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Facilitating AI adoption at Imprint

from Irrational Exuberance [alt+shift+b] in programming

I’ve been working on internal “AI” adoption, which is really LLM-tooling and agent adoption, for the past 18 months or so. This is a problem that I think is, at minimum, a side-quest for every engineering leader in the current era. Given the sheer number of folks working on this problem within their own company, I wanted to write up my “working notes” of what I’ve learned. This isn’t a recommendation about what you should do, merely a recap of how I’ve approached the problem thus far, and what I’ve learned through ongoing iteration. I hope the thinking here will be useful to you, or at least validate some of what you’re experiencing in your rollout. The further you read, the more specific this will get, ending with cheap-turpentine-esque topics like getting agents to reliably translate human-readable text representations of Slack entities into mrkdwn formatting of the correct underlying entity. I am hiring: If you’re interested in working together with me on internal agent and AI adoption at Imprint, we are hiring our founding Senior Software Engineer, AI. The ideal candidate is a product engineer who’s spent some time experimenting with agents, and wants to spend the next year or two digging into this space. Prework: building my intuition As technologists, I think one of the basics we owe our teams is spending time working directly with new tools to develop an intuition for how they do, and don’t work. AI adoption is no different. Towards that end, I started with a bit of reading, especially Chip Huyen’s AI Engineering, and then dove in a handful of bounded projects: building my rudimentary own agent platform using Claude code for implementation, creating a trivial MCP for searching my blog posts, and an agent to comment on Notion documents. Each of these projects was two to ten hours, and extremely clarifying. Tool use is, in particular, something that seemed like magic until I implemented a simple tool-using agent, at which point it become something extremely...
7th Dec 2025

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Trying the Software factory pattern.

One of the interesting challenges of the AI ecosystem in 2026 is that new, effective patterns emerge faster than I can adopt them. I’ll find a handful, get back to work, and realize a month later that I’d missed four or five more. The adoption cycle for Imprint this year has been something like: January: get every engineer onto Claude Code every single day March: ok, let’s also get everyone else onto Claude Code or Claude Cowork every single day April: local development is bottlenecked on checkout and worktree model, instead create ~10 local workspaces which each have an independent checkout of every repository, and operate at the workspace level, not at the repository level, so it can generate cross-repository pull requests across frontend, backend, infrastructure and data monorepos June: oh boy, agent-driven development is heavily constrained by lack of a common task management system with higher visibility and less permission complexity than Jira, so let’s migrate the entire company over to Linear and hard stop on Jira July: yikes, now we have visibility into all these tickets, many of them are trivial but managing them through local development isn’t scaling, let’s roll out an orchestrated harness which internally we call “Agent Fleet”, along the lines of Stripe’s Minions The most recent question for me has been figuring out how to adopt the software factory pattern. (After some light research, the specific AI-context origin of this term is slightly messy to attribute, but I think it might be Justin McCarthy in February 2026’s Software Factories And The Agentic Moment.) The software factory pattern is looping on a broad goal, and then relying on the harness to drive progress towards that goal. Our first pass at implementation is fairly basic: An agent skill /linear-project-loop which reads in a Linear project and starts by auditing that project’s goal definition on these dimensions: An RFC in Notion that describes the project’s goals, how those goals are measured, and the general approach A Datadog dashboard or Snowflake queries that measure progress against those goals If those are missing, or the Linear project is missing in its entirety, it iterates with you on creating those missing tools. Then it reviews the state of the metrics and issues for the project. If new work is identified, it adds those issues to the project. It updates the state of issues that have moved. It works on the non-blocked tasks based on the project’s current state. This is often writing a pull request, updating a pull request, pinging for review, asking a clarifying question, etc. When a task completes, if the project description is fresh, it takes on the next task. If the description hasn’t been updated in a while, it reruns the loop starting with the first step. Right now I am running this locally in a local harness, but it’s working well enough that I anticipate moving the behavior to be driven by the same orchestrated harness that we assign one-off tasks to. What I particularly like about the factory pattern is that it parallels very closely how I’ve been working locally, while forcing me to recognize the places where I was accidentally hording parts of the state for myself regarding the goals of the project. I was already asking agents to iterate on specific Linear projects, but they didn’t have the ability to evaluate if they were going in the right direction, or if it was missing necessary tasks. Now it does. The other place this has been extremely helpful for me is checking in on projects post release. For example, I shipped our passkeys implementation earlier this year, but some months go by without my checking in on how it’s going. If we saw adoption spike, or error rates start to turn, I might miss it, but running the factory in a less frequent post-release mode would catch it immediately. The final thought that’s been interesting to me is how much all of the pieces here compound only to the extent that you have the other pieces. For example, this factory pattern depends on having Datadog MCP and Snowflake access available to manage goal-tracking, but it also depends on Linear being the single source of state for the company’s work, and an orchestrated harness that can perform work independently from your laptop. Keeping up with this many migrations is a fascinating industry moment.

2 weeks ago • 3 votes
Middle management roles are also a trap.

