Ladybug Podcast
9/8/2025

The Transition From Engineer To Engineering Manager

Stepping into management for the first time can be both exciting and overwhelming. In this episode, we explore the critical shift from individual contributor to engineering manager.

Transcript
Emma Bostian

My job is to help you in your career. I would ideally like that to be here with us. But if it's not, I want you to feel comfortable coming and talking to me about it and not feel like you have to hide anything.

Kelly Vaughn

Welcome to the Ladybug podcast. I'm Kelly.

Emma Bostian

And I'm Emma.

Kelly Vaughn

And we're debugging the tech industry. Hi, Emma.

Emma Bostian

What are we talking about today?

Kelly Vaughn

We're talking about the fact that we're dressed exactly alike.

Emma Bostian

This is true. And this was unplanned, but welcomed.

Kelly Vaughn

I'm not mad about it. But also, I guess it's not that impressive because, hey, you're wearing a black top and so am I. The stakes are pretty low here.

Emma Bostian

I mean, who doesn't look good in black? Let's be honest.

Kelly Vaughn

That's true. That's true. Yeah. I walked downstairs and my husband was like, oh, you're going for Steve Jobs today. Like, I can't wear a black turtleneck. Ish.

Emma Bostian

I used to have this. I used to wear this, like, gold chain necklace. There was no. No pendant or anything. It was just gold chain with, like, a black shirt. And I look like that picture of the Rock from, like, the 70s. Do you know the one I'm talking about?

Kelly Vaughn

That was my Halloween costume last year.

Emma Bostian

Was it really?

Kelly Vaughn

Yes. Here's the laziest costume.

Emma Bostian

I unintentionally have showed up to work looking like that multiple times.

Kelly Vaughn

I love it. I mean, it's great. It's so easy. Like, just like pick pin a fanny pack to you as well. And, like, you're good to go.

Emma Bostian

If any of you listening know the exact image I am referring to, please leave a comment.

Kelly Vaughn

It should be pretty awesome. Pretty. Pretty obvious. But yes. What are we actually talking about today?

Emma Bostian

Today we're actually talking about the transition from individual contributor, also known as ic, to em, which is engineering manager. I think this is a. Were you ever an IC officially, or did you just immediately jump into running.

Kelly Vaughn

A company that was an ic? Yeah.

Emma Bostian

Yeah.

Kelly Vaughn

Because even when I was freelancing as like a. There was one. One company I worked with for probably two or about a year or so that I was. I was doing ic, like individual contributor work for before I started my. OR while I was still running my company. And then I also was an IC in college as well.

Emma Bostian

Mm. Okay. Nice. Yeah, I made this transition, I think last episode we mentioned this, but about two and a half years ago. No. Yeah, about two and a half years ago with a parental leave break in between. But I know this is a Common question that many people ponder as an engineer, which is like, how do I know if I'm going to like engineering management? It's kind of a big deal to just jump into it without having any semblance of an idea whether you'll like it or not or be good at it or not. So what drew you to engineering management? I. I always actually wanted to get my master's in business and go through like an MBA program. I really like learning about leadership and I never was a manager like in any other respect, but the idea of managing people and dealing with people problems as well as technology problems was really intriguing to me. So I always knew I'd end up in management. I just thought I would be a little bit more experienced tenure wise before doing so. Although frankly, is there ever a right time to get into anything? Not really right and, but I was on parental leave with my daughter and my manager informed me that there was an open position on our team. We were growing, would I like to apply? And I said absolutely. So when the opportunity arises, you can't always say no. And it worked out.

Kelly Vaughn

Yeah. And here you are stuck in this role now.

Emma Bostian

Mm, indeed. But I love it. I love it. Um, should we talk really quickly about some of the responsibilities of a, an individual contributor versus an emergency?

Kelly Vaughn

Yeah, yeah. I mean on the, on the IC front, I mean your job is to write code to deliver on the projects and solve some, you know, potentially gnarly technical problems to, to meet business goals. Like your responsibility is code the deliverable. It's very tactical. Engineering management on the other side is your responsibilities. People, your responsibility is the delivery of these projects by enabling your team to do that tactical work. Occasionally you do, you know, you write code as well depending on the organization you're in. But it's not your core purpose in life anymore.

Emma Bostian

Right.

Kelly Vaughn

Anything you'd add?

Emma Bostian

Yeah, I'm just thinking about like the day to day, what my day in the life was like as an engineer versus a manager. I had a lot more free time. That's something that people are generally pretty aware of is as a manager you're gonna have a lot more meetings. But the way that I look at like my day to day breakdown now is kind of in a few different buckets. It's like there's the people management side, so meeting with your team, one on ones, stand ups, things like that. Then there's meeting with your peers. If you've got like other engineering managers in your organization that you have to meet with. There's also like reviewing documents And I can't remember the three buckets that I like used to chunk my work but it's like it's not going to be opening pull requests necessarily. It might be but very likely not.

Kelly Vaughn

Basically never for me. How about how many meetings do you have a day?

Emma Bostian

Oh my goodness. It really varies like depending on where we are in the year because we're on six month planning cycle. So if it's planning time or we're planning for six months I have no free time during the day. I'm in meetings from nine to, to four straight. I leave at four to get my, my kid from school. So I don't generally do a ton of meetings after that. But I've also because my team is so senior many of them don't need like weekly guidance from me and they, I have an open door policy. They can check in whenever but So I have one on ones alternating every two weeks. So like oh my gosh, at least 60% of my time is, is taken up by meetings. So I have to be a bit more selective with how I spend my time.

