The Stoic Negotiator™

“Most powerful is he who has himself in his own power.”

—Seneca

I used to work with a boss who was the master of the conversational pause. Do you know anyone like this? It can get pretty uncomfortable talking with people who use silence skillfully.

My boss left lengthy gaps between thoughts as she considered what to say and what had been said.

Three seconds here. Five, six seconds there. The intermittent silences felt like an eternity, each awkward and mildly jarring.

Without fail, during these pauses, the other person would jump in or just keep talking to fill the space. Trust me, I know — because I was one of those people. I couldn’t help myself and would start babbling or over-explaining, invariably weakening my message or leverage in the conversation.

“The Pause” as Negotiation Tool

In every negotiation, there’s a moment of silence—a pause where the next words could determine the outcome. Most people rush to fill that silence, fearing the discomfort it brings.

But what if I told you that this pause can be your greatest ally?

Seneca, the Stoic philosopher, said, “Most powerful is he who has himself in his own power.” In the silence of negotiation, power shifts. The person who controls the pause controls the narrative.

Control the Pause, Control the Narrative

Here’s why:

1.    Silence Builds Pressure: When you pause, you create a psychological tension that compels the other party to fill the void. Often, they’ll reveal more than they intended or concede ground.

2.    Silence Signals Confidence: Rushing to speak can signal desperation. A calm pause, on the other hand, demonstrates control and confidence—qualities that earn respect in any negotiation.

3.    Silence Gives You Clarity: In the quiet, you can reflect, consider alternatives, and craft a response that aligns with your goals.

Next time you’re in a negotiation, remember: Don’t fear the pause. Embrace it.

For more Stoic-inspired negotiation tips, read and subscribe to The Stoic Negotiator newsletter on Substack. And don’t forget to check out the new book, Time-Tested: The Stoic Negotiator’s Five Keys for the Modern Deal, now available in paperback, digital and audiobook formats.

Thanks for listening, and see you again soon.

Suppose you’re offered a bet based on a single coin flip: If it’s tails, you lose $100. Now, to make this gamble worthwhile, how much would you have to stand to gain if the coin were to come up heads?

Think about it for a few seconds.

According to studies of renowned behavioral scientists Daniel Kahneman and Amos Tversky, noted for their scholarship related to cognitive biases, most people would require at least $200 for a winning flip. But why? If the odds of winning or losing a coin toss are 50-50, why wouldn’t we accept the possibility of winning $101, or $150?

The answer is rooted in our tendency towards loss aversion and the prospect theory Kahneman and Tversky developed. Their research suggests that most people feel the sting of loss more intensely than the satisfaction of gain, so that they’d require the possibility of winning $200 to offset potentially losing $100.

So why wouldn’t we rationally accept a coin-flip wager where a loss would cost us $100 but a win would give us $101 or $150? In short, we hate losing more than we like winning. That is, it’s better to not lose $100 than to win $100.

This concept, called loss aversion, is an important psychological principle that skilled negotiators can use to their advantage. On the flip side (yes, a pun), if you’re not careful, loss aversion can cause us to fall for sunk cost and similar logical fallacies that lead to suboptimal decision-making.

The bias of loss aversion can impact our negotiations in various ways. For example, is it rational to refuse a negotiated offer – say, a dollar amount to settle a lawsuit – because, though not a bad deal, it is below your stated “bottom line” and you can’t bear taking a “loss”? Surely not. You might find it difficult to walk away from a lawsuit unless you receive an offer with a significantly higher expected value, even though your reluctance could mean making an illogical decision and leaving money on the table.

We hate to lose more than we like to win.

How would you feel about selling a stock or, say, your house, for less than what you paid, even if the proposed deal reflects current market conditions and an objectively reasonable offer? And have you ever noticed that it’s harder to give up a product or service after using it for a trial period? If so, your instinct to keep the product might be driven largely by your desire to avoid a loss.

Most every negotiation decision involves a trade-off: Each side has to give up something to get something else. Thus, the extent to which a proposal is framed as an avoidance of loss, or rather as a potential gain, can greatly influence how it is perceived and evaluated.

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It’s silly to try to escape other people’s faults. They are inescapable. Just try to escape your own.”

— Marcus Aurelius

As a mediator, I frequently encounter parties that just plain don’t like each other. Sometimes, they actually hate and can’t stand to look at one another. Often, they can’t bring themselves to speak directly and choose instead to communicate completely through me as a third-party intermediary.

“I’ve got nothing to say to her and don’t want to hear it. She’s rude, self-centered, and obnoxious,” one litigant recently explained to me of an adversary.

