What to do when tech jobs go bad

No matter how many companies I go to, work eventually sucks. In the tech companies in which I’ve worked, sooner or later a similar set of problems becomes apparent that would require either a change of management, or rapid extreme changes in the style of the existing management to resolve. Typically, neither of these things happen and I seek other places in the hopes of encountering better management.

I’ve worked as an individual contributor web backend software engineer in several tech companies, from small and medium-sized startups, to large corporations. This is my humble attempt at describing what I’ve seen, what the problems are, and what some possible solutions could be. I write this to organize my own thoughts, but also in the hopes that someone finds these stories familiar, and understands that they’re not alone in their experiences. In some cases, these may seem like issues with developers, but developers work in the environments that management creates, and so I’ve included them here as well.

If you’re busy, I’ve laid things out as bullet points which should cover the gist of things. However, know that the meat matters as much as the bones here.

For more comments, see the Hacker News thread.


  • No roadmap, or a fluffy roadmap

Having little or no idea of what success looks like, you will never achieve it. Vague ideas of projects lead to vague code being written, running “late” (how do you know without a roadmap?), and all kinds of frustration.

Solution: Make a roadmap.

  • Roadmap with no basis in reality (no engineers/stakeholders asked for estimates, no checkpoints in place for progress)

Management decides on a list of things they want, and they decide it must be done this quarter. With no input from the people actually doing the work, this is likely to be wildly ambitious. With no checkpoints to know how things are coming along, projects will be very late, often too late to rescope them in hopes of finishing something meaningful.

Solution: Force those responsible to break down and justify timelines. Drag them away from coding (many developers see only coding as productivity) and make them do this. Incentivize good and thorough estimates.

  • Roadmap built too late (during development)

Work begins on projects and roadmaps are built after roads. Suddenly it’s realized that the project being worked on doesn’t make sense. Time and effort goes out the window along with morale.

Solution: Take time to build the roadmap well ahead of doing the work. No, you don’t have to predict every potential future, but it’s easier to steer without crashing when you know the lay of the land.

  • Extreme changes in roadmap not a result of environmental changes, but a result of shortsightedness or lack of thoroughness in initial planning

One day the business team wakes up and decides they think another project should be prioritized to make hockey stick graphs, because they failed to spend time to prioritize things ahead of time well. Months of work go down the drain, and it was entirely avoidable.

Solution: Take the roadmap seriously. Prioritize things well. Unless an extreme shift in business occurs, stay the course. More is lost in indecision than bad decisions. Work on the projects you say you’ll work on. That’s measurable productivity. If you regret a previous priority, don’t repeat the same mistake next quarter.


  • Lack of a Directly Responsible Individual (DRI) for a project

A project is created and assigned to a team. Perhaps someone makes tickets to track the work to be done. A few people work on these tickets as they come to them. A manager comes by and asks for progress in an email. Nobody responds. The manager is frustrated and yells for answers. Developers answer questions individually. It turns out the project is way behind and much of the work on it is broken.

Solution: Choose 1 person whose job it is to ensure that progress is made. They have the authority to talk to managers to get more resources if necessary, but at the end of the day, they answer questions of progress, and drive things forward.

  • One lone engineer on a big project silo’ed away

Everyone is busy on projects. One person has spare time, and is assigned to work on a project that’s important. Hurray parallelism right? Wrong. The engineer tries to get answers to how things work and gets limited assistance since others are busy. Nobody reviews her work. They ask what the delay is and she responds, but nobody’s satisfied with the answers. She asks for help and is told nobody is available.

Solution: Unless you are a startup with absolutely no money and are dying in a few weeks, always assign at minimum 2 people to a project, and ideally 3. They are far more likely to raise problems since they can discuss the work, move things forward together. A third can break ties in design decisions and code reviews.

  • Lack of taking responsibility in code reviews, not thorough, blaming the author of the code

A pull request comes in. You’re busy, this person probably knows what they’re doing, just approve it and move along. Who doesn’t love easy approvals, right? Think again. Things will break in prod, tests will be missed, and you’ve revealed yourself as a lazy individual. Oh, also you’ve just set a precedent for others to likewise not review code. When things break in prod, are you really going to say “oh, I didn’t write that” if you reviewed it? Guess what, you approved it, you bought it.

Solution: Take code review seriously. If you don’t have time, assign to someone else, or ask the pull requester if they can wait longer for a review. I promise you, you’ll be happy you did.

