How to Prevent Miscommunications

Summary

Help Wanted — "How to Prevent Miscommunications"

Podcast: Help Wanted
Host: Money News Network
Episode Date: July 9, 2026
Hosts: Jason Feifer and Nicole Lapin

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Episode Overview

This episode, hosted by Jason Feifer—a seasoned media professional—and money expert Nicole Lapin, dives into the root causes of miscommunication in professional environments. Jason shares a personal story of being misunderstood by his readership and introduces a practical, two-question exercise to help listeners communicate more clearly at work. The discussion blends personal anecdote, actionable advice, and anthropological context to help listeners prevent misunderstandings in both personal and professional settings.

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Key Discussion Points & Insights

1. The Problem of Being Misunderstood

• Jason opens with a relatable scenario: You’ve shared something—an idea, work, or message—that seems clear to you, yet others find it confusing, unimpressive, or even annoying (03:28).
• Acknowledges that miscommunication is a universal workplace problem.
  • Quote: “Everything you do makes sense to you… But the problem is that the world... does not have the same training, context, experiences, and desires.” — Jason (05:25)

2. A Personal Anecdote of Miscommunication

• Jason recounts the incident of his newsletter, One Thing Better, being mistaken for AI-generated content by a reader named Pam (03:50).
  • Pam’s email: “I was hoping it was written by you. I’m out.” — (04:25)
• The misunderstanding stemmed from a caption under an AI-generated image reading “Made with ChatGPT,” which Pam interpreted as referring to the entire newsletter, not just the image.
• Jason’s panic grew as he considered others might share Pam’s misconception.

3. The Two-Question Clarification Exercise

Jason introduces two reflective questions to prevent miscommunication (06:20):

1. What experiences or knowledge of mine shaped my actions now?
   • Example: Jason’s magazine background led him to always caption images, a practice not universally understood.
2. Do my actions make sense to someone else if they don’t know the backstory?
   • Pam didn’t have Jason’s media context and misinterpreted the caption.

• Application: Rethinking his newsletter’s image policy, Jason surveyed readers and learned most didn’t like the AI image, with one person saying: “When I don’t care for that particular image, I am prompted to skip your article. That’s terrible.” — (09:45)
• Result: Jason removed the illustrations and saw no complaints, reinforcing the importance of challenging one’s assumptions.

4. Context in Communication: High vs. Low Context Cultures

• Jason delves into anthropology to explain cultural differences in communication (10:45):

  • Low-context cultures (e.g., American, British): Communication needs to be explicit.
  • High-context cultures (e.g., Japanese, Arabic): Communication often relies on shared, unspoken understanding.

• Most of us operate in-between, assuming some shared context and thus creating potential blind spots for misunderstanding.

  • Quote: “We cannot assume a shared understanding. We cannot leave things unsaid.” — Jason (11:45)

5. Actionable Takeaways

• Use self-reflection to anticipate misunderstanding before it happens.
• Explicitly clarify your reasoning, context, or intent, especially in unfamiliar or diverse environments.
• Solicit feedback to understand if your communication is landing as intended.
• Recognize and bridge the context gap; don’t assume others see the world as you do.

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Notable Quotes & Memorable Moments

• “Everything that you do makes sense to you… But the problem is that the world... does not have the same training, context, experiences, and desires.”
  — Jason Feifer (05:25)

• “Do my actions make sense to someone else if they don’t know the backstory?”
  — Jason Feifer (06:40)

• Listener feedback:
  “When I don’t care for that particular image, I am prompted to skip your article. That’s terrible.” (09:45)

• “We cannot assume a shared understanding. We cannot leave things unsaid. Instead, we must rigorously consider what we know and what other people don’t know. Because when we do that, we will appreciate them more, empathize with their viewpoint more, and most importantly, we will be understood.”
  — Jason Feifer (11:45)

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Timestamps for Important Segments

• 03:28 – Introduction to the episode's main question: Why are we misunderstood?
• 04:00-05:15 – Jason’s newsletter anecdote and reader misinterpretation.
• 06:20-07:00 – Introduction of the two-question exercise.
• 09:00-09:50 – Newsletter illustration feedback and decision-making.
• 10:45-11:45 – Explanation of high vs. low context cultures in communication.
• 11:45-12:30 – Takeaway: Being explicit to bridge context gaps.

