How to Win People’s Trust

Summary

Help Wanted – “How to Win People’s Trust”

Podcast: Help Wanted
Hosts: Jason Feifer (Entrepreneur Magazine Editor-in-Chief), Nicole Lapin (Money Expert)
Date: September 4, 2025
Theme: Unlocking one of the most essential skills in work and business: how to earn and maintain other people’s trust by diving deeper into “knowingness” in your communication and marketing.

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Episode Overview

In this episode, Jason Feifer focuses on the art of communicating with “knowingness”—going beyond being specific and demonstrating deep, nuanced understanding of your audience’s real-life experiences and emotions. He breaks down strategies and real-world examples to show how “knowingness” builds genuine trust, whether you’re marketing a business, pitching ideas to your boss, or just trying to connect more powerfully with colleagues and customers.

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Key Discussion Points & Insights

What Is “Knowingness” and Why Does It Matter?

• Three Levels of Communication:
  • Generalities: Too broad/vague, fails to connect.
  • Specifics: Clear and focused, often sufficient but not profound.
  • Knowingness: The highest level—“When you say things that only your target audience would understand, displaying your deep knowledge of their needs.” (Jason, 03:13)
• Knowingness is demonstrating that you not only understand what people need, but why and how it feels to need it—creating “felt understanding.”

The McDonald’s Ad Example

• Jason recounts a favorite McDonald's ad from 2010, where a dad repeatedly circles a drive-thru, whispering his order to avoid waking his sleeping baby.
  • The staff finally helps him get his food, showing McDonald’s awareness of parents’ real-life challenges, not just food needs.
  • Insight: The ad connects on an emotional level, reflecting not just a generic problem (hunger), but the nuanced struggle of parents.
  • “McDonald's didn't just show a hungry customer getting food. They captured a hyper specific challenge that every parent understands...” (Jason, 06:50)
• Highlights how the emotional experience of the ad draws people in and makes customers feel seen and understood.

More Examples of Knowingness

• United Card Ad:
  • “If your vacation doesn’t start until their movie does, you should probably have a United card.” (Jason, 07:46)
  • Speaks directly to parents’ lived reality on flights with kids.
• StreetEasy Subway Ads:
  • Images showing “cool” New Yorkers looking lost in the suburbs with captions like “Never become a former New Yorker.”
  • These capture the anxieties of city-dwellers afraid of losing their identity if they move to the suburbs.
  • “I saw these and I texted them immediately to friends of mine who had made the move from New York to the suburbs.” (Jason, 09:15)

How To Cultivate and Communicate Knowingness

• Step 1: Hear Their Nuanced Complaints
  • Talk to your audience, listen for what truly bothers them.
  • Go beyond superficial gripes—dig for the things people would admit after “maybe two drinks in.”
  • “It is personal, small, but also meaningful. It should make their peers say, ‘That happens to me too.’ That right there, that is the core of knowingness.” (Jason, 10:07)
• Step 2: Reflect Their Reality With Specificity
  • Speak/write in ways that scream, “I know your problems at a granular level.”
  • Triggers psychological “felt understanding”—people feel genuinely seen.
  • Examples:
    • “I help founders who lie awake at 3am wondering if they made the right decision about that product, while also feeling guilty for how tired they’ll be with their kids the next morning.”
    • For busy executives: “...every time they leave the office before their team, even though they know they need boundaries to be effective.”
    • For LinkedIn: “...the expert who knows they should be posting, but stares at a blank screen for 20 minutes before giving up...”

Personal Application: Jason’s Own Story

• When pitching himself for speaking gigs, Jason tells the story of “Gary,” a long-time company man who said:
  • “In the decades I’ve been going to these things, I’ve seen a lot of speakers do empty cheerleading. But you’re the first one to give us practical, useful things to do. So I just wanted to thank you.” (Jason quoting Gary, 11:47)
• Jason uses this story to show he understands what executives and employees actually value—practicality, not flashy motivation.
  • “Clients love when I say this. You know why? It's because it shows how well I understand their needs and it shows I can deliver.” (Jason, 12:08)
• Takeaway: Knowingness “closes the deal” by making people feel deeply, emotionally understood.