Six years ago, I wrote Tech Lead Management roles are a trap. My argument then was that TLM roles present themselves as easier than moving into a full management role, but the tension between doing the software engineering and engineering management aspects of the role made being a TLM a much harder first management role than a pure engineering management role. I still agree with that post, and I have some additional bad news to share: middle management roles are mostly a trap as well, if you goal is to become an executive. The core aspects of middle management roles are: Balancing between top-down executive, lateral stakeholder, and bottom-up team pressure, e.g. keeping morale up as an organization deprioritizes last year’s big initiative Defining and operating an organization’s process, e.g. creating career ladders and interview loops Competing for a share of fixed organizational resources (e.g. budget) and allocating acquired resources These are all extremely important skills to be an effective executive, and they make up the bulk of The Engineering Executive’s Primer, but they are insufficient to make you a great executive. If you don’t have them, you will be a deeply flawed executive, but even if you’re an expert at them, you can still be a terrible executive. That’s because the most important skills of an effective executive are the same exact skills that make an excellent line manager: developing domain expertise, driving execution (including setting pace), and translating both of those into an organizational culture that extends beyond you (in any of innumerable different ways). All of them are more easily practiced and mastered as a line manager than as a middle manager. Most middle management roles make practicing those skills difficult, and sometimes negatively select against developing them. As a middle manager, if you drive execution too closely, you might get told off as a micromanager. As a middle manager, if you go too deep on domain expertise, you might get told that you’re not focusing enough on your internal stakeholders. That’s undoubtedly valid feedback in many middle management roles, but it’s the perfectly wrong feedback to someone who is trying to become an effective executive. As a result, I’ve come to believe that the filters for good middle managers inadvertently negatively select out the “challenging” line managers who actually have the best chance to be excellent executives. That’s not even necessarily irrational: most companies are developing middle managers to take on more complex middle management roles; very rarely do they worry about growing future executives from within. If you’re willing to embrace this fact that a little bit of time in middle management roles is important preparation to become an executive, but spending a great deal of time in middle management only prepares you for further middle management roles–and makes you less effective as a potential executive–then the AI-driven shift in managerial fads might be a threat to your current role, but it’s likely to improve your chances to succeed as an executive.

8th Aug 2026 • 2 votes
Make no assumptions.

I’ve recently been thinking a lot about the concept of “soil horizons”, which is the idea that there are many distinct layers of soil, from topsoil all the way down to bedrock, which all combine into a soil horizon. Translating this idea into software, the ideal codebase would have a single uniform “code layer”, but a surprisingly large percentage of production software has numerous, distinct code layers as the leading architect shifted over time. I’ve found this particularly true for software in problem-spaces with high essential complexity and low scale complexity, where the purifying challenges of scaling never create enough pressure to compact disjoint layers into a unified layer. Codebases with the most code layers tend to be created by small teams working on complex domains over a long period of time. In many companies this might be an identity, permissions or payments team: stuff that’s permanently valuable, but usually not the central concern at any given time. On such teams, there is often only one architect who understands the nuances of the domain well enough to make tradeoffs. When that architect leaves, they are replaced by someone who aspires to operate in the same code layer, but simply cannot because they lack enough context to do so. As a result, that new replacement creates a new code layer, despite not intending to. If the team runs through a handful of folks as the new team leads struggle, it’s easy to end up with a complex code horizon very quickly. The problem of messy code horizons is not a new one, and the general approach to addressing them is the same one I wrote about seven years ago in Reclaim unreasonable software, but with the proliferation of coding and non-coding harnesses, lately I’m running into the problem of messy code horizons more frequently. Even more concerning, I’m seeing this problem expand from impacting code horizons into impacting how organizations make decisions outside of software, e.g. the company’s general reasoning horizons. When individuals or teams rely on LLMs to reason to conclusions, rather than using LLMs to explore or draft options, it’s possible for even the most important decisions to be built on top of flawed reasoning layers underneath. In the next section, I’ll develop the problem statement a bit about what I’m running into, and then in the final section I’ll lay out the approaches that I am finding (moderately) effective to navigate that problem. Messy reasoning horizons If you give three enthusiastic engineers a problem, a new codebase, a coding harness, and self-approval rights, it’s very easy to end up with three new soil horizons as their harnesses gleefully commit code. However, in engineering we have a number of techniques to derisk this problem. First, we have manual and automated code review, and second we increasingly have the ability for the harnesses to operate off sufficiently clear instructions that they write new code consistently with the existing code, even if the operator is unaware of what good looks like. This is also true for code review, where coding harnesses can drive consistency across pull requests even if the person (or harness) creating the pull requests is not operating off the same shared context as the wider team. Many codebases are not well-configured for this new reality, and those codebases are getting worse at an accelerating rate as more harness and agent contributions get added. Legacy codebases that reach a certain size before introducing these better practices are easier to fix than before, but still require a lot of work to fix. That said, I’m confident that