The Bosshole® Chronicles

Jeff Harry - Rediscover Your Play (Part 1)

Jeff Harry, a champion of play in the workplace, joins us to unpack his journey from toy industry disillusionment to founding RediscoverYourPlay.com. Inspired by the movie "Big," Jeff embarked on a quest to infuse workplaces with the joy and creativity he found lacking in his early career. He now leads the charge against toxic work cultures, especially in Silicon Valley's tech scene, by using play as a transformative tool. Learn how his workshop, "Dealing with A-Holes in the Workplace through Play," is creating more engaging and healthier work environments by challenging detrimental behaviors and promoting psychological safety.

  • Click HERE for Jeff's LinkedIn profile
  • Click HERE for Jeff's website Rediscover Your Play
  • Click HERE for Jeff's Speaker Playlist


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John Broer:

Welcome to all of our friends out there in the Bossh ole Transformation Nation. This is your co-host, John Broer, which means yes, indeed, I'm being joined by none other than Sara Best, my friend and business partner. Sara, how are you doing and what the heck is going on today? Who are we talking to?

Sara Best:

Hey, John, I am so good, always real good. It's always a delight to spend time with you, and I'm sure our listeners get sick of hearing how great our episode is going to be, but this one is a fun one, it's one for the books, I think. Our guest today, John, is Jeff Harry, and let me just tell you, last April, when I attended the Work Human Live conference in Austin, Texas, Brene Brown was the keynote speaker, by the way. I attended that and I got to hear Jeff's breakout session, which was you know, the lessons we can learn about leadership and psychological safety from the Barbie movie. So I'm like, oh it just the session description.

John Broer:

It drew you in.

Sara Best:

It drew me in yeah. And so I went to hear Jeff speak to a packed room and he was so fun and engaging and on point and just witty and had such a great delivery and, based on what he talked about, I knew he would be a really powerful guest for the Bossh ole Chronicles because he works to prevent that. He is a Boss hole prevention expert for sure. Let me just tell you real quickly a little bit about Jeff and he'll tell a little bit about his own story in our episode but, he created RediscoverYourPlay. com and he is a keynote speaker.

Sara Best:

He's an author. He's a coach and facilitator. He talks on some very important things, such as working with our inner critic. Dealing with a-holes is one of his great topics. He does talk about psychological safety and other things that definitely make it challenging in the workplace and, by the way, Rediscover Y our Play his main focus is how to create well-being and psychological safety and other important outcomes with play at work, but how he gets to that, I think, is worth a listen.

John Broer:

Once again, Sara, you're bringing in some amazing subject matter experts. I say, we just jump in. What do you say?

Sara Best:

Let's play.

John Broer:

The Bossh ole Chronicles are brought to you by Real Good Ventures, a talent optimization firm helping organizations diagnose their most critical people and execution issues with world-class analytics. Make sure to check out all the resources in the show notes and be sure to follow us and share your feedback. Enjoy today's episode.

Sara Best:

Well, Jeff Harry, welcome to the Bossh ole Chronicles. This is so great to have you.

Jeff Harry:

I'm so excited for this. I love the title of this podcast.

Sara Best:

Well, when I first heard you speak and got to meet you, I knew you would be perfect for an episode here on the Bossh ole Chronicles. Without, you know, spoiling anything, let's have you share. How did you end up doing what you're doing today and focusing on what you focus on?

Jeff Harry:

Yeah, so the Batman origin story is, did you ever see the movie "Big with Tom Hanks?

John Broer:

Oh yeah.

Jeff Harry:

You know back in the day, yeah. So I saw that in third grade and I was like you can play with toys for a living. And I was like, oh, my goodness, I need to play with toys. So I started writing toy companies. First I went to FAO Schwartz dance on the piano. No one discovered me, like in the movies.

John Broer:

So they just lie.

Jeff Harry:

They lie about that. And then I just started writing toy companies and I wrote them for the next like 15 years until I got into the toy industry and I don't know if you've ever gotten exactly what you've always wanted, right, and then been so disappointed when you got there. But you know, there were, you know I arrived in the toy industry no toys, no high fives, no joy, no, no kids, no play, and also just and also just, and so many, so many Boss holes, so many Boss holes, like everywhere. So I left my dream industry, my dream job, and I came to the San Francisco bay area and I bumped into a job on craigslist and if you know anything about craigslist like that's where you get furniture in a dark alleyway, so I don't think you should get a job from it. But I found a job teaching kids engineering with Lego, hence the bow tie that I'm wearing today. They were just teaching kids engineering with Lego.

