I’ve been working on a project where I need to plot points on a map. I don’t need an interactive or dynamic visualisation – just a static map with coloured dots for each coordinate. I’ve created maps on the web using Leaflet.js, which load map data from OpenStreetMap (OSM) and support zooming and panning – but for this project, I want a standalone image rather than something I embed in a web page. I want to put in coordinates, and get a PNG image back. This feels like it should be straightforward. There are lots of Python libraries for data visualisation, but it’s not an area I’ve ever explored in detail. I don’t know how to use these libraries, and despite trying I couldn’t work out how to accomplish this seemingly simple task. I made several attempts with libraries like matplotlib and plotly, but I felt like I was fighting the tools. Rather than persist, I wrote my own solution with “lower level” tools. The key was a page on the OpenStreetMap wiki explaining how to convert lat/lon coordinates into the pixel system used by OSM tiles. In particular, it allowed me to break the process into two steps: Get a “base map” image that covers the entire world Convert lat/lon coordinates into xy coordinates that can be overlaid on this image Let’s go through those steps. Get a “base map” image that covers the entire world Let’s talk about how OpenStreetMap works, and in particular their image tiles. If you start at the most zoomed-out level, OSM represents the entire world with a single 256×256 pixel square. This is the Web Mercator projection, and you don’t get much detail – just a rough outline of the world. We can zoom in, and this tile splits into four new tiles of the same size. There are twice as many pixels along each edge, and each tile has more detail. Notice that country boundaries are visible now, but we can’t see any names yet. We can zoom in even further, and each of these tiles split again. There still aren’t any text labels, but the map is getting more detailed and we can see small features that weren’t visible before. You get the idea – we could keep zooming, and we’d get more and more tiles, each with more detail. This tile system means you can get detailed information for a specific area, without loading the entire world. For example, if I’m looking at street information in Britain, I only need the detailed tiles for that part of the world. I don’t need the detailed tiles for Bolivia at the same time. OpenStreetMap will only give you 256×256 pixels at a time, but we can download every tile and stitch them together, one-by-one. Here’s a Python script that enumerates all the tiles at a particular zoom level, downloads them, and uses the Pillow library to combine them into a single large image: #!/usr/bin/env python3 """ Download all the map tiles for a particular zoom level from OpenStreetMap, and stitch them into a single image. """ import io import itertools import httpx from PIL import Image zoom_level = 2 width = 256 * 2**zoom_level height = 256 * (2**zoom_level) im = Image.new("RGB", (width, height)) for x, y in itertools.product(range(2**zoom_level), range(2**zoom_level)): resp = httpx.get(f"https://tile.openstreetmap.org/{zoom_level}/{x}/{y}.png", timeout=50) resp.raise_for_status() im_buffer = Image.open(io.BytesIO(resp.content)) im.paste(im_buffer, (x * 256, y * 256)) out_path = f"map_{zoom_level}.png" im.save(out_path) print(out_path) The higher the zoom level, the more tiles you need to download, and the larger the final image will be. I ran this script up to zoom level 6, and this is the data involved: Zoom level Number of tiles Pixels File size 0 1 256×256 17.1 kB 1 4 512×512 56.3 kB 2 16 1024×1024 155.2 kB 3 64 2048×2048 506.4 kB 4 256 4096×4096 2.7 MB 5 1,024 8192×8192 13.9 MB 6 4,096 16384×16384 46.1 MB I can just about open that zoom level 6 image on my computer, but it’s struggling. I didn’t try opening zoom level 7 – that includes 16,384 tiles, and I’d probably run out of memory. For most static images, zoom level 3 or 4 should be sufficient – I ended up a base map from zoom level 4 for my project. It takes a minute or so to download all the tiles from OpenStreetMap, but you only need to request it once, and then you have a static image you can use again and again. This is a particularly good approach if you want to draw a lot of maps. OpenStreetMap is provided for free, and we want to be a respectful user of the service. Downloading all the map tiles once is more efficient than making repeated requests for the same data. Overlay lat/lon coordinates on this base map Now we have an image with a map of the whole world, we need to overlay our lat/lon coordinates as points on this map. I found instructions on the OpenStreetMap wiki which explain how to convert GPS coordinates into a position on the unit square, which we can in turn add to our map. They outline a straightforward algorithm, which I implemented in Python: import math def convert_gps_coordinates_to_unit_xy( *, latitude: float, longitude: float ) -> tuple[float, float]: """ Convert GPS coordinates to positions on the