Kelly Vaughn

It's, it's one of the biggest, the, the easiest traps you can fall into. Yeah, I mean I am, I'm in Probably anywhere between 6 and 12 meetings a day because I have project status meetings. I've got leadership meetings. I've got one on ones. I've got those peer one on ones as well. And then I've got the, I've got customer calls. I've got, I mean I've got so many especially right now it's, it's end of quarter as we're recording this right now. And so I have no empty space on my calendar. Yeah, yeah. I have to schedule my lunch as a meeting so I don't lose enough time.

Emma Bostian

I do that too. Not for any other purpose than sometimes I forget. But I will say though that like generally I don't have meetings most of the time I don't have meetings before 10 or after 4. So like I do get some good amount of focus time in the morning and can in the evening if I need it. But like we try to keep Wednesdays as focused Wednesday so that we have plenty of time. Um, but yeah that's a dream for me.

Kelly Vaughn

It's never going to happen.

Emma Bostian

It's not something that generally always happens. But, but yeah, I think your schedule is less your own now. Your schedule is more for other people. But frankly I find it less mentally taxing to have a day full of meetings than a day where I would be working on code. So like for me it was, it gave me energy to meet with people, even as an introvert.

Kelly Vaughn

So I think that's a good, like a good sign that management might be for you. Because for me, I mean I'm in meetings, I get, I am mentally drained by the end of the day just because I'm in so many meetings and I have to context switch a lot for these meetings. But I would be even more mentally drained if it was. I'm staring at my co editor and I'm writing all day.

Emma Bostian

I agree. I will say though, because I am an introvert and social engagements very much drain my energy. My therapist was like, why do you like management then? Because mostly meetings I'm like, it is, but actually it's not. It doesn't drain my energy because it's focused around work. And I, I mean some of them are social, but for the most part, like I don't leave the end of the day feeling exhausted.

Kelly Vaughn

So I, I guess my, my situation is a little bit different just because my team spans from California to India and my manager is in San Francisco. But I am starting my meetings in the morning and I'm ending my, my meetings in the evening. So on. Sometimes like there are some days when I know I have to do an early start. Like I start meetings at like seven, but I will block off two or three hours in the afternoon before resuming meetings again because I know I'm just going to need a, like a mental break and that way I'm preventing myself from working 12 hours in a day.

Emma Bostian

Yeah, yeah, that makes total sense. I always tell my team too, like, get outside during the day if it's sunny. Especially living in Sweden where it's dark for half the year.

Kelly Vaughn

It feels like like a sun doesn't.

Emma Bostian

Come up until like nine, if it ever does in the winter, and then sets at three. So we have. I'm very fortunate that we have a very flexible work schedule which doesn't always happen. But in any case, yes, you will have less quote, unquote free time. But it's still quite important that you. Yeah, you do attend these meetings.

Kelly Vaughn

Yeah. So thinking through some other responsibilities, one I would love to kind of talk about at length is delegation because this is one that I think a lot of people struggle with, whether you're an experienced engineering manager or not. Because basically you might go from I have all these things and I own all these things to I now need to take some of these things off my plate and I need to trust my team to be able to deliver. And that can be challenging. How. How are you with delegation?

Emma Bostian

Really good. I try to get rid of all of my work. To other people?

Kelly Vaughn

No, just all of it. I actually don't do anything. This is true.

Emma Bostian

No, I am actually kind of a control freak in, like, my personal life. Like, I like to have control over things. I have high standards for certain things at work. I'm really good at matching people based on skillset or where they want to grow their skill set with opportunity. So I'm also really good at taking the tasks that nobody wants to take. Like we Europe right now is enacting, like the Digital Services act, which is essentially people or consumers of products are allowed to turn off personalized recommendations or not have profiling turned on for certain applications, which. Yeah, it's for data privacy. So we have to make sure that our product is legal and compliant. And it's not a very, very fun task to do all the testing on our platforms with different types of accounts at different regions. So it's something that, like, I'm totally fine to like, you know, just take the tasks that aren't so exciting for the team if I have bandwidth, of course, or at least to pair up with them. So I try to delegate the things that are impactful to someone's career or interesting to them. But this is something that I talk about all the time because the skills that made you a really great engineer are not always going to translate into management. And sometimes they can actually hurt your performance. Right. Delegation is one of them. You're used to taking on tasks, many tasks, doing them really well and reaping the direct benefits. But now your performance is measured in terms of the success of your team, the delivery of your work items. So as long as you can shift your expectations about your own performance, I think you'll be okay. And in the last episode, we also had briefly mentioned making sure that you're preventing bias by giving opportunity to the same people over and over based on proximity or familiarity, et cetera. So make sure you're delegating in a fair or equitable way.

Kelly Vaughn

I think one of the other things that is probably trickiest about moving from a place of taking action and doing the tactical work to trusting your team to do it is that they often will do it a different way than you. And it can be very challenging for you to say, this is the project scope. Do the thing. Instead of saying, here's the project scope, here's how you need to do it. Now do the thing. You're. It's important to empower your team to be able to learn and try to, you know, reason through a solution for themselves instead of you telling them what to do and like dictating that. Because that's how they, that is how they grow. And when this happens, they're going to make mistakes and you're going to make what you can deem to be preventable mistakes. But we learn so much more from our mistakes than we do our successes. And so it's important to give your team the space to try and fail and learn and try again and you'll, you know, eventually get to a good solution. There are times when you need to step in. Like if you start to see like the, the trains kind of get going off the tracks a little bit, you need to push things and nudge things back on. That is okay. But there's a line you need to balance between being supportive of your team and empowering them to figure things out in like micromant managing. You don't want to micromanage them either because again, nobody likes a micromanager.