The Broader Impact

• Practicing knowingness doesn’t just help you sell or persuade—it makes you a better human.
• “We should never want to just sell stuff, we should want to make lives better, which means we need to know those lives. So listen closely, dig deep, communicate deeper. You have to live in the nuance.” (Jason, 12:55)

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Notable Quotes & Memorable Moments

• Jason on the definition of knowingness:

  “That is when you demonstrate that you don’t just understand what other people need, but you understand why they need it and how it feels to need it. When people see that from you, they trust you more.” (04:20)

• On the power of specificity:

  “Your words should scream, ‘I know your problems at a granular level.’” (10:56)

• Story about Gary:

  “In the decades I’ve been going to these things, I’ve seen a lot of speakers do empty cheerleading. But you’re the first one to give us practical, useful things to do.” (Jason quoting Gary, 11:47)

• On empathy in business:

  “Help Wanted is a production of Money News Network… We should want to make lives better, which means we need to know those lives.” (12:55)

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Important Timestamps

• 02:23 — Show begins, intro of hosts and show segments
• 03:13 — Jason introduces the idea of three tiers of marketing/communication
• 05:17 — McDonald’s “knowingness” ad breakdown
• 07:46 — “If your vacation doesn’t start until their movie does”—United Card ad
• 08:45 — StreetEasy’s “Never become a former New Yorker” subway ads
• 10:07 — Two-step process: hear nuanced complaints, reflect reality
• 11:47 — Jason’s keynote story about Gary and why it works
• 12:55 — Why knowingness makes you better at work and better as a person

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Overall Tone

• Jason’s style is storytelling-driven, empathetic, and practical.
• The episode is supportive and actionable—full of specific tools, real-life examples, and memorable lines.
• Listeners are encouraged to approach communication (and business) from a place of deep understanding and respect for the other person’s lived experience.

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Takeaway:
To win people’s trust—be it customers, colleagues, or clients—learn their world so well that you can echo back not just their challenges, but the subtle, personal feelings they have about those challenges. That depth builds true connection and trust—the heart of effective communication, leadership, and business.

Transcript

[A]

When I was broke in my 20s, I was so scared to check my checking account because I didn't know how much money was in there, if any. And honestly, I didn't want to know. Part of my journey from money mess to money master was making sure I always knew how much money I had in each account and a plan for every dollar. One of the tools I love for this is Monarch Money. Monarch Money lets me track every dollar that I have and every dollar that I spend, but it's not just for me. It also lets me and my husband both track all all of our accounts. That way we can see what's in our shared dashboard and which bills we have or haven't paid yet. It takes navigating shared finances from an annoying constant back and forth to one easy peasy peek at Monarch Money. It has saved us both so much time. While I use it to share financial information quickly and easily with my husband, it is also simple to share financial information with an advisor at no extra cost. If you've been putting off managing your money, Monarch Money is an easy way to get started. Knowing where you stand financially ultimately makes life so so much less stressful and will save you so much money in the long run. Don't let financial opportunity slip through the cracks. Use Code help [e-mail] in your browser for half off your first year. That's 50% off your first [e-mail] with code help Wanted. Okay guys, I recently had my identity stolen and it was awful. It felt like a gross icky violation like somebody got into my digital house and locked me out. Getting your identity stolen means putting a hold on your card and replacing everything. So when that happens there is no time to wait. You want to be able to get hold of your bank right away. One thing I love about Chime is that they have 24. 7 customer support available. So if you notice an unexpected charge or lose your wallet, you can connect with a real person right away to get it all sorted out. Chime also offers fee free checking accounts and ATMs. No more monthly maintenance fees. Work on your financial goals with Chime today. Open an [e-mail] helpwanted that's chime.com helpwanted Chime feels like progress.

