>> You're listening to Let's Talk Jobs, where we give you practical insights into jobs and careers. Today, Jesse, Troy, and I talk about our experiences with difficult managers, what we did about it, and what we learned from it. All right, let's get started. Dealing with difficult managers. We've all had them, maybe you're one.

If you're self-aware, you know. Have you guys had experiences with just really challenging managers? >> No, they've all been perfect. >> They've all been perfect? Everyone listening? >> No mistake. Not irritating, micromanaging. >> Yeah. Jesse and I are freelancers for a reason, I think. I think I've definitely had some experiences and some are further up the needle in terms of challenging.

But you have to think about it in terms of it's a relationship, not unlike any other relationship that we have in our lives. If there's challenges there, you're a part of that. I think with all of these challenges that we're talking about, my advice is try to lean into it a little bit, and embrace the discomfort.

I know that in the moment, that's a lot easier said than done. But the more you can embrace it, the more you can try to understand it, and understand what's put yourself in your manager's shoes, what's driving the way they're working with you, and then of course, try to take a step back for yourself, and understand what is it that's tying you up and not.

Sometimes it's not the surface level thing that you think it might be, if you take a second to think back. I had a manager at the same company that I mentioned before, I interviewed with her and was blown away. Loved her personality. She had incredible credentials. Interviewed with her team, everybody seemed fantastic.

Early on, I got in, I brought what I thought was a lot of diverse experience to that role, and I sent an e-mail about an area that I was not directly responsible for, but affected the area that I was responsible for, and immediately got a very stern e-mail back, effectively saying, "Stay in your lane." Honestly, I feel like my relationship with that manager spiraled from there.

I think her managerial style was to create clear autonomy for folks, and I tried to salvage that. I felt really insecure about the whole thing afterwards. I probably didn't fully consider what was happening, but I learned a lot from it in terms of I prefer to work with teams in a slightly less structured way where everybody can bring ideas and expertise, even if it crosses over the boundaries of what people are directly responsible for, at least be considered.

I took from that the way I reacted super insecurely to the whole situation. I had some work to do internally to not take that personally. It wasn't a personal statement about my abilities, but it definitely shaped how I responded to her moving forward, and I'm not proud of that.

Yeah, I had one manager – actually, I've had a few bad managers, and they happened to, unfortunately, be all female. There was a time in my life where I fundamentally distrusted just female leadership. Thankfully, that changed over time. But this first one – I was still earlier in my career, but this is on the agency side still, and I've had three to four years of incredible success up to that point.

My confidence and my ability was really, really high. When I went to this other agency, they brought me in to do account management, and the nature of that job, which was different than my previous agency, was I was both the account manager and the project manager, right? So I'm in this cycle where the more successful I am at bringing in business, the more scope I add to my own plate for work to manage, right?

And so there's that dynamic I was wrestling with, and what happened was they brought me in to manage their largest accounts, and then within a month, she went on maternity leave, right? And so I was managing the best that I can and my escalation path for raising issues and concerns because I was under the belief that I was capable.

I didn't raise my hand enough. That's probably my own fault. But what happened was when she came back, the amount of business that our primary client gave to us was not as high as what she'd expected. And her managerial style was both directly aggressive in the words she would use and very, very passive-aggressive as well.

And so I was constantly dealing with self-doubt, and she would pull me into her office and use very direct language towards me. Now, if that would have happened now, I would have responded differently or maybe take more time to ask questions, to understand the truth behind everything she's saying.

But I didn't have the knowledge to do that. I didn't probably even give myself permission to do that. I think her level as a GM really intimidated me. So I really struggled, you guys. I remember, there's a back in the day where cassette tapes were the thing. My dad had a 10 cassette tape deck of self-help video and audio books.

And every day when I left work, I would sit in the parking lot, pop in a tape and listen to it. And then every day before, I like how Zoom just give me a thumbs up there. And then I'm glad Zoom agrees with that decision. Oh, a celebration. Look at you.

You're a star. That was perfect for an audio-only audience. But then before going to work, I would also have to sit in the car and listen to self-help books because I was at that point where my sense of value was so low that I had to seek that. Otherwise, I would go do work and I would break down.

