Soft Skills Engineering

In this episode, Dave and Jamison answer these questions: Hi! Love your show and how casually you talk and make fun of everything! I started my career as a freelancer and then joined a mid-size software development company to learn how the sausage is really made, salary wasn’t that important back then. A few kids and a lot more expensive lifestyle later the compensation has become more motivating, but I’m not sure how to sell myself to my manager if I don’t feel like I deserve a high salary myself. (The manager decides the salaries for all our team members.) For years I’ve been focusing on my family and other life stuff, so I’ve spent a looot of working hours not working and basically doing the minimum progress acceptable. Slow progress has come up once with my manager, from which I wiggled out of with various excuses. I’ve realised that this way of working isn’t really fair for the company and my teammates and I’ve started to take this job and my career seriously in the last few months. The company and everyone working there are super supportive and it’s been a terrific experience for all of those years. I’ve gotten a raise multiple times with always me initiating that conversation. There aren’t any clear metrics to improve that directly ties to the salary: I’ve asked my manager about it and the answer was vague like “we have this local salary survey that we take as the base and work from there”. So long story short: how to ask for a raise while not feeling like a criminal since I feel like I haven’t earned the salary I had thus far? I’m a team lead who’s growing increasingly frustrated with my project manager. Every planning conversation ends up in my private DMs, no matter how many times I’ve asked him to move these discussions to the team chat. When he messages me one-on-one, my team loses visibility into decisions, questions don’t get addressed openly, and important context just evaporates. It’s not only slowing us down, it also makes me feel like the burden of relaying everything falls squarely on me. I’ve tried gently redirecting him back to the shared space, but he keeps defaulting to my DMs. How can I get him to respect the boundaries of team communication without damaging our working relationship? Sincerely, Lost in the PM’s DMs

In this episode, Dave and Jamison answer these questions: How would you handle a situation where a team forms a negative opinion about you from day one — without any clear reason and without ever giving you a real chance to prove yourself? Even when you contribute technically, your suggestions are ignored… until someone else repeats the same thing and suddenly it’s considered valid. Is it possible to stay in that kind of environment without becoming bitter or burned out? Can you keep contributing professionally — or is it healthier to just walk away? You guys are awesome. Jamison, I interviewed with you and it was lots of fun and productive. Which is really rad. Now… I just landed a 12-month contract in big tech role. It’s perfectly aligned with my long-term career goals. My current fintech FTE is perfectly opposed to my long-term career goals. The question — how unethical / despicable would it be to start one week of PTO at my FTE on the same day as Day One at my contract role so that I can onboard without distractions and then put in my resignation upon returning to my FTE? What about two, three, or four weeks of PTO? Also… are two-week notices still the default still in 2025? Also also… I promise I’m not AI — I’ve been using em dashes since the 20th century.

In this episode, Dave and Jamison answer these questions: After a year of trying, I recently got promoted to staff engineer! It’s great to receive recognition for my work, but i’m not actually very happy, because I only got a 4% raise! I spoke with a former coworker about how much a staff engineer in my role should expect, and he said that he would be insulted by less than . My comp is now slightly below ! In addition to this, times are tough for the business, so it seems unlikely that we’ll get annual bonuses, meaning I likely won’t even get to appreciate the larger target staff bonus! What a bummer! How should I approach this? A year and a half ago after getting a below inflation raise, I was told I was at the top of my level’s pay band and would need to get promoted if I wanted to go much higher. Now that I’ve gotten promoted, it seems like that wasn’t true! I should be grateful that I still have a job and got promoted and got any increase, but I feel like I’m being short changed! How can I talk to my manager to see about getting more money? My company does not address complaints. Here are two examples. On my first day, the lead engineer told me not to participate in the project. He was impossible to work with: He’d hold up PR’s for 3 months because of linting and prettier rules. Eventually, I figured out he was exceptionally insecure and wanted no feedback or anyone to expose his technical weaknesses. I conflicted with him a lot and got shuffled to another department. My 2nd example comes from a trainee. I helped him out everyday after standup for 30 minutes. How he passed his interview, I don’t know. He didn’t know what a semicolon was after a 4 years bachelor in computer science and 6 months of being a trainee. I complained to a friend at work who had, I didn’t know, interviewed the trainee. My friend was surprised, and so we hopped on a call with the trainee who didn’t recognize my friend. After snooping around on social media, we found the guy who had done the interview, the trainee’s brother. I told HR & my department head. Nothing happened. Here’s the question: Getting kicked out of a department ruined my confidence. I have a safe, secure job where there’s no pressure. But my firm doesn’t address complaints properly. Time and time again, people will complain about the linting/prettier guy or other issues like the trainee and nothing is done. Should I leave? I work on a greenfield project here. Switching to a (likely) legacy codebase I didn’t build and dealing with higher pay/expectations is very daunting.