unit square, which can be plotted on a Web Mercator projection of the world. This expects the coordinates to be specified in **degrees**. The result will be (x, y) coordinates: - x will fall in the range (0, 1). x=0 is the left (180° west) edge of the map. x=1 is the right (180° east) edge of the map. x=0.5 is the middle, the prime meridian. - y will fall in the range (0, 1). y=0 is the top (north) edge of the map, at 85.0511 °N. y=1 is the bottom (south) edge of the map, at 85.0511 °S. y=0.5 is the middle, the equator. """ # This is based on instructions from the OpenStreetMap Wiki: # https://wiki.openstreetmap.org/wiki/Slippy_map_tilenames#Example:_Convert_a_GPS_coordinate_to_a_pixel_position_in_a_Web_Mercator_tile # (Retrieved 16 January 2025) # Convert the coordinate to the Web Mercator projection # (https://epsg.io/3857) # # x = longitude # y = arsinh(tan(latitude)) # x_webm = longitude y_webm = math.asinh(math.tan(math.radians(latitude))) # Transform the projected point onto the unit square # # x = 0.5 + x / 360 # y = 0.5 - y / 2π # x_unit = 0.5 + x_webm / 360 y_unit = 0.5 - y_webm / (2 * math.pi) return x_unit, y_unit Their documentation includes a worked example using the coordinates of the Hachiko Statue. We can run our code, and check we get the same results: >>> convert_gps_coordinates_to_unit_xy(latitude=35.6590699, longitude=139.7006793) (0.8880574425, 0.39385379958274735) Most users of OpenStreetMap tiles will use these unit positions to select the tiles they need, and then dowload those images – but we can also position these points directly on the global map. I wrote some more Pillow code that converts GPS coordinates to these unit positions, scales those unit positions to the size of the entire map, then draws a coloured circle at each point on the map. Here’s the code: from PIL import Image, ImageDraw gps_coordinates = [ # Hachiko Memorial Statue in Tokyo {"latitude": 35.6590699, "longitude": 139.7006793}, # Greyfriars Bobby in Edinburgh {"latitude": 55.9469224, "longitude": -3.1913043}, # Fido Statue in Tuscany {"latitude": 43.955101, "longitude": 11.388186}, ] im = Image.open("base_map.png") draw = ImageDraw.Draw(im) for coord in gps_coordinates: x, y = convert_gps_coordinates_to_unit_xy(**coord) radius = 32 draw.ellipse( [ x * im.width - radius, y * im.height - radius, x * im.width + radius, y * im.height + radius, ], fill="red", ) im.save("map_with_dots.png") and here’s the map it produces: The nice thing about writing this code in Pillow is that it’s a library I already know how to use, and so I can customise it if I need to. I can change the shape and colour of the points, or crop to specific regions, or add text to the image. I’m sure more sophisticated data visualisation libraries can do all this, and more – but I wouldn’t know how. The downside is that if I need more advanced features, I’ll have to write them myself. I’m okay with that – trading sophistication for simplicity. I didn’t need to learn a complex visualization library – I was able to write code I can read and understand. In a world full of AI-generating code, writing something I know I understand feels more important than ever. [If the formatting of this post looks odd in your feed reader, visit the original article]

This is a re-publishing of a blog post I originally wrote for work, but wanted on my own blog as well. AI is everywhere, and its impressive claims are leading to rapid adoption. At this stage, I’d qualify it as charismatic technology—something that under-delivers on what it promises, but promises so much that the industry still leverages it because we believe it will eventually deliver on these claims. This is a known pattern. In this post, I’ll use the example of automation deployments to go over known patterns and risks in order to provide you with a list of questions to ask about potential AI solutions. I’ll first cover a short list of base assumptions, and then borrow from scholars of cognitive systems engineering and resilience engineering to list said criteria. At the core of it is the idea that when we say we want humans in the loop, it really matters where in the loop they are. My base assumptions The first thing I’m going to say is that we currently do not have Artificial General Intelligence (AGI). I don’t care whether we have it in 2 years or 40 years or never; if I’m looking to deploy a tool (or an agent) that is supposed to do stuff to my production environments, it has to be able to do it now. I am not looking to be impressed, I am looking to make my life and the system better. Another mechanism I want you to keep in mind is something called the context gap. In a nutshell, any model or automation is constructed from a narrow definition of a controlled environment, which can expand as it gains autonomy, but remains limited. By comparison, people in a system start from a broad situation and narrow definitions down and add constraints to make problem-solving tractable. One side starts from a narrow context, and one starts from a wide one—so in practice, with humans and machines, you end up seeing a type of teamwork where one constantly updates the other: The optimal solution of a model is not an optimal solution of a problem unless the model is a perfect representation of the problem, which it never is.  — Ackoff (1979, p. 97) Because of that mindset, I will disregard all arguments of “it’s coming soon” and “it’s getting better real fast” and instead frame what current LLM solutions are shaped like: tools and automation. As it turns out, there are lots of studies about ergonomics, tool design, collaborative design, where semi-autonomous components fit into sociotechnical systems, and how they tend to fail. Additionally, I’ll borrow from the framing used by people who study joint cognitive systems: rather than looking only at the abilities of what a single person or tool can do, we’re going to look at the overall performance of the joint system. This is important because if you have a tool that is built to be operated like an autonomous agent, you can get weird results in your integration. You’re essentially building an interface for the wrong kind of component—like using a joystick to ride a bicycle. This lens will assist us in establishing general criteria about where the problems will likely be without having to test for every single one and evaluate them on benchmarks against each other. Questions you'll want to ask The following list of questions is meant to act as reminders—abstracting away all the theory from research papers you’d need to read—to let you think through some of the important stuff your teams should track, whether they are engineers using code generation, SREs using AIOps, or managers and execs making the call to adopt new tooling. Are you better even after the tool is taken away? An interesting warning comes from studying how LLMs function as learning aides. The researchers found that people who trained using LLMs tended to fail tests more when the LLMs were taken away compared to people who never studied with them, except if the prompts were specifically (and successfully) designed to help people learn. Likewise, it’s been known for decades that when automation handles standard challenges, the operators expected to take over when they reach their limits end up worse off and generally require more training to keep the overall system performant. While people can feel like they’re getting better and more productive with tool assistance, it doesn’t necessarily follow that they are learning or improving. Over time, there’s a serious risk that your overall system’s performance will be limited to what the automation can do—because without proper design, people keeping the automation in check will gradually lose the skills they had developed prior. Are you augmenting the person or the computer? Traditionally successful tools tend to work on the principle that they improve the physical or mental abilities of their operator: search tools let you go through more data than you could on your own and shift demands to external memory, a bicycle more effectively transmits force for locomotion, a blind spot alert on your car can extend your ability to pay attention to your surroundings, and so on. Automation that augments users therefore tends to be easier to direct, and sort of extends the person’s abilities, rather than acting based on preset goals and framing. Automation that augments a machine tends to broaden the device’s scope and control by leveraging some known effects of their environment and successfully hiding them away. For software folks, an autoscaling controller is a good example of the latter. Neither is fundamentally better nor worse than the other—but you should figure out what kind of automation you’re getting, because they fail differently. Augmenting the user implies that they can tackle a broader variety of challenges effectively. Augmenting the computers tends to mean that when the component reaches its limits, the challenges are worse for the operator. Is it turning you into a monitor rather than helping build an understanding? If your job is to look at the tool go and then say whether it was doing a good or bad job (and maybe take over if it does a bad job), you’re going to have problems. It has long been known that people adapt to their tools, and automation can create complacency. Self-driving cars that generally self-drive themselves well but still require a monitor are not effectively monitored. Instead, having AI that supports people or adds perspectives to the work an operator is already doing tends to yield better long-term results than patterns where the human learns to mostly delegate and focus elsewhere. (As a side note, this is why I tend to dislike incident summarizers. Don’t make it so people stop trying to piece together what happened! Instead, I prefer seeing tools that look at your summaries to remind you of items you may have forgotten, or that look for linguistic cues that point to biases or reductive points of view.) Does it pigeonhole what you can look at? When evaluating a tool, you should ask questions about where the automation lands: Does it let you look at the world more effectively? Does it tell you where to look in the world? Does it force you to look somewhere specific? Does it tell you to do something specific? Does it force you to do something? This is a bit of a hybrid between “Does it extend you?” and “Is it turning you into a monitor?” The five questions above let you figure that out. As the tool becomes a source of assertions or constraints (rather than a source of information and options), the operator becomes someone who interacts with the world from inside the tool rather than someone who interacts with the world with the tool’s help. The tool stops being a tool and becomes a representation of the whole system, which means whatever limitations and internal constraints it has are then transmitted to your users. Is it a built-in distraction? People tend to do multiple tasks over many contexts. Some automated systems are built with alarms or alerts that require stealing someone’s focus, and unless they truly are the most critical thing their users could give attention to, they are going to be an annoyance that can lower the effectiveness of the overall system. What perspectives does it bake in? Tools tend to embody a given perspective. For example, AIOps tools that are built to find a root cause will likely carry the conceptual framework behind root causes in their design. More subtly, these perspectives are sometimes hidden in the type of data you get: if your AIOps agent can only see alerts, your telemetry data, and maybe your code, it will rarely be a source of suggestions on how to improve your workflows because that isn’t part of its world. In roles that are inherently about pulling context from many disconnected sources, how on earth is automation going to make the right decisions? And moreover, who’s accountable for when it makes a poor decision on incomplete data? Surely not the buyer who installed it! This is also one of the many ways in which automation can reinforce biases—not just based on what is in its training data, but also based on its own structure and what inputs were considered most important at design time. The tool can itself become a keyhole through which your conclusions are guided. Is it going to become a hero? A common trope in incident response is heroes—the few people who know everything inside and out, and who end up being necessary bottlenecks to all emergencies. They can’t go away for vacation, they’re too busy to train others, they develop blind spots that nobody can fix, and they can’t be replaced. To avoid this, you have to maintain a continuous awareness of who knows what, and crosstrain each other to always have enough redundancy. If you have a team of multiple engineers and you add AI to it, having it do all of the tasks of a specific kind means it becomes a de facto hero to your team. If that’s okay, be aware that any outages or dysfunction in the AI agent would likely have no practical workaround. You will essentially have offshored part of your ops. Do you need it to be perfect? What a thing promises to be is never what it is—otherwise AWS would be enough, and Kubernetes would be enough, and JIRA would be enough, and the software would work fine with no one needing to fix things. That just doesn’t happen. Ever. Even if it’s really, really good, it’s gonna have outages and surprises, and it’ll mess up here and there, no matter what it is. We aren’t building an omnipotent computer god, we’re building imperfect software. You’ll want to seriously consider whether the tradeoffs you’d make in terms of quality and cost are worth it, and this is going to be a case-by-case basis. Just be careful not to fix the problem by adding a human in the loop that acts as a monitor! Is it doing the whole job or a fraction of it? We don’t notice major parts of our own jobs because they feel natural. A classic pattern here is one of AIs getting better at diagnosing patients, except the benchmarks are usually run on a patient chart where most of the relevant observations have already been made by someone else. Similarly, we often see AI pass a test with flying colors while it still can’t be productive at the job the test represents. People in general have adopted a model of cognition based on information processing that’s very similar to how computers work (get data in, think, output stuff, rinse and repeat), but for decades, there have been multiple disciplines that looked harder at situated work and cognition, moving past that model. Key patterns of cognition are not just in the mind, but are also embedded in the environment and in the interactions we have with each other. Be wary of acquiring a solution that solves what you think the problem is rather than what it actually is. We routinely show we don’t accurately know the latter. What if we have more than one? You probably know how straightforward it can be to write a toy project on your own, with full control of every refactor. You probably also know how this stops being true as your team grows. As it stands today, a lot of AI agents are built within