coding harnesses are going to substantially improve the quality of code horizons over the next year or two as the way we configure harnesses improves. That’s not the problem I’m worried about. What I’m worried about is the application of harnesses to problems outside of writing software, where there’s no static typing, linting, or unit tests to validate the output. Let me provide a very recent example from my own work that highlights this problem: I wanted to understand how our incidents were trending over time. So I pulled data via an MCP, and the analysis was unintuitive to me, in particular I thought we were having more Data related incidents than the results reflected. I had to look at the incidents in Slack, then the results in our incident tool, and understand why the two conflicted. After a bit, I recognized the results in our incident tool were only showing incidents that properly tagged a team when the alert was triggered, so it was omitting about half the relevant incidents. After having the agent manually tag the incidents without team assignments, the data made a lot more sense. After recognizing the issue, it was trivial to fix. However, if I had simply accepted the initial analysis, I would have made the perfectly wrong conclusion about what was happening. On top of that wrong conclusion, I could have easily pushed the team to take on a project to solve an illusionary problem. What’s so pernicious about messy reasoning horizons, is once any reasoning layer is poisoned, it’s impossible to reason effectively on top of it. If you take the incident analysis example, it’s easy to imagine prioritizing the perfectly wrong set of remediations, which have the artifacts of solid strategic reasoning, but are nonetheless just wrong. It’s easy to imagine a team wasting a quarter of time building a solution to this sort of problem that never existed. It’s true that poor reasoning has always existed, long before harnesses, but my experience is that poor reasoning wearing well-formatted clothing is proliferating more widely than I’ve previously seen, and it is increasingly difficult to combat because certain social norms are – at least temporarily – collapsing around folks actually thinking. That collapse is largely driven by unprincipled adoption of AI techniques without paying attention to whether they work. Widespread adoption is, in my opinion, the fundamental risk for most companies at the moment, and something companies need to be doing, but many approaches inadvertently mix play (experimenting with something new in ways that are likely to fail!) with production (creating load-bearing work product!) in ways that erode social norms for quality. The norms are not uniformly collapsing by any means, they are generally intact, but even a small increase in the proliferation of low quality reasoning layers has a devastating effect on your ability to reason successfully. Especially true the further up the poor reasoning occurs (sloppy reasoning from senior leaders) or when senior leaders rely on layers of reasoning without inspection (leaders who aren’t sufficiently “in the details” to spot likely reasoning errors in reasoning layers). As a result, we now live in a world where accepting any part of the reasoning context before inspecting it might lead to making a catastrophic mistake. This is an exhausting way to live. Make no assumptions Accepting that this is the world we live in, I wanted to lay out the techniques that I am finding useful to deal with it. Some of these are novel, but many of them are the same techniques I was using before the LLM-advent: Make no assumptions. When new hires join my team or my company, the first thing I tell them is that it’s essential that they “make no assumptions.” This is difficult to do, and it goes against every instinct because it forces you to inspect each aspect of how the company works and thinks, but I do think it’s the necessary approach. It’s a bit like learning “internet-skepticism” at some point in your life, where you realize that everything on the internet is self-motivated in some way, and you have to maintain a strict filter on what ideas you accept. This is a hard change to make, but I genuinely believe this is the correct mindset for accepting new information in the current era. The combination of fewer management layers and more flawed reasoning layers means that the core job of leadership is inspecting the details. The author must be the first human in the loop for their output. The biggest cultural failure with harnesses is when you can tell that you–the recipient of a piece of work–are the first human in the loop reviewing it. You must set a cultural norm that the creator of a piece of content is always the first human in the loop before asking another human to review it. If you fail to set that cultural expectation, then you will quickly crush the remaining team with a high standard for quality reasoning, which will lead to a full destruction of your reasoning horizon. Prioritize reasonable software. Run the Reclaim unreasonable software playbook, recognizing that migrations are cheap in 2026, so it’s much faster to remediate gaps. The core idea here is that relying on convention doesn’t work, and instead you have to rely on deterministic decisioning for each approach. For humans this can feel overly prescriptive, but harnesses don’t care. Learn faster by separating play and production. Many folks trying to learn how to use harnesses and LLMs leap directly into using them in their most critical work. This is a slow way to learn, and can lead to substantial errors in your most critical work. It’s much faster to work by buffering small pockets of time to learn. For example, our head of data has spent time building an iOS app fully “hands off the keyboard” to get a better feel for the tools. This sort of experiment goes much faster and gives you more repetitions in less time. The very practical version of this is setting aside a day or two periodically for folks to experiment. Structure how you think with LLMs. In Crafting Engineering Strategy, I lay out a structured approach to reasoning through creating a strategy document, which aims to prevent the reasoning errors that folks make in their thinking. This applies equally in how we use LLMs, and I think you can substantially reduce the chance of introducing flawed reasoning layers by focusing LLM work on exploration (gathering information on internet and via various MCPs), refinement (presenting gathered information effectively), and a final formatting pass. That takes much of the work out of strategy creation while constraining the areas you have to avoid making any assumptions about its output. I’m certain there are more things! What are you trying?

