The Boss Show

Workplace wisdom with heart and humor

September 11, 2016

Jim’s Biggest Career Mistakes

How many of your bosses have acknowledged their mistakes?  The best organizations lean into transparency; employees should know what’s going on at all levels of the company. And for bosses, “transparency” includes admitting when they screw up.  Jim role models this personal transparency, exposing his biggest career screw-ups.

View Transcript

Voiceover: It’s a Northwest lifestyle weekend on KOMO News, now a show for anyone who is or has a boss. This is The Boss Show with Jim Hessler and Steve Motenko.


Jim Hessler: Welcome to the show. I’m Jim Hessler. I’m the business guy. I’m the founder of Path Forward Leadership Development and the author along with my co-host of the book, Land on Your Feet, Not on Your Face.


Steve Motenko: I would be that co-author. My name is Steve Motenko. I’m the psychology guy. Happy to have you here on the show with us. I’m the Psychology guy because I do life coaching, term I hate, I like personal development coaching better, more accurately reflects what I do, both for individuals’ lives and in the workplace. What we hope to do today is offer you a little bit of workplace wisdom with heart and humor. What are we going to do today, James?


Jim Hessler: Well, we’re going to allow our listeners to experience a little bit of schadenfreude today, the …


Steve Motenko: A little bit of what?


Jim Hessler: The joy that we take in other people’s failures, because today’s show is about my personal, Jim Hessler’s, biggest career mistakes, and I’m going to be transparent here. I’m going to do what in the business world we call “opening the kimono” and I’m going to let you know some big mistakes I’ve made in my career and by sharing them to humanize me, so I get off that pedestal that people have me on and realize that I’m actually just an ordinary guy.


Steve Motenko: It’s hard to imagine, isn’t it? If one of those mistakes is bringing me into the leadership development business with you, I’m out of here. You can do the show by yourself.


Jim Hessler: I don’t know why I didn’t think of that. That probably should have made the list, but we do talk a lot with our clients about transparency and about genuine showing up as your authentic self, and be real and approachable and I think a part of that for any leader is the ability to admit their mistakes and to own up to them and to not tap dance, not to pretend that something didn’t happen that happened, and so we also talk about transparency in other ways as well. The sharing of financial information, the sharing of the company’s strategy, and I find that it’s still a big deficiency in leaders is this unwillingness to be really transparent, so maybe I’ll model that just a tiny bit today.


Steve Motenko: Yeah, I really appreciate you doing that. I don’t know what you’re about to say. I haven’t’ read your show notes for today.


Jim Hessler: Well, I haven’t murdered anybody.


Steve Motenko: That’s a good thing.


Jim Hessler: I haven’t stolen from my employer, so it’s not crimes.


Steve Motenko: Right, yeah, now people are tuning out because they want hear the …


Jim Hessler: Yeah, right, oh shoot.


Steve Motenko: … the really nasty stuff, but I really appreciate the focus on transparency. We have this notion in our culture that we need to be very close to the vest in our corporate culture, that we can’t tell employees, we can’t disclose our mistakes, we can’t disclose even some company strategies or company mistakes because of the impact that it will have. You’ve always been a strong stand for transparency.


Jim Hessler: Well, there’s a story from my career, brief story I think that illustrates that. I’ve done a number of what would be called turn-around projects in my career where I’ve gone into businesses that were performing poorly and spent a certain amount of my life getting the culture and the strategy and the operations of the business healthy again, and I’ll never forget one of the turnaround efforts I made was with a company, it was about a $15 million company, and they had 38 employees, and one of the reasons I was brought in was because the place was just hemorrhaging money, and the place had lost a lot of money. It was about $600,000 in net operating profit lost in the year prior to my arrival.  At the end of the first week, I called all 38 employees in a room and I showed them the ugly reality of the company’s financial picture and I asked them, I said, “Now, be honest with me: how many of you knew that we were losing money?” Three people raised their hands, so we had 38 employees, 35 were coming to work every day without any awareness that the company was on the verge of disaster, and interestingly enough, I was told by the owners of the company not to share that information, and I chose to do it anyway.


Steve Motenko: You see how well it worked for them.


