Sometimes you’re just an unqualified therapist who knows Excel – the emotional side of selling

Understanding the Emotional Side of Pricing: A Case Study from the Sales Trenches

Last year, I experienced a sales call that underscored the essential role of pricing in running a successful business. A familiar restaurant owner reached out to me in a state of distress; her sales had plummeted, her financial records were disorganized, and she was contemplating selling her restaurant while seeking a line of credit—all without having clean financials to present to the bank. As we spoke, I took a step back and allowed her to express her frustrations. In moments like these, you can find yourself playing the role of an informal therapist with a knack for Excel.

For her, the urgency to tidy up her financial records wasn’t merely a logistical requirement; it was deeply emotional. The outcome of this situation would not only determine whether she remained in business but also whether she could exit gracefully if that was her decision. The stakes were incredibly high. In the hustle of assessing and pricing projects, it’s easy to overlook the human element involved. For many small business owners, their enterprises are incredibly personal.

As I reviewed the chaotic financial transactions, I quickly realized that this wasn’t going to be a straightforward cleanup. While I considered her a valued client—having worked with her previously as a serial entrepreneur—I was determined to avoid either shocking her with a high price or underquoting, which could lead to resentment and a lengthy project.

I consulted a simple pricing worksheet I maintain to reflect on my evaluations (available in the comments for those interested) and put together a proposal that came to $4,200. I fully anticipated a negotiation, yet to my surprise, she agreed right away, paid the deposit, and shared that it was the first time in months she felt a sense of relaxation regarding her company’s situation.

This incident reinforced a crucial lesson I’ve learned over time: when clients feel you genuinely understand their challenges and needs, the price becomes secondary. They desire a trustworthy partner to resolve their issues, especially if they are financially capable (which is often the case for established entrepreneurs).

I’ve made the mistake of underpricing similar jobs before, realizing too late that it’s not about the time spent but the value derived from resolving clients’ problems and restoring their control. As seasoned professionals know, tasks rarely take the same amount of time you initially estimate; unexpected issues invariably arise.

Effective pricing is a blend of analytical skill, intuition, and empathy for what the client is experiencing. In hindsight, I could have likely set

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