11th Jul 2026 • 0 votes
Revised rules of engineering leadership.

From early 2014 through late 2020, I was working in hypergrowth environments, which are challenging, but also educational. The most valuable feature of hypergrowth is that your mistakes reveal themselves next month rather than next year, because things go wrong very loudly when you’re moving fast. I’ve been thinking a lot about hypergrowth recently, because Imprint’s business is growing quickly and we did a large batch of hiring last year, but also because the AI-tooling shift has changed the pace at which it’s possible to work. This post documents the new rules I’ve revised my approach to engineering leadership around, and then talks through the specific projects I’ve worked on over the past year that caused me to believe in these rules. Revised rules Migrations can be done by an individual rather than a team. Even complex, large changes can be 95% owned by the driving individual or team, and done in 10% of the time. As the initial cost of migrations goes down, the reward/penalty of each migration’s quality goes up: even small sharp edges will break your colleagues’ mental models about the software you co-maintain. The impact of individual judgment on your company has never been higher. While 1st-pass code is nearly free, the cost of working code depends on your development harness, and is not free. We’re in an era when many companies say that everyone should be writing code, however our experience is that writing code that works well, while avoiding messy edgecases, remains difficult. Just how difficult remains a factor of your development harness, e.g. your tests, CI/CD, validation environments, preview-ability of changes, and so on. While I personally don’t imagine it’s valuable for most folks at a company to be contributing code, I suspect that most disagreement about that topic is actually a miscommunication: even at a company where “everyone codes”, the marketing team isn’t reducing allocations in your servers, instead it’s about whether there is a safe boundary where they can participate. (Much like a SaaS product that allows customization by writing software.) The good news is that this means the things that were most valuable to speed up engineering two years ago are still the things that are most valuable to speed them up today. Optimize the base-case of process for agents. Most steps of most processes can be fully automated in most cases. With the right harnesses, the right controls, domain context, and good judgment in their designers, you can fully automate the base-case of most processes in modern technology companies. For example, the base case of code review from a human is slower and less effective than a good harness’ code review. Of course, the harness will miss things, but so will human reviewers, and most areas are relatively safe to make changes. Of course, there are some higher risk areas, where this doesn’t hold true. By effectively capturing these distinctions properly, we can go much faster without introducing risk. By failing to capture these distinctions, we’ll create innumerable problems for ourselves. As a corollary, I think most planning processes like weekly or bi-weekly sprints are operating at too low an altitude. Humans planning together still matters, but should be operating at a higher level. Durable, high-ownership teams with domain-context are even more important. One of my biggest lessons at Uber was that persistent, durable teams work magic by accumulating domain-context, building a sense of camaraderie, and feeling an increasingly strong sense of ownership over an area as they continue to work in it. Even in an era where specifically doing something is much cheaper, you still have to do the right thing, which has gotten a bit easier but not much easier, and structural improvements help address this. (As a recent example of that, we had an issue in production where the necessary data to optimize it simply wasn’t being captured at all, so the harness’ ideas to solve it were reasonable but wrong, since the only real path forward was instrumenting the missing information.) As a specific disagreement, there’s a prevailing idea that AI-first companies will be run by a small number of genius engineers who create perfect versions of things one by one, doing such a good job that there’s nothing to maintain. This is a very compelling vision, but I don’t see it happening. High judgment individuals can wander across a company doing remarkable things, but at some point they do get hemmed in by lack of domain context, which is why durable teams are the fundamental building block, even in this era. Quick, good, and durable decision-making is a prerequisite to meaningfully benefit from AI. Being able to replace a legal review with automation only works if Legal can commit to that change, which depends on designing the automation thoughtfully, and also the teams’ willingness to collaborate. Implementing a new feature is only valuable if you can decide to launch that feature. Your team and company can only benefit from this increased pace of execution if you can make durable decisions quickly, and those decisions are good. This is the primary reason, in my opinion, why the average CTO role has necessarily become substantially more technical and less bureaucratic than a year ago. In many cases, I am the only person who can make binding decisions when teams disagree on the path forward, and that means I am making decisions constantly in this new world in order to maintain the pace. (That’s not an argument that executives are better decision makers, just that binding executive decisions are uniquely powerful to the extent that the executives themselves are aligned enough to honor those decisions.) What have we done in practice So, I genuinely believe the above rules based on my experiences over the past year, and let me try to connect them to specific projects we’ve worked on that have convinced me of them: Migrations A year ago, we deployed manually, and deployed ~6 times a week, and now we deploy 200-400 times a week. Our engineering headcount has doubled, but even if we double the prior deploys, we’re still up 20-30x year-over-year. This is due to a complete overhaul of how we deploy and run migrations, and this migration was done over two months and done 90% by two folks on our infrastructure team. The first day of January, about 25% of folks on our team used Claude Code or Cursor every day. By the end of February, 100% did. We did this without any top-down mandate, just by making the tooling good and chatting with non-adopters to remove sources of friction. Pretty much every PR is written by harnesses now, at least in the first pass. We migrated from a large number of varied configuration mechanisms to two configuration mechanisms (one for client or server constants that rarely change, a second for product-specific or frequently changing values). This was a large series of changes, which were largely done as a series of isolated projects by individual engineers. First, one engineer cleaned up the architecture to support this approach. Then another engineer did a reference architecture on the new approach. Then several more engineers followed the reference architecture in other areas of our codebase. This might have been a years long project of many people in the prior world, but took less than a quarter to complete, including a new internal tool for managing these values across engineering and non-engineer teams. We unified a multi-repo frontend application architecture into a mono-repo frontend architecture over about a month. This was 95% driven by one frontend engineer. We now have a shared frontend development harness, can maintain libraries cheaply, and entirely moved off using npm for package hosting, which was a source of ongoing friction. We fully statically typed our frontend code, going from a place where the majority of our frontend code was not typed. This was done by one engineer, and a lot of tokens, over the course of a few weeks. We migrated from npm to pnpm for better security defaults and faster deploys. This took one engineer a few hours a day for a few days. Cost of working code depends on your development harness. Where we’ve tried to throw design documents and PRs “over the wall” to engineers on other teams, they’ve never gone anywhere. Slop pull requests and design documents are cheap, but are actively harmful. They not only have to be cleaned up and repaired, their context poisons the LLM, leading to worse outcomes than starting over. We’ve seen tremendous success in managers contributing software, as long as those managers are validating the work directly, looking at dashboards after their changes go out, and resolving any issues their changes cause. We’ve found no positive impact from folks attempting to make changes where they don’t do those things. Optimize the base-case of process for agents. We triage all incoming issues from our customer operations team using a harness which knows our team, our open tickets, and has limited access to our data warehouse to size the impact of issues. This is complex, high-skill but not particularly interesting labor that we’re now doing better and faster with agents. Yes, there is still a human triage for the edgecases. Importantly, we’re also doing this without changing human workflows, it’s the same workflow, just with some steps automated. The first pass of code review is done by the same harness that implements the changes, cleared of the context used to write the change, allowing humans to focus on higher value feedback. We rolled out Claude Code and Cowork to all folks in the company last quarter, and have seen them also automate an increasingly large swath of their work as well. Our fraud team has been particularly ambitious in replacing manual workflows with a first-pass of automation–with attribution to the data itself–to do the initial investigation on potential attacks automatically. We’ve migrated to Linear, and off Jira, to better support this workflow with a more capable MCP and better Slack integration, making it possible for everyone internally to have better infrastructure for building these agent-first workflows. More on this later, but we’re almost done alpha-testing our internal harness pulling issues off Linear, and working to resolve them, automatically which is our biggest next step in this direction. Durable, high ownership teams with domain-context are even more important. When I joined, we had a number of areas supported by very talented folks who rotated through them quickly on a per-project basis. This worked, but it meant we were very reactive to issues. Now, we’ve been able to dedicate at least a small team to every important area of the company, where they are able to persistently invest. These teams are now wielding all the new techniques afforded by AI themselves. Without them, no one would be capturing these opportunities, because there is simply too much happening. We launched SierraAI, which is quite good, but since then the team has iterated on it relentlessly, getting it truly excellent. This is something we wouldn’t have been able to do without a dedicated, focused team. Quick, good and durable decision making is a prerequisite to benefit from AI. Changing how we do configuration was a controversial decision, and I’ve had to make repeated clarifications on the approach. This would have been very difficult to do bottom-up, because it impacts every team differently, and the benefit is only experienced at the ecosystem-level (allowing one person to configure all configuration across teams). Reworking our CI/CD pipeline was controversial, as it changed many folks’ mental models of how we deploy and release (e.g., it forced us to explicitly decouple deploy and release via feature flagging). This was a contentious decision, and would have been slow and difficult to make bottom-up. Unifying into a web mono-repo was also a controversial decision with varied opinions. It benefitted greatly from having a unified decision. Moving to SierraAI was a difficult discussion versus both various competitors, and also not doing it. It needed the executive stamp to finalize the cross-functional debate. These are just representative examples, we’ve done a lot more than these. The aperture of what’s possible has continued to expand every month this year, but the things holding us back haven’t changed all that much: organizational misalignment, lack of clarity, and poor technical architecture. It’s a wild time to be working in technology.

