president’s club recipients. Show them some video highlights of the year. Present how you’re going to invest in them and their careers with the personal improvement programs that will help them (and you) hit your upcoming targets. Share the new marketing strategy that will be sure to bring in the “Glengarry leads.”

An SKO speaker with energy is good – but the energy needs to be backed with real content.

The Inspired

When The Inspired gives an SKO presentation, it often sounds good – as long as you don’t think too hard about the substance (or lack thereof).

One of my favorite strategy books is Good Strategy/Bad Strategy by UCLA Professor Richard Rumelt. In the book, Rumelt describes the 4 hallmarks of bad strategy: fluff, failure to face the challenge, mistaking goals for strategy, and bad strategic objectives.

Fluff. Fluff is a form of gibberish masquerading as strategic concepts or arguments. It uses…words that are inflated and unnecessarily abstruse and apparently esoteric concepts to create the illusion of high-level thinking.

Failure to face the challenge. Bad strategy fails to recognize or define the challenge. When you cannot define the challenge, you cannot evaluate a strategy or improve it.

Mistaking goals for strategy. Many bad strategies are just statements of desire rather than plans for overcoming obstacles.

Bad strategic objectives. A strategic objective is set by a leader as a means to an end. Strategic objectives are “bad” when they fail to address critical issues or when they are impracticable.

Rumelt, Richard. Good Strategy Bad Strategy: The Difference and Why It Matters (pp. 32-33). The Crown Publishing Group.

The Inspired is the personification of these hallmarks of bad strategy (often combined with someone who has read Eat Pray Love one too many times). On the surface they might sound good, dare I say inspiring. But the longer they talk, their presentation is quickly exposed as fluffy garbage (technical term).

Why you don’t want The Inspired speaking at your 2024 SKO

To quote The Sound of Silence, The Inspired is a master of “talking without speaking.” The telltale sign is that you can see one of Rumelt’s hallmarks of bad strategy in what they say.

Fluff: We’re going to help our clients leverage our differentiators to drive digital transformation with our AI and ML solutions (but don’t ask me to explain my technobabble).

Failure to face the challenge: “This year our strategy is to grow revenue by 20% and take marketshare away from our competitors. How will we do that? By being the best. After all: clear eyes, full hearts, can’t lose!”

Mistaking Goals for Strategy: Our strategy for 2024 is to grow revenue and win more deals.

Bad Strategic Objectives: This year, we’re going to transform our business – we’re on a rocket ship to the moon! (but don’t ask me how we’re going to transform our business or what it means to be on a rocket ship).

If part of your SKO presentation is to talk about the year’s goals or strategies, then by all means do so. Your team wants to hear about the direction in which the business is headed. You have an opportunity to instill confidence that your organization is headed in the right organization.

The key, however, is to make sure to give them more than platitudes, quotes, or fluff. Instead, tell them what you’re going to do to achieve your goals. This does not mean you have to lay out every detail of your strategy as that would likely make for a tedious presentation, but give your audience enough detail to know you have a strategy, and make sure to tell them how your strategy will help them sell more in 2024.

The Comedian

While this isn’t quite as common as it used to be, TV sitcoms are often filmed in front of a live studio audience. An audience that is expected to laugh at every joke so the show has a laugh track.

If you’ve been to a sitcom taping, you know that they don’t just bring the cast out and expect the audience to laugh. They have a warm-up comedian who interacts with the audience and gets them in the mood to laugh. In the words of warm-up comic Mark Sweet: “My job as an entertainer is to engage the audience, hold that energy, and then give it back to the stage, and keep that going for three to five hours.”

The live studio audience knows they’re there to see something funny, and even in that context, they often need someone to keep them in the right mood to laugh at the show.

Why you don’t want The Comedian speaking at your 2024 SKO

An SKO audience isn’t exactly primed to laugh. They are there expecting to hear “work stuff,” not a stand-up show. So if a speaker tries to tell a bunch of jokes, the audience often doesn’t know what to do with it, because they’re not in the right headspace for it.

The big risk to The Comedian is that, well, they aren’t a professional comedian*. They often try way too hard to be funny, and it almost never actually lands. Even worse, it’s always more painful than some of the other kinds of speakers. For example, The Inspired doesn’t say a lot, but at least it sounds good. When an SKO speaker tries to be funny, it almost always bombs.

That’s not to say you can’t have some jokes in your presentation. If they’re well timed and well spaced – if, for example, it breaks up a section about financial performance, it can liven the mood. But when an SKO speaker tries too hard to be funny, like challenging someone to a push-up contest, they should probably take a different approach.

*The exception to this is, of course, if you have a speaker who is actually a comedian. A few years ago I went to the Adobe Summit, and Thomas Middleditch from Silicon Valley ran one of the sessions. He was hilarious, but it worked because 1) the session was in the evening, 2) people expected that session to be funny and 3) he was, you know, a professional funny person.

The D-List Celebrity

The D-List Celebrity needs no introduction. Well, a D-List Celebrity might need an introduction as the audience often doesn’t know or doesn’t care who they are. Or, even worse, the audience does know who they are, and they simply don’t care.

If your speaker is any of the following, maybe consider someone else for your 2024 SKO:

  • Anyone whose next gig is a cruise ship or a Vegas hotel that’s not on the Strip
  • Anyone who charges less than $25 for a Cameo
  • Anyone named “Charlie Sheen”

Why you don’t want The D-List Celebrity speaking at your 2024 SKO

The ROI is…questionable. Before hiring a celebrity speaker, you should consider what value they’re bringing to your event. If your goal is to entertain or get your team excited, then they might work. If you have a pile of money to light on fire, then by all means go for it. But if you want to give your team practical advice to make them more successful in 2024? Maybe consider someone else.

What makes a good SKO speaker?

As you think of who you should have at your SKO, here are some traits to look for:

  • Someone whose success is relevant to the audience
  • Someone who can inspire the audience, or teach them something new
  • Someone who has a track record of strong SKO presentations
  • Someone who the majority of your audience knows and would look forward to hearing

Who was the worst SKO speaker you ever saw (you don’t have to name them, but we’d love a good story)? Let us know in the comments.

And if you’re looking for your next SKO speaker and need someone who checks all of the right boxes, we would love to chat.

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