Not Another SKO: The Monday Morning Test

Budgets are tighter, AI is everywhere, and sellers are armed with more. A recent webinar with Workiva's Sales Enablement Leader, Kim Fisher, who has run SKOs for more than 1,000 revenue team members across 22 selling roles, put it plainly: SKOs can be fun, but they must deliver measurable ROI.

Google Trends data backs up this sentiment. Searches for “SKO” spike every December and January, during planning and execution season, but search interest has dropped by more than 60% since 2020.

The phrase “sales kick off” barely registers by comparison. People are losing patience with SKOs as they’re currently run. If leaders want to make them matter again, they must pass what we’ll call the Monday Morning Test. 

ROI-First Mindset to SKO Planning

An ROI-first approach does not mean modeling attribution on every speaker or every dinner. It means building the event so that it drives specific behavior changes that stick once sellers get home. Too many SKOs focus on big-bang launches or product dumps, but the real value comes from clarity and consistency.

That means narrowing the agenda to one or two actions per role, not a laundry list. It means reinforcing frameworks that sellers already know, rather than overwhelming them with new acronyms.

ROI-first planning asks a straightforward question: What exactly changes on Monday morning? If you can’t answer that, it doesn’t belong in the program.

Managing Stakeholder Demands: Say No

Every SKO attracts competing priorities. Marketing wants airtime. Product wants airtime. HR wants airtime. Left unchecked, the agenda becomes bloated, and the seller leaves overwhelmed. The solution is ruthless prioritization. Anchoring all content to top-down priorities keeps the SKO from becoming a showcase for internal politics and instead ensures it serves as a driver of company strategy. Stephen R. Covey, author of 7 Habits of Highly Effective People, put its succinctly, “You have to decide what your highest priorities are, and have the courage, pleasantly, smiling, non-apologetically, to say ‘no’ to the other things.”

Practically Speaking

Sellers don’t need novelty for novelty’s sake; they need clarity and application. The best SKOs resist the urge to overwhelm teams with net-new frameworks and instead reinforce existing ones, applying them to today’s challenges. By narrowing learning to one or two key actions per role and making the application role-specific, an SDR, AE, or CSM can all leave the room knowing exactly “what this means for me.”

Balancing AI Fatigue: Strategy on Products and Productivity

No SKO in 2026 can avoid AI. But AI fatigue is real. The best events frame AI through two lenses: how the company is integrating it into its product strategy, and how representatives can utilize it to work smarter every day. Both matter.

What Makes SKOs Memorable (For the Right Reasons)

The most memorable SKOs aren’t remembered for their celebrities or venues; they’re remembered because they changed how people worked. They achieve this through interactive learning rather than monologues, a design that balances energy with clarity, and facilitation that keeps people engaged from the main stage to the breakout rooms. When these pieces align, SKOs transform from “just another event” into a collective experience that teams talk about for years. And better still, drivers of team and company growth.

The Executive Leadership Factor

Executives must play a hands-on role in SKOs, otherwise, forced optics feel like theater. When leaders merely appear for keynotes without deeper engagement, sales teams immediately detect the disconnect; they can sense when messaging feels scripted rather than authentic. Leaders need to carry the message of change and embody it with enthusiasm, but more importantly, they need to demonstrate they've wrestled with the strategic decisions themselves and can speak to the trade-offs and reasoning behind new directions.

Middle management can contextualize what the new change means for teams, translating high-level strategy into tactical execution. Enablement provides the scaffolding for adoption through tools, training, ,and reinforcement mechanisms. Alignment across these teams ensures the SKO lives beyond the stage, creating a ripple effect of behavior change in the field.

Not Another SKO (What People Really Complain and Rave About)

Scanning online chatter, feedback is consistent; SKOs are too long, lack dimension, and rely on big names and PowerPoint presentations. However, remote workers note SKO may be their only opportunity to meet colleagues face-to-face and most agree that SKOs are critical when done right. The energy and alignment they create are worth the investment. 

SKOs accelerate change at their best, and at their worst, they’re forgettable and fatiguing. Trends indicate interest in SKOs is declining, but our industry could not be more exciting. This is a call to leaders to rethink how these events are designed. Companies that will win with lasting results are those that approach SKO with an ROI-first mindset, managing stakeholder demands, balancing AI strategy, and planning sessions first. 

Looking for some extra help to ensure your SKO passes the Monday Morning Test? Let's chat.