The Stoic Salesman

What would Marcus Aurelius do?

Most salespeople don’t ask that question when facing a bad quarter or a difficult prospect. 

They waste time searching for the latest sales hacks instead of focusing on what actually matters—their mindset. That’s what separates the elite reps from mediocre ones.

The Stoics can teach us about adopting the right mindset. 

Although there are no Ten Commandments of Stoicism, there are do’s and don’ts that will help you maintain balance, and a more fulfilling career. For example, Epictetus reminded us not to get consumed by things we cannot control. Zeno told us to listen more than we speak. And, Seneca believed there is no time like the present.

Sales can be a grind. And, though it is a team sport, it’s not uncommon to feel alone, especially when things aren’t going your way. Stoicism provides us with the framework to prevail. But, reading the words of Epictetus, Zeno, and Seneca won’t matter unless you put them into action.  

Don’t get consumed by things you can’t control 

Imagine ejecting yourself from a warplane after getting shot down, only to land in the middle of enemy territory. Next, you’re brutally assaulted and taken prisoner. That’s what happened to James Stockdale. He was a prisoner of war for more than seven years during the Vietnam War. 

Fortunately, prior to getting captured, he was recommended a book written by Epictetus titled “The Enchiridion.” This book helped save his life and inspired him to write several books about Stoicism. 

Epictetus taught Stockdale how to master the art of compartmentalizing. He knew exactly what was in his control, and what was not. While his fellow prisoners fantasized that they would be freed soon, James focused on surviving.

While it’s unlikely you’ll need to endure the same challenges as Stockdale, adopting a similar mindset can help you overcome the adversity inherit in Sales:

  • You can’t pick your territory.
  • You can’t pick your manager.
  • You can’t see or set your prospect’s budget.

The Stoic Salesman’s Approach: 

  • The only way to have sustained success is to show up everyday, and take extreme ownership when things go wrong. Is there anything you could have done differently to win that deal? Make a habit of listening to your call recordings and share snippets with colleagues for constructive feedback. The same strategy can be applied to your emails.  
  • Your quota will increase. Your territory will shrink. Your market will be invaded by new competitors who will low-ball you. This is to be expected. But, none of that should concern you. It’s out of your control. You can only control your effort.

Listen more, speak less

Zeno, the founder of Stoicism, famously said “we have two ears and one mouth, so we should listen more than we say.” 

The number one mistake I see junior reps make on calls is talking too much. I remind them salespeople don’t get paid based on the number of words they expend. They get commission on closed deals and there’s an inverse relationship between talking and closing deals. 

Shortly after I joined Teleport, as the first sales-hire, we received a demo request from one of the hottest pre-IPO companies. My solutions engineer said, “Let’s just try to close this deal for $50k. If you put anything higher in front of them, they’re going to build this internally.” He sounded certain and I almost acquiesced since he had been at the company for much longer than me. But, then I remembered there’s a reason we have two ears and one mouth. Plus, we were still finalizing our pricing model, and I thought it would be wise to ask the prospect how much they had paid for similar solutions.

After listening to them, I discovered that the ballpark figure was $200-$300k annually. Not only did they enjoy educating me about the market, but we ended up closing a quarter-million dollar deal instead of a $50k one. 

This is not a sales hack. This is a necessary skill. If you find yourself zoning out when other people are talking, you may suffer from:  

  • A big ego. 
  • The inability to ask intriguing questions.
  • Too many distractions.

The Stoic Salesman’s Approach: 

  • Don’t just view your discovery calls as a way to gauge your buyer’s interest. Approach your next call with the desire to learn from your prospect. Sales is one of the only professions that gives you the perk of constantly talking to new and interesting people. Use this to your advantage.
  • Don’t interrupt them after you’ve asked a thoughtful, open-ended question. When it’s your turn to speak, make every word earn its way into the conversation. After all, Zeno also said, ““Better to trip with the feet than with the tongue.”
  • Set yourself up for success. Getting distracted by Slack and iMessage notifications during a Zoom call is a rookie mistake—turn off your notifications!

No Time Like The Present

Seneca once said, “The whole future lies in uncertainty: live immediately.”

As a VP of Sales, my father travelled to more than 100 countries, closing deals and opening offices in places like Ulaanbaatar. When he took my mom along for one of his trips to Beijing, she fell in love with the city and started dropping hints that he should consider retirement so they could travel more. “Just a couple of more years,” he would say. “I want to make sure our kids are set-up for success.” 

In 2009, he was diagnosed with Stage 4 gastric cancer, and passed away a year later. I spent a lot of time with him during his last year, and learned his greatest regret was not traveling more with my mom when he had the chance.

This is why the following quote from Seneca really hits home for me, “putting things off is the biggest waste of life.”

We get a lot of autonomy, but that can be a recipe for disaster. Motivation is fickle, and if you don’t have the right processes in place, it’s easy to let the day get away from you while you’re staring at your screen.

How do you make sure you’re doing the right things today, so you’re setting yourself up for success tomorrow? 

Choose to own each day, or as Seneca said, “As each day arises, welcome it as the very best day of all, and make it your own possession.”

It all starts by having the right systems in place.

The Stoic Salesman’s Approach: 

  • The best way to make sure you’re doing the right things is to reflect on your day. Make it a practice to jot-down what you accomplished each day. Audit your notes and decide if you need to make adjustments.
  • Don’t wait for the empty slots on your calendar to hit you before contemplating what to do with them. Make the most of today by devising a plan before the start of the week and committing to specific actions throughout it—block it off on your calendar: prospecting, account research, and reviewing your call recordings. Seek out another sales rep as an accountability partner. 

Conclusion

Becoming an elite sales professional is about acquiring the right mindset. The best way to do that is to study Stoicism, a philosophy that will make you more resilient. It will teach you to: 

  • Focus on what you can control. Every ounce of energy you waste on things you cannot, inhibits you in areas where you can build momentum. 
  • Talk less and listen more. Not only will you earn more, but you’ll learn more. Remember that you don’t get paid for speaking, but for closing. 
  • Act with urgency—tomorrow is never promised. 

Next time you’re feeling the pressure, ask yourself, “what would Marcus Aurelius do?”