Jeff Harry:

There were seven people. We had no idea what we were doing, but we started to grow it and we took it from seven people to 400 people and it became the largest Lego-inspired STEM organization in the US. We partnered with Lego. We worked with Facebook, Google, Adobe, all the top companies. We built gigantic stuff out of Lego. I helped three staff get into Lego Masters. We did just a lot of really cool stuff. We broke some world records with Lego and then at one point I left, worked on the Obama campaign and then I came back and I didn't want to work with kids anymore. I wanted to work at the organization and I was just like I just want to start doing stuff with adults. So we started running team building events for all the top tech companies in Silicon Valley, because that's where I was residing.

Jeff Harry:

And I realized while I was there, two things, one not as healthy of a workplace as you would think all these top companies are and two, a lot of Boss holes, so many Boss holes. So, ironically enough, the first workshop that I created with my company, Rediscover Your Play, I partnered with a friend of mine, Gary Ware, another really amazing speaker and improv guy out of San Diego, and we made a workshop called Dealing with A-Holes in the Workplace Through Play. That was our first workshop and it got picked up by Inbound. We got to speak at Inbound in front of hundreds of people. And then we went to Australia, and that was February of 2020. And then everything got locked down. And then, after that, I just started making up talks that just challenged the system, that challenged the antiquated system that we currently have, and I've been doing that ever since.

Sara Best:

That's fascinating.

Sara Best:

Well, so I've heard you as a keynote. You're ridiculously funny and very poignant in the points you make. The talk that I got to listen to and this was at Work Human Live last April is what the Barbie movie can teach you about psychological safety and leadership. Of course I was intrigued and I knew I was going to attend that talk, so I made sure to watch the Barbie movie on the way down to Austin where the conference was. But yeah, you have this unique way of making the important things in work and what we'll call Bosshole prevention, making it palatable by creating fun and levity around it. But there's always a ping of truth in there, for sure. So when you think about what's happening in the industry, you're speaking all over the country. You're going to SHRM conferences and you're speaking to executives. What are the things that you're addressing? What are the chief things that are troublesome that you're seeing out there?

Jeff Harry:

And it's not like it just sucks, like it usually sucks, but like it sucks much more ever since 2020. And you would have thought, like with so many people dying, that we would come back and we've been like looking out for another and like caring about each other, but instead it like lifted the veil on how exploitive a lot of companies are of their staff. So when I talk to employees, the main three things that I would hear a lot is like employees feel disrespected, right, employees feel exploited and employees feel used and I mentioned this during the Barbie talk disrespected. Great example is, like you know, there's a story of someone that worked at Google for 15 years and he went into work at 4 am in the morning using his fob key and it didn't work, and that's how he found out he got laid off. Right, and a thousand other people at that same happened the same way, and that wasn't just Google, like many tech companies are now doing that. Why, how is that OK, right? Especially as people that have devoted so much of their life they're devoting two thousand and 2,500 hours a year.

Jeff Harry:

Another company passed out, I think I told you about this, the stale cookies. They reached $10 billion in sales and, instead of rewarding their staff with bonuses and raises, they instead passed out these cookies that they sent out late and they became stale and they had "10 B on them. So they were like congratulations, we got this much money, but you don't get any of it Right. So, like there's just there's just so many stories of just like staff just feeling taken advantage of and it's really bad and that's why, like, union representation is coming back. That's why people are fighting back much more, because people are angry that you would have thought that great example with HR right, that we would get more support because in many ways, we saved our companies Like no one.

Jeff Harry:

It wasn't marketing that figured out what we should do from an epidemiology perspective, it was HR that figured all this stuff out. Were they rewarded with that? No, most of them. When I'm at conferences and I'm like how many of you doing two to three jobs, 80% of the people raise their hands yeah. So where's the support? Where's the money? Where's all this stuff that we spoke of right? Where's the empathy, compassion and humanity? That's what's currently missing. That's currently missing.

