3 Lessons for Sales Reps Who Want To Maximize Productivity and Learning


One of our guiding principles at Drift is to “always be learning”.


To make sure we actually practice what we preach, our incredible Office Manager, Ashlyn, put together the official “Drift Library” in our Boston headquarters. Every book in that library is handpicked by a Drift employee. And for every book someone selects, he or she needs to write a few words on the inside cover about why it means so much to them.

Last week it was finally my turn to make a contribution. So naturally, I looked for inspiration in my past to pick a book that had a significant impact on me and my career.

What did I choose?

For anyone who knows me personally, the following won’t be a revelation: I’m a huge admirer of President John F. Kennedy.

Now, I know what you’re thinking–“Wow, an Irish-Catholic kid from Boston is a fan of JFK?” Shocker, I know. But for that reason, I chose Thirteen Days, Bobby Kennedy’s memoir about the Cuban Missile Crisis, and the tension-filled days during October 1962 when the United States and the Soviet Union teetered on the brink of an all-out nuclear war.

As I was jotting down a few words about the impact the book had on my life, I began thinking about the parallels between the Cuban Missile Crisis and working in sales. This and the recent release of Drift For Sales got me thinking about one thing:

What lessons can we sales professionals learn from this incredibly important moment in United States and world history?

Lessons that don’t simply make us better sellers, but more effective overall communicators, be it in a business context or an entirely different one.

At this point in time, I imagine you’re probably asking yourself some version of this question:

“How the hell does Kelliher think he’s going to make a connection between avoiding nuclear war and selling a SaaS product?”


Frankly, I don’t blame you for thinking that.

But my old man, Jim Kelliher, always taught me to look for lessons everywhere — particularly throughout history, and to see how those lessons apply to my life.

So, what are the three big lessons we sales professionals can take away from the events that unfolded in October 1962? I’ll get to those in a minute — first, an ultra-quick history lesson about what actually happened back then.

The situation: On October 14, 1962, an American U2 spy plane making a routine high-altitude pass over Cuba discovered several Soviet medium-range ballistic missiles being assembled. This presented an incredibly large and urgent problem for Kennedy and his team. These missiles were being assembled only 90 miles off the coast of Florida, and if they were to become operational would be capable of striking nearly any major city across the United States — including Washington, DC.

But there was another element of danger: the mere presence of those missiles in Cuba drastically weakened the position of the United States in the ongoing nuclear rivalry with the Soviet Union.

The end goal was simple: get those missiles out of Cuba.

Looking back on that period of time, the way JFK handled the situation showed me the importance of three elements that, to this day, I use everyday as a sales pro.

#1 – Always learn from your past mistakes (i.e., lost deals), and use those mistakes to win more deals in the future.

The Bay of Pigs was a secret CIA mission that Kennedy inherited from President Eisenhower only three months into his term, but what unfolded during that time would impact his decision-making for the rest of the time he was in office.

The operation called for a group of Cuban exiles — trained and equipped by the CIA — to lead an invasion of Cuba. If all went according to plan, the invasion would ultimately lead to an anti-Fidel Castro uprising on the island.

From the outset, Kennedy was worried that it would become public knowledge that the United States was behind the invasion and view it as an act of war. The CIA ensured Kennedy that they would be able to keep American involvement a secret.

But, as we all know, the Bay of Pigs was a complete disaster.

It made no impact at all in Castro’s power, and worst of all, it did in fact become public knowledge that the United States was behind it all along.

What did Kennedy learn?

That he couldn’t simply listen to and rely on the CIA and his military advisors. Fast forward to October of 1962, and Kennedy was advised again by military advisors that the only answer to Cuba is force. His advisors called for an airstrike on the island to destroy nuclear missile sites. But Kennedy, learning from the Bay of Pigs fiasco, wouldn’t make the same mistake again.

So, what does all of this have to do with sales?

Like most sales reps, I’ve lost hundreds of deals over the course of my career — if they’re being honest, most other reps will say the same. Sometimes deals are lost for reasons that are simply out of our control. But in other situations, deals are lost because of something we’ve done wrong in the sales process: Maybe it was poor discovery. Maybe we didn’t lock up next steps after a call. Maybe we jumped into a pricing discussion too soon. Or maybe we didn’t ask about how their legal, security, and procurement processes work.

Regardless of why a deal is lost, there is always something we as sales reps could have done better. And when we lose a deal (and even when we win a deal), it’s an incredibly helpful exercise to reflect on what went wrong and figure out how to improve.  