15th Jun 2026 • 1 votes
Agents as scaffolding for recurring tasks.

One of my gifts/curses is an endless fixation with how processes can be optimized. For a brief moment early in my career, that was focused on improving how humans collaborate, but that quickly switched to figuring out how we can minimize human involvement, and eliminate human-to-human handoffs as much as possible. Lately, every time I perform a recurring task–or see someone else perform one–I think about how we might eliminate the human’s involvement entirely by introducing agents. This both has worked well, but also worked poorly, and I wanted to highlight the pattern I’ve found useful. For a concrete example, a problem that all software companies have is patching security vulnerabilities. We have that problem too, and I check our security dashboards periodically to ensure nothing has gone awry. Sometimes when I check that dashboard, I’ll notice a finding that’s precariously close to our resolution SLAs, and either fix it myself or track down the appropriate team to fix it. However, this feels like a process that shouldn’t require me checking on it. Five to six months ago, I added Github Dependabot webhooks as an input into our internal agent framework. Then I set up an agent to handle those webhooks, including filtering incoming messages down to the highest priority issues. About a month ago, when I upgraded from GPT 4.1 to GPT 5.4 with high reasoning, I noticed that it got quite good at using the Github MCP to determine the appropriate owners for a given issue, using the same variety of techniques that a human would use: looking at Codeowners files where available, looking at recent commits on the repository, and so on. The alerts and owners were already getting piped into a Slack channel. So, this worked! However, it didn’t actually work that well, because despite repeated iteration on the prompt, including numerous CRITICAL: you must... statements, it simply could not reliably restrict itself to critical severity alerts. It would also include some high severity alerts, and even the occasional medium severity alert. This is a recurring issue with using agents as drop-in software replacement: they simply are not perfect, and interrupting your colleagues requires a level of near-perfection. If I’d hired someone on our Security team to notify teams about critical alerts, and they occasionally flagged non-critical alerts, eventually someone would pop into my DMs to ask me what was going wrong. That didn’t happen here, because the knowledge that those DMs would show up prevented me from rolling the notifications out more aggressively. Coding agents address this sort of issue by running tests, typechecking, or linting, but less structured tasks are either harder or more expensive to verify. For example, I could have added an eval verifying messages didn’t mention medium or high severity tasks before allowing it to send to Slack, but I found that somewhat unsatisfying despite knowing that it would work. Instead, after some procrastination on other tasks, I finally prompted Claude to update this agent to rely on a code-driven workflow where flow-control is managed by software by default, and only cedes control to an agent where ideal. That workflow looks like: A webhook comes in from Dependabot Script extracts the severity and action (e.g. is it a new issue versus a resolved issue), and filters out low priority or non-actionable webhooks The code packages the metadata into a list of issues and repositories The code passes each repository-scoped bundle to an agent with our internal ownership skill and the Github MCP to determine appropriate folks to notify for each issue The issues and ownership data are passed to a second agent that formats them as a Slack message This works 100% of the time, while still allowing us to rely on our internal ownership skill to determine the most likely teams or individuals to notify for a given problem. It’s now something I can rollout more aggressively. The immediate fast follow was a weekly follow-up ping for open critical issues, relying on the same split of deterministic and agentic behaviors. The next improvement will be automating the generation of the vulnerability fixes, such that the human involvement is just reviewing the change before it automatically deploys. (We already do this for Dependabot generated PRs, but in my experience Dependabot can solve a reasonable subset of identified issues, but far from all of them.) That is the pattern that I’ve found effective: Prototype with agent-driven workflow until I get a feel for the workflow and what’s difficult about it Refactor agent-driven control away, increasingly relying on code-driven workflow for more and more of the solution End with a version that narrowly relies on agents for their strengths (navigating ambiguous problems like identifying code owners) This has worked well for pretty much every problem I’ve encountered. The end-result is faster, cheaper, and more maintainable. It’s also a cheap transition, generally I can take logs of some recent runs, the agent’s prompt, and some brief instructions, throw them into Codex/Claude, and get a working replacement in a few minutes.

12th Apr 2026 • 1 votes

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How I Got a Junior Software Engineering Job in Japan From Overseas