John Broer:

And we want to dive into that empathy, compassion and humanity. Why it's lost. But I want to go back to something really quick because at the advent of the pandemic, Sara, you and I were involved in working with a number of leadership teams virtually just to talk about resilience, understanding your behavioral wiring, your leadership DNA. And I'll tell you what, if COVID did anything, it did a lot of things. If it did anything, it really exposed how poorly we sort of vetted out people we were putting in management and leadership roles. And it seems to have been exacerbated, or there's a I don't know if it's resentment, but this incivility that continues to sort of flourish organizations.

John Broer:

It's not a fair equation from the standpoint of we're this company. We want you to feel like you're part of this community until we don't need you and then you're fobbed at work. That's not an even exchange and the emerging workforce they are expecting that connection and that exchange, and this is where we're not seeing that empathy, compassion and humanity. But I wanted to go back to that simply because that was such a tipping point. And one other thing related to that. I'd love to hear about your concept or your perspective on the return to work push that some organizations are saying well, you know, we think it's time that everybody comes back and we're going to mandate that. It's like you've got to be kidding me. Are you that tone deaf to what's going on? So thanks for letting me jump in there.

Jeff Harry:

I just wanted to reflect on that. Just to add onto that right. So a study that just came out in 2024, I think Fortune and Forbes both featured it, about how nearly all bosses are trained to be doing the management job. They have no training whatsoever. So when we talk about nearly all bosses, we're talking about 82% of bosses and it's leading to one in three people quitting. Right.

Jeff Harry:

So, in addition to 85% of the workforce is disengaged, in addition to 81% are looking for other jobs, in addition to 60 or 70% of them don't have a work-life balance, right, and disengagement numbers are to the point that I think businesses are losing 450 to 550 billion a year in disengagement just because people are turnover, absenteeism, people calling in sick, like all that stuff, right. So all of this is going on and many ways I feel like work is like just so broken and so you have people in leadership positions that should not be in positions of power and then when you ask them, what do they hate most? They hate training because of all the micromanagers hate. And no wonder the micromanagers want people back in the office. They have nothing to do, they have no one to like, point stuff to during the pandemic and showed you're not actually necessary.

Jeff Harry:

There's a book that came out with I think it was called "BS jobs or bullshit jobs, a while back, like four or five years ago, and it proved like 45, 50% of jobs probably unnecessary, a lot of middle management jobs, a lot of ones where, like you're just telling, you're just passing paper from one to another person. So of course, micromanagers want people back in the office because they need control, because they're not good at their job, and I think this all ties in with are y'all familiar with the Pornelli's Iron Law of Bureaucracy?

Jeff Harry:

I can't say that I am. I just came across this myself. So, based on Pornelli's Iron Law of Bureaucracy, it talks about how people that support the bureaucracy at the detriment of the organization are rewarded. Meanwhile, anyone that wants to change or improve the organization usually is ostracized or removed. This is what we're fighting. We're fighting this iron law of bureaucracy, of mediocrity, of mediocre leaders that want to keep it together because they don't want to become obsolete. If they have to get better, they're not going to be there, so that's why they keep it as bad as it is.

Sara Best:

I was reviewing the Gallup's recent State of the Global Workforce report that just came out, I think it was yesterday, actually and it wasn't surprising to learn that managers are the pivotal piece and, as you talked about, Jeff, they're most in need of upskilling and the right style of approach to optimize their team members. But they're at least perhaps not open to it in some cases, or it's not available to them, and they're selected for the reasons you indicated, which is hard, John. What were you going to say? For the reasons you indicated?

Jeff Harry:

Something as simple as, like, I'm an engineer, I want a raise and the only job up there is a managerial job. I know a lot of engineers that would rather be engineers. They don't want but they feel they have to because it's the only way they can move up. There's no other position when, if you think of individual contributors, that could mentor in a different way if we were more creative we would have more individual contributor jobs available.

Jeff Harry:

So instead you're forcing people or you're just being like you breathe, you move up like you're just throwing people up there. Why? Because you did the last job well, does it mean that now you can teach others how to do the other job well? It makes no sense.