a snapshot of the current world: one or few AI tools added to teams that are mostly made up of people. By analogy, this would be like everyone selling you a computer assuming it were the first and only electronic device inside your household. Problems arise when you go beyond these assumptions: maybe AI that writes code has to go through a code review process, but what if that code review is done by another unrelated AI agent? What happens when you get to operations and common mode failures impact components from various teams that all have agents empowered to go fix things to the best of their ability with the available data? Are they going to clash with people, or even with each other? Humans also have that ability and tend to solve it via processes and procedures, explicit coordination, announcing what they’ll do before they do it, and calling upon each other when they need help. Will multiple agents require something equivalent, and if so, do you have it in place? How do they cope with limited context? Some changes that cause issues might be safe to roll back, some not (maybe they include database migrations, maybe it is better to be down than corrupting data), and some may contain changes that rolling back wouldn’t fix (maybe the workload is controlled by one or more feature flags). Knowing what to do in these situations can sometimes be understood from code or release notes, but some situations can require different workflows involving broader parts of the organization. A risk of automation without context is that if you have situations where waiting or doing little is the best option, then you’ll need to either have automation that requires input to act, or a set of actions to quickly disable multiple types of automation as fast as possible. Many of these may exist at the same time, and it becomes the operators’ jobs to not only maintain their own context, but also maintain a mental model of the context each of these pieces of automation has access to. The fancier your agents, the fancier your operators’ understanding and abilities must be to properly orchestrate them. The more surprising your landscape is, the harder it can become to manage with semi-autonomous elements roaming around. After an outage or incident, who does the learning and who does the fixing? One way to track accountability in a system is to figure out who ends up having to learn lessons and change how things are done. It’s not always the same people or teams, and generally, learning will happen whether you want it or not. This is more of a rhetorical question right now, because I expect that in most cases, when things go wrong, whoever is expected to monitor the AI tool is going to have to steer it in a better direction and fix it (if they can); if it can’t be fixed, then the expectation will be that the automation, as a tool, will be used more judiciously in the future. In a nutshell, if the expectation is that your engineers are going to be doing the learning and tweaking, your AI isn’t an independent agent—it’s a tool that cosplays as an independent agent. Do what you will—just be mindful All in all, none of the above questions flat out say you should not use AI, nor where exactly in the loop you should put people. The key point is that you should ask that question and be aware that just adding whatever to your system is not going to substitute workers away. It will, instead, transform work and create new patterns and weaknesses. Some of these patterns are known and well-studied. We don’t have to go rushing to rediscover them all through failures as if we were the first to ever automate something. If AI ever gets so good and so smart that it’s better than all your engineers, it won’t make a difference whether you adopt it only once it’s good. In the meanwhile, these things do matter and have real impacts, so please design your systems responsibly. If you’re interested to know more about the theoretical elements underpinning this post, the following references—on top of whatever was already linked in the text—might be of interest: Books: Joint Cognitive Systems: Foundations of Cognitive Systems Engineering by Erik Hollnagel Joint Cognitive Systems: Patterns in Cognitive Systems Engineering by David D. Woods Cognition in the Wild by Edwin Hutchins Behind Human Error by David D. Woods, Sydney Dekker, Richard Cook, Leila Johannesen, Nadine Sarter Papers: Ironies of Automation by Lisanne Bainbridge The French-Speaking Ergonomists’ Approach to Work Activity by Daniellou How in the World Did We Ever Get into That Mode? Mode Error and Awareness in Supervisory Control by Nadine Sarter Can We Ever Escape from Data Overload? A Cognitive Systems Diagnosis by David D. Woods Ten Challenges for Making Automation a “Team Player” in Joint Human-Agent Activity by Gary Klein and David D. Woods MABA-MABA or Abracadabra? Progress on Human–Automation Co-ordination by Sidney Dekker Managing the Hidden Costs of Coordination by Laura Maguire Designing for Expertise by David D. Woods The Impact of Generative AI on Critical Thinking by Lee et al.