And it was just really emotionally tough for me at the time. And I never really handled it well. I ended up getting let go. I remember actually, when I got let go, that was the first time in probably a year that I actually felt relief and joy. My journey through unemployment after that was a little bit rough.

But yeah, that was really, really tough. And it was hard for me at that moment to identify the positives out of that. And I think the lesson I learned in hindsight is I wish I was more proactive in finding mentors to walk me through it, right, in absence of therapy, to help me understand what I could do differently, or maybe even help me separate the things that truly were my fault versus things that were out of my control.

But everything I attributed to my own failure. And so that really, really took me for a loop. I've been listening to you, Troy, and to you, Tim, talk about dealing with difficult managers. It makes me try to articulate how -- I want to articulate how -- some of this is dependent on -- my experience, anyway, has been dependent on my role.

And sometimes it's been dependent on my level of experience. And when I was much more junior, I remember working for this awful import/export company where I was the copywriter. And we worked in this warehouse. We were in a building in Los Angeles where they had a front area with a reception desk.

But then you walked into the team space. It was literally in a warehouse. And there was a cage, like a wire link cage, around the spaces where we sat in our desk. And then behind us were these rows and rows of large stacks of product. And they sold, like, vitamins and all sorts of crazy stuff.

And we were creating marketing. I was creating marketing material for it. And the manager had actually been someone I went to high school with but didn't know. And then inherited a large -- not a large business, but inherited a business. And he was sort of like -- everything about him made me sort of just want to leave the job force forever because he was flashy.

He was arrogant. It was sort of this arrogant confidence. And then when it came to him -- and even though he was the CEO of, like, a very small company, he would review all the marketing materials and everything I'd written. And invariably the work would come back. Like, everything changed.

You know, basically every sentence had, like, some sort of edit on it. But in retrospect, that was one of my very first jobs as a copywriter. You know, maybe they were appropriate edits. And I just took it as, like, a total and absolute criticism and demonstration of how I wasn't ready.

And maybe I needed that. And I needed also to know that in some cases, you know, I think you said it, Troy, it's about the relationship. And I could have -- and I don't know if I necessarily did it. Eventually I got laid off. Or not laid off, but fired.

And I remember my boss coming to me and said it was sort of like the weakest link thing, which always stuck in my head as an awful way to say you didn't quite make the grade. But, you know, I didn't somehow -- I had the connection with the CEO because he had been at my high school.

But I didn't know how to build the connection with him. And it's been the case in lots of different roles where, you know, whether or not I've been an individual contributor or a manager or, you know, a partner at some of the -- I started two boutique agencies where I was founder or partner.

And so I was working directly with founders, other founders of startups, you know, managing directors of large companies. And so my boss -- they were my clients. And, you know, not necessarily -- it wasn't necessarily the case that any of them were difficult. It was just they presented different challenges.

So as an individual contributor, as I moved up, it was about understanding if the feedback I got from whoever was reviewing my work, you know, how did I interpret it? How did I then revise? How did I work with the other, you know, creatives to get the work to a better space?

How did I assert solutions to, you know, ongoing trends in the work? How did I come up with new ideas? And I think as I did that, I became more successful as a contributor. So then when I was in a managerial role, I think I was better able to reflect that back to folks I was managing and help them understand that in the best case when the business is, you know, somewhat on solid footing and we're not, you know, losing cash or, you know, getting ready for a layoff because of, you know, who knows why.

Lots of different reasons for layoffs. And I had to understand then when I was a manager that there's a couple of really important things to convey to the folks that reported to me. And that was, one, that I didn't think they were perfect. They had strengths and weaknesses. I wanted to lean into their strengths and help them grow over time.

I had a manager at Logitech where we all worked, Nancy Morrison, who's now retired. And I very much remember the first week I was there, and she was describing my role and expectations. And she said something that blew me away. She said, "The first year, Jesse, I want you to focus on this." And I was not quite -- I was in my 30s.

I had a lot of jobs before that. No one had ever said anything that suggested I would be around for that long. Like, not that I -- that wasn't the expectation, but it was never articulated so assertively. And it was such a positive statement, I still kind of tear up when I think about it, how generous that was for her to say that.

