The Reality of Becoming a First-Time Manager: What No One Tells You

In this episode of On the Surface, Seth sits down once again with fan‑favorite guest (and unofficial co‑host) Taylor Kirn for an honest look at what really happens when you step into a management role for the first time. From the shock of overnight responsibility to the emotional weight of leading people you once worked beside, Taylor breaks down the challenges new managers face—and the parts no one warns you about.

Taylor shares her early experiences overseeing team members, including her struggle with delegation, learning to trust others’ processes, and discovering that there’s more than one “right” way to get things done. Through stories about mentors, technology mishaps, and even a paper‑folding machine she found way too late, she explains how growth often comes from embracing discomfort, letting go of control, and making room for people to surprise you.

Together, Seth and Taylor unpack the toughest parts of becoming a manager: balancing daily tasks with new leadership responsibilities, navigating the pressure of constant communication, managing personalities, setting boundaries with former peers, and building resilience when the job feels like “getting punched in the face for a year.” They explore why the first management jump is the hardest in any career—and why trusting your team, asking for help, and being honest about what you don’t know are essential skills, not weaknesses.

Taylor also sheds light on the critical role HR plays in supporting new supervisors, from handling sensitive conversations to navigating policies like FMLA, time off, and compliance issues that can quickly go sideways without guidance. She explains why bringing HR in early matters, how communication shapes culture, and why consistency and follow‑through are the foundations of effective leadership.

It’s a candid, insightful conversation about the human side of managing people—the mindset shifts, the uncomfortable moments, the lessons learned the hard way, and the growth that happens when you finally realize: management isn’t about doing the work…it’s about leading the people who do.

Thanks for listening!

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Transcript

SPEAKER_01 0:05

Welcome back to On the Surface. I'm your host, Seth Stevens, and I want to take just a moment to say thanks to everybody who's been listening up to this point. And please follow, rate, and comment on our show on Apple Podcasts or Spotify. It really helps circulate the podcast and recommend it to others. It gets it in the algorithms that they use. This week, I welcome back our most popular guest, possibly co-host at this point, Taylor Kern, to talk about what it's like being a manager for the first time and what people don't tell you. Let's get into it. Co-host now.

SPEAKER_00 0:47

Okay. Whatever you want me to be.

SPEAKER_01 0:50

It's your third time.

SPEAKER_00 0:52

It's fun. I didn't know if I would like it or not because I'm very like a need preparation to kind of gather my mental space. And I think being recorded adds a whole nother element of like, oh my gosh. Why did I say it that way? Or why didn't I say this? Or I should have had notes on this because that was a good example. Like those things go through my mind.

SPEAKER_01 1:19

Yeah. But it's easier than I thought. Oh, you like it.

SPEAKER_00 1:23

Yeah.

SPEAKER_01 1:24

You're having a good time.

SPEAKER_00 1:25

Yeah.

SPEAKER_01 1:26

I guess. It's good practice.

SPEAKER_00 1:27

Yeah.

SPEAKER_01 1:28

I guess. So your management, you haven't really had management experience, but you said that you oversaw two HR generalists at one point. So what was that like?

SPEAKER_00 1:45

So I've never had direct reports. Um, but I have been able to oversee people on my team. And pretty early on, I found out pretty quickly I was pretty poor at delegating. And I think it's just a control thing, right? Like you know that you can do it well, you can do it the way that it's gonna turn out. And um yeah, it's you gotta build trust with people before you start giving them really important tasks.

SPEAKER_01 2:17

Well, delegation requires, yeah, trust. Yeah. And you at some point it has to be blind trust to get it started.

SPEAKER_00 2:27

Yes. And I was super fortunate that both of the people on my team, both Jen and Courtney, I'll go ahead and shout them out because we built trust very quickly. And there still to this day is not anything that I can't give them because I know that whatever comes their way, they're gonna do it well, they're gonna do it on time, they're gonna do it efficiently, they're gonna loop in the right people. Communication's always there. Um and yeah, trust is a big piece of that.

SPEAKER_01 2:58

Yeah, and um there's really like even trust is a part of it, but also like that's how those people end up growing. So you never know if they're gonna be able to make it or grow into other roles if you don't allow space for failure.

SPEAKER_00 3:18

Yes.

SPEAKER_01 3:18

Which is kind of just flipping it on you, right?