In this episode, Dave and Jamison answer these questions: Hi Dave and Jamison, After fleeing a sinking ship of a startup, I became a solo developer at a medium sized college. This role has really allowed me to expand and grow in ways that I haven’t imagined, but I have encountered an interesting issue I didn’t have in the startup world: there isn’t much to do. At my one year mark, I was promoted into a management position, but with no direct report. I will soon have an employee under me doing data integrations. My manager has been reluctant to give me data integrations work despite knowing that I want to understand what my employee will be working with. I’ve found some of my own projects, but I’ve completed them all. I’m getting bored. I’m a competent developer, learn fast, and get things done quickly. Recently I’ve been planning an upgrade to some of our legacy code, but it will take probably a year or more to complete. Some former colleagues reached out about working with them for a substantial pay bump, but I don’t like the idea of leaving after just over a year and a half. Do I keep riding it out here, or is it time to start looking else where? Thank you both for this wonderful podcast. Its a joy to listen to on my walks. I’m sure I get stared at when I try to hide a laugh or grin from the amazing list of Patron names and your commentary. I was recently terminated a few months before my 1 year vesting cliff as an IC2 for being days (not weeks) late on 3 or 4 stories. The late ones were defined incorrectly by management, or were for paying technical debt created by senior engineers, and my manager knew this. I had no IC2 or IC1 peers on my team for comparison. My performance review for the first half of 2025 was not released to me, I was fired when I would have seen it. This means the only reasoning that management has shared with me was my late work. In 1 on 1s before, my lateness has been something my manager has mentioned, but never a warning of termination (or a “pip” as some call it) and no indication that it’s anything more than an area to improve. The org has made poor decisions that left them tight on funds, and I feel the most financially responsible thing for them to do was fire me rather than give me a warning which would let me hit my cliff or lay me off where they’d give more on my way out. Had I been pipped or laid off, I would not be asking about this. Should I go with the confusing justification that my boss was truthful in his attribution of my firing without warning to my lateness (and can you help me understand why that’s professionally justified)? Should I go with the disheartening approach and brainstorm other shortcomings that would better justify an unwarned firing, possibly spurring professional growth or a career change? Or should I say I got instafired because of penny pinching and opaque management?

In this episode, Dave and Jamison answer these questions: (follow-up from question 449) Hello. Return question asker here. You answered my question from episode 449 “my tech lead ignored my warnings”. I want to give a follow up. I sat by and did not say anything else, he shipped the broken feature, and it broke in production. Instead of fixing it he rose the threshold on the datadog alert so high no one would ever get alerted. Then he left the company. When talking to my manager about the bug we agreed it was part of that refactor and I said “I warned him” and they shrugged it off. I assume he is also a long time listener of this podcast and took the age old “leave your job” advice. Kudos. (question below) I am here for more than just an update though. I am starting to think I understand why he left. It sucks here. I am the lowest level engineer on my team and have not been promoted for the last 2 years because “there is no money”. Ok, fine, I understand that the economy is tough. However I have increased the revenue of my department by 4x, have lead the development of our flagship product this entire year, have been teaching engineers new technology and have been working 60 hour weeks. On a team of 6 I do 33% of the work. 2x what is expected of any one engineer. This last week I received a “meets expectations” performance review. And I am mad. In 1-1’s with my boss they explicitly tell me “I am not saying to sandbag but just do less work. Your teammates are getting compared to you and its making everyone look bad.” Don’t worry Dave and Jamison, I am going to quit this job so I don’t need that advice, however you can throw it in if you like, but I’m wondering how do I handle this? Do I confront my manager in the next 1-1 with the data and say I am underleveled and underpaid or do I just take the advice to do less and coast til I find another job? Do I share with HR in the eventual exit interview that this was the straw that broke the camels back? I’m returning to work after a very long absence due to personal issues. How can I ramp back up quickly? It’s a weird situation because I’m not exactly joining a new job, but it’s been so long that it basically is. I haven’t even opened a code editor in months!

