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Salesforce leaders face many challenges, but how they address them often determines their team's performance and growth. Restaurateur Danny Meyer's distinction between unpleasant and difficult problems is a simple yet remarkably powerful framework for leading a modern salesforce. 

Recognizing the Challenge 

An unpleasant problem is simple yet uncomfortable to confront. Common examples include delivering tough feedback, holding team members accountable, or enforcing compliance. The action is easy to figure out, just unpleasant to execute. Ignoring these leads to compounding issues like demoralized teams or declining performance. 

Difficult problems, on the other hand, are inherently complex. Crafting a new sales strategy, sales process re-design, restructuring compensation plans, or responding to disruptive market changes requires strategic thinking, collaboration, and time. These challenges demand more than decisiveness — they call for deep analysis, cross-functional input, and time. 

A recent Wall Street Journal article perfectly described the distinction, "Difficult issues require lots of attention, lots of consideration, more fact gathering and analysis," said Danny Meyer's colleague Steel. "Unpleasant, you kind of know the answer, you just don't want to deal with it, so you pretend it's difficult when it isn't difficult. It's just unpleasant." 

This insight is critical for sales leaders. Whenever you are wrestling with an issue, recognizing the nature of a problem — whether unpleasant or difficult — is an essential first step that can help you approach the challenge with clarity and confidence.  

Common Problems in Sales Leadership 

Sales leaders are often caught between the immediacy of addressing unpleasant problems and the long-term complexity of resolving difficult ones. Let's look at a few examples: 

Unpleasant Problems (Act): 

  • Underperformance: Addressing persistent underperformance in team members, especially long-standing employees, can be challenging but necessary to uphold team standards??. 

  • Conflict Management: Handling interpersonal conflicts within the team or between sales and other departments often involves uncomfortable but essential conversations. 

  • Compliance Issues: Enforcing adherence to policies and procedures can feel punitive but is critical for maintaining organizational integrity. 

Difficult Problems (Analyze): 

  • Market Adaptation: Responding to changing buyer preferences, such as the increasing demand for digital and self-service purchasing among Millennials and Gen Z??. 

  • Strategic Restructuring: Re-designing sales compensation plans or revamping the sales process to align with evolving business goals

  • Cultural Transformation: Building a culture of continuous improvement and accountability through effective coaching and leadership development?. 

Leadership hinges on quickly resolving unpleasant problems. They will never become less unpleasant and will likely escalate into systemic issues. Plus, you have more time to focus on the difficult ones that require patience, analytical rigor, and collaboration. By understanding the nature of your challenges and approaching them with the right strategies, sales leaders can create a high-performing, adaptable sales organization that thrives in any market environment. 

Jim Peduto, Esq., CBSE, is the Managing Partner and the co-founder of Knowledgeworx, LLC. Owners and CEOs rely on Jim's strategic thinking and transformational growth expertise to win market share and achieve performance gains. 




POSTED ON: 5/20/2025