The Hard Parts of Engineering Management  ## Metadata - Author: [[Ladybug Podcast]] - Full Title: The Hard Parts of Engineering Management - Category: #podcasts - URL: https://share.snipd.com/episode/cfd05a4d-0387-43dd-b4f4-e6c3d267734a ## Document Notes ## Highlights - **Early Manager Onboarding Isn’t Instant Impact** - Joining a new company often means your role is primarily to learn, not immediately deliver measurable outputs. - Managers should expect lengthy onboarding and reduced perceived productivity early on. Transcript: Kelly Vaughn Ooh, yeah. This is an interesting one from multiple angles. I think the first part is joining a new company. You are totally out of your element because you don't know, you have no historical context, you have no institutional knowledge here. And your job is literally to learn as much as you can. And that might mean that you're not actually doing a lot of work right now. And it takes time to onboard, like, you know, three plus months. And you were saying, like, for engineers, like, it could take, you know, six plus months to really understand the code base. ([Time 0:06:12](https://share.snipd.com/snip/b2a60755-7068-4a06-bb10-7c304454ec07)) - **Redefine What Productivity Looks Like** - Reframe productivity for engineers: meetings, RFCs, and planning are valid outputs, not just closed tickets. - Teach your team what high-level contributions look like and celebrate them. Transcript: Emma Bostian Yeah, your tasks are now split across different types of tasks, which are perhaps meetings. You'll spend a lot more time in meetings, and that is productive, but often doesn't lead to you feeling like you've had a direct impact on something tangible. Then there are administrative tasks like approving holidays or sick days or, you know, whatever it might be. And then there are actual tangible pieces of work that you can cross off your to-do list to like calculating engineering capacity for the upcoming launch cycle or obtaining your roadmap Or whatever it might be. But yeah, there is a definite lack of immediate gratification, which frankly for me, as somebody who struggles with like impulse control and needing to feel validated very frequently, It was very difficult. Yeah. Kelly Vaughn Yeah. No, it's, it's, it's a tough one that even I deal with now. Like I, and I go through phases of it as well. Like sometimes I'll feel super productive that I'm getting a lot of work done, that my team's delivering on a lot of great things. And there are other times where I feel like I'm totally useless. And it is something that I, I struggle with personally. And this is like a fun topic for me and my therapist because I am a high performer I've always been a high performer and I've always been like a perfectionist pushing myself and when I don't Feel productive it ends up being one of those things where I'm like defining myself by the lack of productivity perceived productivity I'll call it. Right. Emma Bostian This is something that I'm addressing with almost everybody on my team at this point, because it feels like everybody has this feeling lately that they're not being productive and It's very demotivating. And they feel that way because they're not closing tickets or opening pull requests, when in reality they're writing RFCs or requests for comments where they're attending meetings With other product areas to decide how to architect something that we need. So, you know, when I challenged their concept of what productivity is and say, like, maybe we should. ([Time 0:07:03](https://share.snipd.com/snip/9a870305-5000-41b5-b6a2-5efca122ee2b)) - **Be Intentional About Staying Technical** - Intentionally decide how technical you must remain as a manager and schedule time to stay current. - Ask technical questions early and get comfortable being the tiebreaker with enough context. Transcript: Kelly Vaughn Side of things and we just did an entire episode about this last week, if you missed it, on, you know, like being an engineering manager when you're not technical. Staying technical in a leadership role requires a lot of intentionality. And like deciding how technical is actually necessary for you to be is also something that is going to differ from team to team, from company to company. And it could be really tough at times to figure out what that balance needs to be, especially when you need to be the tiebreaker to make a difficult call. ([Time 0:09:30](https://share.snipd.com/snip/cdeb0bea-b100-4751-b034-d1a8a88c04a4)) - **Tough Choices May Cost Popularity** - Handling conflict is difficult because you cannot control people's reactions to tough conversations. - Good management sometimes requires decisions that make people dislike you temporarily. Transcript: Emma Bostian I think yeah i had mentioned this earlier handling conflict and interpersonal challenges has been like the biggest one of the biggest difficult parts of management for me and i think A lot of it just comes down to the uncertainty of you don't know how other people are going to react. You can control how you communicate information to people, but you cannot control their reactions to things. And I can assure you they're not always going to be positive. And the other thing is people are not always going to like you. In order to be a good manager, you sometimes have to put yourself in positions where people will not like you because it's not synonymous. Like being a good manager means people are not going to like you at some times, right? Like let's say you have a team of five engineers and one of them is underperforming heavily, requiring the other team members to pick up their slack. Well, you need to address that with the underperformer. And if they're unable to get it together, you've got to fire them. That person's not going