In this episode, Dave and Jamison answer these questions: Hey skillet nation, long time skilletee first time skilleter here. I started at a scale up about 6 months ago and recently, I was asked to help with a project that was greatly behind schedule. The folks responsible for the original system are no longer at the company, and the team currently attempting to get it over the finish line have struggled greatly. The codebase is full of performance issues and the infrastructure was not set up to scale. Basically things are bad. Since joining, I’ve helped draft a plan to fix most of the performance issues, and then incrementally improve the architecture. Things are going great, except for the fact that we’re 6 weeks out from our deadline with a burnt out dev team. To resolve this, our CTO hast started to rapidly hire contractors to “help out”. As one might expect, this has only slowed us down. But our CTO, lacking trust in the previous team, has found the promises of the contractors very alluring. I, on the other hand, don’t love the idea of building this greenfield system with temporary workers and then dropping it on an already burnt out team to maintain. Am I overreacting? How would yall handle this scenario? How can I convince our CTO that “the mythical man month” still applies here, regardless of what the contracting company says? Listener k pop demon hunters asks, Hello! I’m a senior engineer in a big tech company. I recently got a bad annual review from my manager due to the fact that I caused a delay happened in my last project. It was a compliance process involving multiple stakeholders and one of them didn’t give me an immediate approval for the step they owned. I promptly updated my submission for review after I got the initial feedback, pinged them in a messenger and sent a reminder mail every day until I got an approval from them. I feel absurd that I got a bad review due to the delay of external process. What could I have done this better? Thanks for the great show. It’s making my commute more enjoyable. Keep it up!

In this episode, Dave and Jamison answer these questions: Can you coach self-awareness? I manage someone who seems to believe their skill set is on par with their teammates, regardless of their constant PR feedback regarding the same issues over and over, the extra attention they are regularly given to help them overcome coding challenges, and the PIP they are currently on to address these issues (and others). What are some approaches I could take to help steer them to better understand their areas for growth when explicit measures don’t seem to get through? I work at a small 10-person startup. The company has absolutely nothing to do with AI, but one of the founders has gone full evangelist. He genuinely believes AGI is arriving this year and that there isn’t a single job, task, or process where an LLM isn’t the obvious tool. Day in, day out, he’s posting links to random AI products with captions like “looks interesting 👀”. It’s like Clippy got a16z funding, moved to Shoreditch, and now spends his days flogging us apps we didn’t ask for. He also insists we “use AI more in development,” despite not understanding development in the slightest. The routine is always the same: He asks the engineering team how to achieve some goal (always involving an LLM). We give a sensible answer, weighing complexity, cost, feasibility. He comes back with a massive pasted transcript: “here’s what ChatGPT thinks.” We pick out what’s actually useful, quietly bin the nonsense. He takes our response, shoves it straight back into ChatGPT, and returns with another transcript: “here’s what ChatGPT thinks.” This has been going on for months. At this point, he’s basically a human middleware layer for ChatGPT — no analysis, no original thought, just endless copy-paste recursion. I’m genuinely worried he’s outsourcing his entire thinking process to a chatbot and slowly losing the ability to engage with ideas on his own. How do I tell him — politely but firmly — that this is both rude and a bit tragic? And, half-serious: is there a prompt injection I can use to jailbreak my founder back into being an actual founder rather than a ChatGPT relay bot?

In this episode, Dave and Jamison answer these questions: Hey guys, I have been working for four months at my job and I already don’t like it. This is my first job out of college and I work as a C# backend engineer for a small B2B SaaS company. I really think this company is a dead end. There is a lot of technical debt and antipatterns and we have no automated testing whatsoever. Most of our time is spent manually debugging but no one wants to refactor. I’m already thinking about working somewhere else. However, it took me a while to get this job, and I don’t think the market has gotten any better since. I’m trying to decide whether I should focus on applying to jobs again or if I should work on a bunch of side projects and open source to stand out better. On one hand, I can learn new technologies on my own to make me stand out for my next job, but on the other hand, I feel like as long as I stay at this company I am wasting time, since I’m not learning from my job. I want to switch to more distributed backend engineering in Java anyways, but I’m not sure how to go about it. Listener Ghani asks, “I’m a mid-level software engineer who has trouble communicating with my engineering manager and product manager when there is unclear or missing information about an assignment/story/project. They answer with hostile/dismissive tone/non-answer (e.g it’s on the jira-card, epic, etc). They course correct when they have the information later, harshly my impressions were they don’t have the information at the time they expect engineers to make decision they expect engineers to know something they don’t (e.g architecture, infrastructure, past decision, plans, etc) I really want to look for where we can have a safe exchange of information. How can I do this?