Emma Bostian

Yeah, that's super true. It's a hard line. And frankly, there are many times I second guess myself and I have to explicitly tell them, I promise you, my intention is not to micromanage you. Like, so, for example, when we have different work streams that are ready to pick up, you know, if people need things to do or have expressed interest, I'll typically say, hey, you know this person, do you want to work on this? And then I have to explicitly tell them for my own sanity, like, I promise I'm not trying to micromanage you. If there's something like just tell me to step off. You can do it in public or private, just tell me to like back off. And I actually have had a team member in a very empathetic and kind way be like, hey, you know, like we don't, I don't agree with your, with your opinion on this matter. And like, cool, I'll back out. Like, thanks for letting me know. But there's this type of work, I can't remember maybe you know the term for it. It's basically non promotable work that more administrative, like running team events and landing retros. And it typically falls on the same kinds of people who may or may not identify as women. A lot of times I find myself doing this type of work, like planning retrospectives or team events. And there was another woman on my.

Kelly Vaughn

Team doing the same thing.

Emma Bostian

And I had a senior engineer, he came to me and was like, hey, I noticed that you and the woman on the team are doing all this work and it's really great. You're doing. You're both doing a great job. But I. I want to make sure that, you know, everybody a gets a chance to do it because it's good, like you said, to let people do things the way that they want to do things and not micromanage, but also to make sure the burden is not falling onto the same couple of people. Because it's not promotable work. Right. I can't remember the term for it, though. We can put it in the show notes because I have a link to an article, but as it pertains to delegation. Yeah. Make sure that if there are tasks that happen repeatedly, whether it's regression testing or things like that, give everybody on the team a chance to do it because. And do it their own way.

Kelly Vaughn

Exactly. Yeah. Like. Sure. If there's a process you have to follow for, like, compliance reasons, then. Right. But most of the time that's not the case. Yeah. There's this space for creativity and we want to leave that space for creativity.

Emma Bostian

Absolutely.

Kelly Vaughn

So the other thing that I would say that's very, very important as a manager and shows up differently as an IC is conflict resolution. The types of conflicts you deal with change as you become a manager. And I have a whole lesson in my course on conflict resolution that goes over how to handle conflict between two people on your team, between you and a person on your team, between your peers, and then with your manager as well, because they all require a different take. Now, between two peers on your team is probably the one you're going to see most often, actually, before we get into that. Conflict is like the defining conflict, I think is important because we often think of conflict as like we're having an argument or something negative is happening. And conflict can simply be. We are. We don't know which tech stack to use. We don't know which direction we want to go down in this project. We don't know which project is higher priority according to, like, the business objectives. And so it's important to not shy away from conflict and the idea of a conflict because conflict leads to discourse. And discourse is healthy.

Emma Bostian

Absolutely.

Kelly Vaughn

Anything you'd add to that?

Emma Bostian

No, I agree with you. I mean, where we see the biggest innovations are on teams that are quite diverse in many respects. And diversity will naturally lead to a difference of opinion, which is a good thing.

Kelly Vaughn

That should be the case. Yes. You're always in agreement, then you're not bringing in new ideas. That is absolutely a Problem. So looking at interpersonal conflict as an individual contributor, what kind of things would you say kind of stand out as an IC versus an em?

Emma Bostian

I mean, I've had like, conflict with team members as an ic, and I remember running to my manager and I mean, all feelings are valid. Right. So I don't want to downplay my feelings, but at the same time, he did kind of reflect it back to me and he helped me. He validated my feelings and he was supportive in that respect. But he ultimately put the responsibility back onto me to continue the conversation. And in the moment I was like, I feel like I'm not getting enough support from him. And now looking back on it and reflecting, I'm like, why? Like, I was like a 27 year old adult. We're both adults. Like, we owe it to ourselves and to our team to sort this out on our own. And if it becomes unsafe, okay, that's a different situation. Right. But yeah, as a team member, I really did not want to address conflict one on one. I was not good at it in my personal or professional lives because it's not something that you see very often.

Kelly Vaughn

Yeah. And you're not trained, like, for the most part, you're not trained on how to handle. Handle conflict?

Emma Bostian

No, not at all. I think a lot, a lot of conflicts at work are not personal either. And I'm. I was always the first person to take things personally as a reflection of who I am as opposed to, like, my behavior, which can be changed. So, like, as an example, I was taking Swedish classes because that was something I wanted to do living in Sweden. And it fell. I accidentally signed up for the wrong course, which placed it like Tuesday, Wednesday, Thursday for like an hour and a half in afternoons. And I was working on a work stream with two other folks and I think one of them was frustrated. That basically, like, prevented us from mobbing or pair programming during, you know, a good period of our day, which was totally valid. But I never heard that feedback from them directly. I heard it through other people that they were talking to. Um, so yeah, it was a little bit tricky to navigate because I'm like, okay, I haven't heard this firsthand, so I'm gonna go to them and like, we're gonna work it out. And it just felt like it was very painful. Like it wasn't fun for either of us to do. Obviously both of our feelings are valid, like in the sense that they were totally correct. Like, I should have fixed the timing of that situation. There wasn't really anything I could do at that point. But I could have at least acknowledged it. Right. But on the flip side, like, we owe it to one another as human beings and as colleagues to give that feedback to one another, even if it's uncomfortable. Because the worst case scenario is you hear it through other people and then it becomes a bigger issue.

