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3 Sales Career Advancement Strategies From A Professional Baseball Player

Brandon Roberts

March 29th, 2019

sales career advancement from baseball player

Transitioning From Baseball to a Sales Career

In September of 2012, I drove eighteen hours straight through the deserts of New Mexico and Arizona with everything I owned. With Colorado Springs and my professional baseball career in my rear view mirror, I headed to my new life in software sales.

My baseball career ended one level below my childhood dream of making it to the big leagues. People said, “You made it further than most,” but I remained disappointed because I knew at my core that I didn’t give it my all. I didn’t capitalize on the big opportunities or devote myself as I should have.

I spent seven years playing professional baseball at four different levels up to Triple-A. I have now spent an equal seven years in SaaS sales in just as many positions. As I reflect on my successes and failures as a baseball player, I have identified a few things that I wish I would have done differently. The lessons I learned from my mistakes in baseball have paved my path in sales and operations. Now, I’m applying career growth strategies I didn’t know as a young ballplayer.

3 Career Advancement Strategies for Salespeople

1. Have Tough Conversations With Your Boss

After a terrible first month in the 2009 season, I remember being benched and wondering: How many games I would sit out? Why is that guy starting instead of me? When would I get another shot?

Even with all these questions, I never sat down and had an honest conversation with my manager. It would have gone a long way for me to say, “I know I had a bad April, but I was an All-Star last year. What do I need to do to get back in the lineup?” Instead, I just waited to see when he would put me in. Every day, I came to the ballpark to see my name left off.

What was I afraid of? If I would have uncovered his perception of me, I could have addressed how I was falling short and how to get back in the game.

Communication is key to understanding where your manager thinks your gaps may be and what you need to accomplish to get what you want. If you think your boss wants you to make more dials, you would pound the phone. However, what if they wanted you to help mentor some of the new hires on the team? You would be completely missing the mark on what they wanted to see for a promotion.

Make a point to understand the gaps your boss sees and how you can improve to get to the next level, even if you do not agree. Even if you’re just a little unsure of the expectations, clarify them with a candid conversation.

Your boss submits you for promotion, just as baseball managers write the lineup card. It ultimately lies in their hands.

2. Study the Success of Others

Even though every hitter has a different style, the same core principles of a swing should be replicated. I only analyzed my swing when I played. I didn’t compare myself to the big league batting leaders. I told myself, “this works for me. It makes me unique.” I should have modeled it after what had been proven to generate success. Now, I catch myself before I say the same thing in sales.

You do not need to mimic others exactly, but you do need to spend more time analyzing and observing successful salespeople. Take the time to shadow the people in your organization that are the top 5-10% on the leaderboard. What are the things they do differently that sets them apart? Reach out to them and ask for a conversation. You will be surprised at how many are willing to help. The hardest part will be to drop your ego and actually practice the things they do differently. Don’t be embarrassed, try something new and fail forward.

3. Maximize Confidence

In baseball, I had a very realistic point of view which made me very self-aware of my capabilities and weaknesses. I remember facing a hard-throwing lefty reliever late in a game and thought, “I only have a 20% chance of getting a hit off this guy, so I don’t have too much to lose.” Although this way of thinking controlled my emotions and calmed me down, if I had used more confident self-talk, I would have been more motivated and increased my chances of getting a hit.

I saw so many players have misconceptions about their abilities and inflated self-perceptions and it drove me nuts. I called it false confidence because they truly believed they were the best hitter in the league, even when their average sat in the low .200’s. I couldn’t understand why they were so blind to their current performance. At the time, I didn’t know the powerful phrase, “You are what you think you are.”

I watched many of those players make it to the big leagues. Their mindset became their strongest asset that allowed them to continually compete at the higher ranks. You can choose to be confident. I misjudged those players because they were setting themselves up for success.

Make the choice to have a confident mindset that can weather successes and failures. Here are some ways to reinforce confident behaviors and thoughts:

  • Envision yourself operating at the next level and fulfilling future goals.
  • Write down some positive self-talk notes about your strengths and past successes that you can reference daily for repetition.
  • Practice positive mental imagery before any cold call, product demo meeting, or onsite presentation. Visualize yourself having success in those particular events and getting good feedback from the prospect.

These simple and quick tricks will boost confidence immediately and set you up for success.

Endings are Beginnings, Mistakes are Lessons

My baseball career ended before I achieved my dream of playing in the big leagues. This failure is my motivation to learn from those mistakes and apply the lessons to ensure future success in my new sales career. Hopefully, you can use these strategies and will never have to experience driving through eighteen hours of desert filled with the feeling of lost opportunity!

About the author

Brandon Roberts

Brandon Roberts currently runs sales operations at MINDBODYand has previously held various sales, sales leadership, and operations roles. He thrives on figuring out how to drive sustainable revenue and hit revenue targets. Prior to MINDBODY, Brandon spent 7 years playing professional baseball for the Twins, Reds, and Rockies where he learned to embrace a mindset of practice and continual improvement.

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