Why is it so hard to teach sales literacy?

Posted March 3, 2022

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By Serena Miller

Editor, Sales Best Practices at Outreach

Sales is not an easy topic for academics to teach. Just ask Frank Cespedes, Senior Lecturer in the Entrepreneurial Management Unit at Harvard Business School. He has so much sales and management knowledge he could write a book on it — and, in fact, he’s written seven, including "Sales Management That Works: How to Sell in a World That Never Stops Changing." Frank also happens to be the former instructor of our fearless leader, Outreach’s CEO, Manny Medina.

In a recent Revenue Innovators episode, we chatted with Frank about why sales poses such a challenge for academics; the challenges revenue leaders face in a world where continuous change is the norm, and how those challenges have shifted in the past decade. Here are some of the key takeaways from our conversation.

Sales is cross-disciplinary

Sales doesn’t exist in a silo (or, at least, it shouldn’t). There are important relationships that exist between sales, marketing, and finance professionals. Those relationships are even more interdependent as companies gain transparency into buying and selling activities through technology.

In the past, it was enough for sellers to simply meet or exceed their quotas. As long as they consistently delivered the goods, they received a certain amount of autonomy from their managers. And in some cases it didn’t matter how they got there, as long as they did.

Today business buyers evolve at a rapid pace. Influenced by their experiences with consumer marketplaces and leaning into their own technological comfort zones – buyers are more than capable of finding information on their own. And when they do interact with sellers they have high expectations for personalized and insightful experiences.

The best sales model in the world cannot make up for a flawed business model

Back in the day, the majority of Frank’s students wanted to go into investment banking and consulting. He told them — if they were serious about strategy — they had to know something about sales. After taking a hiatus from teaching to run a business that was later sold, Frank returned to teaching and found a new generation with a completely different mindset. Students now apologize if they want to go work for an investment bank or consulting firm. According to Frank, almost everyone wants to be an entrepreneur.

“The problem is they don't understand how important strategy is, ironically,” Frank says. “The best sales model in the world cannot substitute for a flawed strategy or a flawed business model. And so now, I find I have to push them in the opposite direction.”

He also explains that sales outcomes are always organizational outcomes. They’re not simply dependent on the smarts or skills of individual salespeople. They’re also reliant on product, pricing, and market conditions. For example, consider tech firms during the pandemic. Many thrived financially due to the remote work world. For roughly two years, they might have been in demand fulfillment mode, but in the coming months, they’re going to have to go back to really selling again, Frank projects.

People still mistakenly use gut instinct to inform sales strategy

Sales strategy has historically been driven almost exclusively by personal experience and anecdotal information. In many cases setting sales strategy has been more of an art versus a science.

“Sales is by far the most context-specific activity in business,” Frank observes. “Selling software is different from selling capital goods, which is different from selling professional services. It also varies depending upon whom, and where you’re selling.”

For some reason, he adds, executives have felt comfortable making huge generalizations about sales that are usually unsupported by data. Instead, they’re often based on one-off experiences. But it’s a different world today. With top-tier sales technologies in place companies can benefit from having large and accurate data sets that can inform next best actions, support equitable territory design, and provide real-time visibility into the health of deals, pipelines and forecasts.

You have to understand the rules of engagement for other key functions

In most industries, you succeed by becoming a domain expert. Success in sales leadership looks a bit different. To succeed as a Chief Revenue Officer, for example, you need sales literacy, but also overall business literacy, too. You have to be able to interact with other functions, explains Frank.

“That means understanding what they do, speaking their language,” he adds. “Not simply, standing up for sales. Any functional leader does that, but understanding what I would call the ‘rules of engagement’ between sales, product, customers, success, etc.”

Today’s revenue leaders must have overall business acumen to thrive in their role. Specialization is great, but unification is essential to orchestrating a thoughtful customer journey.

Want to hear our conversation with Frank in its entirety? Listen to the full episode “The Preeminent Cross-Disciplinary Topic In Academia Is … Sales?” and follow Mary Shea and Harish Mohan on LinkedIn for more insights.


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