2375 - How Leaders Can Create Connection and Joy in the Workplace with Amy Leneker

4 Mar 2026 · 18 min · 11 chapters

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In short

Episode topic: How leaders can create connection and joy at work while reducing stress, using Amy Leneker’s “Cheers to Monday” approach.

Guest

Amy Leneker, leadership consultant, keynote speaker, and certified mediator (helps leaders/teams work well without sacrificing well-being). She’s worked on organizational problem-solving, conference keynotes, and mediating workplace conflict.

Key claims

Organizations face unsustainable change and burnout-driven stress; stress has major financial and human costs, including relationship breakdowns (70% cite work stress in divorces/breakups; 79% for Gen X). There’s a “crisis of connection” (APA: over half of U.S. workers feel lonely). Connection means being seen, heard, and valued; it can’t be scheduled—leaders must be present daily (in-person or virtual).

Notable examples

solo Alaska cruise leading to book-ending creativity; leaders trying to “connect” via holiday parties; Slack multitasking preventing real connection. Book: “Cheers to Monday” (March 24), “see stress differently” via a stress inventory, control/importance lenses, and five types of work stress to break exhaustion/overwhelm/self-doubt cycles.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Amy's Solo Travel Experience

0:46 to 2:16

Amy shares her transformative experience traveling alone for the first time.

“Visit podverified.com if you'd like to be featured as a future guest.”

Creativity Unleashed Through Solitude

2:17 to 4:25

Discussion on how being alone can enhance creativity and self-reflection.

“You know, I think to myself, you know, there's been times when I mean, it's very rare.”

Leadership Consulting Overview

4:26 to 6:04

Amy explains her work as a leadership consultant and her approach to helping organizations.

“I think I heard a comedian say this, you know, it's like, Oh man, punctuality.”

Addressing Workplace Pain Points

6:05 to 7:46

Identifying common organizational challenges related to change and stress.

“Amy, when you are working within an organization, what would be some examples of pain points that your client or the folks that you're working with, what might they be coming in?”

The Cost of Workplace Stress

7:47 to 9:01

Discussion of the financial and human costs associated with stress in organizations.

“And I think what's so important, and I don't think we talk about this enough, is that that type of stress isn't just contained at work.”

The Crisis of Connection at Work

9:02 to 11:14

Exploring the loneliness in the workplace and the importance of feeling connected.

“The American Psychological Association does a stress report every year.”

Creating Connection as a Leader

11:15 to 12:22

Amy shares how leaders can foster genuine connections within their teams.

“What do we do in those virtual environments?”

Seeing Stress Differently

12:23 to 13:20

Amy introduces her book and the concept of reframing how we view stress.

“Amy, your book is coming out in mere weeks.”

Target Audience for Cheers to Monday

13:21 to 14:00

Discussion on who would benefit from reading Amy's book on stress management.

“And so I work with clients to take a full stress inventory.”

Navigating Stress and Expectations

14:00 to 15:49

Learn strategies for managing stress and expectations in the workplace.

“They don't understand that there's another layer that can really shape how you move through it.”
Show all 11 chapters

Book Launch and Author Insights

15:50 to 16:01

Discover the target audience and unique approach of Amy Leneker's book.

“Amy Lenniker, your book, Cheers to Monday, comes out.”
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Transcript

Automatic transcript. May contain errors.

0:03Welcome to the Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15-minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free podverified score, free podverified guest training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests thrive and grow in podcasting.

0:46Visit podverified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it.

1:20talk to because I feel it. I am right there with you. Amy, it's great to have you. Thank you so much. It's great to be here. We'll talk about that in just a moment. Before we do, always love hearing what, you know, successful leaders and entrepreneurs, you know, usually are multi-passionate. And so I generally just ask, what are you geeking out on lately? It's funny because I have two answers. One is the answer I feel like I should say, and the other one is the truth. And I'm just going to tell you the truth. So what I'm geeking on right now is traveling alone. I, as a mom, the thought of traveling alone is not something that's been in my world and I'm having so much fun doing it.

2:03I recently went on a solo cruise to Alaska to celebrate a milestone birthday. And I called it my family of four party of one trip. It was so incredible. I had the best time of my life. That is absolutely incredible. You know, I think to myself, you know, there's been times when I mean, it's very rare. I have gone to a movie by myself. I have gone and gone to a restaurant, you know, with just, you know, just like, you know, my wife's busy, she's working or whatever. Sure. And, you know, and, and, you know, where I've just gone and sat down and, you know, even just that it feels a little, oh, am I supposed to be doing this?