John Broer:

I was just working with a group of business leaders and we were talking about some of the trends, culture, development and so forth, and you can tell that a number of these are more established, perhaps come from the more command and control way of doing business versus trust and autonomy. We use the metaphor of it's the difference between the old stoplight intersection and a roundabout. People freak out at a roundabout. But this is the new way of work, it's the way to reinvent the workplace.

John Broer:

But the thing is one gentleman talked about how important it is for managers and supervisors to be equipped and I asked how much do you invest in each one of your managers to do that? I mean, what's your line item in your budget? And he said we don't have one, we just kind of make it up. And I said you're really not developing people. I mean, if you are not saying we're going to put a line item in our budget and we're going to invest in our supervisors and our managers to make them better people developers, if you're not doing that, you're not a learning organization and you're not serious about developing non-Boss holes developing non-Boss holes.

Jeff Harry:

Exactly. None of your actions. Express your priorities, right, and think about it. What's the first thing that gets cut when, like when, oh, we are not hitting our quarterly numbers? Professional development, so anything that is like feel good. You're like, oh, we actually don't need that. You actually need that more now, when your quarterly results are not hitting. But it's amazing how we run to the things that are more easily measurable than the stuff that actually really matters, right? Sure yeah.

Sara Best:

Yeah, she only would say that's the smart stuff versus the healthy stuff, like the stuff we need to have in place to allow people to thrive. I think the other thing we got to focus on for a smaller to midsize company maybe not the big giants, some of which you've worked in and worked very closely with they're family owned or they're just very old school there hasn't been any development in their operational model and what we often encounter is that behavioral challenges, performance issues just don't get addressed and that breeds a whole other world of problems. But in many cases we're sensing a little patriarchy. You know there's like this is how it works. Yep, what do you? Well, you and I have talked about this, yeah.

Jeff Harry:

Yeah, because I was literally just talking to someone that just works with family-owned companies, right, how to transition, how to transition them out, right, or how to sell them or whatever. Because most of the time the sons and daughters don't want the company, right, but they're being forced to like. And then also there's so much nepotism, so you have someone like that's in charge of marketing and he doesn't care or he's not even really interested in it, but they want someone in a position of, rather than putting someone that's qualified that actually would be really amazing they put one of their kids or one of their cousins in and then they think they can, it can operate that way, right, and I say this all the time we're cultures defined by the worst behavior tolerated. So if you have your son that is just messing around and like maybe does four hours of work a month, you know, and the rest of the time is just, you know, using your expense account, you're sending a message to everybody else.

John Broer:

Oh yeah.

Jeff Harry:

This is what we, this is what we tolerate, this is what we actually support. So I don't care what their mission is, I don't care what your values are. I care about your worst behavior. You tolerate. Address that. That addresses your boss hole problem.

John Broer:

Yep.

Sara Best:

Directly intolerance. Address that. That addresses your Boss hole problem. It's true, whether it's a family member or just an ill-suited person for a particular role. When things like that go unaddressed it really does suck the psychological safety and trust out of the company. Because it doesn't matter what I do. I'm working hard over here, I'm committed, I bring my whole self to the job and I love this opportunity to grow. But look at what I see happening. That doesn't get addressed. So it's unfair and it's unkind. This might be a time to sort of pivot. I mean, we could talk all day about the problems and the challenges, but you make it your mission to talk about what can help inside the workplace in the culture, reducing boss hole behavior. So give us some of those tips and tools.

Jeff Harry:

Yeah, yeah. So there's two approaches to it. I think I'll put the psychological safety part later. Okay, let's talk Boss hole part, right? Okay, so we have to set boundaries. So when I'm running my workshop on dealing with toxicity in the workplace through play, I am all about organizing to challenge that toxic person. So it might start off with simply reframing and redirecting right, meaning that boss hole is not in meetings, because when they are, they affect the meeting.

