How to run a killer sales kickoff
10 ways to make your message stick, build culture, and set the stage for the year
It’s SKO time: the annual tradition where we gather and pretend to listen to a slurry of PowerPoint for way longer than anyone’s attention span can handle.
Fear not! With the right approach, your kickoff can be more than just a caffeine-fueled slog through endless presentations. If you’re on the hook to deliver SKO content that really resonates, inspires the team, and sets the tone for the year, this checklist is for you.
Pick a theme
Beyond setting SKO goals, pick a theme for clarity and direction. A good one creates cultural cohesion around a shared experience — it sets the tone and engages the team. Make it relevant to what you’re trying to achieve. It can be practical, like “the road to $100 million” (ugh, that’s just boring), or wacky and fun, like “Back to the Future,” complete with a midcentury modern aesthetic and George Jetson spaceships, or “We will rock you,” featuring classic rock walk-on songs and music-themed prizes. Weave your theme into the event with bespoke presentation graphics, props, and audience goodies.
Invite collaboration
Invite others to participate in SKO planning. Solicit input early and often, keep people in the loop on agenda changes, and gather feedback on content. Nobody likes a “big reveal,” so keep stakeholders (especially bomb-throwers — you know who you are!) close in both formal and informal ways. Make sure the folks closest to each topic area own the content and session, even if you are the one preparing it. They should feel like it’s their own voice, and evangelize it accordingly. This is tricky since not everyone has your presentation acumen, so start early and turn on your diplomatic charm!
Be ruthless about the agenda
Audiences retain only about 15 percent of what they learn at SKO, so make what you do present really count. Cut everything (everything!) that isn’t great and totally necessary. The past SKOs that haunt me always had those tedious “How to update Salesforce” or “Marketing programs by quarter” sessions. Not that these things aren’t totally important, it’s just that nobody wants to hear about them at SKO, and they harsh the vibe. Keep the event moving and save time by delivering these things as a pre-watch video, or better yet, set up a Genius Bar (with snacks and bevvies) for people to drop in and get their how-to questions answered during event breaks.
Set your content bar high
Be ruthless about content. Adhere to a template. Give specific guidance to creators, e.g., no bulleted lists of more than three points on a slide. Review content like crazy, not just for quality but consistency, too. It should be mutually-reinforcing, but not repetitive. Don’t let anything past you that is too long, confusing, off message, or not beautiful. Don’t just review decks; review the presentations. Give presenters constructive feedback. Have the best speakers speak, and if a so-so speaker must speak, invest in training. Oh, and ideally keep speaking to a minimum: anything that can be made interactive should be. A presentation on competition becomes a pre-read + game. A product demo becomes a contest with silly prizes. Remember that stories, visuals, and video are your friends!
Align your event with new initiatives
For God’s sake, don’t train everyone on the old positioning at SKO if you’re going to turn around and introduce new positioning a month later! Ditto any big initiative, brand change, or messaging introduction. It takes a lot of forethought to line things up, but the whipsaw of big, back-to-back changes takes a huge toll on the team. If you are in the middle of making positioning changes, share as much as you can at SKO with the sales team, and give them a timeline for when new content will be available. If it’s available at the time of SKO, let folks know where they can access, get certified on, and use all the fabulous new assets.
Protect the team’s most precious resource: time
Time is your most precious resource at SKO. Use it wisely. Only give attendees the most critical information as clearly and concisely as you can. Don’t be afraid to assign a pre-read for information that will drag down the energy at the event. Resist packing your agenda to the gills. Build in time for people to breathe, interact with each other, and tackle urgent work. Remind them periodically that they will get breaks so they can comfortably pay attention and not try to work during the sessions.
Use the event to build culture
Use SKO to impart not just information, but culture. Choose activities that reinforce company values and allow people to get to know each other. One simple-but-genius thing one of my former companies did at SKO to forge connection was to put out huge bowls of custom buttons with various things written on them, such as “Monty Python,” “Liverpool FC,” and “Dead Head.” People could take and wear as many as they liked, and they turned out to be an amazing ice breaker, leading folks to learn more about each others’ interests and find common affinities. Another way I saw a company build culture at SKO was to invite the whole company to attend for the first day. They bussed them to the venue and used that day to present higher-level, strategic content and host an all-company lunch. Finally, make sure that your content weaves in contributions from across the company to reinforce the talents and skills throughout. One company spliced together a dance video with contributions from employees around the world. Another created a series of virtual “car karaoke” videos with people across functions. You should ideally start each day of SKO with an upbeat video that gets people laughing and talking.
Celebrate achievements
Lots of companies use SKO to give out awards and announce “club” attendees (for sales and sales-adjacent folks who reach their goals). This is a great idea! It can be a great opportunity not just to recognize individual achievement, but team wins. And it can be a chance to recognize employees that embody company values and build culture throughout the year — within and outside of the GTM team.
Invite customers
One guest that should absolutely make a showing at SKO? Your customer! (At least one, but ideally multiple.) Keep the work light on the customer’s side (don’t ask them to make slides), but do ask them to share specifics (use cases, benefits, anecdotes, and return metrics). If you invite one customer, do a fireside chat with a great interviewer. If multiple, consider a panel. Make the session longer than usual and let the audience ask plenty of questions.
Reinforce the sh*t out of it
Unlike Vegas, what happens at SKO should not stay at SKO! While the event is still fresh in people’s minds, solicit survey responses and anecdotal feedback, and do a readout for your sales leadership. Reinforce SKO messages and learnings to the team all year round. Remind them where they can find the content you introduced at the event. Re-use video and presentation content for company onboarding and ongoing training. If you played a fun game around competitive intelligence or objection handling, do a monthly mini-redux of it on the sales call. And when people win with the information or strategies they learned at SKO, call it out in your company communiques.
A killer SKO doesn’t end when the lights go down. By focusing on clarity, engagement, and follow-through, you’ll set the stage for a year of alignment and success.