Earlier this weekGuileWhippet But now I do! Today’s note is about how we can support untagged allocations of a few different kinds in Whippet’s .mostly-marking collector Why bother supporting untagged allocations at all? Well, if I had my way, I wouldn’t; I would just slog through Guile and fix all uses to be tagged. There are only a finite number of use sites and I could get to them all in a month or so. The problem comes for uses of from outside itself, in C extensions and embedding programs. These users are loathe to adapt to any kind of change, and garbage-collection-related changes are the worst. So, somehow, we need to support these users if we are not to break the Guile community.scm_gc_malloclibguile The problem with , though, is that it is missing an expression of intent, notably as regards tagging. You can use it to allocate an object that has a tag and thus can be traced precisely, or you can use it to allocate, well, anything else. I think we will have to add an API for the tagged case and assume that anything that goes through is requesting an untagged, conservatively-scanned block of memory. Similarly for : you could be allocating a tagged object that happens to not contain pointers, or you could be allocating an untagged array of whatever. A new API is needed there too for pointerless untagged allocations.scm_gc_mallocscm_gc_mallocscm_gc_malloc_pointerless Recall that the mostly-marking collector can be built in a number of different ways: it can support conservative and/or precise roots, it can trace the heap precisely or conservatively, it can be generational or not, and the collector can use multiple threads during pauses or not. Consider a basic configuration with precise roots. You can make tagged pointerless allocations just fine: the trace function for that tag is just trivial. You would like to extend the collector with the ability to make pointerless allocations, for raw data. How to do this?untagged Consider first that when the collector goes to trace an object, it can’t use bits inside the object to discriminate between the tagged and untagged cases. Fortunately though . Of those 8 bits, 3 are used for the mark (five different states, allowing for future concurrent tracing), two for the , one to indicate whether the object is pinned or not, and one to indicate the end of the object, so that we can determine object bounds just by scanning the metadata byte array. That leaves 1 bit, and we can use it to indicate untagged pointerless allocations. Hooray!the main space of the mostly-marking collector has one metadata byte for each 16 bytes of payloadprecise field-logging write barrier However there is a wrinkle: when Whippet decides the it should evacuate an object, it tracks the evacuation state in the object itself; the embedder has to provide an implementation of a , allowing the collector to detect whether an object is forwarded or not, to claim an object for forwarding, to commit a forwarding pointer, and so on. We can’t do that for raw data, because all bit states belong to the object, not the collector or the embedder. So, we have to set the “pinned” bit on the object, indicating that these objects can’t move.little state machine We could in theory manage the forwarding state in the metadata byte, but we don’t have the bits to do that currently; maybe some day. For now, untagged pointerless allocations are pinned. You might also want to support untagged allocations that contain pointers to other GC-managed objects. In this case you would want these untagged allocations to be scanned conservatively. We can do this, but if we do, it will pin all objects. Thing is, conservative stack roots is a kind of a sweet spot in language run-time design. You get to avoid constraining your compiler, you avoid a class of bugs related to rooting, but you can still support compaction of the heap. How is this, you ask? Well, consider that you can move any object for which we can precisely enumerate the incoming references. This is trivially the case for precise roots and precise tracing. For conservative roots, we don’t know whether a given edge is really an object reference or not, so we have to conservatively avoid moving those objects. But once you are done tracing conservative edges, any live object that hasn’t yet been traced is fair game for evacuation, because none of its predecessors have yet been visited. But once you add conservatively-traced objects back into the mix, you don’t know when you are done tracing conservative edges; you could always discover another conservatively-traced object later in the trace, so you have to pin everything. The good news, though, is that we have gained an easier migration path. I can now shove Whippet into Guile and get it running even before I have removed untagged allocations. Once I have done so, I will be able to allow for compaction / evacuation; things only get better from here. Also as a side benefit, the mostly-marking collector’s heap-conservative configurations are now faster, because we have metadata attached to objects which allows tracing to skip known-pointerless objects. This regains an optimization that BDW has long had via its , used in Guile since time out of mind.GC_malloc_atomic With support for untagged allocations, I think I am finally ready to start getting Whippet into Guile itself. Happy hacking, and see you on the other side! inside and outside on intent on data on slop fin