Tech Debt

  • Not taking appropriate action to retire old systems, rewrite and/or move existing legacy systems

At some point, a legacy monolith reaches leviathan proportions, and is such a tangled web of disaster that it harms development. Existing veteran developers have trouble working with it, new developers strafe in the dark morass for months before being marginally productive, and strange crashes lurk causing unknown issues for your clients. But the management keeps prioritizing product, not realizing that the tech debt largely slows the development of the product features they so desire.

Solution: Business must yield priority to tech debt. The most egregious issues with existing legacy must be prioritized and addressed. Longer-term rewrites must be sized and handled over time. This will pay huge dividends in development time of features, and developer happiness and longevity. It’s often said that developers don’t quit their jobs, they quit their bosses, but I think many times, developers also quit their codebases.

  • Writing new systems that don’t need to exist simply to scratch an itch to write (NIH syndrome, etc.)

“Have you heard of that cool new programming language? I’ve been learning it on the weekends and I want to see how it works in production. I’ve heard great things.” Time passes, and a new system is built in a new language, that does something very similar to an existing open source library, only in a more esoteric use-case-specific fashion, and with fewer developers to support it. Sooner or later, the project decays, the developer leaves the company, and much time was wasted on this system that wasn’t necessary which could have been used for business-critical work.

Solution: This one is tricky. It takes a seasoned manager to know when to red-light this kind of project in favor of using existing solutions, and when to green-light things. You don’t want to suppress good developers, but you don’t want waste. The best that can be done is to ask the developer to write a thorough proposal that sells the specifics of the implementation, and to thoroughly vet it. This is, alas, one of the pitfalls of hiring less-experienced managers.

  • Blame the legacy, it’s all the legacy’s fault

Ah legacy systems. Everyone loves to swear at existing code, blaming developers who often are no longer there and can’t defend themselves. Things must have gotten this bad because they were awful, but we’re better. Sure we won’t fix what’s there, and our added hacks were necessary, but we’re better, really, we swear. It’s so much easier to build hacks on top of other hacks, it really makes you wonder how the legacy got here in the first place. This creates a toxic environment of bottomless pits of complaints, and ultimately hurts code quality and team happiness.

Solution: While it may be tempting to endlessly complain about existing systems which may indeed be suboptimal, take the time to remember that the existing code brought the company this far, and that dubious design decisions may be the result of several changes of the guard and business decisions combined with emergent disasters which surround any fast-growing business. Is something awful? Make a concrete plan to make it better. Do it, even if you just chip away at it. The person who comes after you (it might be yourself) will thank you for it.


  • If you spend more code to work around the weakness of a system than the advantages it gives, this is bad design

Someone has a great new design they want to implement which is leagues better than what exists, and the existing design is just so awful. Only, it’s going to require some duct tape here and there, but that’s totally acceptable because overall it’s better. Until it becomes apparent that it’s mostly duct tape, but you’ve gone all-in on this and you can’t go back.

Solution: Start over. The sunken cost fallacy is real. You’ve made a mistake, and that’s ok, you can take those learnings and build something better. Don’t settle for chaos.

  • If most people working on this codebase run into the same set of problems avoidable by a different architecture, this is bad design

You notice the same piece of code gets copy+pasted everywhere this system is involved. You ask someone why, and they explain “oh, that’s because this system expects this thing for a reason that isn’t actually true but sounds good, and everyone has to play along.” You have no idea why they did things this way, but you’re busy, you paste the snippet into your own code and move along.

Solution: It’s painful to hear, but, refactor it. Refactor the whole thing and get rid of the copypasta. It will pay dividends.


  • Shotgun coding. No tests, or bad tests. Not handling of corner cases, mainly happy-path coding.

“This is a startup, we don’t have time for this, we’ll handle it later. This is acceptable,” said the many developers over the years, each contributing their own piece to the chaotic mess that this became. Push out code with no tests, break production and fix it later, write tests to handle only the happy path, or not even that.

Solution: Management can enforce test coverage, but really this is not a good measure of how well-tested a codebase is. What does work is forcing code reviews by thorough people who check for these things, and calling people out for doing superficial code reviews. Unfortunately, this is a case where hiring less experienced or conscientious engineers will hurt you badly, so watch your hiring for this.


  • No agenda, or fluffy agenda with no measurable output

You check your calendar and find you’re in a meeting called “Discuss The System” with no description, 10 people invited, and it’s 1 hour long. Being the good employee you are, you show up, stay silent through the majority of it as 2 people ramble on, and at the end of the meeting, the organizers pat themselves on the back and end it, and threaten to hold another one. Time is wasted, irritation brews, and nothing has been gained, but much has been lost.