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Episode Tone & Style

Jason's delivery is personal, self-reflective, and educational, often using humor and humility (e.g., acknowledging his own mistakes). The tone is conversational, encouraging listeners to think critically about their own communication habits. Nicole plays a supporting but warm role, contributing to a welcoming atmosphere.

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In Summary

This episode of Help Wanted tackles the familiar frustration of being misunderstood at work by pulling back the curtain on why it happens, how context shapes clarity, and offers a simple, repeatable exercise to help anyone—boss or employee—communicate more effectively. Through anecdotes, listener feedback, and cultural insight, Jason encourages proactive empathy: always consider what your audience does not know, and you’ll not only improve your message, but also your relationships and results at work.

Transcript

[A]

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[A]

Entrepreneur magazine and I'm money expert Nicole Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[C]

And on Thursdays, I give you one way to improve your work and build a career or company you love.

[A]

And it starts now.

[C]

Someone is misunderstanding you right now, right? Somewhere in the world someone is misunderstanding you. You shared a great idea with them or you made something wonderful, or you just told them something and they are confused. They are unimpressed. Maybe they are even annoyed. And now you are annoyed. You know, you're upset, you're thinking, why don't they just understand what I am saying to them? But here's the problem. You started in the wrong place. I fall victim to this all the time. So today I'm going to share some of my own stumbles and a powerful two step exercise that will help you make your intentions and ideas clearer so that everyone understands you. Ready? Okay. First, let me tell you about a recent mistake that I made. So I write this newsletter. It's called One Thing better each week. One way to be more successful and satisfied. Build a career company that you love. Maybe you know this because I always read these newsletters, including this one right now on Help Wanted. This thing that you're hearing right now originated as a newsletter. Anyway, okay, point is, I write this newsletter. It comes out every week. And a few weeks ago I got an alarming email from a reader named Pam. She thought that my newsletter was written by ChatGPT. I was hoping it was written by you. She wrote me, I'm out. When I read this, I froze. I thought, why would she think that? Why would she think it's written by ChatGPT? It's not written by ChatGPT, it's written by me. My own human hands and brain. And then I realized the answer. I realized why she thought my newsletter was made by ChatGPT. And as soon as I did, I started to panic. So here's the explanation and why I was panicking. For more than a year, my newsletter would begin with this AI generated image. I always asked AI to make a kind of simple black and white drawing of something that was related to the thing that I had written about. And then underneath, I had written made with ChatGPT. I just wrote it underneath the image. So if you open my newsletter, you'd see the headline, and then you would see the image, and then you would see Made with chatgpt underneath the image. And then my newsletter would start. And to me, made with ChatGPT was just a basic photo caption. You know, it was just the information that you put underneath an image. But to Pam, the phrase made with ChatGPT wasn't related to the image. It was actually the very start of the newsletter. You know what I mean? Like, it was teeing up the entire newsletter as if I had announced, everything that follows is made with ChatGPT. Which, again, is not true. And this is why I panicked, because I wondered, if Pam thinks this, do other people think this too? Now that I see what she was seeing, I can understand how it kind of looks like. My newsletter starts by saying, what follows is made by ChatGPT. And then I realized, ugh, I have made a classic mistake. So let's talk about why we are so misunderstood. Everything that you do makes sense to you. I know that sounds kind of stupid, but it's true, right? Everything you do makes sense to you. Your actions are the product of your training and your context and your experiences and desires. And so the output of all that makes perfect sense. But the problem is that the world, everybody in the world, everyone you interact with, does not have the same training context, experiences, and desires. So we are often blind to what other people don't. No, good news, though. We can solve this problem and even avoid it. The next time that you are being misunderstood or you want to communicate more clearly, just ask yourself these two questions. Number one, what experiences or knowledge of mine shaped my actions now and right, like, just be conscious of what drove the reason that you took whatever action you took or made any