Stick the Landing: Strategic Steps for SKOs that Work

This year, your sales kickoff looms large on your calendar. Whether it’s scheduled for a single day or spread over a week, it carries outsized pressure and comes with a host of tactical challenges. 

Schedules to coordinate. 

Venues to book. 

Speakers, presentations, and A/V equipment to manage. 

Yet when we invited SKO experts onto the Winning the Challenger Sale podcast to share their advice, they encouraged SKO planners to pause and zoom out before diving into to-do lists. Instead, they offered insights to help you align strategy ahead of tactics. Read on to learn how to bring clarity and purpose to your SKO, select an overarching theme, and identify the right speaker mix. 

Start with a diagnosis

Is your SKO designed to be a rallying cry? Can you build an effective event that will leave your attendees feeling confident and ready to sell? After a decade spent carefully observing SKOs, Paul Stansik of ParkerGale Capital says there is one critical component most SKOs completely skip: pausing to get clear about the problems they want to solve.

The best way to build a path toward clarity is to start with a deep-dive diagnosis. On Episode #87: You Need a Chief Reminding Officer, Paul suggests you can’t build an effective SKO until you get clear on where you’re going.

“If you’re planning a compelling SKO…without diagnosis or a plan to remove that biggest obstacle, you’re making a huge mistake,” Paul says.

Paul suggests starting by identifying the bottlenecks. His diagnostic process is quick, and begins by asking sales teams which of two problems they’re dealing with: do they need more touches or fewer drops? The answer lies in your data.

If your close rates are low, you likely need to focus on creating more touches. However, if your sales team closes at a high rate, creating new opportunities may be your focus for the coming year.

“The best SKOs are planned with that diagnosis in mind,” Paul says. “They reinforce a couple of simple tweaks in how the team sells, which could be skills, process, mindset — but it’s all about identifying that gap, and then creating a gap-filling plan to unveil at the SKO.”

Building a foundation of purpose

So you’ve started by ensuring sellers will leave your SKO with an understanding of their goals. Next, you must ensure they can connect to something deeper than their commission. 

On Episode #89: The Power of a Purpose-Driven SKO, Lisa Earle McLeod, author of Selling With Noble Purpose, makes the case for infusing purposeful selling into every step of your SKO. 

Lisa groups SKOs into two buckets: the transactional kind, where organizations encourage sellers to pursue numbers, and the purpose-driven kind, where leaders ignite sellersby the idea of being part of something bigger than themselves. 

She suggests a mindset shift in the way sales leaders approach results. Numbers are important, but they don’t light sellers up. Rather than focusing on that $1M in sales, spotlight the 10,000 customers you helped throughout the year. Better yet, pull in one brilliant customer story.

“Highlight how your product made a difference to a customer, bring the customer in, and have the seller talk about how you made a difference to a customer,” Lisa says. “This seeds a deep belief based on facts and proves that what you do helps people.”

The bottom line? Your SKO shouldn’t focus on closing more business, it should encourage sellers to help more people. The end result is the same, but leading with purpose across the team ensures each seller understands why their work truly matters. 

Set the tone with the right theme

Whether you’re hosting a hybrid, in-person, or virtual event, your work should be guided by a great theme. As Sprout Social’s Peter Zink learned when executing a series of global sales kickoffs for more than 800 attendees, the right theme coalesces everything from speaker selection to reinforcement. 

On Episode #90: Maintain the Momentum with the Right SKO Theme, Peter shared this example: After a recent acquisition, his team needed to move into Q1 with a unified focus. Peter wanted to capitalize on the high enthusiasm across the organization with a theme to help his sellers boldly step into a new chapter.

To center their teaching efforts, Peter’s team built their SKO around a pioneer theme. It was broad enough to allow exploration—pioneers in the Old West, astronauts exploring space, and plenty of fun accompanying visuals. And it was relevant enough to pull in the right guest speakers and underscore important training topics. 

“What I want them to walk out with is that they are going to be a pioneer and try new things this year… I’m a big fan of trying to ground that theme as quickly as possible when you’re planning an SKO,” Peter says.

Perfect your speaker mix

After you’ve gotten clear on your goals, identified your purpose, and selected your theme, you’ll likely start scheduling keynotes, speakers, and activities. At this point, it helps to step back and ask: will my sellers see themselves represented on stage? 

As SailPoint’s Barrett Sellers and Robin Barde shared in Episode #88: A Practical Guide to Creating a Kick-Ass SKO, the right mix of speakers will surface stories from across your company. 

“We highlight our rockstar sellers, men and women,” Robin says. “We give our women leaders a platform to give a keynote or hold a session.”

By representing the diversity of your sales team throughout your SKO, you invite all attendees to recognize they are a critical part of the community and play an instrumental role in achieving your vision for the year. That representation might also mean including stories and leaders from your global offices. 

“We integrate stories and speakers from all over the world,” Barrett says. “We really try to pay attention to our global partners so they have an opportunity to be on stage and talk about how well we work together, how the relationship contributed to [a win].” 

When you’re planning your speaker mix, remember: diversity brings value to your message.

Plan the perfect SKO with these expert strategies

As we explored SKO planning with guests throughout September, one thing became clear: well-executed SKOs come down to strategy as much as execution. And perhaps that comes as a relief. While impressive SKOs feature plenty of bells, whistles, and open bars, successful ones are possible on any budget or timeline. The perfect SKO may not exist, but with a firm foundation of clarity, purpose, and theme you’ll be ready to start the next year stronger than your last. 

For more expert insights, tune into Winning the Challenger Sale. Each week, host and Challenger CEO Andee Harris welcomes industry experts to explore what high-performing sales teams do differently. For deep dives into the biggest problems facing modern sales leaders — including our recent SKO-focused episode with the SailPoint team — check out our Leading the Challenger Sale webinar series.