2:47Is it weird that I'm out here by myself doing this thing? But, you know, I got to tell you, it was really refreshing just to get off the berm. And, you know, Amy, I think that there's something so delightful about that, about being, you know, being your own best friend or being comfortable with yourself and just truly enjoying that me time together. What can I just ask, like some of the biggest revelations that you got from that solo trip? Because that is really inspiring. Absolutely. So one of the biggest ones was just how creative I am when I'm alone. And I think every business person, every entrepreneur listening to this can relate to that, where your brain is always going.

3:30You're thinking about a million different things. And it was out there on the open sea, somewhere between Juneau and a place I can't remember, that the ending to my book came. I'd been struggling with it for months. And then suddenly out there on the open sea, it was like, oh, yeah, this is how the book ends. So what really surprised me was just how creative I could be when I was on my own. to all of our mutual friends who get those flashes of creativity when you're in the shower. Why not build upon that? That's right. Exactly. A three, four day shower and you'll be amazed at what you come up with imaginatively.

4:09So that is so cool. Was there the other one that you wanted to mention too? No, I won't say the one I thought I should mention. Because I think as a society, we're supposed to always say these things of like, oh, here's what I do for fun. Kind of like in job interviews. Remember when they would say, what's your, what's your biggest weakness? And we all said, Oh, I'm a perfectionist. I care too. I'm just like, I just care too much. I think I heard a comedian say this, you know, it's like, Oh man, punctuality. I just cannot get my ass out of bed in the morning. And why should we, it doesn't really start till I get there anyway.

4:45Yeah. That's a perfect answer. I think that's a good enough segue as any to talk about Tears to Monday. Amy, tell us about the work that you do. By the way, your website is amylenecker.com, but share with us your work. Just share your work first, then we'll get into the book afterwards. Sure. Thanks for asking. I am a leadership consultant, so I spend most of my days in organizations helping leaders and teams work well together so that they can accomplish their goals and to do it in a way that doesn't make them sacrifice their well-being or their weekends. That's how I spend my work days. Wow.

5:24And so do you, sir, are you typically engaging from a consultative fashion as well as speaking? Share a little bit more about your tactical work within organizations with leaders. Thank you. So I do three primary things. The first one, I'm a consultant. So I go in and I help organizations solve problems. Secondly, I'm a keynote speaker. So I get to travel all over the world and do really fun conferences, which I love. And then third, I'm a certified mediator. So I help with workplaces who are having hard conversations or they're stuck in conflict and they just can't get through to the other side.

5:58So consulting, keynotes, and mediation. Those are my three books of business. Well, I suspect that that keeps you awfully busy. Amy, when you are working within an organization, what would be some examples of pain points that your client or the folks that you're working with, what might they be coming in? how might their pain present that you're like, oh yeah, yeah, I can help. Yeah. There are two things that I'm seeing the most right now. And I'll be curious if you're hearing about these two. So the first one is just the constant unrelenting change. Even folks who like change, even folks who say, I thrive in change, we've reached a level of change that is feeling unsustainable.

6:43So I hear that a lot. The second one, I always wonder, Josh, am I attracting this or is this just what's happening in organizations? The second thing I hear is around stress. When organizations are feeling stress and burnout, they're not who they want to be. Their performance is now starting to go down. So change and stress, those are usually when I get the calls to come in and be of service. Well, and there are significant operational costs to this being a problem within the organization. Do you mind addressing that? Absolutely. There is the financial cost. There's no question about it. The financial cost, trillions of dollars a year lost in productivity, but there's also a human cost.

7:26There's a human cost of what it feels like to be in a system when you're not successful. And that's when we start to see conflict go up. We see miscommunication go up. You'll start to see an increase in sick leave and leave without pay. So there's a financial cost, but there's also a really painful cost that we're paying as humans. And I think what's so important, and I don't think we talk about this enough, is that that type of stress isn't just contained at work. It doesn't just stay in the workplace. It trickles out into our home lives. And one of the most striking stats I saw recently was that 70 % of people attribute work stress as being a key reason they divorced or broke up with their partner.

8:14And it gets even worse, Josh, if you're in Gen X, that number went up to 79%. So 79 % of Gen X are saying that their work stress contributed to a divorce or a separation. so this it's terrifying so we've got to figure out this work stress because it is rippling out into families and communities everywhere and and amy i know another thing that you've pointed out in your social media is you know work is full of people so why does it sometimes feel so lonely and and i think we again we all crave connection to some level do you mind addressing that sure Sure. Connection. We're in a crisis of connection.

8:59And that's not my opinion. That's the title of a report that recently came out. The American Psychological Association does a stress report every year. And that was the title of this year's report, A Crisis of Connection. And in it, they report that over half of U.S. workers feel lonely. That's striking to me. and it's not as simple as just saying well it's because we're remote or it's because we're hybrid because many of the folks reported feeling lonely regardless of the format of their work and so true connection isn't just about being in the same room with someone it's not just being on zoom with the camera on the definition I love of connection is Brene Brown's where she says it's when we feel seen heard and valued that's connection so even if work is hard even if we're in stress in times of change, can I still operate in a way where you feel seen, heard, and valued in the way that we work together?

