9 Sales Lessons For Entrepreneurs From a Baseball Pro

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Getting a new product off the ground can leave you feeling a lot like this year’s Red Sox crop of rookies: What was once a season anticipated full of success, has turned to one of scratching and clawing for every personal and team accomplishment.

This scenario can be very similar to what young founders, or rookies,  face when launching a company or product. They’ve incubated an idea (single A ball), got through their first product development cycle (AA ball) and secured a small round of funding (AAA ball). But upon entering the marketplace (MLB), find a whole new level of difficulty when it comes to making sales.

I should know. My time with the Red Sox organization taught me more about sales challenges than any book I ever read on the topic. In the true nine-inning spirit of the game, here are the nine most important sales lessons I learned from baseball:

Related: Lights, Camera, Sell? What Your Sales Team Can Learn from Actors.

1. Get a good pre-game scouting report. While most entrepreneurs do their initial market research and identify target customers before diving into the sales process, many don’t bother learning about what it’s like to sell into a particular industry. The most successful salespeople are the ones who take the time to do this scouting homework. Try to find mentors that have sold into the industry in question to learn about potential challenges, and make friends working inside related industries that can offer you insight into your prospective customers.

2. Be prepared to implement “the shift.” No two customers are the same, and you need to be sensitive during each new interaction about what they’re looking for and what they might consider a deal breaker. Remember to ask probing questions early and often when engaging with new customers, and try to avoid playing out of position as a result of a poor scouting report.

Related: To Win More Prospects, Stop Selling and Start Courting

3. Make yourself a five-tool player. Much like professional baseball players are acutely aware of their offensive and defensive strengths, in sales it’s important to recognize as early as possible what you’re good at and what you need to improve. For instance, if you’re great at establishing an initial meeting, but have a more difficult time closing a sale, you may want to seek out a team member or mentor who is particularly good at closing a sale and see what you can learn from their success.

4. Don’t dwell on the failures. Most likely, you won’t make every sale. But you shouldn’t let a loss get you down – after all, the best hitters in baseball fail two out of three times. Try your best to evaluate why you didn’t close a sale, make an effort to adjust for the next prospect comes, and move on.

5. Have an inning-by-inning approach. Just because you closed your first one or two big sales doesn’t mean you’ll be able to close again without putting in the same amount of time, effort and dedication that got you to your first customers. Stay grounded and don’t forget the things that got you those early wins. Don’t fall into the trap of thinking you can cut corners in the sales process the more success you have.

6. Take your cuts. Swinging and missing is part of the game. Whether you’re making or missing sales, stay motivated by your love of winning rather than fear of losing. Fear will force you to play it safe, tighten up and ultimately not connect with the customer as effectively as possible. If you want to hit your sale out of the park, you have to be willing to put everything on the line and not fear rejection.

Related: Not Closing Sales? Look to These 5 Mistakes.

7. Review your stats regularly. When starting out in sales, don’t be lazy about looking at your monthly, quarterly and annual stats associated with the number of calls made, emails sent, prospects visited and deals closed. Much like baseball stats are invaluable for pro players’ learning and improvement, sales stats are invaluable to helping you see objectively what sales methods are working best for you and what you need to work on to improve year-over-year.

8. Do your part AND rely on your teammates. A successful season for a baseball player is judged by both individual and team performance. Individual sales skills will get you a long way in closing initial deals, but as your company scales, you won’t be able to handle all sales single-handedly. You’ll need to build a sales and support team around you as your company grows and provide them with the resources and training they need to succeed.

9. Make sure to take an “off-season.” Baseball has one of the longest professional seasons, and the off-season is invaluable for resting, reflecting and practicing. You might think as a young entrepreneur that you have to work every waking minute for the whole year. But, if you don’t take time off, more of your sales will likely fall flat. As much as possible, try to step away on weekends and make sure to get the occasional day or week away from the “game.” 

Related: Take Time Off From Your Startup