“He’s one of the worst people I’ve ever met, and his company never showed me an ounce of respect,” another party told me of her ex-employer.

In our everyday lives, too, we encounter people who we think are flawed. Maybe you have a selfish uncle, or a rude landlord, or a former spouse in your life that gives you grief. We interact with strangers all of the time, too, and — let’s face it — those encounters aren’t all pleasant.

But what’s the point of dwelling on others’ imperfections? Even if you’re completely correct, and that other person is terrible in every way, how does that help you in a negotiation setting? Does it bring you closer to your goal?

Think about it: How often have you been able to resolve a conflict by changing a person’s nature or character?

In mediations, I try to help people see that focusing on others’ faults (as they perceive them) is counter-productive. Instead of wishing that the company rep was a better person, that your ex- wasn’t so selfish, or that your opposition wasn’t behaving so irrationally, refocus on how you react and respond. Remember, separating what we can control from what we cannot is a bedrock Stoic principal that can guide skilled negotiators.

As Marcus Aurelius reminds us, the only faults we have even a chance of escaping are our own.

In life our first job is this, to divide and distinguish things into two categories: externals I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices.

These words of Epictetus set forth an essential — if not the most essential — philosophical tenet of Stoicism.

Separating those things we can control from what we cannot. Identifying what is worth trying to change, and what is futile. Focusing our efforts and attention on what we can do, in each present moment, to move closer to our goals.

Distinguishing uncontrollable externals from controlled choices just so happens to be a highly effective everyday negotiation skill, as well. For that reason, this theme recurs frequently in discussion of useful negotiating tools.

And it requires practice to train yourself to ask, in the face of a challenging dispute with a difficult adversary, these critical questions:

* Is this something (or, someone) I can control?

* And, if not, how can I control my choices with respect to this immovable force and reach the best possible outcome?

Negotiation and conflict resolution are all, at the core, problem-solving and decision-making exercises. Thus, the lesson we can glean from the Stoics: If it is within your power to solve a problem or create a favorable result, then take action. However, if you are facing an obstacle over which you have no control, then let it go.

The Stoic Negotiator™ is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

We haven’t released a podcast version of the newsletter in a while (as some of you have reminded me!), so we’ve recorded a little something to close out the year. We’re planning a few new things in 2023, too, so be on the lookout and plan to come back soon.

In the meantime, today’s podcast episode:

We talk a lot about negotiation here, to be sure. That’s because we’re negotiating all the time, hoping to influence people or persuade others to see things our way. Trying to settle lawsuits, resolve business disputes, or get the best deal for that used car . . . you know that negotiation envelops us.

Especially as we reflect on 2022 and hope for perhaps a more peaceful, agreeable world in 2023 and into the future, remember: The principles we talk about here are applicable far beyond what you might think of as “negotiation” settings.

Yes, The Stoic Negotiator™ is inspired by ancient philosophies and, heck, its very title references negotiation. But the point of all of this – what we explore each week – is to focus on tools and mindsets you can use to resolve and manage conflict, and communicate as effectively as possible, in broader everyday contexts.

With that in mind, let’s close out the year by highlighting 5 mindset keys you can use – today! – to guide those difficult conversations and keep them from going off the rails:

* Empathy: Great negotiators have a knack for empathizing with their counterparts. Even when they disagree with their adversaries, and whether or not they like their opposing parties at all, these negotiators seem to be able to use empathy – an ability to walk in the shoes of others – to see conflicts from all sides. When you empathize with someone else, and recognize the other’s point of view, the person feels understood. Even more critically, the person feels you understand, which helps build rapport between you. And when you’ve built rapport and expressed empathy, you’re setting yourself up to negotiate effectively and resolve conflict.

* Emotions: Managing, regulating, and channeling emotion is a principal theme familiar to any student of Stoicism. And that theme is common among skilled negotiators and dispute-resolvers, too. Recognize that emotions are involved in and guide decision-making, but strive not to let them divert you from making reasoned decisions. So acknowledge the emotions driving a disagreement. Channel your own emotions, to the extent you can, in a way that allows you sufficient space and calm to make rational decisions. Even though you can’t expect to control another person’s high emotions, you can still help by managing your own responses and at least not fanning the flames on the other side.

* Objectivity: Lacking an objective perspective can lead to prolonged disputes and prevent opposing sides from finding common ground towards resolutions. When you find yourself disagreeing with someone, or in the midst of a dispute, seek objectivity. Is there an objectively right or wrong answer to the subject of your disagreement? Or is your dispute a matter of opinion, so that there’s really no “right” or “wrong”? Whenever you can find objective facts and data to shed light on a dispute, seek them out. Although it can be difficult to change a person’s view of what is “true,” especially with respect to closely held beliefs, it’s virtually impossible to change someone’s subjective opinion.

