7 Lessons From The Challenger Sale That Will Supercharge Your Sales Team

1. Relationships Alone Aren’t Enough—Teach for Impact

Many sales leaders still believe that building relationships is the key to winning deals. But The Challenger Sale’s data tells a different story: in complex sales, relationship builders are the least likely to be star performers. Instead, teaching customers something new—something that reframes their view of their own business—has a far bigger impact. Encourage your team to develop insights and share them early in the sales process.

2. Tailoring Is the Secret to Stakeholder Buy-In

With an average of 6.8 stakeholders in every B2B deal, a generic pitch will fall flat. Tailor your messaging to each decision maker’s priorities, whether it’s cost savings for finance or operational efficiency for IT. Use stakeholder mapping to prepare for every meeting and coach your reps to adapt on the fly.

3. Take Control—Even When It’s Uncomfortable

Top sellers don’t shy away from tough conversations about price or risk. They guide the process assertively, set clear expectations, and help buyers overcome decision paralysis. Train your reps to anticipate objections and lead the conversation, rather than waiting for the customer to dictate terms.

4. Commercial Teaching Drives Loyalty

More than half of customer loyalty is driven by the sales experience, not the product itself. Prepare teaching moments that highlight your unique strengths and challenge the customer’s current thinking. Practice these stories until they’re second nature.

5. Equip Internal Champions

Empower your customers to sell your solution inside their own organization. Provide them with tailored content, data, and arguments they can use to persuade other stakeholders. This internal advocacy is often the difference between a stalled deal and a closed one.

6. Coach Challenger Behaviors—Not Just Activity

Managers should focus on coaching the core Challenger behaviors: teaching, tailoring, and taking control. Use role-plays, feedback sessions, and real deal reviews to reinforce these skills. Recognize and reward reps who model Challenger traits, even if their style is different from your own.

7. Invest in Long-Term Change

Becoming a Challenger organization is a journey, not a quick fix. Align marketing and sales, invest in insight development, and build a culture that values curiosity, courage, and collaboration. The results will be worth it.

Conclusion

The Challenger Sale isn’t about being aggressive or pushy—it’s about leading your customers to better outcomes. Start with these seven lessons, and watch your team’s performance soar.