Kelly Vaughn

Yes. Yeah. And it's so much better. Just get ahead of it and have that, have that conversation. Most people are, you know, are not going to take things personally when you do have feedback. It can happen. Again, we're not trained to give or receive feedback and that's a whole nother section in my course. Because that is another critical thing you need to learn how to do as a manager is how to give effective feedback and how to receive effect or how to receive feedback gracefully even if it's not effective feedback. Even if it's like it's the, it's the, you're doing a great job, keep it up. Or on the flip side, it could be like this, this thing could be better. Like, okay, but how, like what, what's wrong with it? Or even worse, you, you sit like you get told somebody on your team is not pulling their weight on a certain project when it's not even their work to do. It is a completely different team member's work that's not on your team, for example, for a cross functional project. And there was just like a misunderstanding about, you know, ownership of work. And then, you know, I, that's happened to me before and I'd have to get very defensive about my team being like, hey, like my team is doing exactly what they're instructing to do here. If there's an, if you don't think that there's a, you know, if we're not doing the right work, then that's a different problem. But we're doing the work well that we're supposed to be doing, from what I understand. And this is, this comes up a lot more with like your manager and your peers. And I think there's a whole thing that we could do on managing up because that's a. Again, it's really challenging. I think I talked about that in previous episode too. But for, you know, dealing with conflict, especially between you and a team member. So like a direct report, you have to acknowledge that that power dynamic. Right. That is absolutely. Number one, some people are going to feel more comfortable coming to you than others. Again, this is conflict is very cultural. It is deeply cultural. And some people on your team are going to feel much more comfortable coming to you with the with concerns or complaints or, you know, feedback with you for you and others are absolutely going to think that if they give, you know, if they push a, you know, push something into a PR that has a, you know, a typo and it causes something, that they're going to lose their job over it. Like, you need to know how to communicate with your team members, each one individually, and understand how they take feedback, how they handle conflict, and how you can best work with them. It's not a one size fits all thing.

Emma Bostian

No. And I think the resource you mentioned in the first episode, crucial conversations, helped me immensely. Give feedback to my direct reports as their direct manager. But going back to your point about receiving feedback about your team, it's so hard not to feel defensive sometimes.

Kelly Vaughn

Oh, yeah, this.

Emma Bostian

This is another thing. So I remember I had to give feedback to another manager in my, like, organization about one of their reports, and I felt super uncomfortable. I'm like, is this appropriate to do? And I think I messaged them and I'm like, I really hope this isn't out of line. Like, I was so nervous and they were like, why would that be out of line? Like, thanks for letting me know. I'm like, okay, that's really nice. But then one time I got feedback about somebody on my team and a role that they were doing, and I realized it wasn't. It wasn't their fault. Like, they weren't doing nothing wrong. It was my fault because I didn't clarify the expectation on the role for them ahead of time. So immediately, like, I'm like, okay, this is actually not on that person. It's on me. Apologies. But yeah, it's learning. And this is another thing. Learning how to take feedback but also recognizing that not all feedback is valuable.

Kelly Vaughn

Exactly.

Emma Bostian

I tell my team this all the time. I'm like, take it with a grain of salt. If you seriously think through a piece of feedback from all sides and you realize that it's not applicable to you. You know, like, if someone gives you feedback, I don't like your pink hair. I don't like the way it looks. It's like, I don't have pink hair.

Kelly Vaughn

I know that for a fact. So even though you do have pink hair, and it's like, oh, I think your pink hair is unprofessional for the workplace. I'm like, great. That's like your opinion, right?

Emma Bostian

Right. Feedback can be a gift, but it's not always a relevant gift.

Kelly Vaughn

You know what I mean? Some people are just really bad at giving gifts. Yeah, that's Literally what it is. It's true.

Emma Bostian

But I think the biggest thing with giving feedback that I've learned is that it's two of you with a common goal against a problem, and it's not one of you against the other. And as soon as people are gonna have emotions about things. Right. But if you make it very clear up front that, hey, we have the same goal. We want you to be successful. We want you to get that promotion. In order to do that, here are the things we need to improve. And it's uncomfortable, but, like, I'm on your side right at that point. It's not two people against one another. It's two people against a problem. And the heightened emotions or, like, the, you know, the part of your brain that's, like, animalistic when it, like, responds to the reptilian part. I don't know. I don't speak very good English anymore. But, yeah, the part that, like, immediately gets defensive if they feel attacked, that part is not gonna, like, show up if. If you have a common goal. So.

Kelly Vaughn

And even if it does show up, because, again, it is a little cultural, and I can tell you, like, from my upbringing, I get. I can get defensive very quickly. Um, and. But I. It becomes awareness of that. It. You know, it. It's. It's your emotional intelligence. It's being able to recognize your own emotions in a situation and be able to say, like, okay, I'm. Now. This is not a time to be having a conversation. Yeah, we, like, regroup in five minutes.