* Humility: Humility is an under-the-radar secret weapon of some of the absolute best negotiators and problem-solvers. Humble negotiators – those who recognize that they don’t necessarily know everything about a dispute and could learn from the opposing view – benefit from being open-minded and have a knack for seeing both the strengths and weaknesses of their positions. Knowing what we know, as well as what we don’t know, helps us define the limits of our expertise in professional and personal endeavors. 

* Control: Finally, one of Stoicism’s most basic charges is that we separate that which we can control from that which we cannot. Distinguishing uncontrollable externals from controlled choices just so happens to be a highly effective everyday negotiation and conflict-resolution skill, as well. If it is within your power to solve a problem or create a favorable result, then take action. However, if you are facing an obstacle over which you have no control, then let it go.

And there you have it. As always, thanks for being part of The Stoic Negotiator™ community. We sincerely appreciate your support of this space and wish you all the best for 2023. Happy Holidays, and see you next year.

Thanks for reading The Stoic Negotiator™! Subscribe for free to receive new posts and support my work.

“Start from the presumption we know nothing.”

— Rick Rubin

At the breakfast table a couple of weeks ago, one of our middle-schoolers was busy at work. He was reviewing 10 or 12 pages of notes, organized into what looked like an elaborate grid or spreadsheet.

“Wow,” I wondered aloud, “what is all of this? Impressive!”

“Oh, yeah, we’re learning about debate in school. We’re debating another team today that’s going to be tough. Plus, they have a much easier position to take,” he explained.

“What do you mean? And how do you use these blocks of notes?”

“They get to argue for why every school day should start later — which I actually agree with — and our team has to argue against a schedule change,” he sighed. “To get ready, I’ve made a chart of ‘pros’ and ‘cons,’ because we need to know their arguments even better than they do themselves.”

I learn something from these kids every day.

Upon closer look, I saw that he had collected notes supporting both sides of the debate, including citations to primary and secondary sources. On the morning of the debate, the boy was reviewing every angle of the discussion he could imagine, rehearsing his approach, and preparing to counter any tack the competition might lob his team’s way.

People sometimes ask me how they should prepare for mediation or negotiation. Of course, adequate preparation will vary by context, but this debate prep technique highlights some key points that will help you from the jump:

* Do your research. Before entering that car dealership, perform your due diligence thoroughly. Know all about your target vehicle’s features, options, and price range. As you prepare to negotiate a salary increase, understand well the market for those offering similar services. If you’re preparing to buy or sell a house, there’s no excuse these days, with all of the information at our fingertips, not to examine comps in the house’s area and other relevant background details.

* Anticipate the other side. Consistent with sound debate prep, consider how you’d approach the discussion if you were on the opposing team. Why? You want to get in their heads so you’re prepared to present counter-arguments, of course. In addition, particularly when your discussion is part of a negotiation, considering the other side will help you empathize and appreciate the motivating factors that must shape your strategy.

* Rehearse. As you lead up to a negotiation, practice what you’ll say and how you’ll say it. The more confident you are in your presentation, the more persuasive you’ll be. Apart from your substantive points, presenting with confidence engages the other side and gives you an extra air of persuasiveness.

* Keep your mind open. Even when you have a difficult argument to make — or, in the case of our young debater, you have to advocate for a side you’re not completely sold on — try to remain open-minded. First, you might learn something that could change your mind. What if you’re actually mistaken about a fact or have been lead to a faulty conclusion? Then, if the other side has a good point, acknowledge it. You’ll gain credibility with them and, in turn, give the other side permission and incentive to listen to your contentions.

"No role is so well suited to philosophy as the one you happen to be in right now."

— Marcus Aurelius

Negotiation as Essential Element

A good friend was recently confiding in me and lamenting his need to shop for a car. “I’m excited to get a new SUV, because our sedan has been nothing but trouble,” he acknowledged, “but I just can’t stand shopping at these dealerships. Even using the online car-buying services, you still have to NEGOTIATE with these folks. Everything, right down to the floor mats!”

Viewed broadly, every transaction into which we enter is a negotiation. Sometimes the nature of the negotiation is readily apparent – like haggling over a new car’s price – and in other instances the negotiation is more implicit, like when we go to the grocery store, see a gallon of milk marked $3.50, decide that offered price is reasonable and pay the cashier.