SPEAKER_00 3:21

It is because there's more so when I was learning to drive, um, my grandpa taught me how to drive. And we would get in the car, you know, we go through all the basics and I would say, okay, where are we going? And he's like, let's go out to, you know, Target. And I'm like, okay, well, what which way do you want me to go? And he's like, There's multiple ways to get there. You just pick one. And that always made me so anxious because I'm like, oh my gosh, I'm sure there's a faster way, and I'm just blindly driving.

SPEAKER_01 3:49

Explains everything about you.

SPEAKER_00 3:51

Yes. And I just don't know. There's something internally that I'm like, oh, like I feel like I'm just wasting time. Um, but he's a super laid back. There's multiple ways. Um, and that's another piece about management, is there's more than one way to get to successful results. It may not be your way or the way that you had pictured it. Um, but yeah, you need to be open.

SPEAKER_01 4:16

It's healthy actually to see the different ways.

SPEAKER_00 4:18

Yeah, for sure.

SPEAKER_01 4:19

Because if you get stuck in a box of looking at only your ways, like sure, some things that you do are the most efficient or best way, but there's guaranteed to be some of the stuff you do that it's actually terrible. Yes. It's just what you're familiar with.

SPEAKER_00 4:35

Oh, absolutely. Especially looking at things that um, so like for example, Courtney, um, she is always trying to find a more efficient way to do things. Yeah. And she loops in technology into just about everything. And I had a really hard time jumping on that bandwagon because technology was something I wasn't as familiar with. And this is super basic, but like utilizing Excel to do different things that wasn't my strong suit. And once I figured out that she could do it super quickly and away we go, I was like, yeah, I would never would have done that.

SPEAKER_01 5:09

Have you ever like done something one way and then you've thought about it for like a day or something, and then you're like, man, I'm so stupid. Why did I do it that way?

SPEAKER_00 5:18

Absolutely. Um, do you know there's a machine that folds paper to put it into an envelope?

SPEAKER_01 5:25

I just found that out a couple days ago.

SPEAKER_00 5:27

So there is such a thing.

SPEAKER_01 5:30

We have one.

SPEAKER_00 5:30

We have one. I've I've used it, but you want to know when I used it after I folded like a hundred papers to send to employees. Um, and had I've just been a little bit more patient and asked around, yeah, I could have found that out.

SPEAKER_01 5:45

I'm the same way though. I'm just like, let's just get it done. Yeah. So I found out I found out that those machines exist and that we have one like two weeks ago.

SPEAKER_00 5:54

Nice. Yeah.

SPEAKER_01 5:56

Yeah. So did you know that delegation was gonna be a part of that role before going into it?

SPEAKER_00 6:08

I mean, I assumed that there was going to be pieces that I was going to have to delegate. As I climbed the ladder, I got a lot more involved on the strategic side and not as much involved on the day-to-day. Um, and at the time I report I reported to um Phil Heibecker and he was the HR director. And essentially, one of the things that he told me was you're either gonna have to figure it out or you don't. And it was you're either gonna climb the ladder or you're not. If you're gonna stay stuck in the day-to-day block and tackle, as we call it in the HR, um, then you're not gonna be able to grow outside the box into that creative thinking and looking at things at different perspectives because you're being bogged down. Um, so you're gonna have to figure it out. And if you don't, you're gonna be stuck.

SPEAKER_01 6:53

That's a good point. It's like um kind of teaching problem solving and resiliency or like um testing somebody to see if they have it, right? Because like your perspective is different than everybody else's. So you can as much as you want to try and teach somebody how to do a position, they're still gonna do it slightly differently. And whenever you get in those situations and you like feel like you're drowning or dropping the ball and things, like you have to figure out how to claw your way out of it and be resilient and problem solve and make yourself better so that you know how to operate in these positions in the future. And it does require like thinking outside the box a lot and trusting people. Like you have to rely on people to be able to move up for sure.

SPEAKER_00 7:46

Yeah.

SPEAKER_01 7:47

Because it takes teams of people to do things.

SPEAKER_00 7:49

Yeah. I read somewhere, I can't remember where it was, but they were talking about like when you become a manager, it's far less about you doing the work and it's more about leading your team to do the work. And I think that's tough for people.

SPEAKER_01 8:03

Yeah. So you have like insight into positions, managers, employees outside of HR. So what's like a typical uh like success or challenge that people have moving into management roles?

SPEAKER_00 8:20

I would say the number one thing that trips people up is people.

SPEAKER_01 8:26

Yeah.

SPEAKER_00 8:27

I don't mean to be smart about it. Um, but it really is you are leading people, you're managing people, you're working with different personalities. You're the one now in charge of all the paperwork and the time off and the vacations and multitasking in ways that are completely different than what you were originally doing.