to like you, but the rest of the team will respect you and probably appreciate you a lot more. So as a lifelong people pleaser, that was difficult for me. ([Time 0:10:22](https://share.snipd.com/snip/309011d5-9797-47bf-865b-18edf48fc1d4)) - **Address Patterns And Pull In HR Early** - Address patterns quickly: if an issue repeats more than twice in short order, start a conversation. - Involve HR for mental-health or serious performance issues—don't handle them solo. Transcript: Emma Bostian Because you're moving from being friends to being friendly. And it's also, that's different it's also not knowing when is appropriate to give constructive feedback right like yeah how many times does something need to occur for it to become A pattern i would say if it happens more than twice within a short period of time it's something that you should address like if somebody continually shows up to meetings or forgets to Join or just doesn't show up okay once fine like life happens twice okay it's starting to look like this could be a pattern but let's figure out why and then by the third time i'm like okay I need to address this um i think another big thing that i struggled with during my first years in em was how to work through other people's mental health journeys. Because we've talked about this previously, you are not a psychologist. You are not there to diagnose them, to help them through these tumultuous times in their life. But at the end of the day, you are responsible for the success of your team. And while there are certain measures you can put in place, like let's say somebody struggles with getting up in the morning due to a mental health challenge that they're facing. Okay, maybe we can move stand up a little bit later in the morning. It still works for everybody on the team. Like maybe 10 in the morning is a better time than nine, right? So there you're trying to make concessions to see if we can meet in the middle and find something that works for everybody. ([Time 0:11:50](https://share.snipd.com/snip/efb78563-5d2b-486d-91fe-322acc02b9d0)) - **Using Scheduled Time Off To Protect Performance** - Emma adjusted her schedule during pregnancy by taking two fixed days off each week to protect health and consistency. - That plan improved her wellbeing and demonstrated leading by example to her team. Transcript: Emma Bostian It's also like, I mean, I try to lead by example, right? So like the past few weeks of my pregnancy have been really taxing on me physically and emotionally, like to the point where I feel like I can't do my job well. And I found that I was just taking like sporadic sick days to try to remediate this. And it just wasn't consistent. So instead, I was like, okay, well, that's not fair to my team to have like, you know, mental and physical health difficulties that I'm not doing anything about, right? Like, that's not a good example for them. And so I came up with a plan with my manager. I said, here's my plan. I want to take two days off vacation time per week. Like, look, I've got over 30 days of vacation to use this year. I'm going to be off on seven months parental leave anyway. I need to use them. So why don't I take two days off? Here are the days each week I want to take off and that way like i tell you what this is the second or third week of me being off two days a week it has drastically improved my mental and physical Health good and so like leading by example recognizing that hey i've got something i need to work through and i need to be an example to others on the team that if they're also struggling Then they should address it themselves and it's okay. ([Time 0:14:06](https://share.snipd.com/snip/8cb58994-033c-46fe-9742-6fc15e5014db)) - **Choose Battles And Pause Heated Talks** - Choose your battles; not every annoyance needs intervention if delivery isn't impacted. - Pause heated conversations and revisit later when emotions settle to keep them productive. Transcript: Kelly Vaughn Yeah, absolutely. And I think another one that I have learned over time is choosing your battles. This is definitely on the conflict side of things where not everything needs to be addressed. Some things can stay annoyances um and so long as it's not preventing the team from being able to deliver if somebody is changing the font and you don't like the font that they're using It's probably not worth your time i'm not saying like changing the font product i'm saying like changing the fonts on like a word doc or something like that. Like it really doesn't matter if it's just like an internal thing. There are much more serious battles that you probably should be fighting. Emma Bostian As well because shocker I'm an emotional person and I also have very quick and often angry and frustrated responses to things like I'm just impulsive by nature and um so I will say having A three-year has drastically changed how I respond to situations and ironically parenting books has helped me more in my management career believe it or not um being able to handle My own emotions like not suppress them but not to recognize like hey i'm feeling a little bit pissed off at the moment i'm not going to respond to the like my colleague and tell them why I'm pissed off i'm going to sleep on it and if i wake up and i still feel compelled to have a conversation about something that was inappropriate at work or like I would have liked to see Differently next time. Okay, but let's sleep on it and come back from a logical, rational point of view as opposed to the reptilian side of my brain that is telling me to set fire to everything. That's been hard. But I've gotten a lot better at it. Yeah. Kelly Vaughn And you're not always going to get it right either. Like there are times when I say something that I regret saying, like that's just