decision. And then question number two, do my actions make sense to someone else if they don't know the backstory? As soon as you think this, as soon as you run your actions through these two questions, you will start to see breakdowns, places where something makes sense to you but appears weird and arbitrary to others. Now that we know that, let's apply what I just said to my mistake with my newsletter. I had Written, made with chatgpt underneath the image. And Pam misunderstood me. Why was that? Well, let's take the first question. What experiences or knowledge of mine shaped my action? Here's the answer. I've spent my career working in magazines where I was trained to write captions and attributions for all images. Right? Any image that appears in a magazine or on a traditional media website has some kind of attribution for the image. It says where it came from, you know, getty images or whatever. To me, this is just natural and expected. So it was just what I did in my newsletter too. You know, image came from ChatGPT. I said it came from ChatGPT. Now let's ask the second question. Does my action make sense to someone else if they don't know the backstory? The answer here is maybe, but not definitely. Pam is a copywriter and she told me that she opposes AI writing. So she was primed to interpret my caption the way that she did. And she wasn't thinking about photo captions. Maybe nobody else thinks about photo captions. Maybe that's not something anybody notices in the world world anymore. Maybe it's something nobody ever noticed. So no wonder we miscommunicated. Now, now that you have heard this, you can start doing this proactively. You don't have to wait for misunderstandings to arise. You can ask my two questions all the time and improve your work as a result. For example, once I cleared up this confusion with Pam, I started to wonder, why do I even have an AI image at the top of my newsletter? Again, the answer to that, the answer to why I made that decision goes back to my media background. At magazines, words are basically always accompanied by some image. So when I started a newsletter, it seemed improper to hit publish without some visual at the top. But does that make sense to other people? Do people need or expect that? No, I don't know. So I wondered, do I really need it? And here's how I decided to answer that question. A few weeks ago, I asked readers of my newsletter, I said, do you like the illustration at the top? Responses flooded in. It was fascinating. Some did like the illustration, but the vast majority did not. They did not like this AI created thing that I was putting at the top of every newsletter. One person even said, when I don't care for that particular image, I am prompted to skip the your article. That's terrible. So I decided to stop running the illustrations altogether. And you know what happened after I did? After I stopped? Nothing. No complaints at all. What this all comes down to in one way or another is context. So let's zoom out for a moment and ask one final question. How much context do we actually need to understand each other? I don't know if you've ever heard this, but it's fascinating. In anthropology, there is a fascinating concept called high and low context cultures. Some cultures, like American and British cultures, are defined as low context, meaning that we must communicate explicitly with each other. We are understood through the literal definition of our words. But other cultures, like Japanese and Arabic cultures are defined as high context, meaning that a lot of communication is unspoken and cultural expectations are shared and understood. Here is my theory after thinking about that. In our day to day lives, as we just kind of move through the world, we are operating somewhere between high and low. We want to communicate clearly and explicitly, but we also expect to be understood. And as a result, we have these blind spots for when we're being unclear. The truth is, we cannot assume a shared understanding. We cannot leave things unsaid. Instead, we must rigorously consider what we know and what other people don't know. Because when we do that, we will appreciate them more, empathize with their viewpoint more, and most importantly, we will be understood. And as I'd mentioned earlier, I always read my newsletter here on Help Wanted every Thursday. And that came from my newsletter. If you want to subscribe, you can do so at one ThingBetter email. That is a web address. Plug it into a browser. Onethingbetter email I say to you very explicitly with all the high context, so that you know I'm not misunderstood. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason

[A]

Pfeiffer and me, Nicole Lapin. Our executive producer is Morgan Lavoy. Do you want some help? Email our [e-mail] for the chance to have some of your questions answered on the show. And follow us on Instagramoneynews and TikTokoneyNewsNetwork for exclusive content and to see our beautiful faces. Maybe a little dance?

[C]

Oh, I didn't sign up for that.

[A]

All right, well, talk to you soon.

[C]

Sam.