Become a Student: Mastering Sales Through Lifelong Learning & Why I'm the Best I've Ever Been at Sales at 45 (Excerpt from "The Show Must Go On")

The Show Must Go On, AVAILABLE NOW! serves as the comprehensive follow-up to Salesman on Fire : an extensive guide on sales strategies, personal development, and leadership.

It provides insights into building a successful sales career, overcoming obstacles, and achieving personal and professional growth en route to the story of how LinkedIn, AI and a Moneyball approach to sales has generated over $1B in revenue.

Carson V. Heady discusses the significance of personal branding and how it can differentiate a salesperson in a competitive market, the role of a leader in fostering a collaborative and empowering environment for team members, strategies for dealing with setbacks and failures, and methods for effective prospecting, including leveraging social media, AI and personalized messaging to connect with potential clients.

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Be a Student

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Sales – like life and career – is a never-ending pursuit of growth, knowledge, and self-improvement. No matter how much success you've had in the past, every day is a new challenge, and there's always something more to learn. That’s the mindset I’ve embraced throughout my career, and it’s what has allowed me to continue evolving and staying relevant and staying at the top of my game.

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Some of the greatest lessons I’ve learned in sales didn’t come from my successes—they came from experiences that did not go my way and unexpected failures, like deals that went sideways. There’s immense value in doing a post-mortem on deals that didn’t go the way you expected and analyzing situations where you had blind spots.

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Why didn’t it close? What went wrong? What could I have done differently?

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The pain of losing a deal often teaches you more than the joy of winning one. It gives you insights into the process, the customer, and most importantly, yourself.

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In sales, there are so many variables that are beyond your control—changes in leadership, shifts in priorities, economic fluctuations. But there are also key elements you can control, and it’s those controllables that will make or break your success.

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First and foremost, you control your mindset. Your attitude, your preparation, your level of curiosity—these are all within your sphere of influence. If you approach every deal with a commitment to add value, to listen actively, and to stay focused on the customer’s goals, you increase your chances of success exponentially.

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You also control how you communicate. I always recommend using the customer’s own words to frame the conversation. If they told you that a certain milestone was crucial, remind them of that in your discussions. If they mentioned budget constraints, acknowledge that and work within those parameters, or look for other lines of business who might also have budget. It shows that you’ve been paying attention and that you’re invested in their success.

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Finally, you control the consistency of your efforts. Sales isn’t about one-off wins; it’s about showing up day after day, building relationships, and delivering value over time. Success is a byproduct of perseverance and discipline. Just like a coach in the middle of a game, you may need to tweak your strategy or adjust your approach, but you don’t abandon the fundamentals. Stay the course, and the results will follow.

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I’ve had the privilege of working with some of the best salespeople in the world, and the one thing they all have in common is that they never stop learning. They stay curious, they stay humble, and they never assume they have it all figured out. That’s what makes them great, and it’s what I strive to emulate every day.

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In sales, you’re never truly an expert. There’s always a new technique to learn, a new challenge to overcome, and a new customer to understand. But that’s what makes this profession so exciting and rewarding. If you commit to being a lifelong student of sales, there’s no limit to what you can achieve.

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Embrace the uncertainty, lean into the challenges, and never stop learning. Because it’s in those moments of discomfort and growth that you’ll find your greatest successes.

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When I describe myself in podcast episodes, I often convey that I view myself as a lifelong student of sales.

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When I think about where this concept originated for me, two distinct places emerge: (1) Michael Jordan and his talking about being a student of basketball and (2) my favorite sales movie, The Color of Money, where Fast Eddie Felsen talks about how all the greats are students of human moves.

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It’s pretty fascinating to reflect on the evolution of my mentality of a seller, comparing my approach in my 20’s and 30’s to that of my 40’s.

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When I started out, I had success due to sheer drive, competitiveness and relentlessness.

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I chased a deal on every call and was creative, opportunistic and persistent; not to be confused with rude or unethical with customers, as some were, but I looked for every single approved way to make a sale on every call. I conquered the inbound call center game and was unbeatable as a rep and sales manager due to perfectionism and freakish drive to be the best.

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Each time I was promoted or made my way into a new foray – whether moving to an inbound call center I wound up running or to retail division leadership, a consultant firm or to technology – I wondered if I could actually, legitimately sell. There is so much of sales that is also uncovering the loopholes or the game within the game: how to master the metrics that matter or get you paid. Was I a good salesperson, or was I just a master of manipulation of the playing field? Or, hopefully both.

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Whether it was phone packages or buying people out of cell phone contracts before that was a thing to advertising bundles to hardware and software, there was always some element of game within the game that also had to be mastered.

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Being an excellent salesperson matters, but sales excellence is about far more. It’s about being a student of how to strategize and execute in the most impactful ways.

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There are a number of ways to sharpen your sales axe and master your craft. When I was younger, I almost scoffed at the concept of reading sales books – I felt like I didn’t need it or it wouldn’t apply. Now, I voraciously read and consume books in physical form in my hands, on my Kindle and via Audible constantly. There are typically 3-to-5 going simultaneously to adjust for my shifting moods or preferences – often at least one on career or leadership, one fiction, and one nonfiction. Do I want to be motivated today? Do I want to study a famous leader? Or do I want escapism?

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Podcasts are another thing that took a while for me to latch onto; now I love listening to the podcasts from some of my sales heroes.

