Want Honest Feedback? Here’s How to Get It

Summary

---

Help Wanted Podcast: “Want Honest Feedback? Here’s How to Get It”

Host: Jason Feifer (Entrepreneur Editor-in-Chief)
Contributor: Nicole Lapin (Money Expert)
Release Date: August 6, 2026

---

Episode Overview

In this episode, Jason Feifer guides listeners through the art of receiving honest feedback—why it’s tough, and how to bridge the invisible gap that keeps team members, friends, or clients from speaking up. Using real-life stories and actionable advice, he explains how to create deliberate “permission structures” so people feel comfortable sharing what they really think. The episode provides practical strategies for leaders, colleagues, and friends to proactively invite communication that will strengthen togetherness and success.

---

Key Discussion Points and Insights

1. Why People Don’t Speak Up

• Fear of being a burden, discomfort, or not wanting to hurt feelings keeps people from voicing concerns or feedback—even in low-stakes scenarios.
• Jason illustrates this with a personal story from Jenny Wood, a former Google exec, who endured a freezing Lyft ride rather than ask the driver to turn on the heat.
  • “The truth is I didn't want to make the driver uncomfortable, even though I had every right to avoid frostbite.” (Jenny Wood, quoted by Jason, 05:07)

2. Permission Needs to Be Explicit and Ongoing

• Hosts argue that simply saying “open door policy” isn’t enough; people won’t assume you still mean it months later.
• Jason:
  • “Whether you like it or not, it is your job to continually create the opening. You must give other people permission to approach you just like that Lyft driver did and then reinforce it over and over again.” (08:51)

3. Concrete Examples of Giving Permission

• Jenny Wood’s Office Hours at Google
  • Created a weekly calendar slot, sent to her entire team, specifying what could be discussed—ranging from major roadblocks to “something fun you did this weekend.”
  • This design lowered the threshold for starting a conversation, making it clear that both big and small talk were welcome.
  • “No need for prep work or fancy slides.” (Jason quoting Jenny’s invite, 07:32)
• Alternative Approach:
  • Another Google manager used five-minute slots to signal that no topic or duration was too minor.
• The Friendship CRM
  • Jason’s friend, Jordan Harbinger (podcast host), sends regular check-in texts, explicitly offering to help. He tracks people in a CRM (like sales professionals), sending regular nudges that make it easy to ask for a favor.
  • “Jordan literally keeps track of people in a CRM the way salespeople track their clients. I know I am in that CRM and I still like it because although his system may be automated, the connection is human.” (10:46)

4. The Importance of Renewing Permission

• People assume your previous invitation to connect might have ‘expired,’ so it’s vital to renew it—just like Jenny’s Lyft driver’s sign.
• “Relationships are like bridges...most people will eventually wonder, hey, can I still cross that bridge? So it is time to put up a giant flashing neon sign that says yes.” (Jason, 11:20)

---

Actionable Advice

Jason’s Challenge to Listeners:

• Give someone explicit permission to connect or share honestly, whether it’s your team, partner, or a friend. It could be as formal as office hours or as casual as “Hey, anything I can help with?”

Suggestions for Implementation:

• Invite candid feedback regularly, not just during annual reviews.
• Lower conversational barriers with informal prompts (talk about weekend plans, for instance).
• Use tools (like CRMs or recurring reminders) to periodically renew contact and offers of help.
• Remember: The more accessible and welcoming you seem, the better the communication and relationship.

---

Notable Quotes & Memorable Moments

• On why people stay silent:
  • “If people want something from us, yeah, okay, fine, they should just ask. But let's deal with reality. They probably won't ask.” (Jason, 06:59)
• On the impact of deliberate permission:
  • “The sign gave me permission. It’s permission I didn’t even realize I needed.” (Jenny, as quoted by Jason, 05:32)
• Bringing it home:
  • “When you renew people's faith in the bridge, they will cross it and you will both be stronger for it.” (Jason, 11:34)

---

Timestamps for Important Segments

• Introduction and Theme: 04:08–04:29
• Personal Story—Permission in Small Moments: 04:29–06:00
• Why Explicit Permission Matters: 06:00–07:32
• Google Office Hours Strategy (Jenny Wood): 07:32–09:19
• Regular Renewal of Permission (Jordan Harbinger): 09:19–10:46
• Challenge and Summary: 10:46–11:34

---

Summary Takeaways

This episode underscores that truly open communication doesn’t happen by accident. Routine, authentic invitations to connect are not just nice—they’re crucial to fostering a culture, workplace, and relationships where honest feedback flourishes. Small acts—like posting a sign, sending a calendar invite, or initiating a check-in—signal real openness and build lasting trust.

---

For more actionable career wisdom, subscribe to Jason’s newsletter at onethingbetter.email.

