You’re not convincing anyone (at work)

Trying to convince someone is like giving them an undesired gift. If you want to break through, you need to change your story.

An unwanted gift

In a classic Simpsons episode, Homer is looking for a last minute gift for Marge, his wife. He ends up buying a bowling ball for himself and gifting it to her. Marge gets angry with Homer, understandably, because he selfishly bought himself a gift thinking that she would like it. She did not like it.

Related, I was talking to my boss about ideas I had for our company. We were looking for a breakthrough that would get more customers to stick with our products.

I told him about the conversations I had with our customers and what I learned from them. I said that they would do more business with us if we took on more of their burdens — if we did more to help them succeed.

I was hopeful this would be met with joy and acceptance — it was something I had done a lot of research about and had thought about for a long time. I was confident it was a good idea. And yes, I had absolutely rehearsed how I’d present it to my boss.

“No,” he said, “I don’t want us to take the blame if our help backfires. We could hurt ourselves a lot more than we helped them.”

I failed.

What does a bowling ball birthday present have to do with pitching my idea? They were both bad gifts.

Most attempts at convincing are like giving someone an unwanted gift. We take our best idea, wrap it up, and deliver it to the people around us. We hope it’ll be well received.

But often it’s not the gift they were expecting or wanting. They don’t like our ideas for whatever reason. They reject your idea, your gift. When they reject your gift, it hurts. A lot.

Trying to convince someone is a lot like giving them a gift. If you give someone a gift that would make you happy to receive, it often will not make them happy. Similarly, an argument that would convince you will not convince someone else.

This might make sense intuitively, but let’s understand it one level deeper. What’s really happening in your brain when you try to convince someone?

Reflex machines

It’s really hard to convince others because their brains fight against it.

Imagine what happens in the recipient’s brain when you’re trying to convince them. You might picture them being thoughtful and deliberate about your idea, considering the pros and cons, and trying to see if it makes logical sense.


Most of our decision making is automatic, reflex, and intuitive. Around 98% of our decisions are made by our automatic decision making system (“System 1” from Thinking Fast and Slow). You are not the rational, deliberative thinker that you might believe.

“But wait,” you say, “when I make a decision, I always have good, rational reasons for making that decision.”

Bullshit. It was a post-hoc rationale. Your brain came to an automatic decision, and afterwards it invented a rational-sounding justification for that automatic decision.

I know it doesn’t feel that way, but that’s what’s really happening between your neurons. You have a gut feeling, and then you rationalize your gut feeling. And then you feel good because it seems like you made a rational decision, but nope — it was just reflex thinking.

What forms that automatic decision making? Our intuition, perception, deeply embedded experience (like how you don’t have to think about walking or riding a bike, you just do it). The more practice and exposure we have to something, the more likely we’ll use this automatic decision system than our analytical, rational thinking system.

Why does this happen? Because brains are lazy. They take shortcuts based on scant evidence and leap to conclusions. They have to. That rustling sound over there? Maybe it’s a bear about to attack you. Run!

That same mechanism which had to make a snap judgement so that we wouldn’t be killed by imaginary bears? That’s the same mechanism that responds to your attempts at convincing.

So when you start trying to convince someone — with a new idea, differing opinion, or anything — it triggers this automatic system which makes a snap decision based on experience and internalized knowledge. New things that we learn get sorted against our existing opinions, experiences, and biases. Anything that doesn’t fit is rejected.

I know that you put tons of effort into your research and crafted the perfect argument. Too bad. You’re not convincing anyone.

So how do we break through this? How can we actually be convincing when other people’s brains are conspiring against you?

Empathy, the real convincer

To convince someone, and to sneak past their reflex machine — er, brain, you need to create a new set of feelings, experiences, and intuitions around your idea.

In short, you need them to empathize with your idea. You need them to feel it, not to think about it. This is the path towards convincing. Here are a few methods for doing that.

Ask what they want

One way to give a great gift is to just ask what someone wants. The same applies to convincing people. Go ask the people you need to convince, “What would convince you to [support this idea]?”

This is Empathy 101 of convincing. You need to get into your audience’s head.

You’ll often get answers like, “I want to see the data,” or, “show me how much revenue we’d generate.” Do not let them get away with these bad answers. Pin them down for specifics. What do you think about using a survey? What if we find only 10% of users want this feature?

It’s like if you asked your friend, “what do you want for your birthday?” Their response of “just a gift certificate” is not good enough. What kind of gift certificate? What store? What types of things would they want to buy? “Gift certificate” is not enough to go on.

So ask. And pin them down for a specific answer. Simply asking will create empathy between you two — they’ll like you better for reaching out — and you’ll have a better starting point for getting them the right gift, er, convincing argument.