9:54Seen, heard, and valued. I love it. Isn't that beautiful? Leaders, like we want that. Yes. And we might be talking about it. Amy, where does the rubber hit the road as a leader where we can ensure that we are doing our part to create more of this within our organizations? I think it's in the small moments every day. So I work with leaders who are really well-intentioned, really well-intentioned. And so they'll plan an event, and this time of year we see it a lot. There's an end-of-the-year holiday party, or there's an end of the year some kind of event. That's not connection. You can't schedule connection.

10:34You can't say, Josh, I'm going to connect with you every Wednesday from 1 to 105. Does that work for you. That's not how humans are wired. We are wired for connection. So for leaders, it's you can't postpone it. You can't schedule it. It's really about how you show up at work, how you move through work every day. It has to be part of how we work, not something that we add to our to-do list. Yeah. And how do we, you know, I think there's quite a few of us, especially, you know, the SMB founders out there. I think a lot of us work virtually and, you know, my, I've listened, I've got zoom on this window.

11:10I've got Slack on that window. And that's how I pretty much connect with my team on a, you know, throughout the day, but you know, it's at the end of the day, it's pixels and sound. Yes. Which can work. What do we do in those virtual environments? I think it's the exact same thing. I think it's about being present. I think it's about really being where you are. And so if you're on, if you're on Slack and you're just sort of not being thoughtful or you're trying to do five or six or seven things at one time, it's almost impossible to truly connect. I was talking to a leader a few weeks ago who said that they could multitask and I said that's amazing.

11:50You can do something that neuroscientists all over the world have said it's impossible. Like you've got to be telling people that you can do this thing that everyone has deemed impossible because as humans we can't. We can't do it. So my advice whether whether you're in person or virtual or on Slack, is just to be present in that moment. And I say that as a recovering workaholic. So I say that with no shame, with no blame, as someone who has made every mistake there is to make, that if we can slow down and be present, the connection follows. You don't even have to think about it. It's just a natural outcome of that kind of engagement.

12:26Amy, your book is coming out in mere weeks. It's called Cheers to Monday, the surprisingly simple method to lead and live with less stress and more joy. And one thing you share here is you say, see stress differently and finally break the cycle of exhaustion, overwhelm, and self-doubt. Amy, don't keep me in suspense. I'm going to get the book, but tell me just basically what you mean by seeing stress differently. Absolutely. And it's going to seem counterintuitive because everyone that I talked to, and I did hundreds of interviews. I led dozens of focus groups and everyone that I had talked to had tried to overcomplicate solving stress, where stress management almost becomes part of their problem.

13:13Their job is to manage stress and I think we're missing it. Our job isn't to manage our stress, it's to lead our life. And the way we do that is we've got to see what's out there. And so I work with clients to take a full stress inventory. What is everything contributing to your stress at work right now. And folks are hesitant to do it. They'll say, this feels awful. I don't want to write this stuff down. But that's actually the first step in seeing what is causing all of this underlying stress. And then we see it through a couple different lenses. I help them look at what's really important. I help them look at what it is they can control.

13:50And I help them look at which of the five types of work stress they're feeling. Because most of the people I work with don't even know that there's different types of work stress. They just think, well, I'm experiencing stress. They don't understand that there's another layer that can really shape how you move through it. Yeah. You know, it's almost like, I know for those of us who sometimes struggle with sleep or we wake up and want to get back to sleep. If you get worried or you start getting upset about, oh, now I'm awake. Oh, now I'm going to be tired all day. You can't do that. If you do that, it makes it way worse.

14:28The best thing I've learned is just like, okay, you know what? I've had low sleep days before. It's going to be all right. And then I usually find that that increases my ability to go back to sleep much better than if I start getting upset that I can't sleep. So it's a little bit like that. Amy, I want to make sure that our friends who could really value from this book, who else should be reading this book, Cheers to Monday? Thank you for asking. I think it is for every employee who is feeling overwhelmed by expectations. It's for every manager and leader who is trying to keep it all together.

15:06And it's for every leader who is wondering, is this really what success looks like? So to me, it's for everyone in the workplace who wants not just something different for themselves, but they want something different for the people around them and that's what this book is designed to be there are so many leadership books that are designed just for the leader or just for the ceo and that's not this book this book is designed that we read it together and then we figure out how are we going to do things differently around here what's the culture that we want to create because unfortunately when stress starts getting high it becomes a blame game you'll see employees start to blame leaders Leaders start to blame employees and then stress actually goes up.

