The Emotional Landscape of Pricing in Sales

In the world of sales, the art of pricing is crucial—an insight I was reminded of during a recent call with a distressed client. Late last year, a restaurant owner I had previously collaborated with reached out in a state of panic. Faced with declining sales, disorganized financial records, and thoughts of selling her business, she was applying for a line of credit without clean documentation. As we spoke, I allowed her the space to express her concerns, employing a strategy I often find effective: sometimes, you just play the role of an unqualified therapist who happens to know a thing or two about Excel.

For her, tidying up her financial records was not merely a logistical step; it was an emotional lifeline. Her business represented more than a source of income—it was her passion, her future, and the possibility of either continuing her entrepreneurial journey or extinguishing it. In the hustle and bustle of pricing proposals and adjusting numbers, it’s easy to overlook the human element on the other end of the line. For small business owners, their ventures are often deeply personal.

As I assessed her financial situation, I realized the extent of the work required. Her records were tangled with personal expenses, and given the urgency of her situation, I knew this wouldn’t be a simple task. I didn’t want to overwhelm her with shockingly high prices, especially since she was a repeat client—a seasoned entrepreneur I respected and enjoyed working with. At the same time, I had to ensure I didn’t undervalue my services, risking a labor-intensive project that could sour our working relationship.

Using a straightforward pricing worksheet I often rely on to evaluate my proposals (I’ll share a link in the comments for anyone interested), I drafted a proposal for $4,200. To my surprise, she accepted immediately and secured the deposit. For the first time in months, she expressed a sense of relief when discussing her company’s plight.

This experience reaffirmed a principle I’ve encountered time and again: when clients feel genuinely understood and their pain points are acknowledged, pricing often becomes a secondary concern. They’re seeking someone they can trust to resolve their issues—especially when they have the means to invest in solutions.

In the past, I’ve undervalued projects and learned through experience that the time required is often unpredictable. The true value lies not in the hours spent but in the resolution of the client’s challenges and the restoration of their control over their business. Additionally, it’s