This is helpful for one simple reason: History will likely repeat itself.

Makes no mistake — we will find ourselves working a deal in the future where a problematic scenario from the past pops up again. Then, we have two choices: Make the same mistake again, or like Kennedy, take a better course of action.

#2 – Avoid consensus and groupthink.

Managers and fellow sales reps always have a ton of insight to share when I face challenges working a specific deal. A good manager can coach you, and show you how to avoid common pitfalls when trying to close.

That said, when you’re working a deal, there’s really only one person that knows the ins and outs of it completely, and it isn’t your manager.

It’s you.

This is why: It’s rare that a manager or another sales rep has the full context of what’s happening with a specific deal. For this reason, the right course of action may seem clear to them — offer an incentive, tell them about this feature, or some other recommendation.

How many times have you heard, “Why don’t we just tell them we can discount 10% if they sign this week?”

While this may actually work some of the time, most of the time, it doesn’t. But you can’t blame a manager for saying this — he or she may be juggling the exact same scenario across a team of 8, 9, or more reps. A manager can never have the full context on every deal his or her team is working. Ultimately, it’s up to the rep to own it, and make the decision about how to drive urgency and do what’s right for customer.

When Kennedy was told by nearly every single member of his team — including his military advisors — that the United States needed to call for an immediate airstrike on the Cuban missile sites, they didn’t have the full context. They were thinking about the problem from one very biased point of view. Kennedy knew this.

He also knew an airstrike could lead to a nuclear exchange that would put millions in harm’s way. While he considered their opinions, and thought deeply through all the options, he ultimately had the courage to take the action he believed to be right, implementing a blockade of Russian ships coming in to Cuba. No airstrike.  

The lesson?

If you’re a sales rep, you need to consider advice from managers and others on the sales team. But in the end, you’ve got to trust your instincts, and then take the action you believe to be right. Others may disagree with you, but if you’ve truly give your decision the thought and analysis it deserves, that shouldn’t matter. Act decisively.

#3 – When in a negotiation, think ahead and always consider the impact your potential actions could have on the customer.

For me, the most fascinating part of the Cuban Missile Crisis was President Kennedy’s ability to put himself in the shoes of his counterpart, Premier of the Soviet Union, Nikita Khrushchev.

In what has to be the most pressure-packed moment faced by any American President, Kennedy had the presence of mind to consider his counterpart’s mindset before making a decision. Facing similar pressure to Kennedy, Khrushchev would have no choice but to respond aggressively if the United States launched an airstrike on the missile sites in Cuba. He’d feel like he was being backed into a corner — and that could’ve provoked a nuclear response, or perhaps the seizure of Berlin.

Kennedy understood the potential outcomes, and decided against an airstrike, instead enforcing a blockade of Soviet Union ships, which prevented them from arriving in Cuba. Kennedy was giving Khrushchev a chance to save face.

As sales reps, this story serves as an important reminder to always consider the repercussions of the actions we take. For this reason, we must always consider the position and mindset of our customers and prospects before we act.

If we tell a customer that a price expires at the end of the week or month, for example, are we actually helping our customer get that deal done? Or are we potentially putting our customer in a bad spot and forcing them to go back to key stakeholders and appear weak? As sales reps, we must always ask ourselves whether we’re making our customer look good, or if we’re backing them into a corner just to get a decision.

What The Bay of Pigs and Being A Sales Rep Have In Common

After the Bay of Pigs invasion, Kennedy learned that he couldn’t always rely on the CIA and military advisors to guide his decision-making processes in world affairs. He learned that sometimes, those perspectives are secondary to the context-specific info a president has on an emerging situation.

To this day, I apply this lesson to my work as a sales rep.

I understand that while extremely valuable, the perspectives of my colleagues are just a piece of the puzzle. I’m the one who’s closest to the prospect or customer in a deal. And ultimately, I’ve got to act decisively with the info only I have, and be confident in that decision — no matter the outcome.

This lesson takes on even more significance at a place like Drift, where staying close to the customer isn’t just a saying — it’s something we live and breathe each and every day. Just like in Kennedy’s dealings with Khrushchev, I’ve got to be mindful of not backing my customer into a corner, or making them feel anything less than 100% heard and understood. After all, without that alignment, the modern customer has the freedom and information to go elsewhere.

P.S. Can we send you an email?

Once a week or so we send an email with our best content. We never bug you; we just send you our latest piece of content.

Leave a Reply

Your email address will not be published. Required fields are marked *