In this episode, Dave and Jamison answer these questions: Two junior engineers recently joined my team, and I’ve been tasked with onboarding them. This is the first time I’ve been responsible for junior devs, and I’m struggling with how to coach them up. For context, we’re a small engineering team where self-sufficiency is highly valued; processes/overhead is minimal, and we have a real bias for action. As such, when they ask me for help, my intuition is often to respond “Keep looking, figure it out!”; in my mind, walking them to the answer would be anthithetical to our culture and set the wrong expectation for how they should go about solving problems. This is especially the case when they throw their hands up and say “Help, I’m stuck, what do I do”. Though, I don’t want to be so unhelpful that it frustrates them or legitimately impedes their progress. I’ve also noticed them sometimes going “behind” me to ask others engineers for help, which makes me think that I am being too unhelpful. The number one question I ask myself is: How much help should I be giving them? How do I find the right balance here? I’m seeing more and more AI slop in my org’s code base that I fear will have meaningful impact on the integrity and maintainability of the application we deliver to customers. Everyone talks the talk of “Ultimately, it’s the implementer’s responsibility to audit and understand the code they ship,” but few seem to walk the walk. How can I best work with my team to address this, especially in a context where leadership is prioritizing velocity?

In this episode, Dave and Jamison answer these questions: Hi! I’m currently working for a big tech company and I’ve just accepted an internal transfer to another team. At the same time, an external company reached out, offering me a job for a role I’m interested in and twice my current compensation. I’m not sure what to do. The offer from the new company is very interesting and I wouldn’t think twice at accepting it if I still was in my old team. But now that I’ve accepted the internal transfer, I don’t know what’s best for my career: stay with my current company and lose out on a great offer, or go with the new company but likely burn bridges with my current manager, possibly closing off future opportunities to return to my current company (something that I’m open to in the future)? How do I politely but firmly stop a project manager colleague, who has vast open plains in their calendar compared to my Tetris-stacked week as a senior software engineer, from parking themselves at my desk for 45-minute vent sessions about everything that’s frustrating them about our project? It’s never just the weather; it’s a full-blown TED Talk on their annoyances, which makes me feel defensive and frustrated in return. I’ve tried the headphones-on-and-look-intently-at-the-screen-approach, and sitting on the other side of the office, booking a smaller meeting room to hide, and carrying on working as they tell me about their troubles with both leadership and members of my team. Nothing seems to work. They find me every time. Is there a way to escape without faking my own death or staging an office fire drill? Thanks!

In this episode, Dave and Jamison answer these questions: Hi Dave & Jamison, Long time listener, first time google-form filler outer! I work in a hybrid role as a lead developer and manager of a small team (less than 5). I’m new to management and most of ny experience so far has been with smart, motivated engineers. . . UNTIL! My new recruit is driving me crazy, they are clearly very capable, but just do not do the work. They are frequently late for work, frequently sign off early, and constantly evasive when I ask for updates. I have spoken to them about these issues a bunch, and everytime they are apologetic and say they “have some personal issues but are working on it” - and nothing changes. Urgh! I am pretty sure I will have to fire them, but I feel terrible about it! I know I can’t keep them on and pay them to do nothing, but what’s the best way to let somebody go? How do I break the news to the rest of the team? How do I avoid feeling bad for the rest of my life? Yours guiltily, Anon A listener named “erm what the sigma” asks, Do you have any advice on how to reduce the ramp-up time when context switching? I’ve always felt like context switching comes at a high cost for me—it just takes so long for me to mentally shift between tasks. This wasn’t much of a problem before, but I’ve recently become a tech lead and now my calendar is cluttered with meetings (why did I ask for this again??). I’m struggling to complete my coding stories because just as I hit my stride, I get pinged by someone on my team to help them or have to jump into yet another meeting. pls send help

In this episode, Dave and Jamison answer these questions: Hi Jamison and Dave! I am not a developer, but my question is hopefully transferable. I sit in between lawyers and developers. I advise on technology that can be applied to legal processes and I support our teams in using a range of platforms and AI tools to be more efficient across their work. I have ADHD (late diagnosis at 22) and often have trouble with executive function, remembering details, progressing large projects with no deadlines, and remembering verbal instructions. Have either of you ever had a neurodivergent person on your team? If so, how did you support them? What environment helped them to work best? Also, what frustrations did you have and how could they have mitigated them? Any help would be appreciated to help me avoid driving my manager insane (I live in constant fear that one day she will snap and I’ll be fired even multiple years in). 😂 Hi Dave and Jamison, you’ve made my runs very enjoyable over the last years, thank you so much for that - even though I doubt that laughing out all the time is great for my performance. I’ve been in web development for 7 years now and a Lead Fullstack Engineer at a consulting firm. Being a “lead” currently only means that my team mates seek my opinion and guidance on topics, without me having any increased responsibility. In September, I’ll move countries (Europe to Australia) and will be on parental leave until mid ‘26 when I’ll have to look for a new job down under. I feel quite stressed by recent developments (AI), already have the feeling of not being able to keep up with all the new things (ask my 300 open tabs of articles I want to read), and fear that I could loose touch in my time off. How can I deal with this FOMO? And which topics would you look into in the upcoming months if you were in my place? Show Notes https://blog.jsbarretto.com/post/software-is-joy https://medium.com/@djsmith42/the-3-highest-roi-technical-skills-for-software-developers-21b412d79aff