Emma Bostian

Yeah, totally. I recommend everybody take. If you're going to get into management or leadership of any sort, take one of those. Like, I got homework for my therapist yesterday that was like, please take this online survey about your strengths and your weaknesses. And I'm like, cool. So my top strength is that I'm kind and I approach things with a sense of humor. And my, like, negatives are that if I feel like someone's offended me, I can hold a grudge. So, like, I'm also very short, and I make very impulsive. Oh, yeah. I can hold a grudge, like, until the day I die. But if you come and try to, like, repair the situation, okay, no problem.

Kelly Vaughn

I forgive you. Right.

Emma Bostian

So. But, like, being aware of how you are as a human being outside of work, you can actually like those issues. They don't translate into work for me. I keep that very separate because I'm aware of how I am and like it outside of work. And I. I make a huge effort to not let that spill over.

Kelly Vaughn

Yeah. And and that is a really, really important thing for showing up to work is, is knowing, you know, when to pull things in and when to keep things, you know, in inside voice or with a, you know, respected group of people that, you know, I know a lot that happens at my company because I'm also in it. And so as a result, I am a, like, bucket full of, like, rumors and drama and whatever's happening. And I'm like, I can't talk about any of this with anybody. Yeah. Except for, like, you.

Emma Bostian

Well, that's the hard part too, is, like, you're going to be privy to a lot of information about people, about decisions being made that you can't share with other people. And frankly, as a leader, you should not be gossiping anyway. But sometimes it's really hard to not be able to, like, let out your emotions or your feelings about a situation with people anymore. Like, as an IC situation there, the stakes are less high. Right. But as a lander, you're expected to have a standard. Um, so, yeah, that's been a little bit tricky because you don't want to tell people, like, personal things going on.

Kelly Vaughn

And.

Emma Bostian

Yeah, not that I, like, I don't struggle with it because I know it's not even an option on the table, but it's more like, how do you de. Stress otherwise then?

Kelly Vaughn

Yep. You have to find a. You have to find an outlet somehow. Yeah. You can't keep all that internally.

Emma Bostian

Mm. Mm. But how do you know if you're doing a good job? Right. Yeah, we talk about, like, performance. Individual performance is pretty easy to measure. How do you. How do you know that you're doing a good job as a manager?

Kelly Vaughn

I think you need to understand from your manager, you know, how you're being like, what. What does success look like in your role? Because, you know, success in my role is not going to be exactly the same as success in your role. So understanding, you know, what you're working towards and, and then asking for feedback and just checking yourself along that. So for examp example, you know, I am responsible for making sure the. The charter for my team is being delivered on time and with a high quality bar. If things are slipping, I. It is on me to make sure I turn those things around. I also need to make sure that my team is feeling empowered and they feel like they're, you know, they're growing in their career and they're happy. And so I'm maintaining a strong team culture that will, you know, contribute to whatever happens to come up in the organization. So those Are the two like two of the main things? And I have a million side quests that I have because I'm also head of IT or security officer. I do all of our compliance, I do all of our cybersecurity. So I wear a million hats at a smaller company. And so big success in my role has to span all of those. And then I say the third thing that it should be across every organization is how you show up as a leader across your organization, how you're representing the company, whether you know, if you're meeting with customers or you're even just talking to other teams within your organization, outside of your organization. Like, if you have to, you know, work with finance on something, you have to work with a different engineering team on something. Like, how are you representing your. Your org is also really important, like.

Emma Bostian

Your sphere of influence.

Kelly Vaughn

Absolutely. What would you add?

Emma Bostian

Yeah, I think like, how the team is doing. Like, we do health checks every three months to check in. It's all anonymous, but it covers things from psychological safety to efficiency to work life balance. And then we have discussions, if need be, so kind of measuring that performance over time. But I find that I like, put a lot of emphasis internally without knowing that I do this, on how people view me. Like, do people like me as a manager? And the harsh reality is people aren't gonna always like you. And in order to be a good manager, sometimes they're really, really not gonna like you. And you have to be okay with that. Right? But one of my, like, fellow managers, like, you know, like the whole organization will be able to submit like anonymous comments like twice a year. And that goes up the chain, et cetera. And sometimes like, people have frustrations and they're totally valid, but that means that sometimes they maybe will write things that are not productive or kind, but you don't know who it's about. It's all anonymous, you don't know who wrote it, et cetera. And of course, immediately I start reading these things and I start spiraling over thinking, like, is this me? Are they talking about me? Like, could this pertain to me in any way? My fellow EM was like, you gotta stop putting so much emphasis on like refining value. Now let me rephrase this. You have to stop defining your self worth as a leader by how people are viewing you or how they could view you. And I'm like, dang, that's totally true. I need to find another metric to like gauge my performance. Right? So like, is your team delivering on time? What quality are they delivering to things like that also play into your performance?