Narratives for empathy

Storytelling is one of the best ways to convince someone. Stories force you to stop thinking like yourself. Instead, just for a little, you think like someone else. It’s enough that you’ll turn off your intuition, expectations, and experiences just for a bit.

When coming up with the right story, you need to consider your audience, weave in the right evidence, and have a clear and memorable point. But make sure that your narrative is true — fiction is far worse than non-fiction here.

Once, I used a story as the opening to pitch a feature. Imagine you’re selling items online and suddenly some of your items were pulled because of “terms of service violations.” You contact support but they can’t tell you anything more. You’re angry. You thought that your items were fine, but they’re not, and nobody can explain why. It sounds awful, right? How frustrated would you feel if this was you?

Well, that happens to _,000 people a day, tying up support agents, costing us goodwill and revenue, and making customers angry. That number could be a lot less if [insert idea here]…

You get the point. A story evokes emotion and takes you out of yourself for just a bit — just long enough to convince them about your idea.

A great narrative is better than great data.

Be there

Instead of telling a story, bring the story to them. Let them see the reality of the problem for themselves.

I was working on a new product and had just completed some usability tests. There were some clear issues, and it would have been easy for me to list them out.

Instead, I showed my audience part of that usability test. They saw and heard people attempting to use the product. The struggle was obvious, and the frustration was real. The audience was convinced, and we made important fixes before we launched.

You can tell your audience a story about how someone got frustrated, or you can show them that person’s frustration. The difference is night and day.

Go beyond storytelling. Show them what it’s really like.

Offer a choice

Part of empathy is realizing that the person you’re convincing might not agree with everything you’ve said. So give them an out.

We often frame “convincing” as a black and white thing. You’re either with me or you’re against me. This is very much not true.

We agree or disagree in degrees — sometimes a little, sometimes a lot. But when we’re in the middle of trying to convince someone, we’re aiming for their complete adoption of our point-of-view.

Instead of going for the total victory, aim for a partial one by offering choices. “Here’s my main idea, but here are other versions of it that might suit you better.”

It’s like being a salesperson. You don’t want the super deluxe package? The deluxe package costs less, doesn’t have as much, but might be a better fit. Here’s the basic package too, just in case you’d prefer that.

Put differently, are there key details you need this person to agree with? Aim for the whole thing first, but then pull back so that they can meet you in the middle.


One final, very important digression… You can’t convince someone to ignore their fear.

Fear cancels out any attempts to convince someone. Fear is not rational, it can’t be explained, and it can’t be overcome. Empathy can’t pierce it at all.

But worst of all, fear does an amazing job hiding in plain sight. When someone tells you why they weren’t convinced, they’re not gonna say “fear”, but fear might just be the reason.

Going back to the conversation I had with my boss, I tried to convince him about my idea, and his response sounded rational — that deeper ties could backfire. The truth is simply that he was afraid. He was under pressure to grow the company. He was afraid that the idea might not work, and he was afraid of having to sell this idea to his higher-ups.

Fear biased his decision making. If there was any chance this idea would fail, it had to be rejected. I’m not saying my idea was right. I am saying it was rejected out of fear that it might not work.

Fear is a powerful thing. It hides itself in rational thought. Remember, our devious brains come up with rational-sounding justifications for our reflex decisions. When fear is the basis of those reflex decisions, it can cause people to make choices that go against their own best interests.

The only thing that can overcome fear is… the person who’s afraid. They need to change the narrative about their fear. No amount of your convincing will make them unafraid.

If you think fear is the culprit, the simplest thing to do is talk to them. Empathize with them. Don’t talk specifically about fear. Just talk about the issues around their fear. And do not try to convince them. Make that person articulate the fear. In time, hopefully they’ll realize that the thing driving their decisions is not rational.

Convincing – it’s not just for work!

The gift model of convincing is the one that we were raised on. Start with your opinion or idea, bring evidence, and you’ll convince other people.

This is not how it works in reality. Other people have minds, experiences, intuitions, and biases of their own, and those are going to fight your attempts to convince them.

Like the title of this piece implies — “You’re not convincing anyone (at work)” — this is more than just advice for work. This is advice for life.

Too often, instead of trying to convince others in healthy ways, we revert to the worst practices — repeating our same points over and over, offering evidence that would convince you but not others, and not listening to the people we’re trying to convince. It’s infuriating when it happens.

You’re trying to give them the gift of your idea, but it’s probably not a gift they want.

The real way we convince people is not by lobbing presents at them. The real way to convince someone is to change their narrative around it. Give them a new story to tell. Create empathy. Find middle ground. Acknowledge their fear.

Do that, and you might just convince them.

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