conceptual inage of salesman looking up at a stack of powerpoint presentations representing SKO season

It’s that time of year again:

Flights are being booked. Ballrooms are being reserved. Executives are pretending they’re motivational speakers.

Yes, it’s Sales Kickoff (SKO) planning season.

SKOs should be the ignition point for the year’s go-to-market strategy. They should inspire, align, and sharpen execution. But too often, they deliver fatigue, confusion, and a branded Yeti mug.

Let’s break down the five most common SKO mistakes companies make—and why they turn the most important sales investment of the year into a glorified networking event with slides.

5 Most Common SKO Mistakes

1. The Overstuffed, Underfunded Agenda

You made the right call: you’re not going virtual. You want to bring the team together in person. Respect.

But then you try to cram a year’s worth of strategy, product updates, enablement, and executive therapy into 1.5 days—because “hotels are expensive” and “people are busy.”

So what do you get?

A wall-to-wall schedule that runs from 7:45 a.m. to 6:00 p.m. with short breaks, no reflection time, and absolutely no chance that anyone will remember what they heard. It’s like speed-dating with your entire tech stack.

Result? Cognitive overload. Zero absorption. And someone from Product crying in the hallway because their breakout session had three attendees and a buffet tray.

SKO Truth #1: If you can’t afford to do it right, you definitely can’t afford to do it wrong.

2. PowerPoint Palooza 2026

You’ve seen it. You’ve done it. You may be doing it again right now.

Every function demands “just 30 minutes” to present their slides. Marketing. Product. HR. Finance. Legal. The janitor. Everyone gets a turn. No one gets remembered.

Before you know it, you’ve got a 124-slide agenda and no idea what the theme of the SKO actually is.

There was a branded theme and logo for the PowerPoints and signage, which included a word like Ignite, Growth, Together, One, Transform, Motivate, Celebrate, Winning, Together or Connect [insert yours from last year if you remember]. Just a pile of content stapled together with a conference badge.

Here’s a fun test: Take last year’s SKO agenda and replace your company name with a competitor’s. Still works? Then it wasn’t built around your strategy. It was built around your org chart.

SKO Truth #2: If your kickoff could double as a shareholder meeting or TEDx Suburbia, you’re doing it wrong.

3. Senior Leaders Do a Flyby

Let’s say the CRO gives a rousing 45-minute keynote on stage. Applause. Maybe even a standing ovation. Then… gone. Execs vanish into “VIP dinners” and side meetings.

Meanwhile, the people doing the real work—the reps, the managers, the enablement team—are left navigating a maze of panels and product talks with no strategic through-line.
When leaders appear but don’t engage, the message is clear: “This is your event, not ours.”

SKO Truth #3: Your presence isn’t leadership. Your participation is.

If your exec team isn’t sitting in breakouts, answering hard questions, and reinforcing priorities, then your strategy isn’t being communicated with the required clarity and reinforcement.

4. All Sizzle, No Steak.

We get it. You want to create a moment. The DJ’s spinning, the lights are pulsing, someone’s shooting t-shirts into the crowd like it’s a SaaS spring break.

Cool. But unless your reps are leaving with a better way to sell, not just a branded fleece and a hangover, you’ve missed the point.

Fun is fine. Culture is critical. But without application, your SKO is just a pep rally. A very expensive, very well-catered pep rally.

SKO Truth #4: Sellers don’t need more hype. They need help becoming more effective.

That means practice. Role plays. Deal reviews. Real conversations about what’s working and what isn’t. If your reps don’t leave with clarity on how to win deals this year, why are you flying them to Vegas?

5. No Plan to Reinforce Anything

You crushed the event. People clapped. Drinks flowed. The exec team gave it a 9/10.

And then… nothing.

No follow-up. No coaching. No field reinforcement. Managers have no idea how to reinforce what was taught. Reps go back to doing what they were doing before.

Three weeks later, the SKO might as well not have happened at all.

SKO Truth #5: An SKO is not an event. It’s the start of a campaign.

If there’s no post-event plan to reinforce, coach, and measure the behaviors you rolled out—then don’t bother doing it at all. You’re lighting money on fire.

The BETR Way: Make Your SKO a Strategic Weapon

Here’s a wild idea: What if you built your SKO around your sales strategy?

Not your internal priorities.
Not your product roadmap.

Your actual strategy for how you’re going to grow, differentiate, and win this year.

Then, you used the SKO to:

Teach it.

Apply it.

Practice it.

Align managers to coach it.

And build conviction around executing it.

That’s what high-performing companies do.

That’s what BETR helps companies do.

And yes, it’s what the rest of this blog series is going to explore.

Final Study: Your SKO Can Be a Joke… or a Jumpstart

You’re spending a small fortune to bring your go-to-market engine together.

Don’t waste it.

Don’t over-stuff the agenda.

Don’t let leaders disappear.

Don’t settle for hype over clarity.

Do less. BETR.

We’ll help you turn your SKO from a PowerPoint palooza into a strategic mobilization event your competitors will regret you held.

👉 Contact BETR to make your SKO a strategic advantage.