SPEAKER_01 8:49

Yeah.

SPEAKER_00 8:50

Um, and if you don't work well with others, if you're not able to lead people um in a way that gives them the autonomy to do good work, um, it starts to bog you down. And that's when people start getting into that failure zone.

SPEAKER_01 9:05

Mm-hmm. Cause you kind of burn out and you're not able to keep up with stuff. Yeah, for sure. It's wildly different work than you've ever done before. Like, especially if you've not been in a management role before, you're working on all of your daily tasks, they're assigned to you, you're working with peers, all this kind of stuff, and then you think that you want to be at the next level because you can do that job better than your boss can. Everybody thinks this. Oh, yeah. Right? Everyone wants to be the boss. Is doing, I can do better than them. You step into that role and you think that it's gonna be so easy, and then you just keep getting punched in the face for a year, basically. Right.

SPEAKER_00 9:49

It's tough. That first year is tough.

SPEAKER_01 9:52

Yeah.

SPEAKER_00 9:52

Yeah.

SPEAKER_01 9:53

Because you realize, oh, I'm not just doing daily tasks anymore. Like you said, now I am in charge of all of these people. I need to feel responsible for all of these people. I have to do all their paperwork. I have to listen to everything that they have to say, basically. Uh, if I don't want to listen to what they say, I have to put up with the repercussions of that.

SPEAKER_00 10:14

Oh, yeah.

SPEAKER_01 10:15

Um I am not only now in charge of them, I'm also still getting punched in the face by people above me. Yes. And getting requested from all different angles, likely. Um, and I don't have any time to actually do any of these daily tasks that I used to do. So now I have a whole nother level of this trust that we talked about to delegate things, which is not a skill that you practice. You don't practice delegating before you become a manager. And it's a it's a developed skill to delegate and delegate effectively.

SPEAKER_00 10:51

Yeah. And the way you just put that, everyone wants to be a manager, but the way you just kind of spit that through was like it's tough for everyone. It's tough.

SPEAKER_01 11:00

Yeah, it's tough.

SPEAKER_00 11:01

You really got to think if you're wanting to be a manager, all those things come into it. And all of a sudden you're expected to know the finances. You're expected to know the legal percussions, you're expected to be able to communicate with executive leadership, senior leadership, HR, accountant. There's all these different business units that we're expecting you to be able to communicate to and run your job and manage people.

SPEAKER_01 11:27

Yeah, that's true. I didn't even bring up communication like you're doing. Like that's a huge part of it because you have to keep everybody in the loop. And you used to think it was just a big problem because you didn't get communicated to. But now if it doesn't happen, you're the problem.

SPEAKER_00 11:40

Exactly. Yeah. Hindsight's 2020. Yeah.

SPEAKER_01 11:45

Uh I have told any bot any time that we're hiring for like a regional controller position, which is basically our first management position in accounting and finance. Um, or I'm talking to people that internally that want to be a regional controller, I always tell them that this is the hardest jump in the track you will ever make, is from any level of accountant where you're not a manager to being a manager. Because up to this point, you know all the technical stuff, you know all the processes, you think you can do all of them, and then you sit in the seat for six months, and it turns out you really don't need to know any of that.

unknown 12:27

Right.

SPEAKER_01 12:28

I mean, you need to understand it so that you can supervise the processes, but that's not your job anymore. Like your job is now all the extra stuff that we've been talking about, and you're getting questions from all managers, all other managers now asking you about finances or calling you to on somebody else's phone to tell you that their phone doesn't work, or they ran over it with a loader, or hit it with uh you just never know what you're gonna get.

unknown 12:59

Yeah. Yeah.

SPEAKER_01 13:01

Or hit it with a tie-down strap on a low boy. Like I can't tell you how many times I basically told people, I swear, if you break another phone, I'm just taking it away from you.

SPEAKER_00 13:13

It happens that often.

SPEAKER_01 13:14

It's with some people. Oh, geez. Yeah. Um, but no, it's a it's really the hardest jump for sure. Because after that, I'm not saying that those aren't hard jumps, but it's just a more difficult level of what you've already been doing. Like now your work is similar. You're just doing it on a grander scale. You have to delegate more or different projects, you might have to learn different technical skills, you might have to communicate with more people. Um, but it's still the same type of work. Right. So it's um I think the feedback that I've gotten from that a lot of times is like surprise.

SPEAKER_00 13:58

Mm-hmm.

SPEAKER_01 13:59

But hopefully people are thankful that they heard that. You know what I mean?