In this episode, Dave and Jamison answer these questions: I’m the CTO of a small startup. We’re 3 devs including me and one of them is a junior developer. My current policy is to discourage the use of AI tools for the junior dev to make sure they build actual skills and don’t just prompt their way through tasks. However I’m more and more questioning my stance as AI skills will be in demand for jobs to come and I want to prepare this junior dev for a life after my startup. How would you do this? What’s the AI coding assistant policy in your companies. Is it the same for all seniority levels? Hi everyone! Long-time listener here, and I really appreciate all the insights you share. Greetings from Brazil! I recently joined a large company (5,000 employees) that hired around 500 developers in a short time. It seems like they didn’t have enough projects aligned with everyone’s expertise, so many of us, myself included, were placed in roles that don’t match our skill sets. I’m a web developer with experience in Java and TypeScript, but I was assigned to a data-focused project involving Python and ETL pipelines, which is far from my area of interest or strength. I’ve already mentioned to my manager that I don’t have experience in this stack, but the response was that the priority is to place people in projects. He told me to “keep [him] in the loop if you don’t feel comfortable”, but I’m not sure that should I do. The company culture is chill, and I don’t want to come across as unwilling to work or ungrateful. But I also want to grow in the right direction for my career. How can I ask for a project change, ideally one that aligns with my web development background, without sounding negative or uncooperative? Maybe wait for like 3 months inside of this project and then ask for a change? Thanks so much for your thoughts!

In this episode, Dave and Jamison answer these questions: I’m a senior developer on a small team, and I’m feeling frustrated with a junior developer I work with. They’re smart and perfectly capable, but they stick very strictly to the confines of their assigned work. They’ll finish their tickets, but unless they’re directly asked, they don’t offer to help with other areas, pitch in on shared responsibilities, or step up when the team is trying to work cross functionally. This engineer seems content to stay in their lane and do “just enough.” I know they’re junior, so I don’t expect miracles, but I expect some initiative. This is most frustrating because it’s a small team and it often feels like we’re working with half of an engineer when they disappear into a corner and leave the pressing issues for the senior developers to handle. How can I encourage them (or maybe push them a bit) to see the bigger picture and contribute more to the team’s success without coming across as bossy or micromanaging? Is this really my responsibility to fix, and am I expecting too much of a junior? I had my first day yesterday as a senior developer and dozed off at an hour meeting at the end of the day today. The meeting was about planning the next year on a zoom call with the leadership I was following in the beginning but at some point they started to talk in something I can‘t really understand(to excuse myself, I had had mant meetings throughout the day and still new to their product). I should’ve turned off my camera but I kept it on while I was definitely zoning out and got my eyes closed few times. I am so embarrassed and don’t know what should I do and feel. I like this new workplace and people so far but should I already look for another job? Help!!!

In this episode, Dave and Jamison answer these questions: I was on a meeting with a team generally regarded to be pretty annoying to deal with and not particularly useful. The meeting was pretty annoying and not particularly useful. I audibly said to myself after leaving “holy crap what a waste of time.” Turns out I hadn’t left and may not have been muted (?) but I’m really not sure. I left immediately without checking due to cringe overload, so I have no way of knowing. How do I even go about this? I have to meet with this team regularly. My spirit has left my body, this question was typed by the husk that remained. I am almost 2 years into my software development career. A few months ago, I was moved to a team where I was the only frontend developer. My team responsible for maintaining a large, legacy angular project and building a new internal in React tool to support the ML engineers at our organization. Our organization hired some contractors to help with building the new tool, all of which have the same or less dev experience as me. Our project manager is not engaged in our project. He is on multiple teams. I have to communicate with our customer, gather requirements, create user stories, and QA the contractors’ work. This is not the type of work I am particularly good at or enjoy. This is on top of me being the de-facto frontend tech lead. I am STRUGGLING to keep up. I can only do a little bit of work on our project each iteration and doing required maintenance of the legacy application has become very difficult to do because of how little attention I am able to give it. I don’t want to do all the other stuff, I just want to write code. What should I do?