Jim Hessler: Yeah, exactly, and it changed everything. The behavior in that organization changed immediately after that information was shared, so I’m going to share some other stuff with you. Things that may make you cringe a little bit. They certainly made me cringe. Jim’s mistakes. You’re listening to The Boss Show.


Voiceover: It’s a Northwest Lifestyle Weekend on KOMO News. The Boss Shows continues.


Jim Hessler: I’m Jim Hessler. I am the business guy.


Steve Motenko: And I’m Steve Motenko. I’m the psychology guy. Thanks for joining us. If you like the show, or if you don’t, we’d like to hear from you, so we’ve got a listener comment line: 206-973-7377. Call it. Leave a message for us. Tell us what you like. Tell us what you don’t like. Tell us what topics you’d like us to consider on the Boss Show, and if you’re maybe a little more hesitant, then we have email address that you can hide behind. Send us an email: Talk to us.


Jim Hessler: If you’re selling client, you can do what I’m doing today which is to share disaster stories and things that didn’t really go well for you in your career, because that’s the theme today is Jim’s biggest mistakes in his business career.


Steve Motenko: Jim, I can’t decide whether to hammer you for your mistakes just to show my superiority or to acknowledge you for the courage to admit them.


Jim Hessler: I’ll leave that up to you. I pretty much ignore you no matter what you do, so …


Steve Motenko: Yeah, good point.


Jim Hessler: … It doesn’t really matter.


Steve Motenko: Okay, excellent.


Jim Hessler: Mistake number four: my fourth worst mistake, so I even have them ranked so the worst one is at the end, so my fourth worst mistake in my career, and this has happened more than once, and you’ve seen it happen, and that is losing my cool, losing my cool, letting my emotions get the best of me, lashing out, saying some things that I regretted. Now, I think most people who know me would say I’m a pretty nice guy. I’m compassionate. I’m a loving spirit, but I do have a temper and I’ve worked pretty hard over the years to temper that, but boy, I’ll tell you sometimes, a few times over the years, it’s gotten the best of me, and several times, it was in situations where it really did a lot of collateral damage, where people lost respect for me, frankly, because of the way I did that. Now that doesn’t sound like something you would do. I’ve never seen you do it, and so I don’t know if that’s anything that you can look back on in your career.


Steve Motenko: I’ve done it. I actually did it more when I was … This is probably one of my biggest mistakes in life. I did it more when I was teacher dealing with children, and also as parent, I feel terrible about the times that I’ve lost my cool as a teacher, as a parent.


Jim Hessler: Yeah, I did that too.


Steve Motenko: What I want to say about that is that we teach something called “the ladder of inference” to our workshop participants, and we don’t have time to go into it this show. Maybe we’ll do a show on it. Maybe we’ve already done a show on it, but the notion is that each of us sees reality through a very narrow window with a very heavy filter on that windows, and if you Google “ladder of inference”, you’ll understand this, so if you always keep in mind the fact that you’re quote-on-quote reality is actually a very narrow filtered perspective, then you’re always aware of the fact that when you get angry, there’s probably something that you’re missing in someone else’s reality that if you knew, if you were curious about, would curb that anger.


Jim Hessler: Yeah, and there’s three things that I wrote down that I think are origins of these sorts of behaviors, these “losing my cool” behaviors. One is just power tripping, just wanting to exert your power over another human being, and when you lose your cool and I’m a big guy and I’m tall and I’m large and …


Steve Motenko: And confident.


Jim Hessler: And confident and I have a …


Steve Motenko: And strong opinions.


Jim Hessler: … Authoritative voice and a good vocabulary, and I can lay people low. I can make people feel very very small if I’m so inclined and I have to say that there’s probably been a few time when the impetus for it. Also, just immaturity, not being enough of a grown-up to understand how much that sort of behavior is problematical, and also …


Steve Motenko: What impact it has on others.


Jim Hessler: Yeah, and then the other’s just being over-stressed, letting circumstances get the best of me, and not recognizing that in that moment, I’m not at my best and I need to go back and be at my best before I interact with other people. We talk in our workshops also about how important intention to communication, in general, and so I think there were times when I didn’t check my intentions before I lashed out, and it turns out my intentions were probably not good intentions. I wanted the other person to suffer. I wanted the other person to feel put down by me, frankly. Now, I don’t do that much and I’ve hardly done it at all for years and years, but it is something certainly I have done, and so I’m not happy about it, but I’ve learned. I’m moving on, but I’m going to share another big mistake in just a minute after the break. I’m opening the kimono and you’re listening to The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO news.


