Why Relationship Builders Rarely Win Complex Sales—And What to Do Instead

For many years, the standard advice to those in sales, consulting, or any customer-serving role was to focus on building strong relationships. People believed that being friendly, accommodating, and quick to meet customer needs was the gold standard of success. But as the marketplace grew more complex and the stakes of purchasing decisions increased, something unexpected happened. The sales reps—and by extension, the advisors, coaches, or leaders—who succeeded were not the ones with the strongest rapport or the friendliest reputations.

Instead, the winners were those willing to push back, bring new perspectives, and introduce a degree of healthy tension. Customers routinely reported that while they enjoyed their interactions with likeable, reliable vendors, these relationships did little to influence their purchasing unless something more substantial—a fresh idea, a new way to save or make money—was on offer. It turned out, through massive surveys and interviews, that the most valued professionals were those who could teach their customers something they didn’t know, helping them rethink their own strategies.

This switch didn’t come easy. It meant accepting discomfort from time to time, risking being less 'nice' in the moment in order to create lasting value. One account rep who made the shift found herself nervously watching for signs of customer irritation as she challenged a long-standing process, but discovered, to her surprise, that initial skepticism gave way to appreciation and trust once results were delivered. The relationship deepened—not because she was agreeable, but because she guided the customer to a better outcome.

Behavioral science supports this. Studies on cognitive dissonance and learning show people are more likely to change when they’re gently pushed out of their comfort zones, especially when presented with compelling, relevant evidence. Deep, trusting relationships in the long run follow from helping others grow and succeed—not just keeping them comfortable in the moment.

The next time you’re preparing for an important meeting, reflect on how you usually interact. Are you aiming for ease and approval, or are you ready to offer something that might shake up the conversation? Gather a piece of insight or fresh data about your stakeholder’s world, and bring it into the discussion. When tension rises, don’t backpedal—see it as a sign you’re on track. Use it as a springboard for open exploration, and notice how much more memorable and valuable your interactions become. Try it once this week and watch for genuine engagement.