human nature. Again, we're not perfect people. But being able to stay calm under pressure or recognize when you are starting to slip and you're getting to a place where this is not going to be a productive conversation, being able To hit the brakes and say, hey, we need to take a time, like a breather here. Let's let let's regroup about this tomorrow or this afternoon because this is no longer a productive conversation. And that is the thing to say as well. ([Time 0:15:15](https://share.snipd.com/snip/dccb96d4-7ac4-4377-b5ad-121d1d710d58)) - **Repair Fast And Stay Receptive To Feedback** - When you mess up, repair quickly with humility: apologize, avoid excuses, and propose fixes. - Stay open to receiving feedback and don't react defensively as a manager. Transcript: Emma Bostian Yeah. Also repair after like you are going to mess up and being able to acknowledge that and approach it from a humility perspective. I don't know how to rephrase that in English. That's proper grammar. Being humble about it and saying, you know what, like I could have handled this better and I apologize for it. Not making excuses. Just, hey, here's my behavior. It wasn't appropriate. I regret it. And I'm sorry. And let's here's what we can do next time to avoid it. That's important in personal relationships with parenting, with working relationships. And then also like not getting defensive when people give you constructive feedback, especially as a manager. People are not going to want to give you feedback, like constructive feedback. So when they do take it a little bit more serious, like not all feedback is valid, right? You have to discern like what is actually valid or not. But at the same time, you're going to get less feedback as a manager because people are maybe more afraid of the implications of it. So being more receptive to it and not getting defensive right off the bat is difficult, but necessary. ([Time 0:17:43](https://share.snipd.com/snip/be394905-0350-4097-bae7-768409bcee3d)) - **Expectation Management Is Perpetual Work** - Balancing expectations requires managing up, down, and sideways constantly and never fully mastering it. - Pushing uncomfortable conversations upward can be a forcing function for necessary change. Transcript: Kelly Vaughn Let's, you know, something that's a little bit more business oriented, that is one of the most challenging parts of your job is just balancing stakeholder expectations. Because you're managing expectations from the top down, your team has expectations of you, your peers have expectations of you, the cross-functional relationships, especially As you continue to move up in an organization, you know, making sure your cross-functional peers are getting what they need to do, you're enabling them to be able to do their job is so Incredibly important. And so figuring out how to manage up, manage down, manage sideways is one of those things that takes a lot of time. And even in my 10-ish years that I have been in management, it's still a very challenging thing for me. As far as managing up goes, I had a situation back in December that I really got to put this to the test for myself, and it was the most uncomfortable situation that I think I've had professionally In a very long time. Like I was really pushing, pushing the boundaries of what was acceptable to, not to say, but like to ask for. But I was very serious about it. And I'm grateful that I actually got through that opportunity because it did serve as a forcing function for what I needed. But it was really uncomfortable. ([Time 0:18:54](https://share.snipd.com/snip/9f3f0f03-2dc3-4c4d-92ee-c3793b024d86)) - **Explain Promotions With Performance And Business Context** - Explain promotion decisions clearly: separate performance from business constraints like budget or role availability. - Advocate for your reports while transparently setting realistic timelines and criteria. Transcript: Emma Bostian I think another one of the harder parts for me has been taking accountability for failures. I hate the word failures because it feels like such a be-all, end-all. It's like terminal. Yeah. Yeah, yeah. It doesn't need to necessarily have this negative connotation. Kelly Vaughn Being willing to acknowledge that and say like hey i messed up and i'm sorry for that um is important and i think the other side of this and this goes a little bit to interpersonal challenges Is if somebody like if somebody wrongs you in some way and they take accountability for that professionally you move on like and this might change you know things might change like personalized Wow think like your personal life may change like that dynamic of of how you communicate depending on what it is but like if they take accountability you say okay and yeah it sucked but We're moving on like you shouldn't be dwelling on this because this is one of the the fastest ways for you from a from a manager perspective from a leadership perspective to hold yourself Back because it takes i mean you know this like it takes a lot to you know have that conversation to take accountability it's very uncomfortable A lot of this is uncomfortable. And if you're like, you know, I'm just going to hold on to this grudge and be mad about it forever, then it's going to hold you back professionally. This one is this is a challenging one, both for yourself and for your team. One of the most difficult things that you can do as a manager is tell one of your team members why they're not getting a raise or promotion. And it could be it could be, you know, performance related and hopefully even having performance conversations because of that. But sometimes it could be business related. Maybe there's just like not the money or, know, a promotion comes from two things. One, the employee is operating at