What to Do When Your Boss is Irrational

I’m often asked a funny question. “I think Communifire is perfect for us. It has everything we need. But how do I convince my boss to sign off on the purchase?”

Now, considering I’m most often the salesperson in this context, this is not a question I can answer easily. Or so I thought.

This question has come up so often in the last few years, it got me thinking. If our customers are asking this question of me so frequently, they must think I have the answer. It turns out, I might.

I’ve made a study of persuasion and negotiation, purely for the fun of it. I find that these topics come in handy every single day in so many different circumstances—from getting a discount at my local coffee shop to giving prospective customers the Communifire sales pitch.

In a sales conversation, using the right persuasion and negotiation principles can mean the difference between a happy customer and a frustrated prospect. And it turns out that’s exactly what our customers were asking for: Persuasion and negotiation techniques. Preferably techniques that helped them avoid conflict with their boss.

Introvert or extrovert, manager or individual contributor … no matter our personality or position, most of us want to avoid conflict in the workplace. We want to avoid getting emotional.

It’s no wonder that traditional business negotiations best-practices revolve around keeping situations unemotional and rational. “Keep your feelings out of it.” “What’s your BATNA (best alternative to a negotiated agreement) if things get heated?”

So what do you do when your boss is acting irrational, but you need to convince him or her of something? You might be tempted to slip a valium into his or her coffee … resist that urge. There’s a better way to deal with an irrational boss—especially when you want to persuade him or her to your side on an issue.

Embrace the fact that your boss is human.

Human beings are irrational. Every one of us. Across the board. We are all emotionally driven creatures whose rational, logical minds are forever on the back burner. Philosophers have been saying this forever. Recently, though, researchers and psychologists have sought to prove it.

In his book The Happiness Hypothesis, Jonathan Haidt has a wonderful analogy for this irrational/logical dilemma. He says that our irrational, emotional side is an elephant, and our rational, logical side is the rider. Reins in hand, the rider may appear to be in control. However, that rider is so tiny in comparison to the elephant, if the elephant decides to go in a different direction than where the rider wants it to go, there’s nothing the rider can really do to stop it.

That doesn’t mean you’re out of luck when dealing with your boss, however. No matter how irrational he seems to be, there are things you can do to get the results you want.

In this article, you’re first going to learn more about how emotions work with and against the rational mind, and how embracing emotions is the key to getting your way. This will give you a foundation. Following that, I’ll share effective communication and negotiation techniques that you can use with your boss (even when you think he’s being completely illogical).

Emotions Aren’t the Enemy — They’re the Means

First, a little reassurance: Emotions are good things. Emotions are not elements to fight against or overcome—and believe it or not, they don’t get in the way of good decision-making. Emotions are actually critical for everyday decision-making and life. They fuel intuition and problem solving, they help us make quick judgments in risky situations, and they help us conserve our cognitive energy.

Most researchers agree now that there are two different thinking modalities, though the names for the modalities differ between experts. For the sake of this article, we’ll use logical and irrational.

Logical thinking is slower and deliberate. It’s what kicks in when we have a complex problem to solve.

Irrational thinking is fast and automatic. It’s intuitive. It quickly sifts through past experiences and comes up with a snap judgement for quick decision-making. “Fight or flight” lives here. Emotions, of course, play strongly into irrational thinking.

Both types of thinking are necessary for human life to exist. They both use different parts of the brain, but they inform one another. They’re interconnected. Where we get in trouble is when we believe that the logical mind is in control. It’s not. Our irrational mind—the lizard brain—leads the charge. Always. That’s not a bad thing.

We need emotions in order to make decisions.

Elliott is a true-life case in point. Elliott was a successful businessman who developed a brain tumor. The neurosurgery he underwent to remove the tumor left him with irreversible brain damage. The part of his brain that enabled him to feel emotions no longer functioned properly. He was devoid of emotion from that point on.

You might think that this was a good thing for Elliott, and that now he could make decisions more easily. After all, emotions just complicate things, right? Wrong. Elliott became unable to make the smallest decisions. He would deliberate endlessly. His IQ remained high, but his decision-making ability was lost right along with his emotions.

Do you see how your boss’s irrationality could be a good thing in your situation? It means he’s capable of making a good decision, quickly. Now that you’ve got that reframe, it’s time to learn how to work with your boss’s emotions instead of seeing them as a hurdle.

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5 Ways to Work With an Irrational Boss

In all my years of working with organizations, the most important thing I learned is that empathy will get you everywhere. By empathy I mean embracing your counterpart’s emotions—understanding where they’re coming from and using that as your starting point for conversations.