And I was there for a few years, and, you know, I had some -- you know, and it also kind of reminds me of, in the case of Logitech, that sometimes it's my manager's manager that is the problem. And such was the case there. And I've been at other places where I've been in agencies where, you know, I've been in the rank and file, but the account folks are trying to sell stuff.

And so they're sort of semi-managing in a sort of dotted line way to the creatives because they're bringing us work. But often they would, you know, have, like, hallway conversations with the client on a Friday afternoon and say, "We got this great idea, and we're going to spin it up for you by Monday morning," and the creatives work all weekend.

I remember in one case this happened. We put together a presentation, and then Monday morning meeting comes with the client, and he leans over to the account person and says, "That thing I said on Friday, yeah, that was stupid. I hope you didn't do anything about that." Meanwhile, the creatives have worked all weekend.

So it's just -- it can be a mixed bag in terms of how to distinguish between managing both your clients' and your managers' expectations. Yeah, you know, there are two instances, at least that I'm aware of because it was brought to my attention, where I was the difficult manager.

Interesting. The first one was actually that agency I was talking about. So I was able to finally get help. I got a project manager. And you would think that the project manager now, like, that with half my responsibility taken off my plate, I should be able to thrive, and I did not.

And she really struggled working with me. And she wasn't on my direct report, but this is the first time I had a true dotted line. And what I learned after the fact -- so she and I never had a conversation while I was employed. And that's, I think, mistake number one.

As a manager, I didn't have open channel of dialogue, nor was I open to my own vulnerability, nor was I openly transparent with her. And I never realized that my issue was delegation. Like, I didn't know how to delegate work. And I kept stuff close to my chest. And maybe that was maybe in response to my fear of losing my job.

So I wanted to hold stuff to maybe increase the company's dependency on me. But she really struggled. And as a project manager, if you're not given information or if you're removed from meetings with the client, then, like, you can't succeed as a project manager. And I didn't set her up for success for that one.

And actually, I've since reached out to her afterwards and apologized because that was not good. And I didn't realize how terrible it was for her. When we finally reconnected on it, she was, like, crying. And I had no idea that I was impacting her that much. The second one was maybe at Rubrik, which is only two companies removed from where I am today.

And I thought I was a good manager. You know, by then, this is post-LinkedIn. I've learned all I could about compassionate and empathetic leadership. And I thought I was a good manager. And the feedback from a few folks on my team confirmed that. And there's this one person I brought on to run search engine marketing.

And, you know, she replaced a previous employee. And she really struggled. And what I realized prior to her choosing to leave the company, she told me that I didn't allow her to make decisions. And that really boggled my mind because I was like, "I thought I was an empathetic leader where I'm – I thought I'm empowering my individuals." And what I realized was I was drawing goals and outcomes that she had no control over.

So I was defining some benchmark that was, in hindsight, very unrealistic. But I wasn't – like, search engine marketing is not my primary wheelhouse. Like, I know enough to manage it, but I definitely do not know it well enough to run them by myself. And the problem was I wasn't self-aware enough.

I thought I could skate by by my knowledge of the industry. So I would draw goals that just did not make any sense. And she really struggled. And on top of that, she didn't have the right assets to convert with. So, again, I'm equipping her with the tools to succeed in paid search, right?

And then the metrics, the day-to-day metrics, also didn't make sense. Like, the benchmarks just didn't make sense. But, again, I thought I was bringing her in to contribute to the goal setting. What was happening was, in part, she was trying to scrounge together goals to try to meet those KPIs, but ultimately she was set up to fail, right?

And it was chipping away at her sense of value because she felt like she wasn't performing anymore. And I wasn't self-aware enough to notice that. And even though I was the interpersonal leader at the time, I did not do well there. And so when she left, similarly, she was like, "This is the hardest job I've ever had.

And it's probably one of the worst situations she had." And I was the director of all of that, right? And so I learned a lot about trusting your team and knowing your limitations and you're hiring people for a reason because they know something you don't, you know? So lead and guide, but let them do what they're good at.

Hey, guys. Thanks again for watching and listening. Next week, we'll be talking about dealing with career low points. So make sure you hit like, subscribe, and hit the notification bell so you don't miss the next episode. Thanks.