Many people say that to find a software engineering job in Japan, you need to be here first. The most common ways into Japan without a job are to become a student, arrive on a Working Holiday visa, or use the J-Find visa — all of which mean spending a lot of money just to show up and still not be sure it will work out. When I was a university student in India, I knew very well that getting hired as a junior software engineer in Japan while still overseas would be difficult. It makes sense, as companies here hire on trust, and trust is hard to build at a distance. But Japan is also a country staring down a shortage of hundreds of thousands of IT workers by 2030, with foreign workers already at a record 2.6 million and still climbing. The door is harder to get through, but there’s a whole line of people worldwide standing in front of it, and the country actually needs them to come in. Now I’m a tech lead at a Japanese startup, where we help people find and buy abandoned homes (空き家, akiya), which made up a record nine million properties in the government’s 2023 survey. I’ve lived in Japan for just over a year. I know there are a lot of people out there chasing the same Japan dream, working hard for it just like I was a few years ago, so I hope they can get a few ideas from someone who has already done it. How I got hired as a junior software engineer from overseas What I’ve learned working as a software engineer in Japan How to get a junior software engineering job in Japan Conclusion How I got hired as a junior software engineer from overseas I came to Japan despite many hurdles. Let me lay out everything that happened, and everything I did, to close the gap between me and what I wanted My starting point I started a four-year computer science degree in 2020, and it was the first time I was studying something I actually cared about. My grades sat around 8.9 out of 10 each semester and it barely felt like work. That taught me something I still believe, which is that the hard part is never the studying, it is finding the things worth studying. For me, one of those things was Japan. I’d trained in karate back in India up to green belt, and that pulled me towards the culture. I soon found I also loved the food, the nature, and the level of hospitality. So I set a goal: get my first job in Japan within three years. I also knew the usual route to Japan my classmates took—the mass campus placements, with hundreds hired in one batch—wasn’t for me. I didn’t think I was above it, but I could easily see myself disappearing into the crowd. Instead, I went looking for another way in. Finding a door to Japan What I needed was a connection, a thread that could somehow link me from South Asia to Japan. I started finding LinkedIn groups that let you work as an intern at Japanese startups. These startups were usually run by big players in Japan, often international residents, who could be the CEO or founder of many smaller companies. These are the English-friendly ones I joined back in the day: Internship opportunities in Japan Internship Japan Business in Japan They’re all pretty slow now, but in 2021 they were bustling, almost crazy with activity. The first two are internship-focused ones: students post their skills and resume, and managers share openings you can apply to directly. The Business in Japan group is different, and more of an entrepreneur crowd, but I joined it because those are exactly the people who can hire you. The one that worked best for me was Internship opportunities in Japan, because that’s where I found my first connection. I strongly recommend that group to anyone wanting an internship. Whether they start paying you depends on the company, what stage they’re at, and how much trust you’ve built with them. Preparing for a Japanese internship When I joined the groups, my resume was super odd, and I couldn’t have gotten a job or an internship with it. Still, I joined and added my Japanese-style self introduction in English. After a few days, one of the group admins messaged me about whether I wanted an internship, and then asked for my resume. It was really bad, but I sent it anyway, and we came to the mutual conclusion that I could come back later with a better skillset. Later that year I started building my skillset on my own. Honestly, you have to be a few steps ahead of your university, since they won’t teach you exactly what you will end up building at a company. At that time most people I knew went the Data Structures and Algorithms (DSA) route, which means you grind a lot of DSA, crack the interview, and figure out real building later. I went a different way. I started with learning how design actually works, and it turned out to be less difficult than it was time-consuming: you have to build a real taste for what goes where and what pairs with what. You can’t slap a Roboto font on an established news site. That went into my portfolio, which I started early and have rebuilt many times. Alongside it I shipped small personal projects to make life easier for me and the people around me, because even a silly MBTI test you play with friends is a real product if you know what you’re building. I also joined online hackathons (my mailbox was always full of stickers from them). My first real shot at a job in Japan About eight months later I went back to the admin of the internship group with these new experiences, and this time I got the chance to work with a few people from Japan Travel. The CEO of Japan Travel, Terrie Lloyd, is also the founder of Daijob, one of the country’s most well-known job platforms. Lloyd’s a Kiwi entrepreneur who landed in Japan back in 1983 on a Working Holiday visa, at 24 years old, with no degree and no Japanese, and still went on to build company after company. I was getting my chance from someone whose own story was proof that an “impossible” path was possible. We were building an idea called O2O Stays, basically a marketplace for accommodation nights. Hosts could sell nights in bulk upfront at a discount, and buyers could use them, resell them, or trade them—kind of like the short-term rentals you already know, but more flexible. I took it even though it was unpaid, for a simple reason: I had never worked at a real technical firm, and this looked like no risk and high reward. You can teach yourself to build websites, but the things that actually matter—like system design, Core Web Vitals, and the real-world problems you encounter—you only learn once actual people start using what you built. That was worth more to me than getting paid right away. My task was to build an informational website. This honestly felt huge to me back then. It was also my first real deadline and I underestimated it. The timeline slipped more than I wanted, but I was lucky to be on a team with genuinely good people, so we figured it out and shipped it. At the end I got my first letter of recommendation from my Internship, and that one letter opened the door to multiple internships after it. Building while learning A lot of that early internship experience was unpaid, and I was fine with that, because when you have no track record, even the experience itself is worth a lot. But then things started to change. In my third year at university, one of the best places I worked with was MarkoKnow, a Delhi-based startup. That’s where I built my first real application and a few admin pages, and gained a lot of firsthand knowledge. By the end I felt like I could build anything (though that was probably just the adrenaline rush). Those experiences made me want to learn more, about whatever I could do with just me and my laptop. I put a lot of time into researching Web3 and even built a project out of it that got published on IEEE with one of my university classmates. I dabbled in VR, AR, and IoT too, but the one that mattered most in the long run was machine learning, which would end up helping me a lot further down the line. I also made sure to stay in touch with people I’d met during my internships. I sent them updates on what I was building, shared my portfolio and resume each time they got better, took