In this episode, Mike and Eric interview Jake Brown, author of Leadershit: Tales & Tools to Survive a Bad Boss & Have Fun at Work. Jake shares his journey of escaping a toxic job and how 200 conversations with friends dealing with less than ideal bosses inspired his book, which breaks down the four roles we play in bad workplaces. With humor and insight, Jake reflects on both the absurdities of office life, and the power of sharing stories to survive and thrive in tough work environments.
In this episode, Mike and Eric interview Jake Brown - Author of “Leadershit: Tales & Tools to Survive a Bad Boss & Have Fun at Work”
Jake recounts his journey of surviving a soul-crushing job that nearly ruined his relationships—and his weekends. After escaping the grind, he noticed his friends were just as exhausted from their jobs, barely able to function outside of work. Cue 200 conversations with people venting about atrocious bosses, which led Jake to write a book that breaks down the four roles we all play in toxic workplaces. Along the way, Jake shares some of his maybe inappropriate but certainly memorable office moments, like the “No drinking till 10 a.m.” rule that raised more red flags than a bad email subject line. It's a candid, funny take on work life, recovery, and the healing magic of swapping bad boss stories around a metaphorical campfire.
Links Mentioned in the show:
https://airballoonadvisory.com/ Visit Jake's Website
https://leadershit.co/ to get the book
The whole book's about me not falling. Rules and helping people do creative things outside of the rule. It's not like we didn't break a moral model. We did not break laws, but we did break the rules in order to succeed and survive. It's really it should be called why Jake is unhireable, right? Oh, that's not true.
But it's totally not true.
Welcome to the marketing team of one podcast, where we have conversations about the issues one person marketing team space when trying to meet their goals with limited time and budgets. Now here's your hosts, Eric and Mike. We know a lot of the stress of being a solo marketer can come from above. So, and what by above, I mean, comes from your boss.
And so we wanted to talk today about surviving a bad boss. So we called in a heavy hitter here. Got someone who wrote a book on it. It's called leadership. And I'd like to welcome to the podcast, Jake Brown. Hey guys. Hey, how's it going? Doing all right. You know, no bad boss. We're good today. You currently don't have a boss.
Is that what you're saying? Yeah, I am my boss right now. Um, so, you know, the worst boss I've ever had, you know, so grinding myself pretty hard now. Um, Yeah, it's a different world these days. Well, first of all, I think we should start off by saying you might have worked from the stories in your book.
You've probably worked for one of the worst bosses ever, but. You learned a lot and you learned how to get through that and make it fun. I mean, I'd love to hear kind of what started your, you know, what was the genesis of trying to write this book? First off, I lived it. That was the worst part of the whole thing.
But then, um, I got out, like in the book, I actually talk about, it goes from day one to day last in the book. But when I got out, um, a couple of years into it, you know, I was out for about two years and then I noticed that people were quitting. Every conversation I was having, people were complaining about work.
Their boss, it was horrible, you know. And what happened is I was around friends and I got tired of my friends just being bad friends because work was sucking everything out of them. And it's kind of like I just got tired of them not being whole anymore, you know, like outside of work. When we go hang out, we go to the bar, we play Frisbee, like we do something.
And it's kind of like even camping. It's like we can't even camp with our kids because you're not a whole person. Like you're - you're still recovering. So when I noticed that happening, I started having conversations with people. And in the course of about three months, I had 200, like I documented, I had 200 conversations, whether they'd be zoom calls or meeting with people, just hanging out where people just started railing on their bad boss.
Like they were just. Stuck. They're oppressed, like they couldn't figure out how to deal with their bad boss. And I just started sharing my stories over and over again because I had gone through it and I talk about the four different phases, like the four different roles that we play. I have lived all four of those roles.
And then when I got out, I started healing and looking back. And it was this idea that was like my stories. I hated living them, but they were kind of this like light in the darkness. For other people, they gave them hope of what they could change because we can't change everything, but there are things we can change.
And as I started sharing these stories and talking to people, I was like, man, I kind of got tired of sharing the stories over and over again. So I recorded them and then I wrote them down and put it together as the book that was really just made it available to people and started talking to people. And it's been a blast.
The book has been a blast living the stories in the book. Now, I had a lot of fun through the book. I'm not going to lie like there is a lot of stuff in there that you're just kind of like this guy is the worst employee ever. But I made the boss a lot of money, you know, like I accomplished my job. And I helped the other people around me survive.
So living it was horrible. Pulling together the book was hard work, but that was actually a lot of fun. And then sharing the book has been it seriously just feels like play all the time because who doesn't want to sit around a campfire, hop on a zoom call and just talk about their bad boss experience?
Yeah, I I found it so funny how many of the stories in the book relied on, you know, Making a stop at the fridge to grab some beer and house. It's like beer was a central part of the work experience. We had a kegerator in the office. Yeah, and Eventually a sign went up above the kegerator that said you can't drink all day if you don't start in the morning And then another sign went up that said, another sign went up underneath that because we worked at a design agency.
So, you know, we're designing hand lettering, like doing nice signs. And then underneath it, there became, uh, there was a sign that was just handwritten because it wasn't by the designers. It said no drinking till 10 a. m. And I remember when they put up a sign that says no drinking till 10 a. m., you We have a problem.
Like there's a, there's a problem in our culture. If that rule has to be said.
I'd love to hear like that transition about the phases that you're talking about in like how, cause I think. There are some unredeemable bad bosses. I think you might've had one of them is what it sounds like. But I do think there probably are some who don't just don't know, but I'd love to know how those phase, could you explain those phases for everybody?
The big thing that I came to is I was actually working through this and I didn't understand it until people who worked for me. We're having a rough time either with the way I was managing or the big boss, you know, coming down and stand in the book. It's like their relationship in there. And what happened is as I was doing reviews, as I was helping them, I started asking the same questions over and over again.
And really it boiled down to there are two questions. It's, are you aligned? And the idea there's, are you a part of the mission, the vision, where this company is going? Are you a part, aligned with the team? Are you aligned with your co workers? Are you aligned with the boss? Like, is this company, you know, this work that you have, this job, is it taking you somewhere where you want to go?
And if the answer is no, we've got, there's a bigger problem there, you know, like, but if the answer is yes, then great. That's one question. And, uh, that's, you know, uh, on the grid it's, are you aligned? That is, um, the horizontals on it. And then the other one is, are you able, so do you have the skills, you know, are, are you capable of doing your job?
And on the other one, it's like, are you allowed? And that's my favorite one to talk to people who have a bad boss is. Are you, do you have the skills to do your job and are you allowed? And then it's again, those are the vertical columns. Yes, I'm able and allowed. No, I'm not. And the allowed is kind of the kicker for a lot of people because it's like if the boss is meddling, if this is happening, if you're not like you're the expert, you're hired to do this job and you're not allowed to do it.
That's the one that grates on us more than anything. It's also the easiest one to fix because it's usually a conversation. There's an unmet expectation. Yeah. Where you're expecting something out of the job, the boss is expecting something out of your job, and if you don't talk about it, and you don't make sure that you have alignment, then you're never gonna, you're never going to be able to, um, be allowed to do your job, and the biggest gap in that one is, uh, trust, and the idea is either that we think that the boss doesn't trust us, but what I found specifically when I was a boss managing people, I realized That it wasn't that I didn't trust them.
I didn't trust my ability to delegate or to communicate what I wanted. So I was holding on to stuff and I was interfering in projects because I didn't trust that I had set it up or I had enabled them to do their job well. And I had to fix that for myself. And then I started thinking, well, how do we do that?
How do we fix that trust? Um, when we aren't the one who gives it, like, how do I fix the trust with my boss? And I went back and looked at the patterns that I had, um, my coping mechanisms for working in this company. Um, which is really what the book is. It's a collection of my coping mechanisms and how I grew because of them.
Um, the way I define trust is that people like somebody knows that you do what you say. So if you want to earn trust, what that means is say something, do it and make sure they know. Oh, you have to walk backwards. So even with clients, we would do this. Um, or when you go to your boss, you can say, remember when you asked for this project, you asked for A, this is where I did it.
B, this is where I did it. C, this is where I did it. Because the boss will almost never circle back and notice things that were done right. So if you want to build trust, you say, I do my job all the time. Well, they're over there facing 17 different, you know, fires and a client or, you know, a customer that's, you know, off the rails and they're not going to notice that you saved the files with the right format and you got it done a day early and you put it into, you know, Dropbox or wherever.
You didn't save it as a PDF because Mike hates PDFs, but you like you actually do your thing and you put it in the right place. If you do your job, the fact is, if you do your job, nobody should notice that. That is how our work environments are set up. But going back and saying you ask for these things, I did them.
See, see, see, see next time. Like you can ask for growth, but that's how you're going to build. Trust is people know that you do what you say. Okay, we'll say it, do it, and then make sure that they know. And that was my favorite hack that I found out was. Once the boss realizes that, because worst case scenario, they want to stop having these meetings with you.
So they will just give you stuff and then stop checking up on you because they don't want to follow up meeting, like annoy them into letting you do your job. You know, um. It's better than being, being meddled with all the time. Um, but that was really the idea of that trust. So anyway, back to the two by two matrix, if you're allowed and able to do your job and you're aligned, that's the winner.
