Dealing with Difficult Managers - Insights and Personal Stories

00:00:00.000 | [MUSIC]

00:00:07.800 | >> You're listening to Let's Talk Jobs,

00:00:09.760 | where we give you practical insights into jobs and careers.

00:00:13.080 | Today, Jesse, Troy, and I talk about

00:00:15.840 | our experiences with difficult managers,

00:00:18.320 | what we did about it, and what we learned from it.

00:00:20.880 | All right, let's get started.

00:00:22.720 | Dealing with difficult managers.

00:00:25.920 | We've all had them, maybe you're one.

00:00:28.660 | If you're self-aware, you know.

00:00:31.160 | Have you guys had experiences with

00:00:32.720 | just really challenging managers?

00:00:34.600 | >> No, they've all been perfect.

00:00:36.320 | >> They've all been perfect? Everyone listening?

00:00:38.640 | >> No mistake. Not irritating, micromanaging.

00:00:44.560 | >> Yeah. Jesse and I are freelancers for a reason,

00:00:48.840 | I think. I think I've

00:00:56.760 | definitely had some experiences and

00:00:59.000 | some are further up the needle in terms of challenging.

00:01:02.120 | But you have to think about it in terms of it's a relationship,

00:01:07.520 | not unlike any other relationship that we have in our lives.

00:01:10.880 | If there's challenges there,

00:01:12.520 | you're a part of that.

00:01:14.640 | I think with all of these challenges that we're talking about,

00:01:22.240 | my advice is try to lean into it a little bit,

00:01:25.760 | and embrace the discomfort.

00:01:28.880 | I know that in the moment,

00:01:30.560 | that's a lot easier said than done.

00:01:32.440 | But the more you can embrace it,

00:01:36.040 | the more you can try to understand it,

00:01:38.720 | and understand what's put yourself in your manager's shoes,

00:01:45.520 | what's driving the way they're working with you,

00:01:52.440 | and then of course, try to take a step back for yourself,

00:01:55.920 | and understand what is it that's tying you up and not.

00:02:02.000 | Sometimes it's not the surface level thing that you think it might be,

00:02:07.600 | if you take a second to think back.

00:02:13.400 | I had a manager at the same company that I mentioned before,

00:02:22.360 | I interviewed with her and was blown away.

00:02:26.680 | Loved her personality.

00:02:28.840 | She had incredible credentials.

00:02:31.840 | Interviewed with her team, everybody seemed fantastic.

00:02:36.200 | Early on, I got in,

00:02:42.240 | I brought what I thought was a lot of diverse experience to that role,

00:02:47.880 | and I sent an e-mail about an area that I was not directly responsible for,

00:02:54.880 | but affected the area that I was responsible for,

00:02:58.120 | and immediately got a very stern e-mail back,

00:03:02.160 | effectively saying, "Stay in your lane."

00:03:05.320 | Honestly, I feel like my relationship with that manager spiraled from there.

00:03:16.400 | I think her managerial style was to create clear autonomy for folks,

00:03:27.720 | and I tried to salvage that.

00:03:32.240 | I felt really insecure about the whole thing afterwards.

00:03:35.000 | I probably didn't fully consider what was happening,

00:03:40.400 | but I learned a lot from it in terms of I prefer to work with teams

00:03:49.000 | in a slightly less structured way where everybody can bring ideas and expertise,

00:03:55.040 | even if it crosses over the boundaries of what people are directly responsible for,

00:04:01.160 | at least be considered.

00:04:03.200 | I took from that the way I reacted super insecurely to the whole situation.

00:04:15.000 | I had some work to do internally to not take that personally.

00:04:20.360 | It wasn't a personal statement about my abilities,

00:04:24.360 | but it definitely shaped how I responded to her moving forward,

00:04:27.720 | and I'm not proud of that.

00:04:30.000 | Yeah, I had one manager – actually, I've had a few bad managers,

00:04:36.200 | and they happened to, unfortunately, be all female.

00:04:38.480 | There was a time in my life where I fundamentally distrusted just female leadership.

00:04:44.280 | Thankfully, that changed over time.