Jeff Harry:

And we've talked about how your boss has more of a psychological effect on you than your spouse, than your therapist, than your doctor. So, like, these people are actually making you sick, on top of the fact that you might be more stupid because you're around someone that's toxic, and you might be more mean. There's all these studies that communicate that. So the reframing and redirecting right. So like, can we not have them in the meeting? Or being like hey, I'm sorry if there's a Chad listening to this, but I'm just going to say Chad. Hey, Chad, let me save you a meeting. To come to this meeting. It's not a, it's not a good use of your time. I'll summarize it and then share it with you afterwards, right, so that. So I'm giving from easiest to implement, not as impactful, to hardest. Then the second one is actually challenging them directly. Challenge that toxic person directly. So either at the meeting, when they cut you off because they will, or they cut off your colleagues and they're speaking 80% of the time, you jump back in and you watch out for each other. So you're like oh, I'm sorry, Chad, I know you have something really important to say, but Samantha is like the lead on this project, so I think we need to hear from her. And you do that over and over again for the next three months. You even talk to the facilitator to manage it and set the ground rules so Chad can't run a muck during the meeting. Because right now, people are just giving up and being like let Chad speak, we don't care, because that's what. That's what toxic people want. They want you to just give up. That's their strategy. They're just going to tire you out. Until you just are like you can do whatever you want, because I'm just done, right, yeah, and I even say that to people. I'm like you.

Jeff Harry:

Before we even figure out these boundaries, you have to decide whether this is even healthy for you to fight? Do you want this fight? Or what is? Does it make more sense for you to start looking for another job, right? Or look for another? Or you want to stay in the company? Just start looking for another department, because this is not a healthy situation.

Jeff Harry:

So you got to first decide whether it's worth it, right. But then you reframe, redirect and then challenge, and then the third is then. So you confront them as well. You confront them after a meeting and you go what do you want to get out of this meeting, chad? Do you want to talk most of the time or do you want other ideas? If you want other ideas, when you do this, when you say Samantha's stupid or Jeff is stupid in the meeting we're not going to share, like, the impact is that we're out. So you say that to him, so you set the boundary. Now he might just be like whatever I'll do, whatever I want.

Jeff Harry:

That's when you're going to their boss and being like does this person fit the values of the organization, does they fit the mission? And, more importantly, because they won't care about that, is this person make us money? We're trying to make money. Oh, Chad brings in a million dollars a year. Well, let me show you the documentation of the last seven people that have quit because of Chad. If you look at the exit interviews, all these people reference this person. How much did that add up to? Oh, $1.5 million. So actually it's costing us half a million dollars to keep this guy. Is that something we're cool with? So you challenge their motivators, you figure out the decision makers, priorities, and you're like does this fit the values of the mission, the organization, if that's important to you, and does this fit our financial goals? Because clearly it doesn't, right? So then that's that If the manager's manager is also a Boss hole, then you have to go to other departments or to the C-suite executives and you have to really determine whether or not they believe in their mission and values or not.

Jeff Harry:

And it's great, because if you find out that they love Chad and his friend from the same fraternity, then you know you need to go right. Right, and if they don't, then you're like do you know this is what's going on in your organization? Do you know in this department, this is what, how your company is represented. Are you cool with that? Right, and I say it all the time any, any building or any room that has all the leadership posters on their right leadership with the eagle. And the more posters you have, the more toxic the place is like. If you because if you need to tell people to have integrity with a poster, then you're already done Right.

Jeff Harry:

And then, finally, the last part is you have to address the inner Boss hole in yourself, so the inner critic, that inner, because somehow you have to identify. Why does this person trigger you? Because if you don't address that and you don't address every time they call me stupid or every time they say you shouldn't get promoted. If I believe that stuff, then I will act a certain way and even if I leave this organization, the next organization I'm going to be with, it's going to be the same issues because I haven't addressed my inner boss or my inner critic.

Jeff Harry:

Once you do that, and then you really are like wait a minute, I should get paid more than Chad, I should be actually his boss. The next time he disrespects you, you can be like Chad, don't ever speak to me that way. And that empowers everybody else to be like oh look, Jeff just stood up to Chad, maybe I can stand up to Chad, right. And then each and every one of us is standing up to this person and then they can't act that way anymore, because it's not a fun place for them to work, because they can't bully people, and that's when they consider leaving. So that that's my approach from a boundary standpoint road from a boundary standpoint.

John Broer:

So if you want to know what happens to Chad, you better tune in next week for part two of our discussion with Jeff Harry. What a great way to kick off this two-part episode. Make sure you check out all of the links in the show notes to learn more about Jeff and this really cool work that he does. We'll see you next week.