And honestly, when you find yourself in that square, when I found myself in that quad, I found that my job was actually to help other people get to that space. And when I made that a part of my job every day, going in and helping move people in that direction, I started enjoying my work. Um, I just had to insulate people from the bad boss, but I could help move more people in that direction.
And at times, I could help the boss get in, get toward that space as well. Um, had to find ways to do that and get really creative with how we did that. The next one is, if you're aligned, but you're not able, like you don't have the skill set to do your job, I call that the intern. And the idea there is like, you're just an excited puppy that pees all over the kitchen floor.
Like, if you keep peeing everywhere, you're gonna get thrown out. Like, you have to realize that the interns are the first ones to go. The fastest way to get alignment is to join the fan club. It's not healthy, but if you join the fan club and you, like, are eager to learn from other people, that is a quick way to start to grow.
Um, like, you're really aligned. How do you learn from them? Well, take on that intern where I'm going to learn from people. I'm going to get better. Because they're teaching me, that is the fastest way to grow in that intern role. And then the next one, you're not aligned, you're not able, that's the prisoner.
Um, and usually, it's not so much that you're not allowed, you're not able to do the job, that one usually is you're not allowed to do the job, and you have no alignment with the company. You really, it is a dark, dark place. Um, we've all, I'm sure had days where we just kind of don't, it's like a Tuesday morning and you're like, I think I'm feeling sick today.
Like, I just can't get out of bed and go in like that's that prisoner role. There's no hope. And you feel like your skills are even getting worse. Like you're losing your skills. So you don't even feel like you could go find a new job because you're outdated or you're, you know, just everything is against you.
It's, you're most likely to hit that kind of victim mindset when you're in that prisoner role. Um, but in the prisoner role, You can do a couple of things really quickly. Um, you can learn from other people. Um, my book actually is great for the prisoner role because if nothing else, you're going to laugh and you need laughter in your life at that point.
Um, but the idea is like either learn from other people or get alignment. And if you're in the prisoner role, it's a lot easier to learn things and sharpen your skills. Um, one of my favorite ways to do it is just ask somebody who's doing a project. If you can watch them work. Hey, can I watch you work on this?
Can I, can I just watch how you go through that? Um, I had, uh, one guy was telling me that when he read the book, he actually asked his boss to record himself working. So he did a screen, you know, I basically did screen share, recorded it and worked through a project. It was actually a coding project. He worked through it.
And then the employee, you know, the, the employee said, okay, he went back and watched that over his lunch break, like watched how his boss worked. And he was like, oh, now I understand his logic. I couldn't understand what he was doing, but I just watched him do it for 30 minutes. And now I understand how he thinks and that helped him get out of that prisoner role where he's like, okay now That actually fixed alignment and his skill level because now he could do things where the boss looked at it Now this wasn't a bad boss.
This was just You know, boss, but he's like the boss looks out and goes, yes, like the boss could approve things because it was the way he expected to see them. So that's one way the prisoner and then the last one is the expert. This is kind of the mercenary. You're really, really good at what you do. Um, but yeah, there's no alignment.
And the thing is, this is kind of the loneliest role. And it's also, I think, the most dangerous role, because as long as you are not seen, as long as the boss sees you, the bad boss sees you as a hired hand that is working toward their cause, then you're great. But as soon as you become the other or the enemy or something like that, you've got a target on your back and they are going to, you know, they're going to open fire.
They're going to cut you loose very quickly. Um, so you have to find a way to work on alignment. Um, and for me that was investing in other employees, uh, figuring out how I could make the company better. Cause it's really hard to fire somebody who's constantly driving revenue up. So I was like, okay, if the bad boss wants more revenue, I'm going to drive the revenue I'm going to invest in these employees so that we drive the revenue.
So I found ways that when I was in that role, I found ways to, um, almost keep the bad boss addicted to me. Um, you know, it's like, we, we can't let him go because that's where the revenue is coming from. Um, but that also becomes a very lonely and it becomes this battle. Um, it wasn't true alignment. What I found out afterwards, you know, once you get out of the toxic place and you look back and you're like, yeah, the number one question people ask me is.
Why did you stay so long? And the fact is, it never dawned on me to leave because I had to provide for my family. So I was providing for my family and I thought, well, I'll look for another job. I can't let go of this job. Maybe I'll look for another one. But every day when I got home from work, I was too tired to even get on LinkedIn and look for jobs or anything.
There was none of me left. So it just became this cycle that, uh, well, you had a difficult spot too. Cause you were playing that middle role, correct? I mean, that's a, you're basically living in no man's land because you're that insulator and you've got us all done. Got to bring in a team and for them aligned as well.
Right. For sure. Yeah. Getting trapped in there. And when I started working there, I wasn't, I was in a, I was on a team by myself and then what happened is I, once I started finding joy, like I was At the darkest point, I kept going to work looking for happiness. And then I remember that I can still remember the day that I realized I will never find happiness at work.
There's a reason that they pay me, because this isn't a like where I was. They paid me to bribe me to keep me coming back. Like in my mind, I was like, that just became very clear to me. It was like, if this was like Disneyland, if this was Disneyland, they wouldn't be paying me to be here. Like, like, I just remember having that thought.
And. Once I realized that it kind of became this thing where I was like, okay I'm not gonna I'm not gonna come into work to find my happiness I in the book I talk about like I have to pack it like a sack lunch and bring it with me every day And when I started doing that in the way that I did that was fun.
Just goofy things that I did to survive I invited people in on these inside jokes and pranks and things that we did and The more I did that people were like drawn toward me and toward that hope so then we actually had this like joy And And the more people that followed me and were drawn to me, I just moved up in the company like super fast because, um, I became the kind of like defunct leader.
Like, you know, there was the boss who controlled things and I was the leader that was bringing growth. So it was kind of like on accident. I didn't mean to, and I was bad at it at first. But that's how we learn, right? You have like your practice team. You're like, Oh, I'm going to practice on them. And they're like, OK, now it's the real the real deal.
So, yeah. But being stuck in that middle, that was I saw. A big part of my job was making sure that everybody else was allowed to do their job. And there's, there's a chapter in the book called The Friend, and there are, there's the, the boss, and then three of us that are on the management team. And we would literally, there was a bottle cap, a uh, McGlobe Ultra bottle cap, that we would pass around, and if it was on your desk, you were the designated friend.
And it was your job to go in there and be friendly and distract the boss, so the rest of the team could get their work done. Like. Keep completely distracted out of the way. We'll get two hours, like sit in there and talk to the boss for two hours. You can hang in there and do this. And that was one of the tactics that we did, like when it got bad, when we got into a crunch, when we were in a project, it was like, we don't have time for the boss to meddle or give feedback.
You know, like we're rounding third. Don't don't send signals now. Like it was so late in the game. We're like, we can't do that. We just have to finish this and get client approval. We don't have time to change our plan. Well, we would sacrifice a senior, like sometimes a senior leader, like a higher salary, we'd sacrifice that person for two hours to go sit in there and distract and hang out with the boss while we worked.
That was one of the strategic tactics that we did. Um, there were others as well. Um, but the idea was once I found that idea of building trust and I could get the boss to trust me, then I stood in that gap of I will get things done. And. Actually, that was another big change for me. Um, I learned this back when I was, you know, a C, like a single person marketing team.
Uh, and I realized there was one day that I realized, like, it's my job to get things done, not to do everything. And I was like, okay, well, there are other people on the team, outsource vendors, contractors, like my boss wanted me to get stuff done. And I started bringing in rallying team. So as long as the stuff got done, I was trusted to get it done.
Then that that was like. A huge moment in my career, then I go to this agency and I'm working there and I realize I'm just going to step in because none of us are allowed to do our job. So I stepped into that gap and said, I will make sure it gets done. And then I let everybody else like there were, I can't tell you how many hundreds of meetings I sat in there and listen to the boss.
And then didn't actually have to pass that information to the people who were working on it because they already knew how to do their job. So the year's 2019 and I walk in to a meeting and the boss is like, You know what we really need to do? We probably need to focus on making this website responsive.
And I'm like, In 2019? I'm like, We haven't not done that for six years. What are you talking about? You know, it's like, Okay, did you like, did you read a blog that you hadn't read before? Like it was things like that that was like, I mean, for a history lesson though, right? Like the iPhone came out in 2007, responsive websites really started catching on in 2009, 2010.
So nine years later, we're talking about it. Yeah. It was a lot of things like instead of having an all company meeting or the, you know, the boss going in and talking to the designers and the developer, like instead of stepping all the way down into there, it became my job just to take the hit and let them keep working.
While I took the hit. Right. Um, but that was in that middle manager role. But when it came to doing my own job, when the boss would ask something, it would I would always have to go back to, you know, trust their meddling. They don't trust themselves. Like the boss didn't trust the boss or the boss doesn't trust me.
I need to know which one it is and fix that. So that was always whenever those meetings, whenever that meddling sort of happened, I was like, OK, what is it? I would say that the third thing that I found is we created a document. We called it the gold medal, uh. Delegation because we couldn't get projects handed down.
But Metals, M-E-D-D-L-E, 'cause the boss kept meddling and everything and we just never wrote it out where the boss could see it. Um, but we had a series of questions and really the idea there was that, can we get everything that we need to work on this project? And then when we came back to presenting it, we would go back to it and say.