Jim Hessler: I’m Jim Hessler. I’m the business guy.


Steve Motenko: I’m Steve Motenko. I’m the psychology guy. Today on The Boss Show, Jim is airing his own dirty laundry of his biggest career mistakes, and Jim, I just want to take a minute to really applaud you because what you’re doing today is you’re role modeling and if you heard the last segment, you know this to be true. You’re role modeling the courage that every leader needs to admit their mistakes.


Jim Hessler: Yeah, thank you for that, and trying to be perfect sucks.


Steve Motenko: Believe me, I know. You know that about me better than …


Jim Hessler: Yes, I do. It really sucks. It’s hard. It’s stressful and I think you lose a lot of what’s good about yourself when you’re so obsessed with what’s wrong with yourself, so let it go. By talking about this stuff as a way of sharing with other people, that makes it less scary and more manageable, so my third worst mistake and I think you’ll be interested to hear this one. I allowed the recession of 2008, 9 to defeat my spirit. I really got down. I felt defeated and I think there were some things that I didn’t do for my business, our business during that period of time that I could have done, and I think I became a little bit of a victim, and I’m sure there’s a lot of people listening out there that could share that, and may it still be there to some degree.


Steve Motenko: It becomes a habit.


Jim Hessler: Yeah.


Steve Motenko: What you’re talking about.


Jim Hessler: Our sense of optimism our sense of possibility was shaken by a series of external events, which we couldn’t have anticipated and couldn’t have done anything about. It was tough.


Steve Motenko: Frankly, what we offer in Path Forward, our leadership workshop, is a big ticket item. We don’t believe in one shot leadership workshops. They don’t work. All the research proves that, and so we do a year long, actually now a an 18-month long, process and it costs a fair chunk of change and in the recession, that was a difficult thing to sell.


Jim Hessler: Yeah, there was one week in which I received a series of three telephone calls cancelling sizable contracts, and our revenue, as a business, went down about 65% in about a two-month period, and what I will say about that, the good side of that is that I think you and I both had managed our own personal finances well. We weren’t over-extended financially. We weren’t in debt.


Steve Motenko: We both had working wives.


Jim Hessler: We both had working wives, which helped a lot, and so we were never in a position where we were really in trouble, because of that loss of income and revenue, but psychologically, it just really worked on me, and I don’t think I stood up to it, leaned back against it as much as I could have, and not even just in terms of going out and finding business to replace what had been lost, but just keeping myself in good fighting spirit and metal. I think I just really definitely lost some of that.


Steve Motenko: I still see you doing that sometimes, get discouraged, but I also, every time you get discouraged, I see you rebounding …


Jim Hessler: I do.


Steve Motenko: … In a reasonable period of time.


Jim Hessler: Yeah, I’ve told many people that if I have a strength as a business person and a leader, that I would want everyone to share with me, it is resilience.


Steve Motenko: Resilience, that was the word [inaudible 00:13:53], yeah.


Jim Hessler: Yeah, there’s some times that that’s all that I can muster. I call it putting one foot in front of the other.


Steve Motenko: Sometimes, it’s all you need to muster is resilience.


Jim Hessler: It is. I think there’s a lot to be said for that, but when something bad happens, it can knock you down in ways that you … Get back up, get back up, don’t let things like the recession, even losing a job, not getting your budget approved, things like that. Don’t let them knock you down. Get back up, and I didn’t do that quickly enough. More of my mistakes when we come back. You’re listening to The Boss Show.


Voiceover: KOMO News: The Boss Show is back on a Northwest Lifestyle Weekend. Here’s Jim Hessler and Steven Motenko.


Steve Motenko: I’m Steve Motenko. I’m the psychology guy. Welcome back to The Boss Show.


Jim Hessler: I’m Jim Hessler. I’m the business guy. Today’s your day to have a little schadenfreude, a little bit of joy at my mistakes, and I’m sharing my four worst business mistakes. My first four worst career mistakes. The first was losing my cool, which I did more than once in ways that I really regret. The second was letting the recession really defeat my spirit. I think would be the way I would say that, and then the second worst mistake, and I’ll get to the worst one in the next segment, is sharing confidences that shouldn’t have been shared.


