05 Aug THE MOST IMPORTANT SURPRISING LESSON I LEARNED IN SALES
What Surprised Me Most About Sales
I have been asked this question many times over the years, and it has never been easy to answer. After more than three decades in enterprise sales, sales leadership, and executive management, I have learned countless lessons. But because the question asks what surprised me most, one experience stands above the rest.
I entered sales in an unconventional way. I was an accountant for a major hotel chain and had recently passed the Certified Public Accountant (CPA) examination. My career path seemed well defined, and I had no intention of leaving the accounting profession.
Then an unexpected opportunity changed everything.
An applications software company offered me a sales position. I had recently led the implementation of its Fixed Asset Accounting System and knew firsthand that it was a superior product. I believed in the software, respected the company, and decided to take a leap of faith. Despite having a secure job, an excellent manager, and a promising future in accounting, I moved my family back to Chicago to begin an entirely new career in sales.
I started with absolutely no formal sales training.
What I did have was confidence. I understood the product in depth, knew how it solved customers’ problems, and was convinced it was the premier solution in the marketplace. I could explain its value, demonstrate its advantages over competing products, and answer virtually any technical or accounting question a prospect could ask.
I assumed that would be enough.
Fortunately, I quickly learned that successful selling requires far more than product knowledge. Building relationships, asking insightful questions, uncovering business issues, understanding buying motivations, navigating organizational politics, and earning trust would become just as important as understanding the product itself.
Another surprise came as my career progressed.
Large versus newer mid-sized manufacturers
Early in my sales career, I primarily called on mid-sized manufacturing companies throughout the Midwest. As I became more successful, my responsibilities expanded to include Fortune 500—and eventually Fortune 50—organizations.
I expected these global corporations to be the gold standard of business management. I assumed they would employ the most talented executives, embrace the newest technologies, analyze opportunities objectively, and make well-informed decisions quickly.
Instead, I often found exactly the opposite. There was often an inverse relationship between the size and age of the company and how well it was run by its management.
Many of these large organizations were burdened by bureaucracy, layers of management, internal politics, biases towards long-established practices, and decision-making processes that moved at a glacial pace. Long-tenured executives frequently preferred maintaining the status quo over taking calculated risks. Many in management were in their positions because they had been with the company for decades.
Even when significant operational problems were obvious, and the financial justification for change was compelling, many organizations delayed making decisions for months—or even years.
What surprised me most was not their lack of intelligence. Many employed brilliant people. It was their reluctance to act in a timely manner.
Too often, they chose temporary workarounds instead of permanent solutions. The cost of inaction was frequently greater than the investment required to solve the problem they knew existed, yet “doing nothing” remained the safest political decision. They lacked the initiative to act. And they seemed comfortable with remaining with the status quo. The effect of this was demonstrated by the complete takeover of the automotive and motorcycle industries in the 1970s and 1980s by Japanese manufacturers due to the American companies’ inability to quickly respond to the changes in market shifts and fix quality issues.
Ironically, many of the mid-sized companies I had called on earlier in my career behaved very differently.
The mid-sized manufacturers were far more adaptive to change
They were leaner, more agile, and far more decisive. Their executives typically understood the financial impact of delays and were willing to make timely decisions that improved productivity, reduced costs, or created competitive advantages. They often had younger leadership teams who welcomed innovation and viewed change as an opportunity rather than a threat. They disdained the status quo.
The physical environment reflected these differences.
Many of the older, established corporations featured elegant wood-paneled conference rooms with massive tables seating twenty or more people. Traditional artwork, rich furnishings, and executive décor projected stability and history.
The newer, faster-growing companies were far less concerned with appearances. Their conference rooms were simpler and more functional, equipped with the latest collaboration tools, presentation technology, and communication systems. They invested less in impressing visitors and more in enabling employees to work efficiently and make decisions quickly.
Over time, I realized that an impressive headquarters, beautiful conference rooms, or a famous corporate name tells you very little about how well an organization actually operates.
Some of the world’s largest companies struggled to make relatively simple decisions.
Many much smaller companies consistently outperformed them because they moved faster, listened to customers, embraced change, and empowered people to act.
That was the biggest surprise of my sales career—and one of its most valuable lessons.
Success is rarely determined by the size of the company. More often, it is determined by the speed, courage, and willingness of its leaders to make decisions.