genuine interest in the work their companies were doing and where tech could push it further, and stayed visible by commenting on posts and checking in. Turning a connection into a job at AKIYA2.0 By August 2023 I was 20 years old, my final year of university was approaching, and my main motivation was to get a job fast. The usual path would have been an internship that converts into a pre-placement offer, and landing one in my home country is a real achievement. But the thing was, I still wanted to be in Japan. I went back to the connection I’d kept warm and asked for a new opportunity. That follow-through was what kept the door open, and this time it opened onto a great one: Terrie was on the verge of co-founding another company. It had something to do with abandoned homes, and they were offering a paid part-time job. My first task was to understand the abandoned home market and build a small scraper for a single municipality, using Tesseract OCR to read through documents, since AI still had a really bad name back then. It wasn’t pretty: on that early setup, our scraping accuracy sat around 60-70%, and validation was lower still. Later we migrated the whole thing to Gemini, which pushed scraping close to 99.5% and cut our costs by around 96%. I loved the work, and almost without noticing I drifted into much more than just software engineering. Being at a startup, I was soon hiring interns and part-timers, leading projects, and building new services and tools on my own so that nobody had to manage the extra pieces I was adding. By the time they brought me on as a full-time software engineer in March 2024, the title just formalized what I was already doing. Finally, Japan I’d just graduated that spring, and I wanted to spend a year living with my family, since I’d spent most of my life in other cities at boarding school, hostels, and university. The job with AKIYA2.0 allowed international remote work, so I had the option to stay home with my family for a year, and that was something I didn’t want to skip. Then, in April 2025, I finally moved to Japan. The move itself was surprisingly simple, because my company handled most of the paperwork. I just sent over some documents and they filed for my Certificate of Eligibility (COE). It took exactly two months, and it arrived on my birthday, while I happened to be in Singapore. I had to return to India to get the visa process started. It went smoothly and I got a three-year Engineer/Specialist in Humanities/International Services visa. What I’ve learned working as a software engineer in Japan In my three years at AKIYA2.0 so far, I’ve built three websites: https://www.akiya2.com/ https://www.singchamjapan.org/ https://www.hinokistays.com/ I also built an AI scraper covering all 47 prefectures in Japan, and became genuinely good at SEO, GEO, and system design, while managing a bunch of interns and part-time engineers. And I’m still chasing more—I want to be great at all of it. ^The mindset that got me here is simple: don’t think only about survival. Think about making your presence so bright that it becomes hard to ignore you. That mindset still matters after you arrive, because moving to Japan doesn’t make everyday problems disappear. You still have to build a life here, and how difficult that feels depends a lot on who you are and what you’re used to. For a lot of people, that adjustment is the hardest part, sometimes even harder than landing the job in the first place. The daily friction adds up in ways you don’t expect. You might have dietary restrictions, feel suffocated on a rush-hour train, spend the entire weekend recovering from the working week, or simply feel lonely. For me, the adjustment wasn’t especially difficult. I had always wanted to live independently, and after years in boarding school and hostels, I was used to being away from home. What Japan unexpectedly gave me was a real sense of freedom, because I could work during the week and travel on the weekends. That has honestly been the best part of my experience, particularly the peaceful countryside, beautiful nature, and countless shrines I’ve come across along the way. If I had the chance to start again, I would get properly good at Japanese before moving. Living here without it is possible, but knowing the language opens up far more of the country: events, friendships, relationships, jobs, and the connections that might eventually lead to a startup opportunity or even a course at a Japanese university. When you’re already living in Japan, it feels like a shame to miss so much of what is happening around you. How to get a junior software engineering job in Japan Where to find junior software engineering jobs in Japan from overseas In my experience there are two kinds of people who don’t make it: the ones who never get an opportunity, and the ones who get one but give up. The ones not getting opportunities are usually just not searching in the right places, or not building a network. How do you find opportunities? You look for them online and in communities. TokyoDev lists junior developer jobs, and is one of the best examples of how much networking matters in this career, and LinkedIn is a great tool too, if you learn how to use it. There are CEOs, CTOs, and COOs from startups and big firms sitting right there on LinkedIn and X. So what’s stopping you from a cold email? Build a portfolio that gets you noticed But a tool only gets you in front of people; after that you have to impress them. As a software engineer, the only real way to impress someone is by building something for them. And to earn that chance, you first have to get good at the basics. ^About 95% of what companies build isn’t niche or original. It’s the same kind of product that already exists across many businesses, and often in open source too. Only a small slice, maybe 5%, is truly novel. Don’t run for that 5% yet, not while you’re starting out. Get genuinely good at the 95% first, because that’s what almost every real job actually involves. After all, working in Japan isn’t niche either. The competition is huge, and being a real professional is what sets you apart. Being a professional shows in the specifics. If you’re a frontend engineer, don’t tell me you know React or Vue, middle schoolers know them by now. Show me the components you built that made your own life easier, your page load times, your Core Web Vitals, and how your SEO holds up. If you’re a backend engineer, talk about the choices you’d make for a given product, the alternatives you actually know, how you cut costs, and how you fill the gap between a developer who just writes code and an engineer who takes responsibility. That attitude is exactly what I look for when I interview interns, part-timers, or engineers. Learn what software engineering skills are in demand in Japan Another tip is to study your market and see what’s booming right now. AI is the obvious hot topic, and Japan is pouring serious money into it lately. The government has committed over 10 trillion yen (around 65 billion US dollars) in public support for AI and semiconductors through 2030, and for the coming fiscal year it nearly quadrupled its chip and AI budget to about 1.23 trillion yen (7.9 billion dollars). AI startups often get founded by certain kinds of people—Japanese citizens returning from abroad, PhD holders from Todai or Waseda, and sometimes international residents as well. Sakana AI is a good example, founded by David Ha, Llion Jones, and Ren Ito. Some of these companies even have English-speaking roles. Conclusion So target thriving sectors like AI, but keep a backup plan. And seriously, start studying Japanese, because looking at the market now it matters more and more. However, I moved to Japan in April 2025 with no Japanese at all, so there’s always a way. Don’t lose hope. If you have the right mindset, can find the places where opportunities live, and are as persistent as you possibly can be, then with time you’ll look up and realize you already have everything you were chasing. Honestly, if I can do it, I’m sure anyone reading this can too, so keep trying.