Steve Motenko: In a gossip sort of sense?


Jim Hessler: Yeah, yeah, I think one incident in particular where, and I don’t want to get into the details of it, but somebody told me something in confidence and I shared that with somebody else and it came around the circle and the casualty wasn’t me. The casualty was the person who’d shared the information with me, because it was pretty clear that it was only person who could have had that information, and so they were able to track it back other, and I made her look terrible, and I can’t remember a moment in my career where I felt worse as human being than when this came out, and it was discovered that I had put her in that untenable position by sharing something that she’d shared with me in confidence, and again, why do we do that, Mister Psychology Guy, why do human beings like to gossip? Why do we like to share private information? What’s the impulse there?


Steve Motenko: What occurs to me is that it’s about our own egos, and it’s about …


Jim Hessler: There’s some power in having that information, maybe that we enjoy a little too much.


Steve Motenko: Yeah, I’m trying to wrap my mind around how to articulate this. I think you use that German word, schadenfreude.


Jim Hessler: Schadenfreude, yeah.


Steve Motenko: There is part of that to our lower selves. There’s a sense of a relief, maybe, about [crosstalk 00:17:02] didn’t happen to us.


Jim Hessler: We elevate ourselves by putting other people down.


Steve Motenko: Right, clearly it’s human nature and it’s something to be really aware of, but the other thing I think is that in a way, gossip creates a dysfunctional, but nevertheless, a bond with another person. When you’re sharing someone else’s suffering, there’s a connection that you make with this person. It’s not the healthiest connection, but it’s there.


Jim Hessler: I think maybe we just like that little bit of drama. We like having something interesting and juicy to talk about with another person.


Steve Motenko: Right, the whole reason that news exists, right, is to capitalize on drama that happens in human life.


Jim Hessler: Yeah, so it’s interesting. I appreciate what you just said, because as I think back to who I shared the information with, this was a person with whom I had a lot of very lively conversations. This was a really smart person, very witty, and I always enjoyed talking to him, so it was like in a way, I couldn’t wait to share this information with him, because it was juicy. It was about somebody in the organization that had a serious alcohol problem and how it was affecting their work performance, and I remember feeling very much that, “Oh, I can’t wait to talk to so-and-so because he’ll like hearing this.” When you have that kind of information available to you, I think in an immature way, you feel like it makes you more important, more interesting, and then you hope that they come back to you again and again as a person who has special privileged, interesting information that they should seek.


Steve Motenko: Reminds me of the Don Henley song. I think it’s called The Evening News.


Jim Hessler: I don’t know.


Steve Motenko: Where he talks about the prurient interest that’s stirred up by the media and how that taps into our base or human desires, needs, instincts, and one line goes, “It’s interesting when people die.” It’s interesting when bad things happen.


Jim Hessler: It is. It’s people looking at the car accident off the side of the highway, so that’s my second worst mistake, and you’ll want to stay tuned to hear my worst one, and, again, I think a lot of you will share the experience or relate to it.


Steve Motenko: I can’t wait.


Jim Hessler: Number one Jim’s mistake coming up. You’re listening to The Boss Show.


Voiceover: It’s a Northwest Lifestyle Weekend on KOMO News. The Boss Show continues.


Jim Hessler: I’m Jim Hessler. I’m the business guy.


Steve Motenko: Welcome back to The Boss Show. I’m Steve Motenko. I’m the psychology guy, and today we’re exploring Jim’s worst career mistakes. His choice, not mine, although I do have to say …


Jim Hessler: You’re enjoying the hell out of it.


Steve Motenko: … I am enjoying the hell out of it, and I can’t wait until this number one worst mistake you’ve ever made, because I’m going to share it with everyone I know. It’s going to go on Facebook, Instagram, you name it.


Jim Hessler: I got to say: it’s not juicy though. I wish it was juicy.


Steve Motenko: Ah, darn.


Jim Hessler: I think it’s very relatable for a lot of people.


Steve Motenko: All it matters to me is will it make me feel superior to you?