Kelly Vaughn

Yeah. Yeah, I love that. I think that's. I think that's really important. Again, as a transition from IC to em. Like, that is one of the most challenging things that you'll do is if. Especially if you're going from being an IC on a team to being the. All of your previous peers now manager. That is a. That is a tough transition because you're going from, hey, these are my friends, to I am responsible for the. Their work. I'm responsible for them and making sure they deliver. And that means having difficult conversations with them sometimes. And I remember when my husband transitioned into a management role a couple companies ago, when he went from IC to manager on his team, some people were not happy about it. One could be like, they wanted that role and he got it. So, you know, that's disappointing. And two, some people just don't work well together. And when that transition happens, it is possible that people will leave or move to a different team, and that is okay. And, and this is. This is a common theme in leadership in general, is not being afraid of churning on your team. If somebody's leaving it, it's probably not personal. It could be like, maybe you two just clash and you do not work well together. And that is possible. But most of the time, there are other reasons that people are leaving. There's a better opportunity elsewhere. They can get paid more elsewhere. They're bored, they're looking for a new challenge. Whatever it is. Like, it's. Again, you can't take it personally and have that be a measure of how you show up. Now, if, like, half your team suddenly leaves, maybe it's a red flag. Maybe something's actually up here, but if it's just like one or two people or, you know, whatever it is, like, it's okay to. To have that happen. And in fact, a good leader is going to enable your team to be successful no matter where they are. You want to do whatever you can to help them grow in their career. And if that means leaving your team, then that's what it is. Yeah.

Emma Bostian

Yeah. That's what I. That's my. One of my core values is like. And you know what? This came from the very first manager I ever had, like, back in the day, first out of college. Like, my job is to help you in your career. I would ideally like that to be here with us. But if it's not, I want you to feel comfortable coming and talking to me about it and not feel like you have to hide anything because it's not Personal. Right. Most of the time it's a business decision, just like you had mentioned. But also a lot factors into that. Right. Like maybe they want to move countries to be closer to their family and they're not allowed to work in a different time zone. Like there's so much that goes into it. You're not responsible for other people's feelings and their actions is a big one. So like if you are getting to the point with an employee, for example, where you have to put them on a performance improvement plan, it's going to suck. Like they're going to be mad at you because you're the one essentially saying it's time to do this. However, you know, it's there. You know people, you're not responsible for their actions. Something that they have done, have, has led them to this point. I will say your job is not to make people like you. Right. They don't have to like you. You do have to make them feel psychologically safe and included. That is very, very important. And you generally should have their best interests in mind. But they don't have to like you. Right. Ideally, that they would respect you and trust you is the big thing. Trust is a big thing. But. But yeah, that's not. Everybody's gonna like you. And that goes for everything in life.

Kelly Vaughn

Yeah. And one of the hardest things you can do is, is when you start to get into those performance conversations. Having a performance, like the performance improvement plan conversation with somebody, usually that means things have escalated to the point where their job is at risk if they don't turn things around. Hopefully there are conversations like check ins on, like, hey, let's have a performance conversation before you even get to the pip. Because you know, I have had people come off of pips before and turn things around. I've also had people who did not turn things around and we had to let them go. And firing people never gets easier. No, I have, I have done it so many times in my career and it's never easy, especially if it is somebody who you like as an individual. But they're just, you know, they're just not showing up the way they need, the way you need them to. And things are falling behind.

Emma Bostian

Absolutely. And the other thing that you might not realize you're going to have to deal with are people's personal and mental health issues that will happen. And it's very hard to set for me personally at least to set boundaries and not sit in their emotions with them. But I'm also not a trained therapist.

Kelly Vaughn

Right.

Emma Bostian

So for me, like and you have to gauge the situation for yourself. But for me, I like to share what's going on in my personal life because I'm comfortable with that. I'll tell my team, hey, I'm going to therapy, like, this afternoon for 45 minutes. Like, I'll be back later. I find that being open about that makes people feel that they can, like, oh, my manager's going to therapy. Is that something I should try if I'm struggling too? Or like, oh, I'm comfortable sharing that side of myself, too. It's not like I'm the only one doing this now. Again, that might not be the case. And that's totally fine. It's not an expectation. It is just. It's the same with being friends or friendly with your team members. You don't have to get along on, like, a personal level. Right. You do have to respect and respect each other. But, yeah, that's kind of how I lead is from, like, a compassion standpoint, you are. You're going to hear people's mental health issues, and it's going to be hard for you not to, like, be there with them or give them advice. But you have to maintain that, like, professional boundary and. And give them the resources if they are available through your company and all of those things.

Kelly Vaughn

Yep, absolutely. Yeah.

Emma Bostian

And.

Kelly Vaughn

And, you know, you're. Of course, you never force somebody to share something they don't want.

Emma Bostian

Yeah.

Kelly Vaughn

Especially personal. Some people, you know, they. They prefer to keep their personal life personal, and they don't want to bring their personal life into the workplace. And that is a perfectly acceptable thing. The only time it starts to matter is when they are not showing up.

Emma Bostian

Right.

Kelly Vaughn

And there's a difference between bringing your whole self to work and showing up for work. Because the whole idea of bringing your whole self to work, if you're comfortable doing that, great. But I would never expect you to just be open about literally everything that's happening in your life. I want you to show up. I want you to, you know, include yourself on the conversations that we're having. I want you to be present, but I would never say, okay, well, now let's talk about all of our, you know, our traumas. Let's trauma bond now.

Emma Bostian

Yeah, no, totally. And it's not necessarily nice to, like, bring all of that to work and put that on other people as well, because you don't know what they're going through. I will say, though, like, if I'm. Oh, my gosh, over the past, like, two years, I've gone through some really really difficult things with my health, especially, like, I was hospitalized with pneumonia and I. I'd gone through eight pregnancy losses over the past, like, three years. And it was really affecting my ability to physically be at work because I had a lot of doctor's appointments or I was in the hospital. And I, you know, I don't want people to, like, speculate, like, what's going on with me or like, why do I. Why is my calendar, like, why do I have a couple private meetings on there? Like, you know, so I made the decision to. To be open with my team about it, and I wasn't forced to by anybody. But I thought, you know, you know, also for me to bring my whole self to work, which I want to, like, I need to be honest with them about what's going on with me because I'm physically just not able to contribute the way I want to right now. And it was very well received. And some actually, like, during one on ones like, asked me further, they asked me very pointed questions which frankly, like, I welcome because I'm like, I'm happy to tell them an open book. However, it's not for everybody. And I always tell people, like, share what you're comfortable with or don't share at all, and it's totally fine and you're welcome here regardless.