A recent book I read that resonated on this topic was Never Split the Difference, by Chris Voss. I recommend it, and many of the tips that follow in this section are adapted from this book.

Voss is one of the most accomplished hostage negotiators in the world, and during his career he realized that empathy (handling emotions with care) is the key to persuasion. The rule of empathy equally applies to buying a car, talking your kids into going to be early, and negotiating the release of hostages in South America. It’s all the same stuff.

Let’s go back to the elephant analogy. How can you empathize with an unruly elephant?

First, find out what it wants.

What is important to your boss?

Your boss is a person—not just a stubborn one. What does he want? What does he value? What is he struggling with? What excites him? What goal is he struggling to achieve?

All five of the communication techniques that follow will circle back to this in some way. Getting more information is the first step to getting your way in any circumstance.

Technique #1: Mirroring

Mirroring means repeating back the last few words your boss says, but in a questioning tone of voice. Like a curious parrot.


Your boss: I need that report by 3:00.
You: By 3:00?

Mirroring does a few important things:

  1. It triggers your boss to answer the question or reword their original statement—giving you more information without directly asking for it.
  2. Matching language sets off a neurological response that makes your boss feel like you are like him. It builds trust.
  3. It makes the boss feel like you are paying attention—but it eliminates the risk of argument that paraphrasing can bring up.

So let’s say that your boss tells you he needs that report by 3:00—but you know that’s not enough time for you to complete it. This is a perfect opportunity to use mirroring to get more information and persuade him to give you more time without directly disagreeing with him.

Here’s how that conversation might go:

Your boss: I need that report by 3:00.
You: By 3:00?
Your boss: Yes, if I can get it by 3:00, that will give me time to go read through it before my meeting with Marge.
You: Your meeting with Marge?
Your boss: I have a meeting with Marge (the head of HR) at 10:00 tomorrow morning.
You: 10:00 tomorrow morning?
Your boss: Well, I guess if you can get the report to me by 9 tomorrow morning, that should still give me enough time to read over it before the meeting.

Voila. You’ve gained insight into your boss’s situation and you’ve gained more time to complete your report … and you didn’t have to think of what to say. Yes, persuasion (and triggering generosity) can be as simple as repeating back the last 1-3 words someone says to you.

Dutch psychologists discovered this when they conducted a study of waitresses and restaurant patrons in Holland in 2002. In half of the tests, the waitress repeated back customers’ orders. In the other half, waitresses responded to orders with a positive statement, like “Coming right up!”

The waitresses who repeated their customers’ orders back to them earned nearly twice as much in tips.

If you’re interested in the neuroscience behind mirroring, just google “mirror neurons.” There’s a whole world of brain science behind this technique.

Technique #2: Listen and Label

Listening might be the hardest thing we do in an emotional situation—but it’s the most important. Your boss needs to feel like you’re listening to what he’s saying, but your natural human tendency is to plan your argument while your boss is talking. If you can overcome this challenge, you’ll be a negotiation rock star.

Labeling will help you meet this challenge, because it forces you to listen—and it will also help you disarm your boss when he’s getting worked up about something.

Labeling is the practice of restating what you just heard, using a phrase like “It sounds like” in front of the statement.


It sounds like you’re worried about impressing Marge. (let him talk)

It seems like there’s tension between you and Marge. (let him talk)

It looks like HR is giving you a hard time about this. (let him talk)

Don’t make it a question. Make it a statement, and pause at the end to let it sink in. Shut up and let him talk.

Labeling indicates to your boss that you heard what he said—but it’s also an act of empathy that softens his defenses and opens him to discussion. This works especially well in high-emotion situations. Label your boss’s emotions—without judgment—and you’ll diffuse the situation quickly.

If you can remember to use only one technique when your boss is showing signs of hesitation or hostility in a conversation, make it labeling. Negative remarks are signs that he needs help. Labeling opens up the dialogue, gives him the opportunity to share more information with you, and creates trust.

Technique #3: Make Your Boss Say No

This is a counterintuitive technique, for sure. Especially if you’re a student of Cialdini’s principles of persuasion like I am—where getting small yeses is critical to getting a big yes. This technique might feel odd. Give this a try anyway— you’ll be amazed at the results:

Put your boss in a position to tell you no.

How is this helpful?

Saying “no” makes us feel like we’re in control. It makes us feel safe.

Being pushed to say “yes,” even on something small, makes us feel defensive. We feel cornered.