---

End of summary.

Transcript

[A]

As entrepreneurs, it's easy to spend all your time thinking about money, but usually that means the money in your business and not the money in your pocket. So let's hit pause and think about your wallet. Do you love all the cards in there? Have you ever considered that there's something better out there? I want you to love your bank as much as I love mine. That's where Chime comes in. Chime is changing the way people bank. They're not like traditional banks that love to gatekeep the best rewards and pile on hidden fees. Unless you have a massive balance, Chime offers the most rewarding fee free banking, all with no overdraft fees, no monthly fees, no minimum balance fees. You get 5% cash back on Chimecard in a category of choice like gas or groceries, all while building credit through regular everyday spending. With no credit check, you can also grow your money faster with a savings rate that's nine times the national average. And if you're ever in a pinch, Spot Me lets you overdraft up to $200 fee free. Join the millions who are already banking fee free with America's number one choice for banking. Have head to chime.com helpwanted that is chime.com helpwanted Sign up now. It only takes a few minutes. Chime is a fintech, not a bank. Banking services and Chime card provided by Chime's bank partners. Qualifying direct deposits required terms and limits apply. Go to chime.com disclosures for details.

[B]

When everything at work is on fire, you know deadlines are slipping and your entire team just disappeared because they won the lottery. Well, you think that this is a job for Sponsored Jobs. When you need a hiring hero, an Indeed Sponsored Job will match you with quality candidates. Phew.

[A]

Indeed Sponsored Jobs gets you quality candidates when you need them most. Stop struggling to get your job post even seen on other sites.

[B]

People are finding quality hires on Indeed right now. In the minute that I have been talking to you, companies like yours made 27 hires on Indeed. According to Indeed data worldwide, Sponsored Jobs

[A]

posted directly on indeed are 95% more likely to report a higher than non sponsored jobs. Join the 3.3 million employers worldwide that use Indeed to connect with quality talent that fits their needs. Spend less time searching and more time actually interviewing candidates who check all your boxes.

[B]

Less stress, less time, more results when you need the right person to cut through the chaos. This is a job for Indeed Sponsored

[A]

Jobs and listeners of the show will get a $75 sponsored job credit to help get your job the premium status it deserves@ Indeed.com podcast just go Indeed.com

[B]

podcast right now and support our show by saying you heard about Indeed on this podcast. Indeed.com podcast terms and conditions apply. Need a Hiring hero? This is a job for Indeed Sponsored

[A]

Jobs Managing the social media for Money News Network is so much more than scrolling on your phone, making sure that each show's account is regularly posting on trend and flagging comments for me to respond to is a full time job. It also requires someone I can truly trust for my team. That person is Daniella. I found her on upwork. You can find your own Daniella or whoever it is your team needs there too. Upwork helps grow your business by giving you fast access to specialized talent across 125 plus categories so you can fill skill gaps, launch projects faster and scale support up or down without committing to full time headcount. You can browse profiles, review past work and get help scoping the role so you can hire with confidence and get started quickly with business. Plus, you can access the top 1% of talent on Upwork and with AI powered shortlisting, you'll get matched to the right freelancer in under six hours. No endless searching required. It's free to sign up and posting a job is easy. Visit Upwork.com right now and post your job for free. That is Upwork.com to connect with top talent ready to help your business grow. That's Upwork.com Upwork.com.

[B]

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 Lapin. On Tuesdays, Jason and I answer the helpline and help callers solve their work problems.

[B]

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.

[B]