Kelly Vaughn

I love that it's such important on. On the communication side of things, you know, understanding again, like, how. How your team communicates, how you want to communicate, how to communicate in a broader audience, and when it's time to kind of like, not talk. Yeah. And with that also comes standing your ground at times, and sometimes you have to do that in public, and it can be very uncomfortable for everybody else around, I can tell you. A couple years ago, I was in a meeting with my team and my product manager at the time, and the product manager was greatly overstepping into my. Into my territory to the point where, like, if it slips, then sure, it's fine. I, you know, even yesterday I overstepped on accident for one of my product managers to, you know, roll something out, because I thought we had already announced it, but we ended up not announcing it yet. Like, there are things that can happen at times, but in this particular situation, it happened so many times in the same meeting that I finally had to, like, stop the meeting and say, hey, I need you to let me do my work, and you focus on your work. And that is a, like, that was really awkward for the team to kind of sit there and listen to that. But they also need to see Me standing my ground and say, like, this is okay to do. And if I overstep in your territory, like, I want you to say, hey, hey, Kelly, like, I got this. Yeah. Like you said, like, let me know. And I'm happy to back off.

Emma Bostian

Right, right. For me, it's like, I'm sure I'll overstep in some regards at some point. Right. The thing is, it's likely not intentional.

Kelly Vaughn

Exactly.

Emma Bostian

So, like, if I, if I suck, like, just tell me, like, hey, back off. Like, I could take it.

Kelly Vaughn

It's fine.

Emma Bostian

I might cry about it, but that's fine.

Kelly Vaughn

Yeah. Most people are not being malicious. Like, most people just don't know where those lines exist. And that is like managing cross functional relationships. Like, that is. It takes time to learn.

Emma Bostian

Yeah.

Kelly Vaughn

Because you're dealing with such different context. You know, I know what my goals are in the engineering Org. I might not know what your goals are in the finance Org. And you might need an engineer to build something very specific to run reports on, something for loss prevention and finance. And you're like, this is the most important thing at this company. And I'm like, no, it's not. Like we have more important things than your project. And it becomes a very difficult conversation at times to be like, you know, where do we actually, you know, need to go from here? And that is, you know, you, you mentioned this before. You don't have to solve these conflicts by yourself. Like, there are times when you absolutely should take ownership of. Like, this is, you know, somebody else is not going to solve this. I need to make a decision. I'm just going to make my decision. If it's wrong, then it's wrong. We move on from there. But if you feel deeply uncomfortable about something, bring your manager in. Bring HR in. Like HR business partners exist for a reason to help you navigate these conversations. If it starts to veer into a territor where you don't feel comfortable having that conversation, you know, with that product manager I had before, we got to the point where my manager at the time and their manager at the time and the two of us had to get into a meeting to hash this out because we just could not work well together. Yeah. Yeah.

Emma Bostian

If you're, if you're feeling unsafe, hopefully there are people around you that can support you in that conversation. One of the hard lessons I had to learn as a new EM was not everything requires immediate action or necessarily warrants feedback. Sitting on things for 30 minutes, an hour, a day, a week. Obviously, if you're gonna get feedback, the More timely the better. However, I've been very careful to not. I don't wanna say pick my battles. Cause they're never battles. But like, pick and choose when I give feedback because. And this goes back to parenting, right. If. If you're always telling your child no about literally everything, they'll never take you seriously when you have a real genuine reason for saying no. Like a safety reason. Right. So I'm very intentional what I say no about to her. Oh, you want to bring your umbrella to school when it's 30 degrees Celsius? Okay, fine, I'll let you do it. There will be consequences, which are that you have to carry it when you realize that it's hot outside, not raining, but like, you know it's not gonna hurt anyone. Right. When I say no, she knows like, oh, the oven's open. Maybe I shouldn't go over there. It's the same with giving feedback to people. Right. Like, if you're constantly giving constructive feedback or criticism to someone, at some point they're just not going to listen to you. Yep. So, yeah, being very intentional about. At least I sit on my feelings for like 30 minutes, an hour a day, even overnight is better. Especially if it elicits in a visceral reaction from me and I feel like I've been personally wronged. You know, I'm like, okay, let me sit on my feelings and evaluate in the morning. That was a hard lesson to learn.