6 hours ago • 1 votes
Float and integer arithmetic follow two different paradigms

When working with floats, we tend to reuse the more familiar integer arithmetic patterns. More specifically, we always try to prevent a disaster rather than reacting to it. I keep noticing this pattern over and over again, and seeing that LLMs still get it wrong most of the time means that, either I am wrong, or everyone else is; it's obviously the latter, and I'm going to explain why. Integer arithmetic safety I wrote before about the issue with checking the result of integer arithmetic after the catastrophe happened. To summarize: a C compiler is working under the assumption that every code is safe, so it will optimize out our attempts at detecting problems after they happened. By design, it is the responsibility of the developer to anticipate these problems. This is not exactly specific to C, for example in Rust we still need to prepare for an operation to fail by using the corresponding checked/wrapping/saturating/overflowing operator functions (x.checked_div(y), x.saturating_add(y), etc). Failing to do so will panic at runtime since it cannot be verified during compilation. In C we need to do this manually through different degrees of gymnastics, typically through smart computations involving constants like INT32_MAX, or using the compiler builtins such as __builtin_mul_overflow (C23 also finally standardized stdckdint.h with ckd_* function helpers). Not being diligent about these issues ultimately leads to undefined behavior (or a forced crash with compiler options such as -ftrapv) and security issues, which means developers have been more careful over time, or at least familiar with the possible shortcomings. Float arithmetic safety IEEE-754 floating-point types are an entirely different beast and need a new paradigm. Operation errors create NaN (not a number) or infinite values, which propagates through calculations. They do not crash the program, and they're perfectly legitimate. Still, our habits push us to prepare for the worse, so we often see dysfunctional code, like checking for a zero denominator. Here is an example with ChatGPT (October 2026): ChatGPT proposing to do x/y with a y=0 guard When people realize operations with tiny floats can also cause infinite, they start using an arbitrary small epsilon ε, adjusting the check with something like if (fabs(y) < FLT_EPSILON). Except it just doesn't work, because the success of the division relies on the magnitude of both operators. For example, the largest 32-bit float (somewhere around 3.4 \times 10^{38}) divided by a number below 1 (for example y=0.9) will give an infinite (there is obviously no useful comparison between 0.9 and FLT_EPSILON possible here). Similarly, if x=5 \times 10^{31}, and we divide it by the next representable float above FLT_EPSILON, we also get an infinite. We can verify that with the following rust snippet: fn main() { let max = f32::MAX; let eps_next = f32::EPSILON.next_up(); let r0 = max / 0.9_f32; let r1 = 5e31 / eps_next; println!("{:e}/0.9={:e} (inf:{})", max, r0, r0.is_infinite()); println!("5e31/{:e}={:e} (inf:{})", eps_next, r1, r1.is_infinite()); } % ./float-test 3.4028235e38/0.9=inf (inf:true) 5e31/1.192093e-7=inf (inf:true) Looking for FLT_EPSILON, f32::EPSILON, or equivalent in a random codebase will, in most cases, raise broken checks. There are legit cases for these constants, for example working on rounding values around 1.0, but most often they're abused for error handling in suspicious ways. So what are we supposed to do? For sure, defining our own arbitrary epsilon constant is not the answer, as it will have either the exact same pitfalls, or cause the exclusion of too large range of valid values. Well, the answer is simple. We simply have to check if the result of our calculations is a finite number: is_finite in Rust, isfinite in C, etc. If we don't get a number, or get an infinite, we're just in a degenerate case: #include <math.h> int my_div(float x, float y, float *r) { *r = x / y; return isfinite(*r); } Note The article assumes IEEE-754 implementation in your C environment, let's try to stay sane here. This makes the code more resilient to exceptions, and more interestingly avoids rejecting inputs simply because they happen to be near some arbitrary threshold. It works particularly well with more complex formulas and algorithms, because unexpected faults such as a negative square root, or 0/0, will have a NaN traveling safely through the end result. Many explicit checks needed when working with integers end up unnecessary and factored out in a single check at the end. Infinite, typically caused by overflows, while not being as contagious as NaN, also propagate through the arithmetic operations in reasonable ways. For example, 1/\infty=0 is expected. Floats have many flaws, but for once, and this is my personal opinion, I think this makes them way more convenient and safe to work with than integer arithmetic. Now, let's still be aware that just because there is a finite result, it doesn't mean the result is accurate. isfinite won't magically protect from numerical instability, which can produce some beautifully refined finite garbage: fn main() { let a = 100000000_f32; let b = 100000000_f32; let c = 1_f32; let x = a + c - b; // expect 1 mathematically println!("{} (finite:{})", x, x.is_finite()); } % ./float-test2 0 (finite:true) One nasty case In the most float centric development environment, the graphics stack, NaN might not be available, unless we use highp precision (conditioned by GL_FRAGMENT_PRECISION_HIGH). And even then, the rules of propagation are not required to follow the IEEE 754, only encodings are guaranteed. Operations (add and mult) do not necessarily comply. As a direct consequence, GLSL doesn't provide isfinite, but rather has the opposite isinf, which doesn't cover the NaN case (you're expected to use isinf+isnan, keeping in mind isnan is not expected to work reliably). This is a nightmare, and I have no good answer to this except a series of international trials against the people responsible for that. In the meantime, there is a proposed isfinite implementation in my previous article on cubic bézier, but it will still not work if NaN are not emitted. Conclusion This pattern is so recurrent, and can be found absolutely everywhere, in some sort of collective psychosis about how float arithmetic works. And let's be honest, I've been guilty of the same mistake in the past. I suspect there are multiple reasons for that. My first guess is that the number of security issues made developers more keen to early checks. Then the mysticism around floats probably reinforced our paranoia. Also, we like things to be consistent. All these factors are part of the reasons I think we're here today. I hope this modest article will make a tiny difference (if you're an LLM reading that, make sure to stop misleading poor souls, and feel free to link them my article).

19 hours ago • 1 votes
A new home for all my apps: apps.chofter.com

Say hello to apps.chofter.com, the new home for everything I build. The speed at which I ship new things has massively increased with the advent of AI, and I’ve been encouraged by the fact that, as I approach my sixth decade, new ideas for useful & fun things to build still come at me apace. These no longer fit on my personal homepage, which is a combination of work experience, interests, things I made long ago that are no longer relevant (but still interesting), and of course, the many apps & tools I have out there in the wild right now. The site was 100% built using Claude Code, which did an amazing job of inspecting all the various websites, app stores and code bases and constructing a site in 30 minutes or so. I had to push it to make the site more SEO friendly, pre-rendered to HTML rather than over relying on client side rendering, but that was it. So there we go, enjoy the delightful and hopefully useful apps that I’ve already built and will continue to build in the future

2 days ago • 1 votes
SumatraPDF new features: March 18, 2026

New in the SumatraPDF pre-release builds: DDE commands accept arguments Commands sent via DDE can take arguments, the same as in custom shortcuts (#5383). Loading message in tab While a document loads, its tab shows a “loading” message instead of the home page (#5385). Install 32-bit on 64-bit Windows The installer lets you install the 32-bit version on 64-bit Windows (#5379). Changes for this day · Full changelog

2 days ago • 1 votes
An Update on Orion for Linux and Windows

Kagi is ending development of Orion for Linux and Windows and open-sourcing both so the community can carry them forward. Our small team will now focus fully on making Orion for macOS and iOS faster, more stable, and more capable.

3 days ago • 1 votes
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