The Curse of the Superstar Salesperson Turned Sales Leader

Over the past ten years, I've led the hiring process for about 300 sales roles. Roughly two-thirds of those hires were for salespeople, and a third were for sales leadership.

There's one recruiting error I encounter time and time again, the kind that inevitably leads to failed sales performance.

There’s irony at play here because it stems from rational decision-making. That’s why it’s such a common mistake amongst executives and business owners.

But if you want a best-in-class sales team, you need to be aware of it upfront.

And, by the end of this chapter, you will be. You’ll have the stable foundations required to build a successful sales team.

But, before we get there…

We need to talk about Bill Belichick, Nick Saban, and Pete Carroll

They’ve collectively coached more championship football teams than all other modern coaches combined. What may come as a surprise is the fact that none of them played in the NFL.

In fact, all three had very forgettable playing careers. Nick Saban played defensive back at Kent State. Pete Carroll played free safety at the University of the Pacific. Bill Belichick played center and tight end at Wesleyan University.

So why are these individuals with forgettable playing resumes more successful coaches than their contemporaries?

I can’t relate to their NFL coaching careers, but I can their playing careers based on my experience of being a very forgettable college athlete.

I was a Division III running back at Sewanee: The University of the South. An average football player on a team that produced zero NFL prospects during my four years of playing. At 5’6” and 175 pounds, I was small even for Divison III standards. I lacked the size, speed, and skill to ever become elite.

To compensate and find my own competitive edge, I had to overcome these untrainable deficiencies with other characteristics and skills. I studied the game, good players, and opponents to identify patterns and insights.

That’s what these elite-level coaches did in their playing careers.

No matter how hard Bill Belichick trained, he wasn’t going to get taller. He could train harder than any superstar athlete, but the modest gains he experienced in strength, speed, and stamina would still leave him undermanned versus top talent.

When a good player doesn’t possess superstar talent, they must develop an unrivalled understanding of the game–it's their only hope at competing with the top players.

The best coaches develop a deep understanding of the game because of the hours they spent studying, not playing. They’re crazed scientists obsessed with mastering the fundamentals of the sport.

In his book Mastery, Robert Greene says, “You must understand the following: In order to master a field, you must love the subject and feel a profound connection to it. Your interest must transcend the field itself and border on the religious.”

That profile is completely different from most elite-level players.

Patrick Mahomes is considered one of the greatest quarterbacks in NFL history.

Through seven seasons in the NFL, he’s led the Kansas City Chiefs to six consecutive AFC Championship Game appearances and four Super Bowl appearances since becoming the team's starting quarterback in 2018.

Watching him play, you don’t need to know much about football to know that Mahomes is dangerous on the field – he’s fast, creative, and can make any throw.

Now imagine if the Chiefs were suddenly in the market for a new coach, with Mahomes reportedly the leading candidate to take the role. The Chiefs fans would be outraged, and most of the football world would be left scratching their heads at the decision. It wouldn't make any sense.

Why would you take your star player, in the prime of his career, off the field?

How does moving your best player into a head coach role give the team the utmost chance to win a Super Bowl? Well, it doesn’t.

But that’s exactly what’s happening in sales teams time and time again

C-suite executives take their best sales rep off the field and give them the responsibility of leading the sales team. In a football context, it's easy to understand how this is a bad decision, but many business leaders miss that, for all the same reasons, it's a dumb decision for your business.

Because just as is the case with playing and coaching…

The ability to sell has nothing to do with the ability to lead a sales team

And I mean NOTHING.

I’d even go as far as to say that the very best sales leaders I’ve worked with and coached were average salespeople at best–myself included.

Early in my consulting practice, I questioned why this obvious career path progression wasn't working after seeing so many great salespeople turned sales leaders fail.

Then I noticed that Michael Jordan, Magic Johnson, Peyton Manning, Chipper Jones, Joe Montana, and many of my childhood sports idols left the sport as players and never coached a professional game in their careers.

Why is this? There had to be a good reason.

That’s when I discovered the work of Dr. Sian Beilock

She’s known for her research on the subject of “choking” and has plenty of great insights into why the best players rarely become good coaches.

According to Dr. Beilock, the leading reason is that the great players know what to do but can't communicate how they do it.

“Skilled performers often have trouble putting their actions into words in the first place. That's why those who perform at the highest levels should think twice about teaching their skills to others.”

When your performance flows largely outside of your conscious awareness, your memories of what you've done are just not that accurate. This makes it hard to teach what you know. As you get better and better at what you do, your ability to communicate your understanding or to help others learn that skill often gets worse and worse. It’s the curse of knowledge.

Part of what makes Patrick Mahomes so good is that he isn’t “thinking” about what to do. It comes naturally to him.

The best salespeople have those same kind of natural tendencies too that separate them from the rest of the sales team. Some are obvious, some are not so obvious (more on that later).

Being a great football player rarely translates to being a great coach, and great coaches are rarely superstar players, but what about the exceptions to the rule?

Demeco Ryans is one of those exceptions

He recently demonstrated that he might have the ability to become a great coach after a stellar playing career.

