The Education of a Salesperson: A Journey from Cold Calls to Strategic Mastery

The Beginnings of a Sales Career: Learning Through Cold Calls

I started selling when I was 15. I made cold calls for a non-profit. I was not given any training, just a script and a list of phone numbers. That said, I was the only person to win two deals. Before that job, I washed dishes, where I learned the discipline of working. Making calls was no different than washing dishes.

Transition to Recruitment and B2B Sales

A few years later, I joined my family’s business as a recruiter. I was taught that if there were no interviews, I was to call companies and ask them if they needed help. I was working there because I wanted to have time to play music, and eventually I found my way to Los Angeles. To make ends meet, I got a day job in staffing, something I knew how to do. The first time I was provided B2B sales training was in Los Angeles.

Learning Sales Techniques through Role Playing

The vice president of operations was doing the training. As she did role plays, she tried to encourage the salespeople to ask for an order. When it was my turn to role play, instead of asking for an order, I explained how I could handle all of the jobs their current provider was unable to fill. It was my nature at the time to push. After my role play, the VP of sales ushered me into the next room and told me that I was scaring people. My manager laughed, as we were rolling up clients one after another.

Overcoming Personal Challenges and Excelling in Sales

After two brain surgeries, I was back in the family business. The next two years was all sales, where I won some of the largest clients in the city. I had learned to sell in Los Angeles, but much of my success was due to the fact that I was in operations. That experience allowed me to solve my clients’ problems.

Evaluating Sales Training: Finding What Works

The next B2B sales training was run by a trainer who was desperate to be Anthony Robbins. He knew nothing about selling. Instead he tried, and failed, to motivate the sales force. It was easy to see that he was not one of us. This was the first time I saw a sales trainer fail because they lacked the experience.

Implementing Major Account Sales Strategy

By this time, I was the VP of sales. The first thing I noticed was that our average deal size was too low for us to reach our goals. I made a list of companies that spent more than a million dollars a year. There was no reason to win small deals if you could win large deals.

Enhancing Sales Skills with SPIN Selling

To train my team, I paid for SPIN Selling, as Neil Rackham’s work made the most sense to me. I found major account sales strategy more helpful for winning enterprise-level deals. The training was fine, but I noticed some of my team had a difficult time changing how they sold. It seemed easier to have a new or less-experienced rep join an effective salesperson, something that provided access to the sales conversation. This helped to speed up their development.

The Limitations of Linear Sales Processes

About this time, sales organizations adopted a linear sales process. This was supposed to ensure that every salesperson would win their deals by following a set sequence of actions. I adopted this process only to find that the people that won deals still won deals, and those that didn’t win deals still didn’t win deals. This B2B training was a bust.

Developing a Modern Sales Approach

When I started writing this humble blog, I steered clear of conversations about the sales process, which was a religion at the time. My experience allowed me to notice that my contacts had a lot of questions. The linear approach was not designed for buyers and decision makers. It was designed to keep the salesperson on track. This was a time when the legacy approach took hold. I developed my version of the “Why Us” slide deck that is the pride of the legacy approach.

Publishing Insights on Nonlinear Sales Conversations

Eventually, I started to teach that selling is a dynamic nonlinear conversation. Different contacts seemed to need different things at different times. One client in Cincinnati threatened to throw me out if I opened up my laptop to queue up my slide deck.

From Sales Guide to Advanced Sales Strategies: A Series of Successful Publications

The first book I published was The Only Sales Guide You’ll Ever Need. I noticed that there were new competencies, like business acumen, change management, and leading the client, but they were not taught in most sales trainings or described in sales books. I still believe this approach is right for sales forces, and that book will make you a better salesperson.

The second book followed eight months later. Rackham taught me the importance of advancing the conversation, but he didn’t publish the advances, maybe because he believed the sales conversation is nonlinear. The Lost Art of Closing outlines a methodology that allows for a dynamic, nonlinear conversation. This book will make you more money.

My experience in sales was one of competitive displacement. To win a deal in staffing, it was necessary to remove your competitor. My third book was about how to steal your competitor’s clients. Eat Their Lunch is a set of practices that will allow you to win competitive deals and displace your rivals.

My fourth book Elite Sales Strategies is about being One-Up, which is to say you know more about your client’s problems and the decisions they need to make. A large part of this book will help you do better discovery.

Most of us who write blogs and books are sharing our experience of selling. If you want to improve your sales results, you would do well to avoid what is not designed for our evolving B2B landscape. We call the opposite of the legacy approach the modern sales approach.