00:04:47.000 | But this first one – I was still earlier in my career,

00:04:51.600 | but this is on the agency side still,

00:04:54.800 | and I've had three to four years of incredible success up to that point.

00:04:59.640 | My confidence and my ability was really, really high.

00:05:03.720 | When I went to this other agency, they brought me in to do account management,

00:05:07.920 | and the nature of that job, which was different than my previous agency,

00:05:12.520 | was I was both the account manager and the project manager, right?

00:05:16.920 | So I'm in this cycle where the more successful I am at bringing in business,

00:05:23.120 | the more scope I add to my own plate for work to manage, right?

00:05:27.120 | And so there's that dynamic I was wrestling with,

00:05:29.720 | and what happened was they brought me in to manage their largest accounts,

00:05:35.320 | and then within a month, she went on maternity leave, right?

00:05:38.920 | And so I was managing the best that I can

00:05:41.000 | and my escalation path for raising issues and concerns

00:05:46.800 | because I was under the belief that I was capable.

00:05:51.120 | I didn't raise my hand enough. That's probably my own fault.

00:05:54.000 | But what happened was when she came back,

00:05:57.600 | the amount of business that our primary client gave to us

00:06:02.800 | was not as high as what she'd expected.

00:06:05.800 | And her managerial style was both directly aggressive

00:06:11.400 | in the words she would use and very, very passive-aggressive as well.

00:06:18.680 | And so I was constantly dealing with self-doubt,

00:06:22.400 | and she would pull me into her office and use very direct language towards me.

00:06:29.200 | Now, if that would have happened now, I would have responded differently

00:06:32.400 | or maybe take more time to ask questions,

00:06:34.000 | to understand the truth behind everything she's saying.

00:06:37.000 | But I didn't have the knowledge to do that.

00:06:43.000 | I didn't probably even give myself permission to do that.

00:06:45.400 | I think her level as a GM really intimidated me.

00:06:50.000 | So I really struggled, you guys.

00:06:52.400 | I remember, there's a back in the day where cassette tapes were the thing.

00:06:57.400 | My dad had a 10 cassette tape deck of self-help video and audio books.

00:07:05.000 | And every day when I left work,

00:07:08.600 | I would sit in the parking lot, pop in a tape and listen to it.

00:07:13.600 | And then every day before, I like how Zoom just give me a thumbs up there.

00:07:19.600 | And then I'm glad Zoom agrees with that decision.

00:07:25.600 | Oh, a celebration.

00:07:27.600 | Look at you. You're a star.

00:07:30.600 | That was perfect for an audio-only audience.

00:07:35.600 | But then before going to work,

00:07:39.600 | I would also have to sit in the car and listen to self-help books

00:07:42.600 | because I was at that point where my sense of value was so low

00:07:47.600 | that I had to seek that.

00:07:50.600 | Otherwise, I would go do work and I would break down.

00:07:53.600 | And it was just really emotionally tough for me at the time.

00:07:56.600 | And I never really handled it well.

00:07:58.600 | I ended up getting let go.

00:08:00.600 | I remember actually, when I got let go,

00:08:03.600 | that was the first time in probably a year that I actually felt relief and joy.

00:08:07.600 | My journey through unemployment after that was a little bit rough.

00:08:13.600 | But yeah, that was really, really tough.

00:08:16.600 | And it was hard for me at that moment to identify the positives out of that.

00:08:22.600 | And I think the lesson I learned in hindsight is

00:08:26.600 | I wish I was more proactive in finding mentors to walk me through it, right,

00:08:31.600 | in absence of therapy,

00:08:33.600 | to help me understand what I could do differently,

00:08:36.600 | or maybe even help me separate the things that truly were my fault

00:08:41.600 | versus things that were out of my control.

00:08:43.600 | But everything I attributed to my own failure.

00:08:46.600 | And so that really, really took me for a loop.

00:08:51.600 | I've been listening to you, Troy, and to you, Tim,

00:08:55.600 | talk about dealing with difficult managers.

00:09:03.600 | It makes me try to articulate how -- I want to articulate how --

00:09:13.600 | some of this is dependent on -- my experience, anyway,

00:09:16.600 | has been dependent on my role.

