Tailoring for adoption, Challenger-style
Older generations love to help younger ones put their problems into perspective—often with some version of “in my day, we had to walk ten miles to school!”
In their day, you had to knock on doors!
In their day, it was all about building relationships!
In their day, you wrote a ‘”thank you” note by hand!
Yet modern sellers know the biggest hurdle in sales today isn’t a lack of effort (or manual labor). Buyers today operate in a fundamentally different environment than they did 25 years or 10 years or even one year ago. A joint Pavilion and Ebsta 2025 Seller Benchmark report found 78% of sellers missed quota in 2025, and win rates dropped 10% over 2024.
Buyers can glean all the vendor information they need in a few minutes, yet still can’t navigate their own buying process. Sellers relying on old approaches might use new tech, but the fundamentals can’t keep up. It’s tempting to jump to new approaches, but the reality is that Challenger was built for this environment.
The key to making that case to sellers lies in personalizing their sales training. Because in selling, tailoring creates a connection, and the same is true for your sellers. They need a strong foundation of Challenger skills and the fluency to apply them to this new era of conversations. But without personalized learning, they risk thinking “this isn’t for me anymore.”
In this issue, we’ll explore how personalization makes sellers sit up and pay attention—so buyers can follow suit.
“Personalization is fundamentally about relevance, and relevance creates resonance.”
If sellers don’t connect with what they’re seeing, with what they’re engaging with, they disengage quickly. So, giving generic examples, generic opportunities to practice, generic show and tells makes it feel like that’s not for me. I don’t do that. My customers don’t act like that. And that immediately builds a wall, and we don’t want to build a wall.”
The solution? Personalized training, deployed at scale. Watch Kate’s full video.
💡 Challenger Moment of the Month
Great perspective from Tim Williton on Challenger’s continued relevance as differentiation shrinks. “The best leaders I’ve worked with challenge people to think bigger, not aggressively or arrogantly, but intentionally. They create Constructive Tension, push thinking, and help people grow. That is what strong coaches, mentors, and advisors do. And in a world where products and brands are becoming increasingly difficult to differentiate, I believe people are looking for leaders and organizations that bring something far more valuable: wisdom, clarity, perspective, and confidence.”
📃 Featured Content
Brief: The Power of Customization in Sales Training
Today’s buyers expect more from sellers. Sellers need to understand their business, speak their language, and connect solutions directly to business outcomes. So why do so many sales training programs still rely on generic content that doesn’t translate into real-world execution? Our brief, “The Power of Customization in Sales Training,” explores why relevance differentiates average training from training that drives measurable performance. Read the brief to see how customized sales training helps sellers apply skills faster, build buyer confidence, and drive stronger results.
Brief: The Problem Enablement Leaders Couldn’t Solve. Until Now
Despite investing in frameworks, tools, training, and tech stacks, they simply couldn’t connect seller behavior to performance outcomes at scale. And that put their training investments at risk. With agentic AI, they can finally connect performance signals to targeted development—and deliver that guidance continuously, at scale, in the flow of work. This is the missing piece enablement leaders needed all along.
Learn how it works in our brief, “The Problem Enablement Leaders Couldn’t Solve. Until Now.”
📢 What’s New with Richardson?
Accelerate Prism: A New Era of Sales Excellence is Here
Accelerate Prism is the next evolution of the Challenger Hub experience — designed to help organizations consistently teach, tailor, take control, and leverage constructive tension through AI-powered practice, coaching, and sustainment.
With Accelerate Prism, you can drive stronger adoption and sustainment of Challenger behaviors to prepare your team for the future of sales, today.
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