Win The Hill! - What Makes Great Salespeople


What makes GREAT salespeople and sales leaders? While I would love to say that there is a simple formula for success, when it comes to identifying talent, there’s not. Over the last ten years, I have had the opportunity to observe some amazing salespeople across a broad array of industries and companies, ranging from Fortune 500 manufacturing distributors, and mid-market energy companies to technology startups. My career, so far, has taught me there is no magic formula. However, when you are in the presence of a great salesperson and see them practice their craft, you know.


So, how can you tell if a salesperson has what it takes to be GREAT? Well, in short, they “Win the Hill.” I was a decent runner in high school, and while many things make runners successful, these four principles below are universal. As a sales leader, these same principles are also consistent in great salespeople.

1. Love to Compete: Great runners and salespeople love competing, and the competitive mindset and internal drive are key to their success. This keeps them going mile after mile or “No” after “No”. Sales can be a lonely sport, and you must enjoy the “Yes” so much that it gets them through the miles of “No’s.”

2. Make the last mile the best mile: Mentally, whether running, selling, or leading a sales organization, it is way more fun and motivating to be passing people versus just holding on. This positive momentum can have a multiplying effect on sales and produces the best performance. It also sets an energizing tone for your team.

3. Run through the finish line: This is about self-accountability. When you finish a race, you know whether you ran through the finish or let up at the end. In sales, you know when you leave a meeting or finish a year, whether you gave it your best. Running through the finish line keeps you accountable to yourself!

4. Win the hill: This is a big one. This separates the good salespeople from the great ones, the salespeople that sprint up the hill and look at challenges as opportunities. These individuals are special. Winning the hill often leads to a significant competitive advantage in the minds of the customer and pushes you way ahead of the competition.

Coach Gower, my high school cross country coach, would sit at the bottom of the biggest hill on the course and yell, “Win the Hill.” I loved it. When challenges come my way, I still hear him yelling, “Win the Hill!” From a coaching perspective, he wasn’t at the bottom of the hill just to cheer us on but to see how everyone responded.


Many other skills make salespeople great. You might have something special when you see these four core principles. Who knows, maybe sales recruiters will start showing up to cross-country races, watching racers run up hills. I have tagged some of the great people in my career that have demonstrated these principles.

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Win the Hill!