Negotiation is an essential part of our daily lives. Whether you’re buying or selling in a transaction, there is a negotiation process involved, even if not explicitly or obviously so.

Think about it. Have you needed to resolve an argument or disagreement, persuade someone to see things your way, or make a decision at home lately? Of course. We all have, and those eventual resolutions – even between parents and kids, for instance, where unequal bargaining power is inherent – almost always require some form of negotiated agreement. How about at work? What determines your salary, or the amount for which you sell your products or services? Have you ever had a disagreement with a colleague that you needed to overcome, in collaborative fashion, in order to work together productively? Naturally, surely, you have.

Ever had to buy a cell phone, or sign up for internet service, and experience the joy of dickering with a customer service representative over an exorbitant enrollment fee, or a shipping add-on there’s no way in the world you should have to pay? Have you ever called your bank or credit card company to dispute a charge that you feel was unjustly or incorrectly assessed? Or has your health insurer balked at paying a complete doctor’s bill, such that you’ve been stuck in the middle between a physician’s or hospital’s billing department and your insurance company?

Let’s leave the rhetorical questions there.

As a mediator, I study and think about these challenges every day and regularly guide people through the negotiation process. In my typical engagement as a mediator, I help individuals and businesses settle their lawsuits out of court by harnessing the power of negotiation. 

Opportunities to Learn and Improve Your Skills

I firmly believe that consciously working to improve negotiation skills is beneficial for both our personal and our professional lives. Negotiation skills are specifically useful — essential, in fact — to lawyers and others engaged in structured dispute resolution processes, like mediation and arbitration, and who must know how to negotiate for just resolutions.

I also believe that these skills are relevant to everyone, and they can certainly be learned. I’ve found that some of the most basic Stoic principles and approaches are surprisingly useful guides to approaching negotiation.

Negotiation will come naturally to some people and seem more foreign to others. We all have relative strengths and weaknesses that make us who we are. And each of us can become more skilled and comfortable using negotiation techniques that suit us, and in simply recognizing negotiation maneuvers we encounter others employing.

That’s why this Substack newsletter is here, and I’m glad you’re reading. All I ask of you is that, if you like something you read, please share it with a friend or two. Thank you for being here, and see you next time.

“Nothing happens to the wise man against his expectation . . . nor do all things turn out for him as he wished but as he reckoned—and above all he reckoned that something could block his plans.”

—Seneca

Studying the Stoics, you’ll surely come across the concept Seneca references in this quote: negative visualization, or premeditatio malorum. In a nutshell, this concept consists of spending time contemplating the bad things that could befall us, or how our plans could go wrong. 

The “negative visualization” technique appears to contrast with some of the more familiar, feel-good, pop-psychology ideas like “the power of positive thinking,” or the notion that if we can imagine success, we can achieve it. Instead, the Stoics teach us through this mental exercise that anticipating calamities, or our worst fears coming to pass — like, say losing a loved one, suffering a disaster, falling ill of an incurable disease — we can gain a greater appreciation for what we have. 

With the perspective we obtain from this Stoic practice, we can make better use of our time and enjoy each moment to its fullest, because we’re prepared for the worst. Also, in the event a catastrophe does strike, we’ll be better equipped to handle it, because we’ve been training our minds to face such an event.

Interestingly, a related tool is useful in negotiation settings, as well. A common practice among skilled negotiators is to prepare for a negotiation, in part, by calculating the “WATNA,” or worst alternative to a negotiated agreement. That is, they assess the worst-case scenario they’d face should they not reach a negotiated resolution to the conflict at hand.

Say you’re locked in negotiations with a house buyer, and you view the offer on the table as less than ideal. But even if not ideal, is the proposed purchase agreement better than your worst-case scenario? If so, perhaps locking in the sale would help you cut your losses. You’re on the verge of being hired for a new job, but you can’t quite get the top salary you wanted. But have you considered your WATNA? How long might you be out of work if you reject the pending offer? How slim are your other available options? What else could become part of your worst-case scenario if you walk away?

I frequently run through this exercise with parties at mediation. You say you don’t like what’s being offered in this negotiation because you were hoping for more. You think you can do better elsewhere, or at another time. But might you do worse if you walk away from the proposed agreement? How would that look, and how would you feel if things take a turn for the worse down the road?

Particularly with loss-averse parties — like most of us by human nature, frankly — there is a powerful draw to this approach. Visualizing what we could lose through misfortune, or other causes outside of our power, helps us prepare for the unexpected by taking action on what we can control today.