You may not realize it, but somebody is afraid to talk to you. If you're a manager, your team might hesitate to give you upd. If you're a business owner, your customers might not give you valuable feedback. If your friends or partners are in need, they might not turn to you first. This sounds awful, right? You want to be warm and welcoming and you don't think of yourself as intimidating. So what's the problem? It's this. You haven't given them permission because you didn't think you needed to. Today I will show you how to fix this problem, making you a better friend, leader and partner. But first, let's look at a small moment where someone was afraid to speak up. My friend Jenny Wood, who has been co hosting a few of these episodes with me. So name might sound familiar. My friend Jenny is a former Google executive, has a great new book out called Wild Go after what yout Want and Get It. In the book she tells a brief story that I really related to. And here it is. She wrote. The other day I got into a lift to the airport. The car was freezing. However, I shivered silently instead of asking the driver to turn on the heat. The truth is I didn't want to make the driver uncomfortable, even though I had every right to avoid frostbite. That's okay. That's from her book. I don't know about you, but that is so me. Like if I'm getting a massage at a spa and the pressure is so intense that I am in pain, I will literally grip my way through it instead of asking the masseuse to lighten it up. But anyway, Jenny, back in that freezing car, noticed something. Her Lyft driver had a sign in the back seat and it said this if you need anything, feel free to ask. And then there was a list of things to talk about including the AC and heat. When Jenny saw that she felt comfortable speaking up. The sign gave me permission. She told me when we talked about this. We were chatting about it after recording a help wanted it's permission she said that she didn't even realize she needed. Now here's why that story is so powerful. We should all be giving permission. If people want something from us, yeah, okay, fine, they should just ask. But let's deal with reality. They probably won't ask. They may fear being a burden, or they don't want to hurt our feelings, or they worry that their request isn't welcome or whatever. That's why Jenny didn't speak up in the cab and why I don't interrupt the masseuse. Instead, we all stay quiet, leading to a worse experience for everyone. If people are not asking you for what they want or need, that is inhibiting your ability to build stronger connections and become a better leader, partner or friend. Maybe you think you've already covered this. Maybe you're a manager and you've already told people you have an open door policy. Or you might tell friends, you know I'm here for you anytime. But as time passes, people might forget that or they worry that your offer expired. So whether you like it or not, it is your job to continually create the opening. You must give other people permission to approach you just like that Lyft driver did and then reinforce it over and over again. I asked Jenny did she ever do this when she was at Google? And she told me yes. People on her team were nervous to meet with her because they they weren't sure what would justify taking her time. So she set out to fix that. And here's what permission can look like. Jenny, for context, ran a large org at Google with many direct and indirect reports, and she wanted them to feel consistently welcome approaching her. So she created a weekly block of time for office hours. And then she sent the invite to everybody on her team. It said that anybody can book a 20 minute slot with her. And then to alleviate any anxiety about what's worth discussing, she provided conversation topics. Here's what it looks like. So she actually sent me a screenshot of it. It just says, like the name of it is Jenny Wood. Weekly office hours. Underneath she wrote, hi team. Please sign up for a 20 minute office hour slot whenever you'd like. There are three available slots each Tuesday. Below are ideas of what we can discuss. No need for prep work or fancy slides. And then she lists a whole bunch of things. A project you're excited about, a roadblock I can remove. A skill you want to develop, something fun you did this weekend. That thing at the end there, the little fun thing she did this weekend, that's because she wanted to lower the bar for conversation. She didn't want people to feel like they had to have some very, very important reason to meet with her. One of her Google colleagues actually went a step further. They offered five minute blocks of time, not just 20, because they wanted to send a signal that you don't have to have some fancy presentation to come talk to the boss. So that's one way to give permission. Here's another. As I was talking to Jenny, I was reminded of my friend Jordan Harbinger, who hosts a big podcast. Every few months, I get a text from him that basically says, hey, how you doing? Anything I can help with? And I love these texts. They prompt us to catch up. And every so often, yeah, I actually do have something that he could help me with. But now I realize something. In those texts, Jordan is really giving me permission to ask him for favors. Yes, in theory, I could always ask Jordan for help, but I might have hesitated otherwise. It's anxiety striking again. I might have thought, well, Jordan offered to help me a few months ago, but maybe he's not in the mood anymore so I won't ask. That's why Jordan needs to renew the permission. And now you want to get next level with this. Get ready. Jordan literally keeps track of people in a CRM the way salespeople track their clients. I know I am in that CRM and I still like it because although his system may be automated, the connection is human. So here's a challenge that I hope you will take today. You should give someone permission. Maybe it's your team, like Jenny, you could find a simple and lasting way to invite them in. Maybe it's a partner you could ask. Hey, it's been a while since we checked in. How are you feeling about the project? Any concerns we can discuss and that could open conversation that they might have kept to themselves. Or maybe it's a friend. If you haven't heard from someone in a while, they might wonder if you're too busy for them or if your feelings about them have changed. So invite a catch up. Relationships are like bridges. Some are big and strong, like a friendship or a partnership. Some are narrow and temporary, like a customer in your lift. But no matter what, most people will eventually wonder, hey, can I still cross that bridge? So it is time to put up a giant flashing neon sign that says yes. When you renew people's faith in the bridge, they will cross it and you will both be stronger for it. All right, that as you may know if you listen to Help Wanted regularly. That comes from my newsletter. My newsletter is called One Thing Better each Week. One way to be more successful and satisfied and build a career or company that you love. You can find it at onethingbetter Email. That's a web address. Plug it into a browser. One thingbetter Email. I do read the newsletter here here on the podcast, but if you want to get it early in your email and along with a whole bunch of other goodies that I tend to include and link to. Then again, one thing better. Email. I give you permission to subscribe or to not subscribe. I give you permission to do whatever you want as long as you keep listening to Help Wanted. 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 helpline@help wantedoneynewsnetwork.com 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?

[B]

Oh, I didn't sign up for that.

[A]

All right, well, talk to you soon.

[B]

Sam.