Solution: Enforce a company-wide policy that all meetings must have an agenda with a measurable output, involve only the necessary people, and have notes taken to show if the output was significantly reached. End all meetings once the goal has been reached, or the time is up. Any meeting that doesn’t obey these tenets, allow people to either leave, or not show up in the future. This will force people to change.

  • Meetings that could be an email or a DM

You’re in a meeting with an agenda with measurable output (yay!), but it’s a simple yes/no question that could be answered through email or DM.

Solution: Yes, this is a shocker: use email or DM. Use your common sense, and use the appropriate medium.

  • Meetings that include unnecessary people, and don’t include necessary people

You’re in a meeting where 10 people are present, except the main designer. People wave their hands and say words, but in the end, all of this will just be overridden by the person responsible. Later that day, you’re in a meeting where for some reason the head of engineering is present to go through a low-level code decision, and nitpicks things out of context, wasting everyone’s time (including her own).

Solution: Have a good reason to invite every single person at the meeting. If you can’t think of one, don’t invite that person. If the chief decision makers of something should be involved, invite them. And above all, stop adding people as “optional” to a meeting. If a person is optional, they should not be invited. It’s that simple. This is a company meeting, not a tech conference seminar.

  • Meetings had for the sake of meetings (standups, what are you really gaining from this?)

You’re at the daily standup meeting. People talk about things that you have no idea about, nor care about. You likewise share what you do that they don’t have any connection to. The few people who do have connections, you’ve talked offline to already, and here you report that you talked offline to them, and will continue to talk offline to them. Wait, why are we here again?

Solution: If you absolutely must know what other people are working on, write it in text in a chat or email. “Oh, but nobody will ever read that!” you say. Correct. That’s because nobody cares. Do you think that hearing it aloud will make them care any more? Are you all now doing a better job as a result of this daily ritual? Probably not. Stop wasting people’s time, and focus on the results. Kill all useless meetings, especially the repetitive ones that are held mainly for ritual.

  • Meetings too early or late in the day. Attention span low, irritation level high. You won’t get good things from these meetings.

It’s 6PM and someone’s holding a meeting. You latch onto your third coffee of the day and pray this is either good or ends soon. Neither of these things come to pass. The next morning you realize someone has put a meeting at 8:30AM. You latch onto your first coffee of the day that you haven’t half-finished and hope this is good. Someone asks a yes/no question, and the meeting ends. Seriously?

Solution: Seriously. This is one of many ways in which we’ve forgotten the human factor. Stop scheduling meetings too early or too late, schedule them during core hours. If a meeting is so important to have, it needs to be done immediately. Otherwise, there’s nothing that can’t wait a day or a few hours. People will be more willing to be present, participate more, and you’re more likely to achieve the desired outcome.


  • Blind adherence to process without evaluation for current situation

Sprints! Who doesn’t love sprints. We do Agile here. What do you mean Agile isn’t a noun? I just capitalized it, it must be so. Anyway, let’s just repeat sprints every week or so, and have people figure out what they’re doing. How do I know this is working? Because we create another sprint every week. What, results measurement? Many tickets were created and closed. What more do you want?

Solution: Process is a great thing to have. It guides work, and leads to desired outcomes on the roadmap (which you of course have!). However, process that does not measurably get you closer to or accomplish your goals is either unnecessary, wrong, a waste of time, or all of the above. Always evaluate your process for what it gives you vs. what it takes away, and ensure the former is always greater.

  • Excessive democracy leading to indecision

Everybody’s opinion matters. We’re not a dictatorship here, ok? Let’s ask for comments from everyone in all of engineering. Wait, two people are disagreeing, that’s not good. One of the engineers isn’t in any way involved in this project, but she has great experience! Until this is settled, we can’t move on. Forget the deadline, we need to do things right! Correctness matters.

Solution: No, corporations are not governments, and they should not be democracies. Fast, good decisions save a company, and slow decisions, good or bad, can kill a company. If you assign someone to be in charge of a project, they get the final say, and they make the decision quickly. Disputes can be resolved more privately without bringing in the entire engineering department. Focus your people, and you’ll maximize your outputs. Give them all a say in everything, and you’ll be gridlocked for no good reason.

  • Excessive micromanagement, manager not taking care of bigger picture, ICs frustrated, bad work comes out

The manager is a people’s person, she’s right there with you in the trenches. She asks you about this line of code and why you didn’t handle it another way, not knowing the context that led to the decision. You spend an hour explaining it to her, and in the end she goes “ohhh” and agrees. Meanwhile, the roadmap is running late and is not accurate, engineers are angry left and right, and the manager is nowhere to be seen on handling these real issues.