It needed to do this, like you said this, we did it, you said this, we did it, you said this, we did it, like we were able to document that, and then my favorite thing at the end was, like, what do we do with this, um, and there's, uh, I can't remember which Olympics it was, it was the Winter Olympics, and I watched this guy come down, like, he was skiing, you know, where they, like, go around the flags and all this kind of stuff, I don't know, some kind of downhill skiing, and he's going down, and he makes it to the bottom, and And then they like show him and he's got this great time, you know He's set up for a medal and he's like just like looking around.
He's like lost He doesn't know how to get out of the bottom because they've moved the exit And I remember watching that and going that's how I feel on every project I do my work I get to the end of the project and then i'm like, but what do I do with it? Like I never know when the boss thinks that I'm done.
So what we ended up doing is at the end of the, at the end of that delegation sheet, it was like, do the project, pass it off, do the project, bring it back to the boss for approval. Do the research, bring it to the boss and the boss will make a decision. We kind of had these different levels of what do you do with it when it's done?
And that streamlined us so much because what happened is people would finish a project and then in project management, you kick it off. Like it's off my plate, it's on somebody else's plate. But if it was a decision, like a company decision or. Um, you know, like, for instance, if you're a one person marketing team and you're working on, say, a content calendar, does the boss have to approve everything on the content calendar, or do they just want you to fill it out and say, I've got it done, and they say, Thank you.
Like, just knowing what is that expectation of the finish line. Because there are a lot of times that we think the boss is meddling, and we say, Okay, well, here's my content calendar. Please go through and review everything and give me your edits. Tell me what you think. The boss may not actually want to tell you what they think.
Okay. But they think that they're helping you by getting involved. Tell me what you think. Let me know if there are any revisions. What they hear is, oh, well, there's probably revisions I need to go find. Like what I like to do is and Mike and I have talked about this before. It's like I will present it.
And I'm like, here it is. I'm publishing on Wednesday unless you throw a red flag. Like, I'm assuming this is approved. Do you want eyes on it? And I found that. Having that conversation with the boss ahead of time to say, this is how I'm going to do this. And then moving in that direction, whether it be with clients or a boss or anybody, it actually takes the pressure off of them.
And then there comes a day where they go, I don't really need to see these content calendars anymore. You've got this. And that's, I mean, that's like one of the happiest days in a solo marketer's life ever when they go, I don't need to see this anymore. And you're just like, yes. But I love that observation.
That's a really clear one. And I think a lot of people just take for granted, like, yeah, this is what it means to be finished. That is such an important milestone that probably isn't clarified as much as it needs to be. You know, what is done? What does that look like is what's the approval process behind it?
I like that. And, uh, Most people, we don't ever think about that because we think about it from our point of view. And if you just have that conversation, it saves so much stress. Now, if you say now, well, what about, you know, what if I fill out the content calendar, I bring it to you and the boss is like, well, yeah, I want to go over every single one of them with a fine tooth tone, fine tooth comb and everything.
That's when you go, yeah, I'm not allowed to do my job. Like that, that was made very clear to me. Okay. That's where we are. How do I build that trust? Can you have that conversation? Because most bad bosses don't want to be bad bosses. They actually think that they're helping. They're just like helicopter parents that are smothering us.
Um, now if they're unethical and like illegal and doing that, like, no, you can't. Run from that like don't go to jail for them. That's the job's not worth it So much of it is about like expectations and alignment, you know, but um one other thing I really liked especially I think if you've got if you're kind of feeling lonely Like you you're the solo marketer and you don't you might not have anybody else I one of the things I really loved about the book is you're where to get inspiration and guidance from people you may not even be connected to.
Like, could you, can you talk a little bit about how, how people might be able to kind of like grow in their learning while they're trying, doing all these things to get alignment and everything. But there's the skill part of it and everything. How can they grow their skills when they're kind of stuck trying to solve some of those other problems?
Yeah. Um, so there's one thing that I came up with that, My wife told me not to include in the book because she's like, Yeah, you can't do this. But I included it anyway, because that's how I am. The whole book's about me not following rules and helping people do creative things outside of the rule. It's not like we didn't break the rule.
We did not break laws, but we did break the rules in order to succeed. It's really, it should be called why Jake is unhireable, right? Ah, that's not true. Um, so one of the, uh, um, one of the tools that I talked about in there is this council of elders. And, uh, my wife is like, yeah, you can't tell people you have imaginary friends.
Like you can't put that in the book. But honestly, what it was is I wanted to grow, but I didn't have access to anybody who was growing me because the first Misaligned expectation I had is that the boss cared enough about me to help me grow to make me better I'm investing my life and spending chunks of my life in your company like in your presence Why am I not a better person?
Like I expected that to happen and then I realized it was not on the boss's radar at all To make me a better person and I remembered that was That was actually really hard. Like I actually like called my grandpa cause I'm like, I think I just figured out something and my grandpa's like, yeah, that's not your boss's job.
And that was kind of like one of those moments that I was like, oh, I wanted to be mentored, but my boss did not see it that way. So that, that wasn't, that was a missed expectation of our relationship. So then what I did is I said, okay, well, who do I trust? Who would I want to be more like? And I found these kind of like, what are the areas I wanted to grow in?
And I found either authors, podcasters, musicians, um, Yeah, Dave Grohl made the list anyway. It's like there are different people that do great things that I was like, there's something about that person that I would like to be more like them. So I created these this council of elders in my mind. It was like this person represents this attribute that I want to grow into.
So I'll go read their blog. I'll listen to their podcast. I'll do these things because I want that to rub off on me. So I started learning these things like Michael Hyatt, uh, so Michael Hyatt, Donald Miller, John Acuff, Bob Goff, Dave Grohl, like there were just all these people that I was like, okay, they're putting information out there.
I'm just going to kind of sit under it and kind of be mentored by them. And now, um, it's shifted. But now for my company, I still have this like it's this idea of like they're at the my board of directors almost and there are times when I'm like, I don't know what to do. And my grandpa passed away, you know, um, several years ago and I was still in my mind.
Imagine like if I was to ask grandpa this question, how would our conversation go? Like I'm pulling from the wisdom that I know that he had or that he put on me or it's like I need to work on the messaging for my website. I'm going to redo the messaging on my website. Okay, well, okay, well, who do I trust for that?
Okay, let's think about the process that I learned from them. And I will often go back and think if I was going to sit down at a table and imagine this conversation, I need to work on this project, but I need the wisdom. I need the information beyond what I have. Well, who do I have access to? How can I learn that?
And that's where I started growing and I started having more answers. And then as I had more resources, a lot of people that worked for us would come to me. Because they're like, how do I get this information so that it gets past the boss? How do I how do I do this? So I started growing myself and that was the first thing that other people saw was that that hope and then Some of the other ways that I would say like that I learned to grow myself or I would ask people how they did things Hey, how do you do this?
Can I just watch you work? Can I watch you do that? I would ask for documents for how people did things and Specifically up and downstream of my job, because what I found is when you have a role and there's somebody downstream that like picks up the work after you're done with it, if you can make their job easier, like that, like ability will be very, like, that's very valuable on the team.
You can build a lot of alignment by just figuring out, like, for instance, if you're say you're working in illustrator. And anybody who's ever worked with an illustrator straight out of college hates seeing their files. It's like, look, 17, 000 layers. Every letter got outlined and put on its own layer, and we hate looking at this garbage.
Like, we don't want to live there. Or Photoshop. Edit photos, all this kind of stuff, and you're like, do you know what a folder is? Please tell me somebody taught you what a folder is. Like, you end up in those messes of just nasty files. Well, when you go to hand off a file to somebody. It should be in a way that they can use it, not just like, you know, like my kid's bed, where everything just shoved underneath and you're like, Hey, where's your missing sock?
I don't know. They pull it out. Everything's flying. You can't find the sock. And you're like, we're trying to go to church and we can't get a sock to go to church. Like, you don't want to be in those situations where you hand off a file. For instance, I'm going to go with design. Cause that's my background.
Um, say you do like a massive cookbook, lots of stuff. You're getting ready to send it to print. Somebody's going over it. They're pre pressing it. They're going through making sure that everything's ready, locking it down, getting it ready to ship out. If they get a messy file with jacked up links and the photos aren't in there, right?
Like, and everything's named different ways, like it becomes very cumbersome and then they have to do a bunch of guesswork and assumption that the files, that they're reco, that they're reconnecting, all this kinda stuff, they're assuming that they're doing it right. Well, that slows everybody down and they don't like you, so that's gonna kill your alignment.
But if you can. What I did is I started reaching out sideways, upstream and downstream. How do I make people's jobs easier? Well, what happens is then those people like you and they start coming to you. Well, that's actually right there. How I got my first promotion at this company was because everybody came to me for answers and they basically like, I mean, like, you know, basically like an earthquake.
They like pushed me up, you know, like they just as they closed in that gap, they pushed me above where they were. That is how I took that first leadership role. Because I was curious about their job and I made their jobs easier. And nobody gets their feelings hurt that the person who made their job easier got promoted over them.
Hey, you're the new guy, but you got promoted. That's a rough situation. But you're the new guy and I like my job better. My job's a lot easier. Hey, you made this happen. Nobody fights that promotion. Um, and if they do, it's because they've got their own issues, but providing value, you provide value in that chain that, uh, that's the secret.