00:09:19.600 | And sometimes it's been dependent on my level of experience.

00:09:22.600 | And when I was much more junior,

00:09:24.600 | I remember working for this awful import/export company

00:09:29.600 | where I was the copywriter.

00:09:31.600 | And we worked in this warehouse.

00:09:33.600 | We were in a building in Los Angeles where they had a front area

00:09:37.600 | with a reception desk.

00:09:39.600 | But then you walked into the team space.

00:09:42.600 | It was literally in a warehouse.

00:09:44.600 | And there was a cage, like a wire link cage,

00:09:48.600 | around the spaces where we sat in our desk.

00:09:50.600 | And then behind us were these rows and rows of large stacks of product.

00:09:55.600 | And they sold, like, vitamins and all sorts of crazy stuff.

00:09:58.600 | And we were creating marketing.

00:10:00.600 | I was creating marketing material for it.

00:10:02.600 | And the manager had actually been someone I went to high school with

00:10:05.600 | but didn't know.

00:10:07.600 | And then inherited a large -- not a large business,

00:10:09.600 | but inherited a business.

00:10:11.600 | And he was sort of like -- everything about him made me sort of just want

00:10:16.600 | to leave the job force forever because he was flashy.

00:10:21.600 | He was arrogant.

00:10:23.600 | It was sort of this arrogant confidence.

00:10:25.600 | And then when it came to him -- and even though he was the CEO of,

00:10:30.600 | like, a very small company, he would review all the marketing materials

00:10:34.600 | and everything I'd written.

00:10:36.600 | And invariably the work would come back.

00:10:38.600 | Like, everything changed.

00:10:40.600 | You know, basically every sentence had, like, some sort of edit on it.

00:10:43.600 | But in retrospect, that was one of my very first jobs as a copywriter.

00:10:47.600 | You know, maybe they were appropriate edits.

00:10:50.600 | And I just took it as, like, a total and absolute criticism

00:10:55.600 | and demonstration of how I wasn't ready.

00:10:57.600 | And maybe I needed that.

00:10:59.600 | And I needed also to know that in some cases, you know, I think you said it,

00:11:07.600 | Troy, it's about the relationship.

00:11:09.600 | And I could have -- and I don't know if I necessarily did it.

00:11:12.600 | Eventually I got laid off.

00:11:14.600 | Or not laid off, but fired.

00:11:17.600 | And I remember my boss coming to me and said it was sort of like the weakest

00:11:24.600 | link thing, which always stuck in my head as an awful way to say you didn't

00:11:27.600 | quite make the grade.

00:11:29.600 | But, you know, I didn't somehow -- I had the connection with the CEO

00:11:34.600 | because he had been at my high school.

00:11:36.600 | But I didn't know how to build the connection with him.

00:11:39.600 | And it's been the case in lots of different roles where, you know,

00:11:44.600 | whether or not I've been an individual contributor or a manager or, you

00:11:49.600 | know, a partner at some of the -- I started two boutique agencies where I

00:11:54.600 | was founder or partner.

00:11:56.600 | And so I was working directly with founders, other founders of startups,

00:12:00.600 | you know, managing directors of large companies.

00:12:03.600 | And so my boss -- they were my clients.

00:12:07.600 | And, you know, not necessarily -- it wasn't necessarily the case that any

00:12:13.600 | of them were difficult.

00:12:16.600 | It was just they presented different challenges.

00:12:19.600 | So as an individual contributor, as I moved up, it was about understanding

00:12:24.600 | if the feedback I got from whoever was reviewing my work, you know, how did

00:12:29.600 | I interpret it?

00:12:30.600 | How did I then revise?

00:12:32.600 | How did I work with the other, you know, creatives to get the work to a

00:12:35.600 | better space?

00:12:36.600 | How did I assert solutions to, you know, ongoing trends in the work?

00:12:41.600 | How did I come up with new ideas?

00:12:43.600 | And I think as I did that, I became more successful as a contributor.