If you can get your boss to say “no” to something, he’ll relax immediately.

In Never Split the Difference, Voss says that negotiation doesn’t start until someone says no. “No” is not the end of the conversation—it’s the beginning of it. Get your boss to say “no” to you at the very beginning of the conversation and he’ll feel more relaxed and ready to listen.

That “no” can also open the door for gathering further information (remember, you need to understand what the elephant wants!). After receiving a no, ask gently probing questions like “What about this doesn’t work for you?” or “What do you need to make this work?”

You might not even need to probe for more information. Saying “no” can also trigger your boss to justify his answer—providing more insight to you without you having to ask for it. This is why sometimes forcing the no can be beneficial.

For example, say you need some information from your boss in order to finish a big project. You’ve asked time and time again for the information, but your emails are going unanswered, and when you call he says he’ll get back to you soon. Your instinct might be to get more aggressive, to tell him that you can’t complete the project without the information he promised. But there’s a better way to handle this.

Send him an email with this one simple question:

“Have you given up on this project?”

Of course he’s going to say no. And if he doesn’t give you the information you need right then and there, he’ll at least feel compelled to justify why he isn’t answering your requests. “No” is a magical word. Learn to love it.

Technique #4: Trigger “That’s Right”

The phrase “that’s right” is almost as magical as “no.” “That’s right” is the turning point in any negotiation. It opens the door to a successful outcome. If you can get your boss to say “that’s right,” you’re on your way to getting him to agree with you.

Please note that “that’s right” is very different from “you’re right.” The former is an acknowledgment that you are on the same page—the latter is a slammed door on any further communication.

Think about it. After a lengthy, heated argument with your significant other, what does it mean when he or she tells you “You’re right”? It means they are no longer interested in discussing the matter with you. They’ve given up on it. They haven’t agreed with you. They’ve just shut you down.

“That’s right” indicates that your counterpart (your boss, in this case) feels heard and acknowledged.

To trigger a “that’s right” response, use mirroring and labeling liberally. Repeat back what you’re hearing (verbatim in the case of mirroring, and paraphrasing with an introductory “It sounds like…” phrase in the case of labeling) until your boss says those magic words.

The conversation isn’t over, and you haven’t persuaded your boss, until he says “that’s right.”

Technique #5: Create the Illusion of Control

We all have a deep-seated need to feel safe. In fact, safety is one of the base human needs in Maslow’s Hierarchy of Needs—created in 1943 to illustrate his theory of human motivation.

(Source: By FireflySixtySeven – Own work using Inkscape, based on Maslow’s paper, A Theory of Human Motivation., CC BY-SA 4.0)

We feel safer when we’re in control.

Make your boss feel like he’s in control, and he’ll be much more receptive to your ideas. You’ll have a lot more power to guide the conversation in your favor.

There are two easy questions to ask that will give your boss the illusion of control:

  1. What?
  2. How?

Voss calls these “calibrated questions.” Here are some examples:

  • What is your goal with this project?
  • What makes you ask?
  • How am I supposed to do that? (My personal favorite)
  • How do we know the rest of the team is on board?

What and How questions put the problem-solving power in your boss’s hands. He gets the illusion of control, and you gain more information to work with. Also, asking these questions forces your boss to have to think about the answers, which may help get him into a less emotional, more logical frame of mind, too.

Whatever you do, however, avoid asking “Why” if you can help it. “Why” puts people on the defensive.

Your Boss is Only Irrational Because He’s Human

Every human on this planet is driven by their lizard brain—and the lizard brain is irrational. (Maybe with the exception of those with brain damage, like Elliott.)

If you can remember that when you’re approaching your boss about anything at all, you’ll be better off. If you can use that emotion to your advantage and empathize with your boss, you’ll get your way.

Use the techniques in this article when you’re convincing your boss to buy Communifire for your organization. (I’m biased.) Use them when you’re negotiating your salary. Use them when your boss is asking you to do something you disagree with. Use them in every conversation, because they’ll help you navigate through emotionally charged waters no matter how they arise.

Conversations will become less like walking across a field riddled with emotional landmines, and more like friendly collaborations.

Internal Communications Strategy

Written by

Tim Eisenhauer is a co-founder of Axero Solutions, a leading intranet software vendor. He's also a bestselling author of Who the Hell Wants to Work for You? Mastering Employee Engagement. Tim’s been featured in Fortune, Forbes, TIME, Inc Magazine, Entrepreneur, CNBC, Today, and other leading publications.


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