I mean, everybody needs that, you know, help. I mean, that's what we're all trying to do is work towards that final. So it sounds like we need to make a poster. What would grave Dave Grohl do as long as it's not a pdf somewhere, right? As long as it's not a pdf. Michael condone. No. So. If it's intended to be printed, I'm okay with a PDF being used.
I do. I need to clarify that. I don't hate all PDFs, but if it's going to be printed, it can be a PDF. If it's intended for somebody's mobile phone, it should not be a PDF. Right. Yeah. Okay. Just, I'm going to repeat that every episode until I start seeing it in the world. Oh yeah. I have sent that episode to so many people because I think it is so funny.
He's such a whiner. That even goes back to that upstream downstream, you know, like. If the end user is using it on their phone, why on earth would you make it so difficult? Like, I want you to know this information and it's going to be in a riddle and too small for you to read. And, you know, I'm going to hate you as I give you this information that I require you to know.
Like, that just doesn't work. Like, just think upstream, downstream. How do you make it to where they can actually use your output? One time we talked before and you had mentioned this, This like metaphor that sticks in my head. It's about and actually it's very relevant. We don't Olympics just wrapped up and Yep, and uh, the u.
s. Is very bad at one event and it's striking if you look at the 100 meter or the 100 meters like this year We had three of the eight competitors like three of the eight fastest people in the world are American Great. So you, you take another guy, you could take almost anybody. You take a fourth person.
I might be able to do, I might be able to do a leg. So you take the fourth person, but you've got three of the eight fastest people in the world. And we can't even qualify. Like, yeah, we are horrible at the relay because we hand off the batons. And I watched this documentary. It was about actually the women's team, how we couldn't make the Olympics like multiple Olympics.
We couldn't do it because we were dropping the baton. We had bad handoffs. And he said, The problem is we think that we push the baton and it's the person who's getting the baton. It's their job to take the baton and run. And he said, The person receiving the baton, he said, their job is to get up to speed and hold their arm out.
That's it. They get up to speed. It's the person delivering the baton. Everything else is on their shoulders. They run, they have to tempo off of the other person's acceleration. They put the baton in the receiving person's hand, and hold it still until it's pulled out of their hand. And I was like, Huh? So he came in and coached him, and then, I mean, like at this Olympics, like, we crushed it.
You know, the women's crushed it. Oh, the women's team. Yeah, the women's team. But the men's team did that. The men's team. It was kind of like one of those things where you were like, Oh, man, it just. It's just sad. Anyway, but the idea is like that is what we have the fastest people But they all and if you watch them, they're all celebrating themselves at the end of the race And when they got to that relay, they're doing enough to say that their job is done And then it's like my job is done.
You dropped it. It's like it Your job's not done until the other person. I mean, that handoff thing is long, like the window where you have to hand off, like your job is not done until they are at full speed with a baton and then you're done. So that's that's the that's the metaphor. And when I started thinking about it's like, if you take that mindset, if you have a team that has that mindset, if you personally have that mindset, you will find a lot of alignment because.
Everybody, if your job, if you, if your job is actually to make the next person's job easier, like it doesn't matter what you have to do, but your job is to make it land so that the next person can be excellent at their job. Like who doesn't want to work with those people, right? I mean, again, if you're doing finalizing files and stuff like that, and somebody's giving you garbage, or there's the, you have two people, the person who gives you just enough to where it looks good and it's done, or the person that gives you the organized files.
And you get to pick which person you're going to like, you walk in there, which project do you want to work in? I don't care how horrible that client is, how anything I want to work with a person that's going to set me up for success. One of your council of elders, which seemed to be very present in the beginning was, um, Jim from the office.
I think it seemed like you took a lot of learnings from that to really kind of help build morale around and kind of. Tuna. Yeah. Yeah. Big tuna. Big tuna. Big tuna. Yeah. We, uh, we actually started, um, I had never heard of the office. Like at the time, it was kind of like one of those things where I hadn't got engaged in with or whatever.
And then, um, somebody mentioned it and we started watching it on our lunch break. We'd go in the conference room, throw it up on the projector and we would watch it while we all sat there and lunch. And it became this like healing place where it was like. Cheers, you know, where everybody knows you're like, you went there and you felt like, oh, we're not in this alone, you know, like, oh, their works a little bit worse than ours, like, like, we aren't going to jail.
They might be like that was that was kind of a big, big difference there. But we started watching it and I noticed how Jim, um, one of my favorite things is that Jim started playing pranks on people, but they're all custom tailored. Like, they're not just mean, like when he does something, it's like from 12 episodes back, like something is there, like the one where he dresses up like Dwight and he's like, you know, identity crime or identity theft is a crime, James, like all the little nuanced things that he did to be Dwight, you know, you start watching, it's like, okay, he actually saw them and he becomes this leader where people are following him and I didn't notice that I was doing this at first, but I was watching The Office and I actually had a notebook where I was taking notes.
Like, I was like seeing the things that Jim did and I was like, wow, that was really good. Like I was being mentored by Jim to bring kind of this joy, this, you know, camaraderie back into the office. And sometimes it's, you know, the boss is gone. Let's do the office Olympics, you know, like let's do random things like, like sometimes it's things like that.
And sometimes it's just like, how are we going to survive this meeting that we, we know that we're just going to get berated and there's nothing I can do about it. Um, or. You know, uh, we just have theme days. I just randomly would send out a note and be like, all right, everybody theme day. And we'd dress like we were all going to a 1980s pool party and sit out on the front porch and eat popsicles.
Like we would just do these random things that I just knew people needed a break. But I was watching Jim because he's also like Jim was their number one salesperson. So it's not like he was 100 percent slacking. Like he was getting all the numbers and everything, but he was keeping everybody else alive.
It's kind of how I watched it and I fell in love with the way that he was doing that and then he kind of became a mentor for me and then there became a point where you kind of outgrow that and you're like, okay, the culture is healthier. We depend on each other. We need to be a little bit more. There are times that it's like, yeah, we need to find three more clients.
We need to put our head down. We need to work on this. I need, you know, maybe it's yeah. You have a grand opening for a building and you're the only person doing all the communication and you just have to head down, work on that project, drive through like there are times you have to do that. Um, and I kind of, I wouldn't say I completely outgrew gym, but I definitely came to the point where it was kind of like I became a gym and then I needed other mentors.
As I moved through there, but, uh, yeah, he definitely played a huge role in, uh, So when you were, when you were searching for that, it sounds like you, you react well, having kind of that council of elders in your life. Did you ever, you needed it to have them kind of virtually exist, um, when you were a solo marketer, but then you, Did you ever gain another kind of, you know, a group that you had talked to actual human beings or was this, uh, do you have a kind of a group of those people in your life now?
Yeah, for sure. Um, you definitely need to build a community. The idea of when I was on my own, it was really rough. When I built the people around me, like when I had a staff, when I had vendors, like there were actually times when like vendors that I hired became my coworkers. They became the group that I was surviving with.
And even going back to when I was the solo marketing person, I was still in that role where I was protecting the vendors from my boss. Like there were a lot of times that I felt and then the vendor was going to come back with stuff. There were a lot of times that like you just feel like a volleyball or a ping pong ball and you're just getting smashed by both sides.
And. It's just kind of like, you know, the great news is this is only 11 points long. Like, I can survive it. Like on table tennis, you're like, I'm going to make it. Wow. Another Olympics reference. So the idea of like figuring out how to turn vendors into partners into co workers, because there were a lot of vendors that I had a lot of stuff I could learn from.
For instance, if we're going large format or we're going digital large format, you know, digital space, experiential type stuff. It's like, what can I learn from them to make their job easier? Because. If I can do stuff to get it out to them, or another one that a lot of individual marketers don't think of is if you have, so you have your print team and you have the design team and you have a copywriter person over here, like if they aren't working for each other, like that's a nightmare.
Like nobody likes you because you've gathered together a group of people who can't get along that are trying to just get the money together just because they're cheaper on the hourly rate. Doesn't mean it's actually going to be a better project because. One of my favorite things to do is, if I know what printer I want to print something, ask them who will get me there, who will set me up.
And they might cost a little bit more, hourly or whatever. That contract might cost more, but it might take half the time. So then it actually ends up being cheaper. Or they might be able to hit my deadline. It's like, if you can build that team where they're going to work together. Um, vendors were a good one.
Um, I, there's a printer that comes to mind that he was just, um, I mean, he almost like in my professional career, I would consider him like an uncle in my professional career where he was there. He helped me. He mentored me. If you asked him, he probably won't even realize that he fully mentored me. It was just that I was there.
I was curious and he would take time when I asked for questions. Um, it was whenever I had new people coming in, I was like, I can teach them stuff. But if you could just give us a tour of the print shop and take us through and my young people, like, An intern or a junior person that worked for me, they got to go to a print shop, they saw the cutter, they saw everything work, and they never had any questions about CMYK or limitations or anything like that because straight out of college, you might have seen some of that stuff.
But if you see something that you designed or that came out of our house, go through, you know, Heidelberg, Awesome. It's coming through, it's coming off the end and it's folded like it's going through the whole process and you look at it and you go, Oh, that's why you keep telling me to do this. That's why you say, check the bleed, because if I don't check the bleed, 5, 000 or 500, 000 prints are going to be wrong.