Demeco was the SEC Defensive Player of the Year in 2005 and was drafted in the first round by the Houston Texans. In his rookie season, he was named AP Defensive Rookie of the Year. He went on to play ten seasons in the NFL and was selected to the Pro Bowl twice.

He was a superstar player.

He retired in 2016, and then in 2017, the San Francisco 49ers hired him as an entry-level coach. Fast forward to 2023, and the team that drafted him in the first round as a player hired him as their head coach. What happened?

In 2023, Ryans' Texans started the season by losing their first two games.[40] However, under his leadership, the team clinched the AFC South and made the playoffs by going 10–5 in their last 15 games. They finished with a final record of 10–7, which marked the team's best finish since 2019 and its first division title since 2019.[41] The Texans defeated the Cleveland Browns by a score of 45–14 during Wild Card Weekend, which marked their first playoff win since 2019, and just the franchise’s third playoff victory since 2013.

So, how might Demeco Ryans defy the odds?

Why is it that this superstar player could become a great coach?

Johnny Holland coached linebackers for the Houston Texans, and Demeco played under his leadership.

Johnny saw characteristics in Demeco as a player that would translate to being a great coach when his playing days were over. He says Ryans had leadership qualities that few young players possessed. He was eager, willing to learn, and could retain information better than anyone he had met, let alone any 22-year-old rookie.

Upon meeting him, Ryans told Holland he had a photographic memory.

Holland thought Ryans was just talking. “I didn’t believe him until after the first two or three weeks of practice,” Holland said with a smile. “Everything I’d give him, he could remember. I told him if he comes in (to coaching), he can work with me, and I’m going to show him what he’s got to do,” Holland said. “He took it and ran with it. He did a heck of a job. He was awesome. It’s no surprise what he’s doing now.”

When Holland says, "I'm going to show him what he's got to do", he's speaking to a skillset required of great coaches that has little to nothing to do with being a good football player.

Demeco's success as a coach is not because he was a great player…

It's despite being a great player

Chances are, your top-performing salesperson will struggle and eventually fail as a sales leader.

As part of my consulting practice, CEOs and private equity investors hire me to assess and evaluate their sales teams. Most of my clients are established companies with a history of year-over-year sales growth, an established sales team, a strong offering, and the resources, namely capital, to fuel growth.

But despite their past success, they have a sense of paranoia about the sales team. Growth has slowed and the C-suite is realizing that the game is changing and they need new plays.

I start my process with a series of stakeholder interviews.

I gain exposure to every aspect of the business–sales, product, marketing, finance, and human resources or people operations. I talk at length with every member of the C-suite before I even talk to anyone on the sales team. While each business is different and nuanced, common themes emerge.

The executive team consistently praises the sales team–particularly the sales leader. It's common for me to hear that the sales leader has been with the company longer than anyone else on the sales team, was in the trenches with the CEO or founder in the early days, and knows how to sell their offering better than anyone else, and, wait for it…was once their top salesperson.

During these conversations, I have to fight the urge to just cut to the chase, and tell them the truth they aren’t yet ready to receive. Many of the reasons why their sales team is sub-optimal is because…

They hired Patrick Mahomes as their head coach

It would save me a ton of time and them a lot of money if they were ready to hear this brutal truth. Still, they aren't, so I gently, objectively, and diligently navigate a process that shows them what I already knew–their beloved top salesperson is failing as a sales leader.

My assessments generally reveal that the sales leader can’t replicate their success as a seller with the salespeople under their tutelage.

No one on the current sales team has been able to produce results similar to the leader’s success as an individual contributor. Some of the team's salespeople are far behind the stated goals despite having desirable characteristics.

I always ask the sales leaders how they were so successful as a salesperson, and most of them can’t give me a good answer. “I worked hard, bent over backward for the customer, I just got the deal done.” Essentially, it came naturally to them and they can’t explain “why.”

They were unconsciously great at selling

When I talk to the sales leader about what makes a seller successful on their team, they don’t really know. Despite not knowing what it takes to truly succeed in selling their offering, they all have very confident answers on their ideal salesperson profile. Some give me a list of character attributes like grit, tenacity, likeability, life experience, work ethic, industry knowledge, etc. Some believe their industry has barriers to entry and that market and company knowledge are key selling success factors.

We review the performance of each member of the sales team. The leader assures me that the team is comprised of grit, tenacity, a good work ethic, and all the behavioral characterstics that should result in individual sales success.

Yet, without exception, sales results vary drastically across the team, and the sales leader can’t explain the variances well. Their success as a salesperson hasn’t translated to becoming a successful sales leader because the skills required to become a successful sales leader differ from those of a superstar salesperson.

That skillset starts with having a nose for talent

Once we acknowledge that elite-level salespeople don’t make elite-level sales leaders, we need to also accept the following: building a remarkable sales team requires great coaching, but you can't coach talent. The elite coaches understand this immutable truth.

Most sales leaders don’t realize that the talent truths of sports have the same implications for sales teams. The best sales leaders have learned that it's better to spend time identifying and recruiting top sales talent than developing it within their existing team.

They become dangerously good at identifying the tendencies required for success on their team and then finding these tendencies in talented salespeople.

How exactly do you identify top talent? That's what we're covering in the next chapter.