Kelly Vaughn

I, you know, I still, I still say choose your battles. You know, of course, not everything is a battle, but it's, it's easy enough to kind of phrase it that way. And a story I often tell one of like that same product manager. I had two particular issues with them. One is they never gave me enough details in the product resource document for me to make a decision on engineering resourcing and how to actually build a product. You know, if we were saying we need to introduce license plate recognition, I needed, I need a PRD for this. And you're like, I'll get it to you. But like on, like, it's, it's simple. Like, just introduce license plate recognition. I'm like, what do we do with that? You know, that requires actual feedback because it is affecting the business and being able to execute on your work. The other thing, this individual just like got under my skin so much. It still does to this day. Every now and then I come across it, this individual. Like we had every six weeks a meeting with the executive team where we would go over, here are the things we did last Six weeks. Here's what we're doing. The next six weeks. Here are blockers that I have, and here are some asks that I have of E staff, like, I need a new headcount, or I need, like, you know, more time on this, or we need to kind of talk through, you know, resource allocation, whatever it happens to be. We have the same template we used on the slide deck every single time. And for whatever reason, the two slides that this. This PM owned, they would change the font. It was so just maddening to be like, there is a pattern here. There's consistency. Why are you changing the font? And they're like, because I like this font. I'm like, but why, like, put this in your own document? Not in, like, the. This is the kind of thing that's not important at all. But it's just. It's a personal thing.

Emma Bostian

I mean, I'm almost on their side. Because sometimes fonts suck in PowerPoint. No, but I mean, I'm actually.

Kelly Vaughn

You saw this. If you saw this, you'd be like, there's one thing about changing your font and there's another one. Like, this is the font you chose.

Emma Bostian

Yeah, I've had to ask people to change font documents before because it was just not. I couldn't do it. I mean, it's one thing if it's like an accessibility issue in the camera. I did, but, like, yeah, I mean, you know, do what you gotta do. I change fonts on stuff. We probably wouldn't work very well together, would we?

Kelly Vaughn

I'm okay. Like I said, I'm okay with. I'm okay with change if it's not just, like, abrupt.

Emma Bostian

And I think for every episode page on our website, I'm gonna go change.

Kelly Vaughn

The font to a different I will cry font family. And the only reason why I'm not going to remove your access to do that is because I don't want to manage the website. So. You need you.

Emma Bostian

I need you.

Kelly Vaughn

This is one of those things where I'm going to choose to just let this one go.

Emma Bostian

This is one of those things. You don't have to like the people you work with.

Kelly Vaughn

You have to respect them. Struggling for this podcast.

Emma Bostian

Well, speaking of things we don't like or do like, do you have any resources of the week?

Kelly Vaughn

Ooh, yes, sure. So the. I'm going to share another book this week, and that is the Manager's Path by Camille Fournier. I think this is a fantastic read for anybody considering getting into management and who wants to better understand that path from IC to Em, to even like a manager of managers or like, being a tech lead. Kind of walks you through the progression there to help you understand more about, you know, what that role would look like and the important parts to being in that role. Absolutely. Love it. So it's one of those books that I recommend to a lot of people who are considering management.

Emma Bostian

What about you? Yeah, it's. It's a classic one and it's decently short, I'd say. So it's pretty short. Yeah. It's a pretty good one to pick up as a first resource. My resource of the week is going to be lead dev this week. They are, I think. I don't know if they started as a website or a blog or they do conferences, they do podcasts. They do. I use them for their blogs most frequently because they have a whole engineering manager section. There's some really great stuff in there, so I would recommend checking them out.

Kelly Vaughn

Have you written anything for them?

Emma Bostian

No, but I was on their podcast once.

Kelly Vaughn

Okay.

Emma Bostian

So of course I'm going to go plug that. No kidding. No, but I haven't written for them. I do read a lot of the articles that come out, though.

Kelly Vaughn

Yeah, there's a lot of good stuff on there, for sure.

Emma Bostian

Indeed.

Kelly Vaughn

I know there are some very familiar names. The GSC who ran here. So it's pretty cool.

Emma Bostian

And they're having a conference in London.

Kelly Vaughn

Oh, yeah, they do. They do lead dev. London and New York, I want to say.

Emma Bostian

Oh, I don't know. But on the locations, but I know that Camille Fournier is speaking.

Kelly Vaughn

Oh. So how relevant.

Emma Bostian

Yeah.

Kelly Vaughn

All right. Do you want to close this out?

Emma Bostian

I don't know how to end. You know, this is an ongoing discussion with my team because I am the most awkward person and I don't know how to end meetings so often. We'll just end it with awkward silence and then one of us says bye, and we all leave.

Kelly Vaughn

That is really funny. Okay, I'm going to walk you through this. Okay, thank you, everyone, for listening. I'm not going. Yeah, yeah, so. But really, you know, we're. We're having a blast recording this. This new season of Ladybug and genuinely appreciate you taking the time to listen to this one. And as always, if you have questions, Ron management or anything that you want us to talk about, or there's anyone interesting you would like to like us to have on this podcast as a guest next season, definitely let us know. Our contact info is on our website. You can find us on any podcasting platform. You can find us on YouTube can find us on Tik Tok for a little, little shorts one day. I'm just going to call it Tic Tac. It's going to come out. But it hasn't.

Emma Bostian

It hasn't yet.

Kelly Vaughn

So with that, we'll see you next week by.

Episode Notes

Stepping into management for the first time can be both exciting and overwhelming. In this episode, we explore the critical shift from individual contributor to engineering manager—what changes, what stays the same, and what new challenges emerge. We’ll discuss common misconceptions, the mindset shift required, and practical tips for navigating your first few months in the role. Whether you're considering the move or already in the thick of it, this episode offers guidance to help you lead with confidence and clarity.

  • 03:30 Responsibilities of an IC vs. EM
  • 09:05 Shifting to delegation
  • 15:04 Conflict resolution
  • 26:31 Team development vs. individual performance
  • 37:31 Communication

Find out more at https://ladybug-podcast.pinecast.co