Yes. Because a robot cuts it. You know, it's like he helped me realize that he helped me by inviting my team in. in solving that problem for me, like massive problem. So then anytime I got a chance, like we'd go through another cycle, new employees, new interns, it's like we're going to the print shop and we'd go to the print shop and learn that from him.
Um, another thing is colleagues, people who had my role other places, they were fun to get together and talk to. Um, they were coworkers. I wouldn't say that they were always a mentor, you know, like an elder type thing, because a lot of times, um, Whenever we would get together and talk, it was like the cesspool of human ignorance.
Like none of us had the answers. So we just like sat together and shared problems. You know, we didn't actually make any progress. It's kind of like, Oh, look, you have that problem too. Or you have it worse than I do. That's that wasn't progress. It was helpful and it was community, but it wasn't necessarily progress.
Um, and then I did join some other communities and I found other people. But the idea for me always was who can help. Like, who can help me and who can I learn from? And I've always had this thing where like gray hairs like I, I've just always been drawn to like, this sounds weird. I was like, I've always been drawn to gray haired men.
But you know what I mean? Like, I've always been like this idea of like grandpas and parents, like these people who are older than me, because I don't want to learn things the hard way, like if I could just learn from them, you know, like nobody wants to be the person who goes and goes, Yeah, well, you know, we got 10, 000 cookbooks back, but The page order was wrong.
So we're going to have to redo this stuff and send it out. You know, that's the thing though is like when you come to people and you're, you're kind of in a vulnerable state and say, Hey, I'm just starting or I'm just trying to learn more. I want to do this, you know, come from a posture of like, like you said, I'm trying to help us get this done as quickly and as efficiently as possible.
I'd love to talk. People, I mean, I've never run into anybody who's like, no, I'm not talking to you. I don't have any time that people love to engage like that. You know, they're teaching, they're showing authority, but then they're also learning and making a human connection. You know, people love that. And if you really, like, if you go to the vendors and the stuff, like I love, you talk about being vulnerable.
I think we're afraid of being vulnerable. Just ask somebody for help. Like, don't think of it as being vulnerable. Just be like, Hey, I want to be better at this. Can you help me? Sure. And especially if you're going to vendors or somebody like that. One of my favorite questions is, Hey, we just got through this project.
How can I make this better for you? Show me how to be a better customer. Show me how to do this better for you. Like, what could we do to make this job easier on you next time? Nobody's not going to help you do that. Like, like my double negative. They're going to just lean in and they're going to be like, you know, how can I make this better for you?
They're like, well, if it showed up this way, let me show you how to do that. Document that and do it next time. Like all of a sudden you just became more valuable to the vendor and to yourself. Now, say you're in a bad spot and you're looking to get out, right? If you have eight vendors that love working with you because they've invested in you and you are their ideal customer, they're going to tell you where to go work, they're going to give you good advice.
They're not going to send you to a bad company. And at the same time, they will be a raving fan and help you get somewhere because you're going to make their job better. They don't want to lose you because they already know if you're leaving this company, then they're going to get back filled with who knows what.
They want you to land somewhere that is beneficial to them. And that's one thing that I found when exiting or when, um, one of the things I did when, like, promoting people is there came a point where they, like, got promoted where they were, like, right here. Like, I'm here, I'm not leaving, I can't promote you, we're going to promote you out of the building.
The first place we would go is to vendors. Like we, like you say, it was a creative director, an assistant creative director. And it's like, okay, in order for your career to grow, like, I feel like your next step, you're ready for the next step. It can't be inside this building. Like you've reached the end of the line where we are as much as it makes my job easy that you're here working.
What are we going to do? And I would all like, we'd reach out to the network. And the first place we would go is to vendors, you know, print shops, web developers, people like that. And we're like, okay, hey, you've worked on all these projects with Tabitha. How, um, She's looking to go somewhere else, creative director or a assistant creative director.
Do you know anybody like that you think would be a good place for her or somebody for her to talk to? And they will like, they will connect you. And it's not this like fearful thing. Like, even if you go to a vendor that loves working with you and you say, Hey, I got something kind of sensitive. I want to talk to you about, like, you have to judge that relationship.
Like, are they going to go tell the boss? If you can't let the boss know, like, if you're looking for an exit, Having people that trust you and are loyal to you. Because they've invested in you, like they will protect you and help you go. So that's my my number one tip. If somebody is looking to leave, like build great relationships with vendors and ask the vendor because that vendor wants you to land somewhere else.
And a lot of times they'll actually know of a place that. So the this specific example I'm talking about, um, they took the assistant creative director. We found another place for her to be. Um, but it was not a client of the print shop, the vendor, but the vendor got us connected. Well, she goes there and starts working at this agency.
Well, guess what? As soon as she got a chance, she connected him to the print shop. So the print shop actually ends up getting more business and everything because of the relationship that had been built in the trenches and the bad boss situation. The idea of the bad boss is there are really bad bosses.
There are some bosses that they're not capable of doing the job. Do they have the skills to do their job? Most of them don't, especially if you're talking to somebody who's a middle manager or at a small company manager. Very few of us received any leadership training except from. Experiences of I don't want to be like that person, and I don't want to be like that person, and I don't want to be like that person.
Right. I mean, We went to art school, right? Eric, you went to art school. How many leadership development classes were in that curriculum? Just yeah, for the schedule was filled with them. Not none. It's funny because there's a in all over the place. There's this weird dynamic where you do a certain thing.
You're really good at that thing. You show a lot of proficiency, you know, proficiency at it. And to to climb the ladder, you ultimately go from doing the thing you're good at to managing the people who do what you do with no management training, with no management training, no nothing. So like there's, I think there's a lot of people who kind of succeed to a point where like, you're like, Whoa, what got me here isn't going to get me much further.
I need to either develop, I need to spend a lot more time learning, a lot new skills. And I don't know, it took me a long time to realize that too. You know, that, that, and so if you're, if you're under a bad boss, it might just be that like they got to that point because they're, they're still working on their own development and they haven't got to that chapter in the book yet or something like, and so like, I think you're right.
Like not there, there are some really bad bosses out there. I'm not in the, they're unredeemable. They're like that, that's just not going to happen. But there's a lot of them who just, You know what? They, they didn't have that role or what would you call it? Anti role role model. You know, the one like, I don't want to be like that, you know, you, they haven't been able to counter that stuff and they haven't got to that point in their development yet.
And so having, I think some of these tricks that you've talked about, about trying to get alignment, I think. Always being like curious and motivated. I think those things will help transcend that a little bit. And then just be. Maybe a little, a little empathetic that what's most important to you when you're working with your boss isn't their main focus, right?
That's not the most important thing to them. Like you said, there's 17 other priorities pulling out, you know, and so just trying to work together to make that bad boss a little less bad. And I'd say in any situation, yeah, you look at that. We talked about the expectations and it's like, are they a bad boss?
They are a bad boss for you for sure. Like you, you know that and it goes, okay, well. Can you have an expectation talk where you figure out what is that relationship like I need more feedback like for me I don't need mmm. I need feedback, but I need it in deep like I need deep feedback But I need it and like pretty big gaps Like it's like if we go two weeks and I get deep feedback every two weeks That's ideal for me.
Like I am running hard But that's not going to work for some bosses. Like if you come to me and interact and try to give me feedback every single day while I'm on one project, like if I'm deep in a project, you're giving me feedback every single day. I'm like, why are you paying me? Like if you're going to do 90 percent of the work, why are you paying me?
Like that frustrates me. And that's where I found out that the boss didn't actually trust that I was going to be at the end of two weeks, that I would be where they expected me to be. So then it's like, OK, it was more about that's a trust issue. that And then I found out it's actually that they don't trust the information that they gave me.
It's not that they didn't trust my work. They didn't trust their communication skills or the fact that they actually had all of the information Like they might launch a project. They have 20 information They launched the project and then a week later now they've figured out what they should have had to launch it That's a fail on their part, but they've been Meddling with me the whole way through because they're getting more information and they're trying to help steer me Because they started me wrong and you look at you from the boss's perspective that's being kind But we need to move past that like we need to have an expectation where we are aligned on a better pathway And when I found out like that meddling was constantly so there's that reason and then there's the other reason that in the book The number one need for bad boss Stan was a fan club Somebody had to be clapping for Stan There was this deep wound that was a need that had to happen there.
And once I realized that it was like, okay, so we can scratch it. The reason that the company existed was because that need like existed in Stan's life. And it was like, okay, took me years to figure that out. And after I figured that out, I'm like, okay, we can play that game. So it's like, okay, that's part of the relationship is, hey, that's really great.
Thank you for handing this off to me. You don't need to worry about it. I'll check back in in two weeks. Like, thanking the boss for giving you an incomplete assignment gave me time to go do my job. Because I acknowledged that it was incomplete. I thanked the boss for that. Like, you kind of have to play the game.
Like, what is the need here? What is the expectation? And then there were certain projects. It was like, the boss needs to play in this one. Like, that is the expectation. The boss is going to be involved. It's going to be a medley. This is going to be messy. We're going to go back and forth. That's fine. It's, they're the boss.
