Stop Treating CS Training Like an Event
It is a familiar pattern in Customer Success teams. Someone attends an external workshop. The team participates in a product training session. A one-time skills course gets scheduled. Everyone checks the box. Then work resumes, and much of what was learned fades into memory.
This is not a problem with intent. It is a problem with systems.
Training that exists as a moment instead of a practice rarely translates into sustained capability. The strongest CS teams understand that year-round learning systems, not isolated events, are what build durable skill and performance.
Why Event-Based Training Falls Short
At its core, event-based training assumes that a single exposure to new information is enough. Research on learning and memory consistently shows that this is not how durable learning works.
A 2025 study conducted at the University of Oregon examined how learning is consolidated over time and found that repeated engagement and reactivation of information are critical for long-term retention. The research shows that memory strengthens through cycles of reinforcement, not through one-time exposure. Learning that is revisited and applied over time is more likely to be retained and transferred into real-world behavior.
This helps explain why event-based training often feels effective in the moment but fails to produce lasting change. Without intentional reinforcement, new knowledge remains fragile. It has not yet been integrated into how people think or act under pressure.
The issue is not the quality of the training itself. It is the absence of a system that allows learning to be revisited, practiced, and strengthened over time.
Without reinforcement, reflection, and application, training remains an isolated moment rather than a foundation for growth.
What Modern CS Teams Actually Need to Learn
Customer Success professionals must stay current on many fronts. They need to understand product changes, internal processes, customer segments, and evolving company priorities. All of these are important.
But product and process training, while necessary, does not automatically translate into the skills required to succeed with customers. Technical training explains what has changed. Skill training explains how to navigate those changes in real conversations.
Teams that invest in durable CS skills find that internal training becomes far more actionable. CSMs are better equipped to apply new information in context, rather than simply repeating it.
What Year-Round CS Training Looks Like
Year-round training does not mean constant sessions or an overloaded calendar. It means establishing a rhythm that supports continuous development.
Effective programs share a few characteristics:
Spaced learning: Topics are revisited throughout the year instead of delivered once.
Practical application: Teams practice using new concepts in real account scenarios.
Role playing: Customer-facing skills are developed through repetition and feedback.
Manager reinforcement: Leaders bring training concepts into coaching and team conversations.
Consistency matters more than volume. Training becomes part of how work happens, not something that interrupts it.
Where External Training Fits Best
External training programs play an important role when they are used intentionally. They introduce proven frameworks, provide shared language, and offer perspective that is not shaped by internal dynamics.
Their impact is strongest when external learning is integrated into a broader system. After a workshop or course, teams should translate concepts into their own context, reinforce them internally, and connect them directly to customer work.
External training works best as a foundation, not a finish line.
The Manager’s Role in Making Training Stick
Managers are the single biggest factor in whether training leads to behavior change.
When managers attend training alongside their teams, reinforce concepts in one-on-ones, and coach to specific behaviors, learning becomes real. When training is treated as something that happens elsewhere, momentum fades quickly.
Ongoing coaching turns knowledge into capability. Without it, even the best training struggles to stick.
Action Items for CS Leaders
Review your current training approach and identify where learning exists as an event rather than a system.
Choose one core CS skill to reinforce consistently this quarter.
Ask managers to lead follow-up conversations after any training session.
Build practice into your training plans, not just presentations.
Measure application, not attendance.
Why This Matters in 2026
Customer Success teams are operating in increasingly complex environments. Expectations are higher, change is constant, and customers notice inconsistency quickly.
Training systems built around one-time moments cannot keep up. Teams need ongoing capability development that evolves alongside the business.
Learning is not something you complete: It is something you sustain.
The Success League is a boutique customer success training and consulting firm. If you’re looking for foundational training for your CSMs or CS Leadership team, we can help! Visit our Learning page to see our full suite of offerings or contact us to learn more about corporate training.
Kristen Hayer - Kristen is the Founder & CEO of The Success League, a global, customer-focused consulting and training firm. Kristen’s background includes leading award-winning sales, marketing, and customer success teams in early and growth-stage tech companies. She is the host of several podcasts on CS and leadership, and has written over 100 articles on the field of customer success. The book she recently co-authored with 5 other CS thought leaders - The Customer Success Talent Playbook - recently hit #1 on Amazon in 5 categories. Kristen received her MBA from the University of Washington and splits her time between San Francisco and San Felipe, Mexico.