Though premeditatio malorum might seem a pessimistic approach, the Stoics did not see it that way. Instead, they used it – just as we can, to confront challenges in negotiation and other settings – to face the future with the confidence and optimism that they were capable of handling any eventuality.

“Objectivity is a virtue, and one that is very difficult to practice.”

—Pierre Hadot

I’ve observed over the years that great negotiators have an ability to empathize with their counterparts. Even when they disagree with their adversaries, and whether or not they like their opposing parties at all, these negotiators seem to be able to see conflicts from all sides.

As so often is the case, negotiation skills that are effective in a conference room or courthouse also work to resolve conflicts in interpersonal relationships. But it takes effort to see a disagreement through the eyes of your spouse, child, parent, or sibling. When you clash with friend or colleague who clings tightly to an opinion you find irrational or outrageous, it can be difficult to imagine what could possibly possess that person to hold such a belief.

People who are able to empathize, though, can use this superpower to relieve conflicts and manage disputes. They recognize that understanding an issue from the other side’s perspective helps them to uncover the motivations, main concerns, and ultimate needs that must be satisfied to reach an agreement.

You know this, because you are an avid reader of The Stoic Negotiator and student of negotiation theory. You realize that empathy is a critical step towards greater objectivity. But what about the person with whom you’re engaged in conflict or sitting across the negotiating table?

You can lead that person to empathy, too, by asking certain pointed questions. We’ve touched on this before, and it bears revisiting. Because it’s an extremely powerful, yet under-appreciated, negotiation tool.

One such question I particularly like to use: What would you do if you were me?

You might be familiar with a flip-flopped version of this question, which we sometimes use to introduce an offer of advice: “If I were you, I would . . . .” Here, though, instead of you opining what action you’d take if you were that other person, you’re asking the person to consider what he or she would do in your place.

The beauty of this “what would you do” approach is that it: (1) is simple to execute; (2) shows deference to the other side, which will often engender reciprocal deference and respect; (3) shows your humility in seeking out the other person’s advice; (4) gives you an opportunity to better understand your counterpart’s thought process; and, finally, (5) subtly forces the other person to consider your perspective.

Ideally, with both sides of a conflict benefiting from a more balanced view of a dispute or negotiation, you’ll then be able to lay the foundations of what should be a more satisfying resolution.

“Fortune falls heavy on those for whom she’s unexpected. The one always on the lookout easily endures.”

—Seneca

You’ve all read those notices on the back of 18-wheelers reminding us, “If you can’t see my mirrors, I can’t see you.” In other words: Get out of my blind spot!

Our cars have rearview and sideview mirrors, of course, so we can see what’s next to and behind us on the road. Newer cars offer blind spot warning systems, using radar or cameras to monitor the sides and rears of our vehicles and indicate when other cars or objects are near. You might notice a light on your mirror or a “beeping” sound when someone or something lurks close by.

What’s the purpose of these blind spot warning systems? Of course, they’re there because, even if we adjust our mirrors just so, we can’t always visualize absolutely everything around us.

In other words, we all have blind spots. We can’t trust everything we see, and we can’t rely only upon what we see.

This “blind spot” analogy is relevant in conflict resolution. We all have individual preferences, backgrounds, and cognitive biases that shape our perspectives and opinions. Each of us has a unique life experience and accompanying lens through which to view the world.

To untangle a dispute, it can be helpful to try to understand the other side of the coin. Why? Because, just like our rearview mirror systems, our points of view are susceptible to missing information. Maybe we’re not getting the whole picture, or perhaps we can’t see it from where we sit. (You see heads, the other person sees tails, and you’re both right — you’re looking at the same thing, but from opposite sides.)

As a mediator, I spend a lot of time with disputing parties helping them realize they have blind spots. Think of me as those warning lights on the side of your mirrors.

You’re saying you’ll win in court if this case goes to trial instead of settling, but are you 100% sure of that? Or could you be missing something? Are you seeing the whole picture, or just what your mirrors are showing you? Similarly, what might your counterpart be overlooking that you could highlight or help explain? Can you trip the other person’s blind spot warning system?

Mediation — a structured negotiation process — gives parties a formal opportunity to turn their heads and actually check their blind spots. You can check your blind spots in everyday conversations, though, too.

Say you’re having a disagreement with a spouse or family member, or with someone at work. What parts of your position — and the other person’s — depend on subjectivity and guesswork? Are you arguing about facts or opinions? What facts might you be missing, and which of your opinions are reasonably debatable?

There’s not always something in your blind spot, but you have to check to be sure. And if something is there, wouldn’t you be better off knowing?