Like that, that's how this works. Like my job is there. How do you feel? Is it fair for the boss to say like, let's go back to your previous example where I've got 20 percent of the information. I want to send you off on this task. What if I said that? What if I said, I've only got 20 percent of the information.
Could you go find the other, is that a fair move? I guess it depends on the person. So you just changed the question in the middle of that. You said, here's 20%. Can you go find the rest of it? . Yeah, you put that on me. Great. Yes. I now know what the expectation is of me. Well, you have to go back in time before you were like nice and knew what you were doing.
So, but the fact that you said, this is what I launch, and you are very demanding and clear of what you want, but you're wrong. Like from where I stand today, I'm launching this project as I see it, this is the information, this is what I want. And then you have another client, like another call with the client and you go, oh, I misunderstood.
I sent my team off running in the wrong direction. How do you handle that situation when you come back? Because if you're honest about that, then a team will follow you. But if you do that constantly, they will learn not to do good work because they have to keep everything in the reserve for the redos.
So if the boss comes in and says, um, depending on the relationship with the boss, I like to ask when something's launched and then when it comes in and it changes, you say, what changed? We launched this way and now we're heading in a different direction. Like, do we have time for a conversation about that?
That was one of my favorite ways. Do we have a conversation to talk about this? Not in the project, but to talk about the project. And then you can say, okay, so what changed? Why were we running South and now we're running West? Like what happened? Because I know that I'm changing my work that I'm supposed to be doing now.
And sometimes I've also said, no, we can't have that conversation right now. Fine. Do what you can to move forward. But if the boss can't have that conversation, the reason you want to know what changed is because. If I make the changes and say, you know. I know that we were headed this way, now we're headed this way in 100 yards, that's fine.
In 30 miles, I could be way off target again because I'm basing it off of a reaction to information. So it's like what changed and they go, we had a project one time where we were working on branding for a company and it came back and said, no, scrap everything that we're doing, the colors have to be silver and purple.
And I'm like, this is for a tow truck, like a mechanic, like it's a mechanic that works on tow trucks and it's like neon purple and silver are the colors. And I'm like, What just happened? Like, how did we change that color palette? Like, I don't understand what happened in from having the conversation.
We've actually we got into deeper conversations. But what happened is the guy who owned the company had just gotten remarried within the last year and his wife likes those colors. Oh, the strategy blew everything out. And once we figured that out, it was like, OK. Everything else that we thought we trusted, we need to figure out.
Is any of this right? You know, not just, OK, take those logos and change them to silver and purple like that. We could have just done that, but it was so far off that I had to go. Hold on a second. Why did this change? Like something foundationally broke. It's different now. So going back to the boss and saying, can we talk about this?
I'm trying to understand like, hey, this task popped up, popped up. I'm trying to understand to make sure that The goalposts changed to make sure that I'm headed at the goalpost, right? Can we talk about what happened in the project? And sometimes the boss can talk to you about it. Sometimes the bad boss just doesn't know.
They just. Had a bad burrito and changed the project. Um, so is there a process at the end where there's a kind of a Review of the project. It's all finished. It's delivered invoices are paid. Do you like to go back and do that? kind of a Study on things. Is that a consistent part of your process? So I do it for myself we did it, you know at the agency and everything like We always would every project was measured by.
Um, Let me double check. Uh Product Process, profit, and the idea is like, was the product, was it quality? Did we reach the goals? Did the product, was it a good product? Did we follow our process? Did the client follow the process? Did the boss follow the process? Like, did we actually do it? Did we do good work?
Did we do it the way that we do it? You know, did we follow the process? And then profitable, like, was it a profitable project? Like, did it reach our money goals? Because if it didn't reach the goal, Say we did good quality work, say we followed the process and it wasn't profitable. Like we needed to know that because we needed to stop doing work that way.
Like, okay, the process is broken. Like this isn't a hobby. Like we had to eat, you know, like I had to, my kids needed to eat. So the business needed to be profitable. So we would review projects on those three criteria. Now, when we would do work, we would use that. Remember I talked about the, uh, the, uh, um, gold medal delegation worksheet.
Okay. Where we would fill that out and say, okay, this is what's expected. This is what's required. These are things that, you know, are optional. We might do, and this is how we know that project's done. We would use that to launch. We actually replaced creative briefs and all project briefs with this document and we would launch it.
And then when we would come back for internal approval, that would be attached. And if we did an internal, like. Meeting on approve like a big project. It was like, these are our goals. We did it here. We did it here. We did it here. So we used that document to launch all projects and to defend the work that was done because when you do that, what happens is you said, this is what you told us to do.
Look, we did it all. And if the boss comes back and says no, then you go, okay, what's different? Either there was information missing, something's changed, You know, while time has passed, while we've been working on this or you lied to me and I will tell you when you change, when a boss changes something, all of the workers, whether it's the boss or the client, everybody assumes I was lied to like, that is where we go.
Like you think about it, like if you work on a brand standards for a company or whatever, like, or they give you the brand standards, you're working on stuff and you send it off and then they come back and like, Oh, the lawyers didn't approve it because it didn't do all these seven things. And here's our updated brand standards.
You were working on one that was six months old and you're like, You lied to me. Like, all of my work was based on a lie. We don't say it out loud, but we feel that. We kind of think that somewhere inside. And if you present something to the client, and the client's like, I know I said I wanted that, but really it needs to be this.
You lied to me. Like, there is that expectation where it's like, you lied to me. But if you have that document where you can go back to it, then it's, they feel a little bit more accountable. Like, yeah, I did say that. Well, if they agree that they said that, they're less likely to back off of it. You know, it's like they go, you know, I don't know.
Yeah, I did say it needed to be a 24 page booklet. Okay. We delivered a 24 page booklet. All right. Like, it's very hard for them to go. Yeah, but I'd really like it to be 28 now or my favorite. Yeah, we'd really like it to be 26. 26 saddle stitch. Awesome. Um, yeah. So. It's not a multiple of four. But yeah, they're going to come back.
And when as the like as the employee, you have to remember, I feel like they're lying to me. Maybe they're not. Maybe they didn't know. But the idea is, like, how can you have those conversations to realign those? Because the more times the boss changes the field, like changes the goalpost, the more time people learn, like we learn not to trust a boss who keeps changing the goalposts.
And then we're not going to do good work, because if you give me a project and I work on it, and then I know that it's going to get changed as soon as it gets back to you, I'm never going to try on the first draft. I'm going to give you something. It's like you gave me some information. I don't trust this.
I'm going to give you junk work so that you will give me the information that I needed to start. So we start this ping pong game of back and forth and back and forth. And then everybody suffers, productivity's down, we don't do good work, we don't like our work, we don't like our boss, we don't like our job, and then you write a book about it.
Um, like I did. I don't know how many people would go that far, I mean, you're, you're, yeah. Unless you're telling me I should start writing a book, like that's, uh, yeah. Everybody should write a book, but that's a side note. When I was a solo marketer, I had. Bosses, and I was alone. There was nobody who worked for me, but I viewed vendors as part of the team that I was trying to corral together and get stuff done.
When I started, there was a boss and there was me. And I was everything. And I thought I had to do everything. And that was the dumbest decision Idea I ever had it was to get things done not to do them. Once I realized that I started getting vendors, volunteers, whatever, just building people to help get things done or reverse delegation is my favorite thing in the world where somebody comes to you and you go, okay, I understand what this is, you know, like you talk to somebody and then you give it back to them.
Like they walk in and you give them the task and they walk out with the task, but they have a clear view of it or they're not afraid of it. So there are a lot of times that somebody would come to me and say, Hey, we need to do this. There's an exhibit coming for the state fair of Texas. We need to work on.
And I'm like, okay, who's the audience? I would actually go into my gold medal worksheet, you know, delegation worksheet. And I would say, okay, so who's the audience and what, what the action do we want them to take when they come back out of that? Well, I don't know yet. Can you get with a client? Can you do that?
Can you figure out what this project? Before you hand me the project, can you figure out what it is? That's really what I was saying, but I would reverse delegate where it's like here are two questions that I need Before I'm ready to accept this from you But I wouldn't say that I was like, do you know these two things?
Can you get that to me by tomorrow? Yeah, I can get that Well, what I just did is I just the boss came to hand me a mess that wasn't ready I punted it back on the boss You To say, Hey, do you think, you think maybe you could go an extra five yards to where I can actually grab the baton, like reverse delegate, you just push it back and say, could you make this a little bit more ready?
Um, that was one of my favorite things to do. Um, specifically when I was the solo person and I had a boss and the boss was full of half baked ideas all the time. And you're kind of like, you know, sometimes the boss is saying things and you're like, I'm going to nod my head. Yeah. And say, can we circle another question?
Hey, can we circle back? Can we talk about this next week? Can we talk about this at a different time? Because what happens is most of those ideas like degrade very, very quickly. And the boss will know that their idea is horrible by the time you have that conversation. I can't tell you how many meetings I've had canceled because the agenda said we're going to talk about these three things so that I can understand them.
And the boss is like, never mind. Okay. kill that meeting. I'm like, that's what I thought. I'm glad I didn't start. Um, so you said something earlier, which I thought was, is really, really a good frame of mind to for solo marketers to get into. And it's that idea that, um, a lot of them might think they have to do all the things, right.