15:49So this is about taking a unified approach. I love it. Amy Lenniker, your book, Cheers to Monday, comes out. Oh, what's the day here? March 24th. March 24th. That's exciting. Well, congratulations. It sounds like a lot of work and effort and research went into this, including some fabulous days on a cruise. Yes. So Amy Lenneker, again, recovering workaholic turned joy strategist, your website, amylenneker.com. Amy, thank you so much for joining us. Thank you, Josh. Great to see you. Thanks for listening to The Thoughtful Entrepreneur. If your goal is to grow your business, increase revenue, and build authority without gimmicks, this show is designed for you.

16:33Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15-minute episodes focused on growth that actually compounds. And if you're interested in being a guest or you want to turn podcast appearances into measurable business growth, visit podverified.com. You can start for free with your Podverified score along with free podcast guest training and a free media kit builder. These tools are built to help you get booked on better shows, deliver stronger interviews, and convert audience trust into revenue.

17:15No more desperate sales. You truly can enjoy all the business you like by generously sharing your wisdom. Everything we offer is built by podcasters for guests with a focus on trust, organic growth, and long-term business success. Thanks again for spending your time with us. I'll see you next time.

17:39We'll be right back.

From the publisher
Cultivating Joy: Leading with Less Stress and More Connection with Amy Leneker

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Amy Leneker, Founder and CEO of Amy Leneker, to discuss the urgent need for a shift in workplace culture. As a leadership consultant and author of the book Cheers to Monday, Amy brings a wealth of knowledge on how to dismantle the staggering human and financial costs of workplace stress. Their conversation dives into the "crisis of connection" facing modern teams and provides a roadmap for leaders who want to move beyond simply managing a to-do list toward leading a life filled with more presence, joy, and authentic engagement.

Transforming Workplace Culture Through Intentional Presence and Connection

Addressing workplace stress is no longer just a "nice-to-have" initiative; it is a critical business imperative that directly impacts organizational health and employee retention. Amy explains that stress often stems from a lack of true connection, where employees may be physically present or "available" on digital platforms like Slack and Zoom but do not feel seen, heard, or valued. By shifting the focus from mere availability to intentional presence, leaders can foster "micro-moments" of connection that build trust and empathy. This transition requires a commitment to slowing down and treating connection as a daily practice rather than a scheduled HR event.

To effectively navigate the complexities of modern work life, leaders must first gain clarity by conducting a thorough stress inventory to identify specific triggers and patterns. Amy identifies five distinct types of work stress—including acute, chronic, and relationship-based stress—noting that a one-size-fits-all approach to management is often ineffective. Understanding the root cause of pressure allows individuals to tailor their responses, moving from a proactive stance of "leading their life." When leaders model this behavior, they create a permission structure for their teams to prioritize well-being, which ultimately reduces conflict and boosts collective productivity.

In today's hybrid and virtual environments, the foundation of a healthy culture is built on the quality of interactions rather than the quantity of meetings. Amy emphasizes that presence is platform-agnostic; whether a conversation happens in person or via video, the key is to eliminate distractions and practice active listening. Multitasking during interactions undermines the fabric of connection and signals to others that they are not a priority. By creating intentional moments for personal check-ins and celebrating milestones, organizations can bridge the digital divide and build a culture where "Cheers to Monday" becomes a realistic reflection of the workplace experience.

About Amy Leneker

Amy Leneker is a leadership consultant, keynote speaker, and the Founder and CEO of Amy Leneker. With a background in organizational development, she helps leaders and teams around the world decrease stress and increase joy. She is the author of Cheers to Monday: The Surprisingly Simple Method to Leave, Lead, and Live with Less Stress and More Joy.

About Amy Leneker (Company)

Amy Leneker’s consulting firm specializes in leadership development and workplace culture transformation. Through workshops, coaching, and speaking engagements, the company provides science-backed strategies to help organizations foster authentic connections and build resilient, high-performing teams.

Links Mentioned in This Episode

  1. Amy Leneker Official Website
  2. Amy Leneker on LinkedIn

Key Episode Highlights

  1. The "Crisis of Connection": Understanding why loneliness persists in the workplace and how to foster genuine belonging.
  2. The Five Types of Work Stress: A framework for identifying stressors to develop targeted, effective coping strategies.
  3. Presence Over Availability: Why being truly present in the moment is the most effective tool for building trust and empathy.
  4. The Cost of Stress: Examining how workplace pressure spills over into home life and the staggering trillions lost in global productivity.
  5. Leading Your Life: Shifting the mindset from "managing" external stress to intentionally leading your own internal experience.

Conclusion

This conversation with Amy Leneker highlights that the ultimate competitive advantage for any organization is the well-being and connection of its people. By treating stress as a signal for adjustment rather than an inevitable burden, leaders can reclaim their time and build environments where people genuinely thrive.

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2375 - How Leaders Can Create Connection and Joy in the Workplace with Amy LenekerThe Thoughtful Entrepreneur · 18 min
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