Bean counters have a bad rep for a reason. And it’s not because paying attention to the numbers is inherently unreasonable. It’s because weighing everything exclusively by its quantifiable properties is an impoverished way to view business (and the world!). Nobody presents this caricature better than the MBA types who think you can manage a business entirely in the abstract realm of "products," "markets," "resources," and "deliverables." To hell with that. The death of all that makes for a breakout product or service happens when the generic lingo of management theory takes over. This is why founder-led operations often keep an edge. Because when there’s someone at the top who actually gives a damn about cars, watches, bags, software, or whatever the hell the company makes, it shows up in a million value judgments that can’t be quantified neatly on a spreadsheet. Now, I love a beautiful spreadsheet that shows expanding margins, healthy profits, and customer growth as much as any business owner. But much of the time, those figures are derivatives of doing all the stuff that you can’t compute and that won’t quantify. But this isn’t just about running a better business by betting on unquantifiable elements that you can’t prove but still believe matter. It’s also about the fact that doing so is simply more fun! It’s more congruent. It’s vibe management. And no business owner should ever apologize for having fun, following their instincts, or trusting that the numbers will eventually show that doing the right thing, the beautiful thing, the poetic thing is going to pay off somehow. In this life or the next. Of course, you’ve got to get the basics right. Make more than you spend. Don’t get out over your skis. But once there’s a bit of margin, you owe it to yourself to lean on that cushion and lead the business primarily on the basis of good vibes and a long vision.

If you talk to enough aspiring leaders, you’ll become familiar with the prevalent idea that they need to be promoted before they can work on strategy. It’s a truism, but I’ve also found this idea perfectly wrong: you can work on strategy from anywhere in an organization, it just requires different tactics to do so. Both Staff Engineer and The Engineering Executive’s Primer have chapters on strategy. While the chapters’ contents are quite different, both present a practical path to advancing your organization’s thinking about complex topics. This chapter explains my belief that anyone within an organization can make meaningful progress on strategy, particularly if you are honest about the tools accessible to you, and thoughtful about how to use them. The themes we’ll dig into are: How to do strategy as an engineer, particularly an engineer who hasn’t been given explicit authority to do strategy Doing strategy as an engineering executive who is responsible for your organization’s decision-making How you can do engineering strategy even when you depend on an absent strategy, cannot acknowledge parts of the diagnosis because addressing certain problems is politically sensitive, or struggle with pockets of misaligned incentives If this book’s argument is that everyone should do strategy, is there anyone who, nonetheless, really should not do strategy? By the end, you’ll hopefully agree that engineering strategy is accessible to everyone, even though you’re always operating within constraints. This is an exploratory, draft chapter for a book on engineering strategy that I’m brainstorming in #eng-strategy-book. As such, some of the links go to other draft chapters, both published drafts and very early, unpublished drafts. Doing strategy as an engineer It’s easy to get so distracted by executive’s top-down approach to strategy that you convince yourself that there aren’t other approachable mechanisms to doing strategy. There are! Staff Engineer introduces an approach I call Take five, then synthesize, which does strategy by: Documenting how five current and historical related decisions have been made in your organization. This is an extended exploration phase Synthesizing those five documents into a diagnosis and policy. You are naming the implicit strategy, so it’s impossible for someone to reasonably argue you’re not empowered to do strategy: you’re just describing what’s already happening At that point, either the organization feels comfortable with what you’ve written–which is their current strategy–or it doesn’t in which case you’ve forced a conversation about how to revise the approach. Creating awareness is often enough to drive strategic change, and doesn’t require any explicit authorization from an executive to do. When awareness is insufficient, the other pattern I’ve found highly effective in low-authority scenarios is an approach I wrote about in An Elegant Puzzle, and call model, document, and share: Model the approach you want others to adopt. Make it easy for them to observe how you’ve changed the way you’re doing things. Document the approach, the thinking behind it, and how to adopt it. Share the document around. If people see you succeeding with the approach, then they’re likely to copy it from