But the boss is really, if you question them on it, they'd rather you get things done. And there's a difference there. I'd love to hear you talk a little bit more about if you've got a boss bridging that gap, convincing them that you are there to get the job done and that it may mean you not doing all the things and that you have to bring in help.
So I'd love to hear your thoughts on how to, how to build that up. So you can build those strong relationships with some of these vendors and other people. Ultimately the company is going to do a lot better because you're going to be able to have Experts in a lot of these places, the product of everything's going to be way better, but there might be some convincing there with the boss.
I'd love to hear your thoughts on all that. Sure. Um, so in the book, I know we've talked about in the book, there's a question that is what if, and it is, it's something that changed how we operated for sure. Um, and it's kind of my go to when things feel stuck. And so if you're walking, working with the boss and the boss is like, First off, if it's your own mindset and you're the one thinking, I have to do all this, they hired me.
I have to prove to myself that I get this done. Get this done. Not I have to do this because the idea you go, what if I could do more? What if we could get more stuff done? What if it was quality? What if it didn't feel rushed? What if. The printer didn't hate us because we keep sending RGB files. Like, what if like everything, you know, what, what if you could read it in a dim light?
Like there are all these things that the, what if you always want to say like, what if it was better? What if, what is the dream of it being done? And once you start thinking like, uh, what if I liked my job? What if I could get more stuff done? What if I could serve our audience? What if people understood what we were getting?
And one of my favorites is what if people stopped emailing me Like hate mail. What if people stopped complaining about everything that we did? Like if you ever have that, like back to Mike's love of PDFs, you send out PDFs and people are replying saying, stop sending me PDFs. Like if people are, if people are taking time out of their life to reply that they don't like something, you should go.
What if we did it differently? What if they didn't complain? You know, what are the staff didn't complain? What if this was easier for everyone? And we talked about, you know, uh, Downstream and upstream, like we talked about that. What if I made their job easier? What if this was easier on other people?
Another thing is like when the boss says, Hey, we need to do this video. We need to start doing these videos for social media. And you go, What if we didn't? Like, that is my number one thing. What if we didn't? What if we didn't have to do that? Like, how much is that for you? What if I didn't have to edit all those videos?
OK. Well, that means somebody else could do it or you don't have to do it. Or do you do raw videos? Well, you see, we just found three options that could get the bosses request done. But there's three different ways to handle it. So that's where I like to go. What if? So it's like if the boss is coming to you and it's like, you know, well, what if we did this project big?
What if instead of doing these three things, we did one that served the whole company? You know, like. For instance, everybody's like, well, this product has a website and this product has a website. This has a product. What if we had one website where people could find us? Like, you see the question is like, well, what if we made it easier for other people?
Um, and then say the boss wants you to do videos. You go, well, what if we had somebody else to do that? We could focus on the content and everything. And what if we had somebody who's good at editing the videos do that so that I'm not wasting, I'm not investing this much time on it. I can be doing other work.
Well, what if somebody who's good at that, who's an expert at that? The idea of like, well, what if instead of having a jack of all trades, like this comes down to that trust and do you feel safe in your role? What if instead of a jack of all trades, you know, we had aces at everything? Like, what if we could pull in, you know, those experts that aren't necessarily part of our team?
What if we could hire them to come in and knock it out of the park, right? Um, you know, DH, just bring in a hitter. Um, so, These are the what ifs that I would go to. So if you're having trouble with the boss, especially saying what is my role and how much should I actually have on my shoulders? The first question is, is that really expected?
Does the boss expect me to do everything? Or am I having a hero complex where I have to do more to prove my worth? For me, that's what I was in, in one role. I've had another role where that wasn't the case. They were like, well, we hired you so that we wouldn't have to hire other people. And I found that that was not a good fit for me.
I did my role. I fulfilled my agreement and everything, but that was not a good fit. I did not need to be there. Um, so have that expectation. What is it? And then you say, well, what if, say you need more budget, you need to grow into something, you need to do something. Um, I'm working with a nonprofit right now.
They're getting ready to do a video that was not in their budget, but we came back and we said, well, what if you had this video that there's this group of people, we want them to take this action. What if we shot a video with this arc, and this is the story that we're telling and then we're just inviting them to take this action.
What if we did a video that did that? And they're like, if we had a video like that, that action would bring in this much money. They were like, yeah, we would have this many donors that would bring in this much money. Okay, so then the executive director went out to one of the donors who constantly gives and says, would you basically be willing to front us the money?
Like in advance on your donation. Basically, would you cover the cost for this video so that we can go into this capital campaign like so we can have our big event and have this video and they're like, absolutely. So the executive director and the communications person have zero to do with this project anymore.
Like, they're just overseeing it. There is a video production, like, it's actually a two guy video production team that is taking care of it, like, we've written, I've talked to them, I volunteer with them, so I've worked with them on the arc, and they're going out, they're videoing it, they're putting it all together, and it's going to be amazing.
Like, they've actually made it so much better than even the dream could have been, because they're knocking it out of the park, because they're bringing all their expertise and everything, and they're not, they don't have to understand the heart of the agency, or of the non profit, what they're actually doing.
One of my favorite things is, is they're bringing their ignorance into this project as well. They're bringing their expertise and their ignorance, which means they connect with the audience more than the people inside the organization can. So they're looking at it like the executive director is like, well, we do this every year and the, you know, video goes like, yeah, what's that?
Like he doesn't know what it is because the audience doesn't know the inside lingo. So they're bringing expertise and ignorance and making this project super powerful. For the audience, they're serving the audience better because of those two things. And if we had not had lunch and I just said, what do you think about that?
Well, what if you could, we don't have the budget for that. Yeah. But what if you did, you know, it was like, well, what if, what if you did, well, if we did, we'd get, end up making all this, we'd have this many more donations. And I'm like, like, you know, that you're going to have, so this donation there, we know that we're going to get 600, 000 of donations.
Like, this is what that would bring And I'm like, So you don't have the 2, 000 to get 600, 000. What if you did? And they go. So what happened is they had an like there was, you know, there was this problem that they couldn't overcome. We don't have the money for a video. But if you go to somebody who has the money and you say, we want to do this video because this is going to be the outcome.
And they go, Oh yeah, let's do that. It was just a what if, well, what if you did have the money? Well, then this would happen. OK, well, we don't have the money. OK, well, who does? Like, what if we found the money? OK, where would we find the money? This guy over here has the money. Why are we not talking to him right now?
Like, pull out your phone and text him. Like, that's kind of the the idea is like, well, what if what if what if is any time you have that like obstacle, if you say, well, what if? And you imagine you're on the other side of it. What happens is that obstacle usually becomes really small. And you can do that with the boss, like with this executive director who is hardcore that we are going to stay in budget.
But when you know, when they daydream and go, yeah, that's the number that this is going to bring in. Like all of a sudden, like. That investment was nothing like I mean, basically, it was like we could send out a text message and get that money. And I'm like. But that's because they saw the outcome when you're on this side of the obstacle, we can't find that money.
Well, that's silly because in five minutes, we found it like that wasn't hard. So asking what if like, what if I didn't have to do this? What if we brought in somebody else? What if we knocked this out of the park? Another thing like. You can do really fun projects. You can make them way more complicated doing what if and you can make them way smaller and either one could be better depending on the project.
You know, well, what if we got to the point? What if we didn't send that, like another one, annual reports? That's a fun one to play what if with. Because it goes, well, what if we made this bigger? What if we went digital? What if we did this? What if we mailed it to them? What if we did all these things? Like, what if there was a video?
What if we sent them a postcard that when they open it up, there's actually a video player in it? Like I mean, that actually started where you go, well, what if it was like Harry Potter and the pictures were moving? Like that's when you know you've gone too far. What if we reinvent the Internet? That would be cool.
Um, but what if can make things bigger, but it can also be like, you know, what if we like for one of them, like we even we never did this, but we went back and said, what if the annual report was handwritten? Like you see how like you just ask that random question, but all of a sudden you're kind of like, wow, this is a personal like leaning into thing.
Like just asking, what if can steer any conversation, it can unlock budgets. It's just the idea of like, get to that dream. So, what if we did this project? What if we hired somebody to do our social media? Well, how much is that going to cost? Well, my favorite thing is when somebody says, what is that going to cost?
Change, um, what you're talking about. Change the currency. Like, hey, what if we hired somebody to do our social media? Well, what is that going to cost? Oh, man, I don't know it. It'll probably free me up about 20, 25 hours every month. Like, oh, that's what it's costing us now. Sorry. You like if you you do that, well, what if what if I talked about my hours?
What have I talked about what it would make possible? So, yeah, we might pay for the social media. They might manage that for us. But I am freed up to do this or. Writing social media, or what happens if we give our sales team access to not necessarily social media, but what if we just tell them, Hey, shoot a quick video when you're out on a sales call, like you're walking into the building, just shoot a, shoot a video.
We may or may not use it on social media. Now, if they shoot four videos and you don't use any of them, they're not going to shoot any more videos. But this goes back to, well, what if, what if we made it our sales guys job to create content? Because they're the ones already talking to customers. Anyway. So you do a sales call, you're walking out to your car, just recap.
