526 episodes
Episode 525: How do I save my company of 500 people and my new company is insane with AI
2026-08-10 | 28 mins.In this episode, Dave and Jamison answer these questions:
Hey Dave and Jamison,
First, I love your show and it has now been part of my Monday evening routine for many years to listen to your podcast while cooking dinner.
I recently joined a mid-sized software company (500 people) as a senior data engineer. The salary is a significant bump from my previous job and I really like the team on a personal level.
Three months after I joined, the company laid off half its employees and announced a strategic pivot away from their previous core business to become an āAI-first companyā and develop new products in novel, more profitable sectors.
The product that my team had been working on until that point was scrapped and there are no new projects coming from the business side. In subsequent communications, it was revealed why: Management has no concrete ideas for the future strategy, neither on what products to develop nor on which sectors to target. Instead, our team (among others) is now tasked with coming up with new product ideas to āsave the companyā. Iām a data engineer, not a business development manager, and while I have dealt with high ambiguity from the business side in previous roles, it was never this extreme.
I was looking forward to working on interesting technical challenges within a great, experienced team, but now I feel like Iām expected to become an āidea guyā, a role that doesnāt really match my personality.
My question is: Should I be patient and try to turn this situation into āan opportunity for growthā, or should I start applying elsewhere? Iām a bit worried that the short length of stay at this company will leave a stain on my CV.
Many thanks to my favorite space lawyers,
an anonymous listener.
Hi!
My current job is at a 10k+ large risk-adverse company that currently has nil, none, nada, nichts ai tools available for coding. I of course did the only reasonable thing. Iāve gotten a new job at a middle-sized fintech company thatās going āAI firstā.
Iām really excited about finally using ai outside hobby projects. I worry however, that my future colleagues will go too quickly ahead while vibecoding, vibearchitecting, vibetesting⦠leaving a mountain of tech debt behind. A lazy colleague would actually be better than an intellectually lazy colleague in this scenario. (I sincerely hope that I wonāt be that coworker)
Are my worries overblown or sane? Any gotchāas to avoid? Maybe you can give a brief survival guide to the brave new AI world?Episode 524: My CTO AI-codes big piles of slop and early mornings, late meetings
2026-08-03 | 32 mins.In this episode, Dave and Jamison answer these questions:
I work for a small software company on a team of about 7 or 8 engineers. I like working here. I like the people, the autonomy, the pay, my boss, and the stack among other things. I try to remind myself of this regularly so I donāt take it for granted. Iāve been here for about 2.5 years and would love to continue working here.
Our CTO, like many, has become a big AI cowboy coder. Every few months, he vibe codes a new project and then decides to interrupt the full workloads that we have a limited number of engineers to do to hand his project off to be cleaned up, worked into the product, and solve all of the problems that remain once actually put into practice. This usually ends up going to a different engineer per project, who is then tied up with the CTOās whims and is no longer available to do the work planned by product. Our EM knows this and knows the frustration and lost velocity, but what can he do? (rhetorical, not the question)
Most recently, I was tasked with implementing some reporting dashboards he did into the product, but he specifically asked me to make it in such a way that he can continue to work on and add to because he canāt be bothered to run the actual product. This is very concerning to several of us. He has no clue what heās writing or how bad it is. Weāve talked about perhaps making him do PRs, but a) who can make him, heās the CTO, and b) heāll have no clue what to do with PR pushback given that he has no clue what he wrote. And again, who can make him actually fix it if he asks us to rubber stamp it? (rhetorical, not the question)
Iāve been listening to the show for years and Iāve talked to friends at other companies, so I know this is everywhere. Is it as everywhere as it seems? Is it worth finding a new place to work where the CTO isnāt running so rampant? As I stated before, Iād rather not leave, but if I talked about that as a concern, I donāt want it to sound like an ultimatum, even if maybe it is at some level. Is this just the new reality for us, or is there something that can be done?
I am a senior software engineer at a big tech company. I live in central Europe but my team is in the US and Iām 9 hours ahead. I have 7:30 pm meetings and sometimes take an hour before and/or after this meeting to prep or follow up. Previously I slept in later and started later to deal with these meetings.
However, now my daughter is starting kindergarten and I wake up early (5-6AM) to be with her, drop her off, etc. Now in the evening meetings my brain is fried and I canāt even articulate myself well. The next day I think about so many things I wish I had said in those meetings.
I canāt quit as I make 160K right now and I would only be making 60-80K tops in my country and have some financial commitments. Relocation to the US is also not an option because I have kids and donāt want them to move.
So far I have been skipping meetings and my manager has not expressed concern but I feel so detached from my team. I donāt even know what most of my peers are working on.
It feels like I am out of ideas to make this better. Please share your space wisdom with me :)- This is a rerun of episode 331.
In this episode, Dave and Jamison answer these questions:
Listener ninjamonkey says,
I am a new grad who is half a year into the role now at a very large company. Recently, a senior engineer on my team asked me to create a ticket for an infra team for a problem with a service. I provided logs and steps to reproduce the issue and did a health check before submitting.
