Can Your Sales Reps Build Insight with Prospects?
To successfully sell complex solutions, sales reps must focus more on customer success than simply closing deals. Buyers are better informed, customers expect more, and differentiation is often harder to articulate. To thrive, sales reps must move from being order-takers to insight providers — trusted business advisors capable of guiding clients toward solutions they may not even realize they need.
Sales rep assessment simulation data suggests that with deliberate effort, targeted business sales training, and meaningful organizational support, sales reps can raise their game.
When sales reps build insight with prospects, they excel at two fundamental sales competencies:
Research from the Harvard Business Review highlights that organizations whose sales teams can offer actionable insights see a 40% higher win rate compared to peers relying solely on transactional sales tactics. Just remember, challenging customer thinking isn’t about pushing a product or trying to close a sale; it’s about sharing valuable perspectives to better help your clients to succeed.
These sales skills matter because building insight requires more than knowledge accumulation — it demands thoughtful curiosity. High performing sales teams ask effective sales questions, uncover underlying issues, and challenge conventional thinking in a thoughtful way. McKinsey research shows that insight-selling approaches not only increase conversion rates but also strengthen long-term client relationships, fostering trust and credibility.
It Takes More than Sales Competencies
While the competencies of “challenging customer thinking” and “thinking through solutions” is the right place to start, we know from training measurement data that truly building customer insights requires more than improving individual sales skills. Organizations play a critical role in enabling reps to generate and deliver valuable customer insights through:
Adding customer value during the sales process typically requires a cultural shift. Traditional sales metrics often reward volume and speed rather than thought leadership and client impact. To encourage insight-driven behavior, companies must cultivate a sales force that consistently adds strategic value.
The Bottom Line
Done right, insights from sales reps becomes a differentiator that turns transactional buyer-seller exchanges into strategic and collaborative problem-solving sessions. To stand apart in the sales process, equip your sales team with the sales skills, sales mindsets, and customer-oriented sales incentives to become trusted advisors. Insight-driven selling strengthens client relationships, enhances credibility, and drives sustainable growth.
To learn more about how to ensure that your sales reps build insight with prospects, download The Top Sales Skills to Challenge Customers

Tristam Brown is an executive business consultant and organizational development expert with more than three decades of experience helping organizations accelerate performance, build high-impact teams, and turn strategy into execution. As CEO of LSA Global, he works with leaders to get and stay aligned™ through research-backed strategy, culture, and talent solutions that produce measurable, business-critical results. See full bio.
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