[B]

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[C]

This is Help Wanted, the show that makes your work work for you. I'm Jason Pfeiffer, Editor in Chief of.

[A]

Entrepreneur Magazine, and I'm money expert Nicole La. 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]

You're not connecting with people the way you want to. Maybe you own a business and your marketing isn't working, or your content feels flat, or your calls with clients aren't landing. Or maybe it's something else. Maybe you work at a business and you just aren't getting your ideas through. Whatever it is, this could be your actual problem. You haven't reached the highest and most convincing level of communication and that is knowingness. There are three tiers of marketing and communication as far as I'm concerned. And here they are. Tier number one is generalities. That's just when you're being broad and vague. Tier number two is specifics. That's when you're clear and focused. And tier number three is knowingness. When you say things that only your target audience would understand, displaying your deep knowledge of their needs. Most people stop at specifics thinking that that's enough, but knowingness goes deeper. That is when you demonstrate that you don't just understand what other people need, but you understand why they need it and how it feels to to need it. When people see that from you, they trust you more. Today I'm going to show you how to infuse more knowingness into your marketing and communications. And I promise you this is useful whether or not you are actually in marketing and communications. And let's start with how McDonald's mastered this technique in one of my all time favorite ads. So in 2010 McDonald's created an ad that had nothing to do with food and everything to do with their customers lives. I'm gonna break it down for you here. Okay so we open on a guy driving a car and he's looking really sleepy and he pulls into a McDonald's drive thru. But he doesn't stop the car. Instead he quickly loud whispers his order into the speaker but struggles to get everything out. Hello, excuse me, I'd like a name with my vanilla. Hello. So he circles back around and he does this repeatedly until he gets the order actually out. And then we cut to the McDonald's staffer who's inside, who is very confused. The guy keeps returning saying his order. I said an egg McMuffin and a large cup of coffee.

[B]

Can you just say that one more time please?

[C]

But eventually the McDonald's staffer gets it.

[A]

Did you say naked McMuffin and a.

[C]