Right after, the manager of the team put me into a group chat with their team, asked why I created the ticket and told me to start doing my job and they canāt debug for me.
From these interactions and comments on the ticket, it feels the infra team will likely not work on the tickets I report or de-prioritize them. This has left me discouraged and hesitant.
I will have to do lots of this kind of infrastructure work in the future. Additionally, one of the goals my manager set for me is to work with more external teams for the upcoming year.
What do I do here? Do I tell my manager about these interactions? Do I tell my team lead, staff/seniors to swap out for different kind of story?
I work for a small startup. I was the first employee other than the 2 founders.
Being the first developer hired, naturally means I have the most knowledge about our application. I also have good organisational skills, which has led to me becoming and being referred to as the āLead Developerā.
I have recruited 2 of the 3 new developers, and have trained both of them and got them up to speed.
At first I was pleased with the progression and was keen to grow into the position, and told the founders so.
Since then, I have changed my mind, I donāt want to be the lead - due to the following:
The communication is absolutely pitiful. Any questions we ask of the founders we get about a 30% reply rate no matter the form of communication.
We get poorly defined tasks and requirements
The CTO will just blast through some of our features over the weekend and say here I fixed it for you
I donāt want to quit my job (just yet⦠its a comin though).
I have actually discussed the above points with them, but I know these 2 founders will never change their ways.
How do I tell them I just want to go back to being an Individual Contributor like my Employment contract states? Episode 522: I stayed too long at my first job and should I get a masters degree
2026-07-20 | 28 mins.In this episode, Dave and Jamison answer these questions:
I stayed too long at my first company and now my career is ruined?
Hi both, long time listener. (Since I graduated university 4 years ago actually and felt I could never find a job but listening to you guys made me feel not like such an outcast in our field.)
I graduated in 2022. Didnāt really apply around much and almost immediately accepted the full time offer from the company I did my internship with during my degree. And fast forward to middle of 2026⦠I am still here.
Iāve long stopped growing as an engineer and have actually been stuck on a simple CLI tool for almost 4 years now with little to no cloud/backend/etcetera experience to show in my 5 year career. I donāt feel I am desirable in the job market at all due to this and waited way too long to look for a job because I was comfortable and happy. I feel paralyzed (no need to put on your space therapist hats BUT some career advice would be wonderful!)
(Also did I mention I am in Canada and want to move to Europe and live the rest of my life there but visa sponsorship with my level of experience is impossible? Maybe thatāll be for my next questionā¦)
Thanks for all you do, cheers!
I have a non-CS engineering degree, and am looking to transition into Software Engineering. I have the option of pursuing a degree with Tuition Reimbursement from my job, but am in a bit of a strange situation deciding which degree. Basically, Iāve figured that with my current Engineering background I could pursue either a second Bachelorās degree through Universities offering a āPost-Baccalaureateā program in Computer Science, or a Masterās degree, with maybe only a slightly longer program to get the Masterās as opposed to the Bachelorās. Otherwise the total length/cost of the programs would be roughly the same.
I have heard though that it might not be a great idea to go into a Masterās program unless you know what specifically you want to study.
I am curious what you think would be more āhire-ableā between the two options for someone pursuing the career change into Software Engineering?Episode 521: negotiating . . . now? and doing good work is not enough for promotion?
2026-07-13 | 31 mins.In this episode, Dave and Jamison answer these questions:
Dwill Ainghell asks,
During the golden era of software development, it was commonly stated that you should always negotiate job offers. The argument was that the company has invested significant time and resources into you as a candidate and there is always some wiggle room for negotiations. A popular article / podcast by Patrick McKenzie likened it to doing something slightly uncomfortable like āreciting poetry while simultaneously standing on one footā with almost no downside. (https://www.complexsystemspodcast.com/episodes/how-to-negotiate-your-salary-package/)
Does this still hold true in todayās environment? Iām a SWE with 10 years of experience and Iāve been unemployed for close to a year. Iām expecting an offer from a large company and I fear that I will look like a fool trying to negotiate in my current position and the current job market dynamics. Even worse, I fear that they might retract the offer and give it to someone else. That being said, I donāt want to leave money on the table.
Whatās the correct course of action in todayās environment?
Listener Stu says,
In episode 500, you said something to the effect of āworking hard and doing a great job with the work youāve been assigned is not the promotion trackā. Iād love to hear you discuss what it does take to get promoted and how to do that.
In my job, we have a jira queue and engineers are tasked with taking from the top of the queue and executing work. Thereās also an expectation to lead pre-defined projects (define the scope, write the tickets, and shepherd it along).
All of these projects have deadlines, so how do you recommend people get the defined work done, lead projects, and still find time to do whatever it is to get promoted?
Why is doing an excellent job not enough?
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About Soft Skills Engineering
It takes more than great code to be a great engineer. Soft Skills Engineering is a weekly advice podcast for software developers about the non-technical stuff that goes into being a great software developer.
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