What are three bullet points that you really, you know, that three bullet points that were value about our product to your client, you know, that you were pitching, if they record those three things, you may or may not be able to use it, but you know, what if the sales guys who already have the content, give us the content, you see now all of a sudden that's so valuable in so many different ways too, right?
Because those. Even if you don't use the video and they're fresh out of that meeting, talking about those three things, those are three potential things that you could talk about in other marketing materials that maybe you're working on. Maybe it goes into it. Maybe it's the topic of an email, part of an email campaign you're working on or something.
Yeah. That so great product development. Like you go up to product development. You're like, Hey, these are the three things we're talking about all the time. It's like, Oh, well, why don't we just fix the product? Like there's that option. There's the CEO, the CFO, or just, okay. Cross training for the rest of the sales team.
Like, hey, these are, I've had five conversations and these are only three things customers want to know about. Yeah, we should probably put that in a slide deck. You know, like, there's just that, that if we share, if we ask what if, if we share, so many good things could come of it. Um, but like you said, you got to be curious.
Um, you got to be open to that. And if, if you're stuck trying to, um, If you're like trying to lead from the second chair almost, you know, like here's the boss and you're kind of below or behind, how do you, sometimes you have to cast a vision to ignite the leader to step into. And that's that's what what if does it opens up the thing?
Well, what if we did this? Well, then they can start dreaming about the future. It's their job to be a leader and move to the future. Like they should be thinking that way. And you say, well, what if we did this? You're actually inviting them back into their job. And it make it in theory, it should make your job easier.
It's the best way to ask for things. Cause I've also been places where I'm like, Hey, I really would like to hire somebody to handle this. You know, I would like to bring in somebody that actually does the edits on the website and just, you know, does minor tweak and all this kind of stuff to update our website.
And the boss is like, you know, no, what is that going to cost? Whatever the conversation. And then I actually have to put in like a, uh, a, uh, purchase request. Like I've actually had to put in a purchase request for vendors. Or for staff that I want to hire, like, here's what it's going to cost. And this is the breakdown.
And this is the revenue that we're going to get. Like, I've had to fill out those forms to hire somebody to update, to hire a retainer, to update the website. And I'm like, if I had just said, well, what if I might have had to do that? But it wouldn't have been so cold and calculated and painful for me to get what I needed if it was more of a.
Well, what if we actually got the website, like right now you put in a request or you ask me to update the website. Sometimes it takes me like two weeks to get to it. What if we had somebody that was basically on standby and we knew it was going to happen, you know, within the week. Or we knew that, you know, we had somebody on retainer.
We knew that it was going to be done right, because remember last time when I tried to update the staff and all the columns? Remember when that happened? Yeah, let's not do that again. Like, you can pitch, you can pitch this thing where it's like, all of this stuff that shouldn't happen, happens. Yeah. What if it didn't?
What if it was better and faster? And that's kind of my thing is, you know, anytime they ask, what's it going to cost? Well, it's costing me this much right now, like set that, like, what does it cost? Well, it costs this currently the investment would be this because the cost is a loss. The investment is a gain.
So I always tried to separate those. We've talked before about the trying to know, like, have that almost business acumen a little bit and shift that. thinking, using a lot, filling in the gaps here, talking a lot of what you're talking about is kind of like an opportunity cost, selling the opportunity costs.
Like, because I'm working on this thing right now, it's taking away from something else I could be doing. So the social media example is perfect for that, right? Like if I'm spending all this time on social media and we've grown our followers by 50 over the last two, two months, right? Like, not, not a lot.
That's an opportunity cost of something else that I could be doing. If we want to keep doing social media, we can find somebody who's really good at that, and they might be able to grow our followers, but I'll be able to do something that maybe has higher leverage, and will bring in more revenue. Right.
And that's, yeah, being, you know, I think that's, that's not something you, I don't know if you learned that in school either. You don't learn in design school, that's for sure. Um, no, we come out, we come out as the product. Like our creative work is our product. And if we don't do it, then we aren't valuable.
It is like we are the machine that kicks out product. And what we have to learn is we're the system that makes things happen. It's the idea like for me. Um, There are certain things that I love doing illustrations. I will never, I doubt that I will ever pay somebody to illustrate something for me because it's just, I'm passionate about it.
I love it. It's something that I'm going to keep doing. Um, but if it comes to like writing social media content or content for like a book, annual reports. I'm going to go back to that one. I, annual reports are fun projects because you're taking boring information and making people care about it, right?
Like that, that is, that is hard. Like most people don't want all of the information that's in there, but you have to tell them a story and engage them and invite them into the possible future. This is the past and this is the future. Like that's the story that you're telling them. It's just that most people try to do it with a spreadsheet and it's like, no.
So I don't like doing those. I like finding people who are really great at taking a spreadsheet and turning it into a story. And letting them and then taking the credit for it. Like, that's amazing. Like, you get it done. Well, I mean, you have the vendors. You have everything. But when the staff, like, say you're working.
There's a staff. There's a board. There's, like, all the people up here. And all they know is that your department, this went through you and it got done. You know what? You're known for the got done person. Like, you got it done. Take credit for that. Don't take credit for somebody else's illustration, their creative work or the video, whatever.
But the fact that, yeah, we got that done. You did like without you, that did not happen. That is your role is to make sure it gets done. And if it gets done poorly, if it gets done haphazardly because you're doing 17 things like do the best you can. But if you're holding it and doing all 17 things, then they're all going to be done like one 17th good.
Like. That's how it's going to come out, you know? So how can you do that? How can you build it in? How can you work with the boss and help them realize that we could be doing more? We could reach further, you know, whether it be marketing and again, websites, design work. I mean, there's so much stuff that falls on that one person's shoulders to get done.
And what I'm trying to say is, There's one that as a one off person, it always bothered me. And then at an agency working with one off people always bothered me presentations like that one off person who does the presentation. You're like, you're going to offer a 40, 000 product. And you threw it together in PowerPoint.
Like that's something that somebody should probably expert on for a little bit. You know, it's all these little things where you're like, Which things are the hardest hitting? Which ones could you outsource? Cause we all think, Oh, I can throw together a PowerPoint presentation. I can get in Google presentation and throw that together real fast.
Um, but should you like, that's the question. Does it deserve a little bit more? Yeah. Yep. The potential ROI. What does that work? Right. What does the return on it then focus on that? And if it's, you know, if it's writing some internal. Staff only emails, you probably don't need to outsource that unless you're really bad at it, you know, or, or if it's a very sensitive subject, but there, there are certain things you look at and you go, what is the weight of this project?
Can I bring in experts? You know, what if somebody hit a home run here? Cause I got started thinking about it. I was like, I'm a solid double, like on a lot of things. I was like, I'm a solid double, but what if I could bring on a home run hitter on this video? What if I could bring on a home run hitter on our social media to where it's like, Maybe you're going into a big season, you know, there, there's a big campaign coming up or whatever.
What if you could bring in somebody to kind of get behind that for social media or a new website launch? Like, if you are a person of a team of one and there's anything website, you need help. Like you need help, even if it is, you're going to go through, even if it's like your old website and you're just updating the copy across your website, like, Hey, we're just going to clean house on the website.
That's it. You need help. There's just so much information architecture and everything. You're about You're about to flip the bird to Google like don't make Google angry Jake so much information. I'm still kind of decompressing from all the all the good stuff here. But um, I wanted to let people know that Leadership is available on Amazon.
So you can get, if you're on Kindle unlimited, it's a free download. Get it right away, but you can get, uh, it's filled with paperback, audible, go get it. It's a lot of fun, great, funny stories. Uh, and, um, you do kind of wonder a couple of things like, wow, how did they pull it off? Two, Like you said earlier, why did you stay so long?
But then there's so many good things, even if, and if you're on the boss's side, you could be like, Whoa, do I have any of those things going on? Do I, am I doing any of that? It's, there's a lot of good from that side of things, but, um, where else can they find you, Jake? Um, the, the fastest, easiest way to find me is if you go to leadership.
co, um, that's a website. It's about the book. You can easily connect with me right there. So, or you can follow me on LinkedIn. Um, So look me up on LinkedIn, but yeah, it's a, um, a lot of doodles, a lot of random stuff that I'm doing there that just help people get back to enjoying work a little bit more. I mean, is it every email you send off?
You've there's there's have fun on every one. It's a good, it's usually my signature. Yeah. It's kind of my go to because I used to say it every time somebody would come in at the office or with my kids. Um, my kids pointed it out, but like I would have a meeting and as people really, I was like, Hey, have fun.
Like just naturally I was telling everybody that was like the, all right, meetings over, have fun, like go back to work and have fun. Like if you're not having fun, you're not going to do great work. So go have fun and produce work along the way. That was kind of the idea that, uh, my personality and what I was saying to people, but yeah, it's kind of, it's kind of a mantra.
And now my kids say it all the time. Uh, and it, it actually comes from a princess bride. When they're leaving, it's like, have fun storming the castle. Like, that's, that was the, uh, the root of where it came from. Perfect. I love it. Cause every time I see it in an email, I'm like, Oh yeah, I should have some fun.
It works. I just want to let you know it's working. So, um, Gosh, thanks for, thanks for your time today. I think we've taken up a lot of time, but it's always, always fun connection with you. And we probably could talk for hours more, but we'll give the listeners a break. Oh, it's been a blast. Yeah. Thanks Jake.
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