Solution: Trust people. If you can’t trust them, get rid of them. Micromanagement is the death knell of any organization, and stops any team from scaling. If the manager isn’t handling real high-level decisions, that one line of code won’t matter, because the house is on fire while you were arguing with the carpenter about the new chair. Stay above it all, use the bird’s-eye view to make great decisions, and even if small inefficiencies arise at the lower levels, the ship is still sailing in the right direction.

  • Hierarchy that hinders but is not used. Managers skipping rungs on the ladder to ask non-direct reports for updates.

You’re working on something, and your boss asks how it’s going, so you give an update. Then your boss’s boss asks, and you give the same answer with less detail. Then her boss asks, and you say “good.” Then a manager completely unrelated to your team asks and you begin to wonder what’s going on here. You decide to just write a company-wide accessible report of what’s going on, wasting your time to give excessive visibility to managers who should have other concerns. What’s going on?

Solution: As always, corporations are not general society. The hierarchy isn’t there to suppress the lower class, it’s there to maintain order and efficiency. If a manager 3 levels up is asking an indirect subordinate about a project regularly, it’s a sign of micromanagement, or too many managerial layers. Both problems are obvious how to address.

  • Lack of useful checkpoints

We’ll know the project’s done when it’s done. We report status in number of tickets completed. Sure, the number of open tickets varies over time, but it’s a rough idea, right? Until the project that was scheduled to take 2 weeks takes 6 months.

Solution: Make checkpoints. “Such and such is expected to be done at the end of week 2.” If a checkpoint is not met, estimates must be reassessed, and possibly more people must be allocated to a project if it’s high priority. Otherwise, you have uncontrolled ballooning of a project’s scope and time taken.

  • Not stepping in to help an engineer when they’re stuck

Everybody knows that Jackie’s working on this long-term project, and that it’s taking a while. You often wonder how she’s doing. Management doesn’t seem to care she’s delayed, because hey, it’s just a difficult project you know? Time passes by, and nobody steps in. She asks for help from time to time, but she’s told that everyone’s busy. The project takes forever.

Solution: Management should have some visibility on the status of projects. If something appears to be taking too long, then at some point, it’s wholly appropriate for management to step in and figure out what information is missing, or if more headcount is required. This is not micromanagement, this is a core part of management, but oftentimes managers who fear micromanaging give so much freedom as to not manage at all. It’s admittedly a tight line to walk, but this is the hallmark of good management.

Note: From here on out it’ll just be lists, as I never got around to fleshing these out, but hopefully they should be somewhat self-explanatory. If it makes sense and time allows, I’ll flesh these out.


  • Overcommunication. Emails to large groups about particular details of everything, in the name of transparency. Floods inboxes, people filter, leads to apathy.
  • Undercommunication. Big potentially breaking changes affecting other teams, other teams not notified.


  • Managers not evaluated by their direct reports
  • Fluffy descriptions of how to improve, usually used to suppress salary by saying that a person never exceeded expectations without making clear what that means
  • Rewarding so-called “firefighters” who respond rapidly to bad code deploys, rather than those who design and code more carefully to avoid issues in the first place
  • No clear path for growth


  • “The company is a family.” No it is not, and if it were, many companies behave like an abusive parent, where the child keeps giving, and the parent keeps expecting and punishing.
  • “Use your social media to spread the company’s posts.” This is disingenuous at best. Expecting people to use their own personal street cred to promote a company is see-through and pushes too hard from work into personal life. This is a huge overreach. If an employee likes what the company does, they will spread it on their own.


  • Process is not aligned with its goals: to find the right people for the job that fit in well with the company and teams
  • Engineers overburdened by conducting interviews as often as they’re doing work
  • Emphasis on hiring more people, without focusing on maintaining existing talent (how well will your engineer sell the company to others, if they feel they’re being badly treated?)


  • Providing regular events with alcohol. Peer pressure to drink, bad health habits, bad workplace environment.
  • Normalizing and glorifying drinking alcohol.


  • Racism, sexism, LGBT discrimination, ageism. Much training given, but subtler forms emerge.
  • Low diversity.

Employee Well-Being

  • Obvious signs of overwork, overstress or burnout ignored, glorified as “hard worker”
  • Ignoring that employees are human beings. Ignoring interpersonal problems, health, etc.