SPEAKER_00 14:06

So let me ask you this. We've talked a lot about how it's pretty brutal to take that jump into management.

SPEAKER_01 14:13

Yeah.

SPEAKER_00 14:14

What do you think, I guess from your experience, is a good way to start learning how to manage people when you don't have direct reports?

SPEAKER_01 14:24

Um, I think making, you know, like expressing your desire to eventually be in that role and want to take on more with your current supervisor is key. Like, you know, we've been talking about that lately. You know, be communicate and be transparent with what you want to do and where you want to go. And, you know, if your supervisor doesn't have the idea for you, then I think great ideas are to like work on improvement projects and hopefully ideally you work within a team of people or like other peers within your group. So like if you're a staff accountant working with other staff accountants and like leading that project, right? And also showing and trying to like build relationships with people in other areas of the business to get to the point where you uh know enough about their business to like ask questions and possibly like influence decisions, I would say. Because it's really the same type of thing managing people, right? Like it's there's more when you're actually managing, you actually have like paperwork and I don't know, all those things, right? But the the actual the soft skills are the same managing the people. You're really just listening to people and convincing them to do something sometimes that they don't want to do.

SPEAKER_00 16:02

Yeah. Right? That makes sense. Yeah. That's a good way to put it.

SPEAKER_01 16:07

Yeah.

SPEAKER_00 16:08

I know that your team has started um giving more responsibility to other members on supervising the interns.

SPEAKER_01 16:17

Yeah. We do that too. Yeah. So anytime that we have interns, which our intern program throughout Reeves is legit, like 30-ish interns. And we do, I don't know, we've done anywhere from like eight to 14 or something like that. Um it's a great opportunity to like have them report to, you know, well, I'm I keep using finance examples, but like a senior accountant or a staff accountant, or um, right now, like Carrie as our continuous process improvement manager doesn't have a direct report, but she's taking an intern to be able to manage them. Um, you could do the same with really any position that's like an assistant or a senior level position that doesn't have direct reports. It's just a great way for them to understand for three months, like, hey, you're in charge of this person. Yeah, you're responsible. You're answering their questions, you're telling them what to do every day, you're building their schedule, you're approving their time card, like this is what it's like.

SPEAKER_00 17:20

Temporarily.

SPEAKER_01 17:21

Temporarily. Yeah. Yeah. Like the stakes are low.

SPEAKER_00 17:24

Yeah.

SPEAKER_01 17:25

Comparatively.

SPEAKER_00 17:26

Did you like it or not? Yeah.

SPEAKER_01 17:28

And some people, um, you know, good on them are honest about it. Like, yeah, this, I don't want to do this.

SPEAKER_00 17:35

Yeah. I mean, it's a great opportunity to see what it's like.

SPEAKER_01 17:39

Yeah. I mean, I have friends that don't work here that um have wanted to move up in roles and stuff before and then gotten direct reports and are then are like, yeah, I don't want to do this. Like I don't want to be in charge of people.

SPEAKER_00 17:56

Yeah. And then what happens? Like that's even more of a tough transition.

SPEAKER_01 18:01

Yeah. Well, you either have to you either have to s uh be super honest with yourself and swallow your pride in if you want to stay with the organization you're with and move roles again, or you have to change organizations, right? Or j and jobs.

SPEAKER_00 18:17

Yeah.

SPEAKER_01 18:17

And then it's kind of starting all over. I mean, maybe it works everybody's situation is different, so maybe it works out good for you at the time, but it's tough. But yeah, interning interns are a good way to get some temporary practice.

SPEAKER_00 18:34

Yeah, I agree.

SPEAKER_01 18:35

We do it a lot. Um what do you think is you know, uh what do you think is something that people should know before like if you were if people asked you for advice on what they should know before becoming a manager, what would you tell them?

SPEAKER_00 18:58

Um, so a couple things I would have to say is um you need to be prepared for everything to change overnight. Like as soon as you show up to work the next day and now you're responsible for people, it's just a whole nother like there's no real onboarding process to figure it out. Like you just have to.

SPEAKER_01 19:21

As soon as word gets out and they have your phone number, it's over.

SPEAKER_00 19:23

It's over, yeah. And everyone's looking at you.

SPEAKER_01 19:27

Yeah.

SPEAKER_00 19:27

And everyone needs an answer.

SPEAKER_01 19:29

Yeah.