a skill where they should get that promotion. And two, there's a business case for the promotion. And quite often, the reason for not getting a promotion is because there's not a business case for it right now, not because they don't, you know, they're not capable of doing it. ([Time 0:20:52](https://share.snipd.com/snip/20f5966c-b4d4-4201-84bb-30d67a6d5999)) - **Expectation Gaps From Fast-Moving Career Norms** - Many peers expect rapid promotions due to career norms, creating misalignment about readiness. - Managers must calibrate expectations versus demonstrated capability and business reality. Transcript: Emma Bostian Yeah. But what happens if somebody thinks that they're performing at the next level and they absolutely are not and you are very misaligned? Because I've seen that happen before where people expect that they deserve a promotion i think we've like now okay let's like acknowledge the fact that for people who are perhaps underrepresented In this industry titles are very important for for you know i wish it wasn't for the sake of like garnering respect from peers but sometimes it can be yeah but that being said i feel that As a whole in the tech industry people around our age group in particular like i'm gonna you know i'm 32 turning 33 this year like i think no i'm 31 turning 32 this is my life right old are You um people around like the millennial generation have been accustomed to like move fast and break things, switch companies every two years, like get a promotion every two years, Right? This like hustle culture, which doesn't have to be a bad thing, but it also sets it, it can set an expectation from someone that they deserve a promotion every two years. And that's frankly, just not realistic in most places, especially if you stay in the company, right? So I've seen cases where people generally around my age, they just expect that they deserve it. They're like, well, I deserve this promotion. And it's like, but are you performing at this level? Because even if there was a business case and this role was open today, I can tell you, I don't think you're ready. And that's very tricky to navigate. It is. Kelly Vaughn It is. And it's never a fun conversation to have. ([Time 0:23:40](https://share.snipd.com/snip/17cc2e39-4baa-447f-b866-cc53c5a86e63)) - **Management Often Feels Lonely—Find Safe Outlets** - Management can be isolating because you often can't vent to team or peers without consequences. - Find outside confidants or therapists to process workplace stress safely. Transcript: Kelly Vaughn Because if you're like deeply under pressure, and you need to vent to somebody, you can't vent to your team, because it's not an appropriate conversation to have with them necessarily. And you can't always vent to your peers either because people talk and you might have some very strong feelings about something that might even be about them. It could, if I was unhappy because they were getting more opportunities than I was, I'm not going to vent to them and be like, well, you're getting all the cool stuff and I'm not getting Anything. That's not an appropriate conversation to have with them. So what do you do? Emma Bostian When you're feeling lonely you need to vent what do you do cry same i honestly i haven't figured out a good solution to be honest it's really hard not to be able this sounds so superficial To say but not to be able to like gossip about about work drama like that's been really hard because like that is a way that you would typically vent like with your friends right but now Like okay my friends also work there so like i can't be doing that that's not appropriate um i try not to like if somebody's getting all the cool opportunities and i'm jealous of it right I try to take my like frustrations uh and turn them into like okay well what am i going to do about it like okay i go to my manager and say uh like i would like to be considered for a tech poc role Next cycle uh it aligns with my goal you know instead of just saying like well this person gets all the cool stuff it's like cool instead of that i'm going to turn it into like a like something That i can achieve turn it into a goal like hey this is my goal my goal is to also be doing stuff like this. Please consider me for stuff like this in the future because it aligns with my growth aspirations. Like instead of just complaining about problems, perhaps try to phrase them as opportunities with solutions. Kelly Vaughn I like that. It's not sexy, but no, it's also something that I'm sure HR would tell you to do as well. So, yeah, it's a good outcome. ([Time 0:26:15](https://share.snipd.com/snip/76da922e-70bb-4719-b831-869fab76aadf)) - **Management Felt Like The Best Career Change** - Emma says management isn't for everyone but calls it the best career change she's made personally. - She urges trying it if curious, since you can leave if it doesn't fit. Transcript: Emma Bostian Don't think so. I think that ultimately this career is not going to be for everybody in the sense of like a lot of people are not they're going to try it out and realize it's not for them. They want to go back to coding or to do something else. It's a lot of responsibility. But I'll tell you right now, this is the best career change I've ever made. I knew I would enjoy it, but I'm enjoying it so much more than I thought. So if you're intimidated by it, yeah, I mean, that's not a bad thing. It means you take it seriously and you should if you're affecting people's lives. But, you know, I suggest everybody. No, this is not true. I don't suggest everybody try this out. I don't think it's for everybody. But I do think if you're interested and think it would suit you, like, go for it. ([Time 0:29:33](https://share.snipd.com/snip/ef92d672-671c-4c01-b7d0-5623352e0290))