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What changed for me? It was the illuminating, eye-opening realization that I knew relatively nothing. That my own frame of reference was limited and narrow.

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When I re-read my first book 5 years after it was first published, I realized a lot of what I had felt about sales and leadership in my 20’s had rightfully shifted, prompting me to re-write and re-release a special, updated edition. I also attribute this to what Winston Churchill deemed, “new facts.” The infamous British Prime Minister changed political parties twice and changed his mind frequently, but always in light of new parameters that shifted the landscape.

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I’ll use Michael Jordan’s career as an example. I loved watching the golden era of NBA basketball that was the 80’s and 90’s. Personalities and rivalries that were larger than life – there were the Bulls, Pistons, Lakers and Celtics, the Jazz, the Pacers, the Magic. There was MJ, Magic, Larry Bird, and then Shaq and Kobe.

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Jordan amazed me, but not just because he was the greatest basketball player of all time. He was also the greatest competitor of all time. It was all about winning for him. He was constantly taking on new elements to his game, learning to better utilize his teammates, and tasking coach Phil Jackson with giving him challenges to keep him engaged – be it to garner more assists or rebounds or master new statistics.

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Jordan left at the peak of his game, which few do in sports; Barry Sanders comes to mind, as well as Sandy Koufax, Jim Brown and Rocky Marciano. He tried his hand at baseball, which had been a lifelong dream of his and his late father’s, and had it not been for a player’s strike he would have made the Major Leagues. Then he came back to the NBA and won 3 more championships before leaving again. He later returned, content to be a sixth man on a team he served in operations, and played 2 more years, returning to the starting lineup and scoring over 20 points per game in his early 40’s to nearly take a cellar-dwelling team to the playoffs.

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I won’t compare my athleticism to Jordan’s, but will compare my drive and will to win. Jordan, and later Kobe Bryant and others, regarded themselves as students of the game in their approaches and quests for improvement and excellence. It was one thing to be great ball-handlers and shooters and quite another to be able to take over a game, to get into the heads of your opponents, to modify your game or your body to better take on a specific team.

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In every role I’ve been in, I’ve studied what works and figured out how to replicate it, studied what doesn’t work and figured out how to jettison it or tweak it so it does, and used the results and outcomes to diagnose the process so I can create a better one. The approach has never failed.

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Even coming into technology at age 35 surrounded by 20-something’s, I was content at first and fully expecting to be a sixth man. I needed a job and benefits and it paid well; I had rebuffed the recruitment efforts made to me at first because I had been slated to start at a massive company I had originally turned down, only to have the role never come available. Remember – nothing’s in the bag until you get paid.

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Fortunately, when I went back to the guy trying to recruit me, their runner-up had backed out and I moved back into pole position.

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It felt like everyone around me was speaking a different language. While I was ferociously scrambling to just contribute at first, once I got the hang of it and the taste of winning, it became about results. Results beget the desire to maximize and optimize those results, and then it became about staying #1. We were #1 in the world 8 quarters in a row which, in hindsight, was unbelievable and unprecedented.

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It's important to point out that this domination was not the original goal – understanding all of the variables in place, creating and executing strategy, and course-correcting amidst each and every change was. You don’t set out to build a dynasty, but it becomes possible when you build strong leadership, play on everyone’s superpowers, and are able and willing to adapt and pivot when needed.

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Learning is so central to everything now. A great seller who worked for me in recent years suggested we add a segment to our weekly team calls called “What are you learning?” We go around the horn where members of the team can share what they learned the week prior – a new internal resource, a podcast, a documentary. Anything they learned from that made them better.

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I’ve learned the value of creating and nurturing a learning culture; shining a light on those who are winning or whose unique strengths can benefit the many.

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Mentors are another great source of learning. Seeking out people who you look up to, who are doing what you ultimately want to do or who are doing well at something you want to improve in can all be great ways to locate mentors. Furthermore, you will ideally have a litany of mentors who serve you for various time periods in different ways; don’t feel compelled to think that every mentorship needs to be formalized or forever. You’ll be drawn to people who can improve you and be honest and candid with you; if their feedback isn’t constructive and designed to make you better, you need more.

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For many years in my career, I thought I was just a man against the world; I had managers who were either intimidated by my prowess or simply weak and unable to better me. I worked for unethical nightmares and incompetent bozos. My problem back then was I did a poor job of playing the politics. However, I was also na?ve to think I did not need mentors at the time.

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Looking back, I would have greatly benefited from someone helping me hone my skills and better play the game. I did not realize what I needed until it was too late in some ways, but in others it’s never too late. Because we are always a work in progress, we can always keep adding new skills, acumen and experiences that make us better and better.

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Mentorship has played a significant role in my development. Transitioning from an individual contributor to a sales leader, I initially lacked formal mentors, hindering my understanding of teamwork and consensus-building. Intentionally seeking mentors who provide candid feedback has been transformative, helping me become a better leader and team player.

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Another crucial aspect of my learning journey is self-improvement. Incorporating insights from time management, organization, and mindset mastery has enhanced my day-to-day efficiency. Studying the mindset of successful individuals, including sports legends like Michael Jordan and coaches like Phil Jackson, has been a source of inspiration.

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In the realm of mindset mastery, I delve into books that explore mindset, winning, leadership and motivation – from business to athletics. Additionally, recommendations from mentors guide me towards valuable reads, ensuring a holistic approach to personal and professional development.

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Seeking learning intentionally and proactively is the catalyst for perpetual improvement.

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