Jim Hessler: Maybe, I don’t know. We’ll see. I hope so for your sake.


Steve Motenko: Thank you.


Jim Hessler: This is directed at largely at young people who maybe are just getting started in their career. You’re going to get opportunities to get promotions. You may get opportunities to re-locate. You may get opportunities to take on a major new responsibility at work, and my biggest mistake, and it’s happened to me twice that I can think of, is accepting career opportunities without having all the facts and assurances that I needed before I took the job.


Steve Motenko: Do you have a sense of why you did that?


Jim Hessler: I was anxious. I trusted too much. I was really anxious for the opportunities. As it turned out, they all worked out well, so it wasn’t like I ended up …


Steve Motenko: Why was it a mistake if they worked out well?


Jim Hessler: Because there was a lot of naivety there and looking back there’s just some more questions I should have asked in each situation. Let me just give you examples. One job I took that required me to relocate my family and I didn’t really have clarity on the bonus structure of my compensation, which was a big part of my compensation, and I ended up actually having an argument with my boss at the end of my first full year there about what I was expecting in bonus and what he told me my bonus was going to be. That was a big mistake. That was rookie mistake.


Steve Motenko: To have the argument or to make that [crosstalk 00:21:38]


Jim Hessler: No, I’m glad I had the argument because he certainly, being the senior person in the conversation, could have been a lot clearer with me up front. Strategy for the operation, a couple of times I wasn’t entirely clear on what the corporate strategy was, what their expectations were in the first or second year. When I did these turn-around efforts, sometimes their expectations for my first year on the job were frankly unreasonable and I should have squared that up. I should have communicated better about that, and then really the biggest one was what exactly I had the authority to do in each situation. I think I presumed some authority to do certain things that I didn’t have. Now, the worst example of that is I took over an operation from someone who ended up staying in that operation and reporting to me, so this is the guy who used to be the boss.


He’s now the second in command reporting to me, and this is a guy that I … Very nice man and nobody knows who I’m talking about, so I guess it doesn’t matter, but he was not effective. He was a disaster, and he had taken the organization in some very bad directions, and I assumed that I would have an opportunity to work with him and make my own judgment about what his value was to the company and as it turns out, I decided he wasn’t a keeper, and then I wasn’t given the opportunity to terminate him. Now, I had to play some pretty tricky politics to work through that, and I eventually did make the termination, and we ended up being very successful in that organization, but I absolutely should have squared that up with my boss before I took the job about how long the leash was for this guy, and how long it was going to be before I was going to make that call, so anytime you take a new position, new job, new responsibility, even a new project, make sure you know exactly what you’re walking into. Ask all the questions that you need to ask. Don’t wait until after the opportunity presents itself. You’re listening to The Boss Show.


Voiceover: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on KOMO News.


Jim Hessler: I’m Jim Hessler. I’m the business guy.


Steve Motenko: I’m Steve Motenko. I’m the psychology guy. Thanks for staying with us. We have a unique event coming up. If you’re in the Seattle area, we’re going to do, for the first time ever, something we call The Boss Show live. It’s actually free. You can go to to register, and we’ll even feed you appetizers and maybe a glass of wine and what it’s about …


Jim Hessler: It’s on October 4th.


Steve Motenko: Yeah, it’s on October 4th. Yeah,, search for The Boss Show live, and what it’s about is we’re going to ask people to stand up in front of a microphone and tell their stories about maybe their worst boss or their best team experience or some interest workplace thing. We’ll respond. We’ll engage in a dialogue, and we’ll just have a heck of a good time.


Jim Hessler: If you have one of those stories, we particularly want to hear from you so we can get our speakers lined up well in advance to the event, so 206-973-7377, or The Boss Show is produced by Boss Media Productions and our sound engineer is Kevin Dodrill.


Steve Motenko: If you missed any of this show and really, you do want to hear all of it, you can get it in it’s entirely online at our website, and that’s also where you can go to talk to us, to subscribe to the podcast, to ask us how to bring us into your workplace to help your leaders.


Jim Hessler: Thanks for listening.


Steve Motenko: Don’t forget: rule number six.


Jim Hessler: Rule number six.



Leave a Comment

Your email address will not be published. Required fields are marked *