00:12:48.600 | So then when I was in a managerial role, I think I was better able to reflect

00:12:54.600 | that back to folks I was managing and help them understand that in the best

00:12:59.600 | case when the business is, you know, somewhat on solid footing and we're not,

00:13:04.600 | you know, losing cash or, you know, getting ready for a layoff because of,

00:13:08.600 | you know, who knows why.

00:13:10.600 | Lots of different reasons for layoffs.

00:13:12.600 | And I had to understand then when I was a manager that there's a couple of

00:13:19.600 | really important things to convey to the folks that reported to me.

00:13:24.600 | And that was, one, that I didn't think they were perfect.

00:13:28.600 | They had strengths and weaknesses.

00:13:30.600 | I wanted to lean into their strengths and help them grow over time.

00:13:34.600 | I had a manager at Logitech where we all worked, Nancy Morrison,

00:13:40.600 | who's now retired.

00:13:42.600 | And I very much remember the first week I was there, and she was describing

00:13:46.600 | my role and expectations.

00:13:48.600 | And she said something that blew me away.

00:13:50.600 | She said, "The first year, Jesse, I want you to focus on this."

00:13:54.600 | And I was not quite -- I was in my 30s.

00:13:59.600 | I had a lot of jobs before that.

00:14:02.600 | No one had ever said anything that suggested I would be around for that long.

00:14:06.600 | Like, not that I -- that wasn't the expectation,

00:14:09.600 | but it was never articulated so assertively.

00:14:14.600 | And it was such a positive statement, I still kind of tear up when I think

00:14:17.600 | about it, how generous that was for her to say that.

00:14:20.600 | And I was there for a few years, and, you know, I had some -- you know,

00:14:24.600 | and it also kind of reminds me of, in the case of Logitech,

00:14:27.600 | that sometimes it's my manager's manager that is the problem.

00:14:31.600 | And such was the case there.

00:14:34.600 | And I've been at other places where I've been in agencies where, you know,

00:14:37.600 | I've been in the rank and file, but the account folks are trying to sell stuff.

00:14:43.600 | And so they're sort of semi-managing in a sort of dotted line way to the

00:14:47.600 | creatives because they're bringing us work.

00:14:49.600 | But often they would, you know, have, like,

00:14:51.600 | hallway conversations with the client on a Friday afternoon and say,

00:14:55.600 | "We got this great idea, and we're going to spin it up for you by Monday

00:14:58.600 | morning," and the creatives work all weekend.

00:15:00.600 | I remember in one case this happened.

00:15:02.600 | We put together a presentation, and then Monday morning meeting comes with

00:15:05.600 | the client, and he leans over to the account person and says,

00:15:07.600 | "That thing I said on Friday, yeah, that was stupid.

00:15:10.600 | I hope you didn't do anything about that."

00:15:12.600 | Meanwhile, the creatives have worked all weekend.

00:15:14.600 | So it's just -- it can be a mixed bag in terms of how to distinguish between

00:15:26.600 | managing both your clients' and your managers' expectations.

00:15:35.600 | Yeah, you know, there are two instances,

00:15:37.600 | at least that I'm aware of because it was brought to my attention,

00:15:40.600 | where I was the difficult manager.

00:15:43.600 | Interesting.

00:15:44.600 | The first one was actually that agency I was talking about.

00:15:47.600 | So I was able to finally get help.

00:15:49.600 | I got a project manager.

00:15:50.600 | And you would think that the project manager now, like,

00:15:54.600 | that with half my responsibility taken off my plate,

00:15:57.600 | I should be able to thrive, and I did not.

00:16:00.600 | And she really struggled working with me.

00:16:03.600 | And she wasn't on my direct report,

00:16:05.600 | but this is the first time I had a true dotted line.

00:16:09.600 | And what I learned after the fact --

00:16:13.600 | so she and I never had a conversation while I was employed.

00:16:16.600 | And that's, I think, mistake number one.

00:16:18.600 | As a manager, I didn't have open channel of dialogue,

00:16:22.600 | nor was I open to my own vulnerability,

00:16:24.600 | nor was I openly transparent with her.

00:16:27.600 | And I never realized that my issue was delegation.

00:16:32.600 | Like, I didn't know how to delegate work.

00:16:34.600 | And I kept stuff close to my chest.