Large coffee with cream and sugar, please. There is a sleeping baby in the backseat of that guy's car. And the guy, the dad, doesn't want to stop the car and risk waking his kid, which is why he just keeps circling around trying to whisper his order. The whole McDonald's crew snaps into action, helping him get his food and they communicate the price. There's this quick handoff of food for money and then the dad drives away with a big thumbs up out the window, grateful for their help. It is adorable. And if you watch it, it's actually really affecting too. Like it's kind of emotional to watch because. Well, let's talk about why it was so emotional to watch. McDonald's didn't just show a hungry customer getting food. They captured a hyper specific challenge that every parent understands and that is the delicate balance of caring for a child while also managing your own needs. This wasn't about convenience or speed in this ad. It was about knowingness. McDonald's demonstrated a nuanced understanding of their customers lives and in turn, parents felt heard and they were reminded that McDonald's is an easy solution for stressful parenting lives. Think about it. When you see yourself truly reflected in ads, don't you take notice? Here are a few more ads that really spring to mind. When I think about knowingness. I was once walking through an airport and I saw this sign. So first of all, what you see is, it's a, it's a, it's an ad and it shows a picture of a cute kid sitting in an airplane, wearing headphones and reaching up to the screen in front of him. And it says, if your vacation doesn't start until their movie does, you should probably have a United card. Oh, that's so good. Because any parent knows that really you cannot relax until you get your kid watching the movie on an airplane. And now here's another one. I really loved this Street Easy campaign which ran in the New York City subway. It was capturing the anxiety of New Yorkers thinking about moving to the suburbs. It's a series of photos of, you know, like cool looking people who really belong in Brooklyn sitting or standing in suburban environments, looking absolutely lifeless, like the life has been drained out of them. And so in one, there's there's this couple and they're sitting there. They're sitting there in a kitchen and on the table in front of them is a big box of pizza that says New York style pizza. And anyway, the big, the big text on the image is never become a former New Yorker. You can just see how much they like, absolutely hate that they've bought this suburban New York style pizza after living in New York and eating New York pizza. There's another one. It also again says, never become a former New Yorker. And this one is just a guy wearing a, like a Brooklyn shirt. You know, he's like dressed really cool like he belongs in Brooklyn. But he's just standing there and he's got a hose and he's watering the lawn. He's just looking out like vacantly into the distance as the water just runs into the grass. Anyway, so great. Like I saw these and I texted them immediately to friends of mine who had made the move from New York to the suburbs. I live in New York. Anyway, notice what all these examples have in common. They don't just identify a problem. They capture the emotional experience of having the problem. That is the difference between specifics and knowingness. So how do you do this in your work? Here is how to show knowing this. You know who you're trying to reach and you know what they want. But before you try to speak to them, you must think, what are their shared experiences? To find the answer, follow this two step process. Step number one, Just hear their nuanced complaints. Talk to your customer or your clients or your colleagues or whoever you're trying to reach. Ask what bothers them the most. Ask how that makes them feel personally. How does it impact them at home? What does it stop them from doing? Also imagine this. If a bunch of your customers were drinking at a bar, what would they complain about? Not immediately, but like, you know, what would they complain about? Maybe two drinks in. You're looking for a specific insight. It is personal, small, but also meaningful. It should make their peers say, that happens to me too. That right there, that is the core of knowingness. All right, so that's step one. Hear their nuanced complaint. Here is step two. Reflect their reality with specificity. Here's your goal. Whenever you speak through content or conversations, you should infuse your language with well earned knowingness. Your words should scream, I know your problems at a granular level. When people see their specific experience reflected back to them, it triggers what psychologists call felt understanding. They don't just think, this person gets it, they feel understood at a visceral level. For example, instead of saying I help overwhelmed entrepreneurs, you could say I help founders who lie awake at 3am wondering if they made the right decision about that product, while also feeling guilty for how tired they'll be with their kids the next morning. Instead of saying time management for busy professionals, try this for the executive who feels guilty every time they leave the office before their team, even though they know they need boundaries to be effective. And now, here's another one. Instead of saying I offer LinkedIn training for consultants, you could say, this is for the expert who knows that they should be posting on LinkedIn, but stares at a blank screen for 20 minutes before giving up, wondering if anyone actually cares what they have to say. In each case, the language is specific and relatable. You want people to think, oh yeah, that's me. Now here's how I applied this to my own work. I do corporate keynotes and to get these gigs, I often take sales calls from prospective clients. And when I do that, I often start by sharing this true story. I tell them this. I say, A few years ago I spoke at a large company's staff retreat and during the Q and A session, a guy in the back raises his hand. His name was Gary. He was an older guy, giant beard, and he told me that he retired a few years ago but misses everyone and so he still comes to the retreat. I don't have a question, Gary told me. I just want to tell you that in the decades I've been going to these things, I've seen a lot of speakers do empty cheerleading. But you're the first one to give us practical, useful things to do. So I just wanted to thank you. After I tell that story to my potential client, I say this. That is how I define success. It's when people like Gary are happy. Gary's have seen it all. Their time is valuable and they deserve something that's unique, practical and memorable. Clients love when I say this. You know why? It's because it shows how well I understand their needs and it shows that I can deliver. Knowingness closes the deal, because above all, everyone just wants to feel understood. Not just intellectually, but emotionally. They want someone who gets not just their problem, but their experience of the problem. The more deeply you understand that experience, the more they'll trust you to help them change it. And frankly, I think that this exercise makes us better humans too. It forces us to think carefully about the people we serve and what matters to them. We should never want to just sell stuff we should want to make lives better, which means we need to know those lives. So listen closely, dig deep, communicate deeper. You have to live in the nuance. Help Wanted is a production of Money News Network. Help Wanted is hosted by me, Jason.

[A]

Pfeiffer, and me, Nicole Lapman. Our executive producer is Morgan Lavoy. 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 Instagram at Money News and TikTok at MoneyNews Network 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.