SPEAKER_00 19:29

Um, I think in those situations, leaning on your team, leaning on your supervisor, and leaning on HR is really important to keep that circle of communication open. Um the company wants to see you succeed. Your manager wants to see you succeed, your team wants to see you be successful. Um, so the resources are there. You should not be afraid to ask questions, to ask a stupid question because you don't know what you don't know. And as soon as you start managing people, they're gonna expect for you to know the answer. And it's totally fine to say, that's a great question. I don't know that yet.

SPEAKER_01 20:10

Yeah.

SPEAKER_00 20:11

But I do know someone who does know and let me find out for you.

SPEAKER_01 20:14

Yeah. Yeah, yeah. No, that's good advice. Well, a terrible thing to do, like one of the I think the worst things that you can do is just assume that people know things. Yes. Right. And don't make the assumption that you should know it so that so then you just make something up or whatever. Like it's okay, like you said, to say, I don't know, and reach out to somebody else. Yeah. It's a better answer, and I think gains you more respect from somebody than to get caught up in some other situation.

SPEAKER_00 20:46

Yeah. Well, I think there's this perception that if you don't know the answer, that it starts to spiral into you're not qualified and you don't have the experience. And are people gonna think that I'm not a good fit? And it just starts to like internally spiral.

SPEAKER_01 20:59

Yeah.

SPEAKER_00 21:00

When really people aren't thinking that.

SPEAKER_01 21:02

No, yeah. That's a BS excuse that you tell yourself. It's really like um It's like imposter syndrome. Yeah, for sure. But I think you actually gain more respect out of saying, I don't know, and then actually going, getting the answer and following up in a timely manner, because then somebody's like, oh, they were listening to me and like found an answer to my question.

SPEAKER_00 21:26

Yeah. To your point, things that'll go south real quick is if you don't follow up and you're inconsistent. Yeah. Those two are going to eat you alive and you won't be successful as a supervisor.

SPEAKER_01 21:39

So yeah. What's you know, you brought up um communicating with HR and asking for help and questions, like what type of support are you providing in that role?

SPEAKER_00 21:52

So a couple examples that come to mind. Our industry specifically, I personally think does a Really good job of promoting from within. And majority of the time that means that you go from peer to supervisor. And at that point, like I said, things shift overnight. You can no longer have the same conversations and the same chit chat and the same venting that you typically would in your day-to-day. Right. Like you have to, you know, the rule of thumb is you vent up, not down. And what you say, how you say it can get you into into trouble, um, especially dealing with employee issues. So I always suggest getting HR involved. If you're getting ready to have a difficult conversation, if you've never done it before, if it's someone that you were pretty close to and now you're having to deliver kind of that boss to worker um conversation, get us involved. Um and then a lot of it is just you don't know what you don't know. Now all of a sudden you're responsible for things like FMLA or um all the policies, right? Bereavement, vacation, time away, um, all those things that come to your attention. You can quickly screw up if you don't do it right. And so I always say bring HR kind of in sooner than later, and and we're here to help.

SPEAKER_01 23:19

Yeah. Well, that's a good point. Don't assume that you have to know all of these policies inside and out. Just be cautious. Like know that they exist and then ask for help on handling them. Yep. Like I don't know them.

SPEAKER_00 23:33

Yeah. It there's a lot.

SPEAKER_01 23:35

Inside and out.

SPEAKER_00 23:36

Yeah. It it's too much to remember and memorize. And especially things change all the time. You may not have the most updated one handy. So yeah.

SPEAKER_01 23:45

You brought up a couple good points. One about the venting, like that whole relationship does change. And they say, like it's an old saying, like it's lonely at the top, right? But I mean, that's true because every time you move up management roles, you're the management team of that level shrinks, right? It's smaller and smaller until you wind up down to just a couple people, and there's less people to vent to. And once you become a manager, I mean, I think you're noticed in any role that you're in, whether you're a manager or not. Like people are watching what you're doing. So you need to be aware of that and be a mentor and a leader, but especially once you're into a management role, like people are watching you. For sure. And looking at for you to set the tone and what you do and how you act and the things you say, the way you handle things. So like you have to be self-aware of that. And it doesn't mean that you have to be some super straight laced, like suit and tie type of manager. You just need to be aware of what of how you show up, basically.

SPEAKER_00 24:58

Sounds so simple, but it's so important. Yeah.

SPEAKER_01 25:02

It does sound simple, but it's not.

SPEAKER_00 25:04

No, it's not.

SPEAKER_01 25:08

If y'all enjoyed the episode, please rate our show and leave a review on Apple Podcasts, Spotify, or wherever you listen, and check out Delta on all social media platforms at Delta Companies, and our website at Delta C O S looks like Deltacos.com. Thanks for listening, and we'll see you next week.