00:16:37.600 | And maybe that was maybe in response to my fear of losing my job.

00:16:41.600 | So I wanted to hold stuff

00:16:43.600 | to maybe increase the company's dependency on me.

00:16:46.600 | But she really struggled.

00:16:48.600 | And as a project manager, if you're not given information

00:16:52.600 | or if you're removed from meetings with the client,

00:16:55.600 | then, like, you can't succeed as a project manager.

00:16:58.600 | And I didn't set her up for success for that one.

00:17:00.600 | And actually, I've since reached out to her afterwards and apologized

00:17:03.600 | because that was not good.

00:17:05.600 | And I didn't realize how terrible it was for her.

00:17:08.600 | When we finally reconnected on it, she was, like, crying.

00:17:12.600 | And I had no idea that I was impacting her that much.

00:17:16.600 | The second one was maybe at Rubrik,

00:17:20.600 | which is only two companies removed from where I am today.

00:17:23.600 | And I thought I was a good manager.

00:17:25.600 | You know, by then, this is post-LinkedIn.

00:17:27.600 | I've learned all I could about compassionate and empathetic leadership.

00:17:32.600 | And I thought I was a good manager.

00:17:34.600 | And the feedback from a few folks on my team confirmed that.

00:17:40.600 | And there's this one person I brought on to run search engine marketing.

00:17:46.600 | And, you know, she replaced a previous employee.

00:17:50.600 | And she really struggled.

00:17:52.600 | And what I realized prior to her choosing to leave the company,

00:17:59.600 | she told me that I didn't allow her to make decisions.

00:18:03.600 | And that really boggled my mind because I was like,

00:18:05.600 | "I thought I was an empathetic leader where I'm –

00:18:07.600 | I thought I'm empowering my individuals."

00:18:10.600 | And what I realized was I was drawing goals and outcomes

00:18:18.600 | that she had no control over.

00:18:21.600 | So I was defining some benchmark that was, in hindsight, very unrealistic.

00:18:26.600 | But I wasn't – like, search engine marketing is not my primary wheelhouse.

00:18:32.600 | Like, I know enough to manage it,

00:18:34.600 | but I definitely do not know it well enough to run them by myself.

00:18:37.600 | And the problem was I wasn't self-aware enough.

00:18:41.600 | I thought I could skate by by my knowledge of the industry.

00:18:47.600 | So I would draw goals that just did not make any sense.

00:18:51.600 | And she really struggled.

00:18:54.600 | And on top of that, she didn't have the right assets to convert with.

00:18:59.600 | So, again, I'm equipping her with the tools to succeed in paid search, right?

00:19:04.600 | And then the metrics, the day-to-day metrics, also didn't make sense.

00:19:09.600 | Like, the benchmarks just didn't make sense.

00:19:11.600 | But, again, I thought I was bringing her in to contribute to the goal setting.

00:19:17.600 | What was happening was, in part, she was trying to scrounge together goals

00:19:25.600 | to try to meet those KPIs, but ultimately she was set up to fail, right?

00:19:29.600 | And it was chipping away at her sense of value

00:19:34.600 | because she felt like she wasn't performing anymore.

00:19:37.600 | And I wasn't self-aware enough to notice that.

00:19:40.600 | And even though I was the interpersonal leader at the time, I did not do well there.

00:19:48.600 | And so when she left, similarly, she was like, "This is the hardest job I've ever had.

00:19:52.600 | And it's probably one of the worst situations she had."

00:19:55.600 | And I was the director of all of that, right?

00:19:57.600 | And so I learned a lot about trusting your team and knowing your limitations

00:20:02.600 | and you're hiring people for a reason because they know something you don't, you know?

00:20:08.600 | So lead and guide, but let them do what they're good at.

00:20:13.600 | Hey, guys. Thanks again for watching and listening.

00:20:16.600 | Next week, we'll be talking about dealing with career low points.

00:20:19.600 | So make sure you hit like, subscribe, and hit the notification bell

00:20:23.600 | so you don't miss the next episode. Thanks.

00:20:26.600 | [BLANK_AUDIO]

Dealing with Difficult Managers - Insights and Personal Stories

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