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Advice for Your Younger Sales Self
Blog / For Sales Pros / Feb 7, 2021 / Posted by Brian Sullivan / 2131

Advice for Your Younger Sales Self


I’ve always been an avid reader of selling books and today, electronic media has dramatically increased our ability to stay sharp through books, posts, blogs, and the like. No excuse for being uninformed. But truthfully, my most impactful sales knowledge has come from real experiences, real colleagues, and real clients. Hold that thought and ponder some country music. Many are likely familiar with Brad Paisley, country superstar, who wrote and performed “Letter to Me”. In the song, as an adult, he offers guidance to himself as a 17-year-old in areas like relationships, education, and other challenging topics. He provides practical advice like “I wish you’d study Spanish” and “I wish you’d take a typing class”….you get the point, I’m sure.

And you probably see where this is headed. What if we, as experienced sales professionals, wrote letters to our young selling selves, offering wisdom gained from years of successes, failures, and hard-earned lessons? How about that for a premise?

In my selling career, I’ve been blessed to get to know countless people over the years – colleagues and friends. Birds of a feather, as they say, flock together. And while that’s true of all professions, I’ve found that the adventure of selling promotes more collegiality and friendship than other more “traditional” occupations. Selling, of course, is not for the faint of heart. And for that very reason, it forges bonds and experiential badges of honor. From my amazing days at Xerox, Capgemini, Sandler, and now in consulting, I’m grateful to have gained a large selling flock of people whose experiences have taught them and changed them. Their lessons learned, in many ways, have made them who they are. I thought, how valuable would it be to assemble from this dynamic group of people the guidance they would candidly share with their young sales selves? And so, I asked them.

Contacting a few hundred of my selling friends and sharing the “Letter to Me” theme, I requested two insights that they would give to their younger selves. Counting on the fact that salespeople love to talk, I was confident that my ask would generate a high volume of responses. And it did. But I was surprised at the number of folks who requested time to ponder the topic in the interest of providing truly meaningful feedback. Yes, the flock took it seriously.

Before I share the most popular response, I must note that, while the respondents represent a diverse selling universe, they are all connected to me. So, to broaden the perspective, I’ll be widening my request shortly. Stay tuned for more on that in a moment.

Responses came from hundreds of sales professionals globally, representing different verticals, business models, selling strategies, and customer bases. And what advice did they most often offer to help their younger sales selves be more successful and to sleep more soundly at night? What was the most common gem of wisdom? A prospecting tip, a closing technique, an account growth strategy? No. It was to listen. Just listen. And there was a great deal of similarity in the context of the responses. Those who live and grow in the sales arena learn the same lessons from the same types of experiences. And beyond the listening, there were six bits of advice cited most often – a Top Six, if you will. And my plan is to share more in future articles so we can all continue to grow.

Let’s focus, though, on the #1 choice – listen. As you might guess, much focus on this top tip highlighted how doing it well increases your chances of learning, especially when the customer is talking. And huge importance was repeatedly placed on the critical connection between listening and understanding. “Understand”, it was shared, is an active verb, driving the exploration that earns you the right to know whether or not you can help a prospect address their pain. Without it, you’re flying blind. With it, anything is possible. And with it, younger selves were promised, your chances of success in selling are greatly increased. For that matter, as was often mentioned, so too are your chances of success in life. Like I said, they took it seriously.

As mentioned, there’s more to come on what I hope you find an interesting and valuable initiative. And to widen the perspective, I invite all of you involved in sales to participate. Follow the theme, thinking of your younger sales selves and decide on your two pieces of advice. Then share them at or directly to me via LinkedIn if you prefer. And stay tuned for more as the learning continues for us all.

About Author

Brian Sullivan is a best-selling author, consultant, and enterprise selling expert. He spent eight years at Sandler Training, developing and growing the Sandler Enterprise Selling Program on a worldwide basis. Prior to Sandler, Brian was in sales, sales management, and P&L management positions with The Capgemini Group for thirty years.

Author's Publications on Amazon

The comprehensive 6-stage selling program from Sandler Training-- "Top 20 Sales Training Company" by Selling Power Magazine Competitively pursuing large, complex accounts is perhaps the greatest challenge for selling teams. To keep treasured clients and gain new ones, you need a system to win business…
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Comments (3)


Ewuola Opeyemi commented...

this is a great automizer, i love it


Busola Florence Ojewale commented...

this is great!!! this article taught me alot.


Dennis Wise commented...

Great Insight! Am definitely doing a letter to my younger self!

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