you. You might be skeptical because this is an influence-based approach. However, as we’ll discuss in the next section, even executive-driven strategy is highly dependent on influence. Strategy archaeology Vernor Vinge’s A Deepness in the Sky, published in 1999, introduced the term software archaeologists, folks who created functionality by cobbling together millennia of scraps of existing software. Although it’s a somewhat different usage, I sometimes think of the “take five, then synthesize” approach as performing strategy archaeology. Simply by recording what has happened in the past, we make it easier to understand the present, and influence the future. Doing strategy as an executive The biggest misconception about executive roles, frequently held by non-executives and new executives who are about to make a series of regrettable mistakes, is that executives operate without constraints. That is false: executives have an extremely high number of constraints that they operate under. Executives have budgets, CEO visions, peers to satisfy, and a team to motivate. They can disappoint any of these temporarily, but long-term have to satisfy all of them. Nonetheless, it is true that executives have more latitude to mandate and cajole participation in the strategies that they sponsor. The Engineering Executive’s Primer’s chapter on strategy is a brief summary of this entire book, but it doesn’t say much about how executive strategy differs from non-executive strategy. How the executive’s approach to strategy differs from the engineer’s can be boiled down to: Executives can mandate following of their strategy, which empowers their policy options. An engineer can’t prevent the promotion of someone who refused to follow their policy, but an executive can. Mandates only matter if there are consequences. If an executive is unwilling to enforce consequences for non-compliance with a mandate, the ability to issue a mandate isn’t meaningful. This is also true if they can’t enforce a mandate because of lack of support from their peer executives. Even if an executive is unwilling to use mandates, they have significant visibility and access to their organization to advocate for their preferred strategy. Neither access nor mandates improve an executive’s ability to diagnose problems. However, both often create the appearance of progress. This is why executive strategies can fail so spectacularly and endure so long despite failure. As a result, my experience is that executives have an easier time doing strategy, but a much harder time learning how to do strategy well, and fewer protections to avoid serious mistakes. Further, the consequences of an executive’s poor strategy tend to be much further reaching than an engineer’s. Waiting to do strategy until you are an executive is a recipe for disaster, even if it looks easier from a distance. Doing strategy in other roles Even if you’re neither an engineer nor an engineering executive, you can still do engineering strategy. It’ll just require an even more influence-driven approach. The engineering organization is generally right to believe that they know the most about engineering, but that’s not always true. Sometimes a product manager used to be an engineer and has significant relevant experience. Other times, such as the early adoption of large language models, engineers don’t know much either, and benefit from outside perspectives. Doing strategy in challenging environments Good strategies succeed by accurately diagnosing circumstances and picking policies that address those circumstances. You are likely to spend time in organizations where both of those are challenging due to internal limitations, so it’s worth acknowledging that and discussing how to navigate those challenges. Low-trust environment Sometimes the struggle to diagnose problems is a skill issue. Being bad at strategy is in some ways the easy problem to solve: just do more strategy work to build expertise. In other cases, you may see what the problems are fairly clearly, but not know how to acknowledge the problems because your organization’s culture would frown on it. The latter is a diagnosis problem rooted in low-trust, and does make things more difficult. The chapter on Diagnosis recognizes this problem, and admits that sometimes you have to whisper the controversial parts of a strategy: When you’re writing a strategy, you’ll often find yourself trying to choose between two awkward options: say something awkward or uncomfortable about your company or someone working within it, or omit a critical piece of your diagnosis that’s necessary to understand the wider thinking. Whenever you encounter this sort of debate, my advice is to find a way to include the diagnosis, but to reframe it into a palatable statement that avoids casting blame too narrowly. In short, the solution to low-trust is to translate difficult messages into softer, less direct versions that are acceptable to state. If your goal is to hold people accountable, this can feel dishonest or like a ethical compromise, but the goal of strategy is to make better decisions, which is an entirely different concern than holding folks accountable for the past. Karpman Drama Triangle Sometimes when the diagnosis seems particularly obvious, and people don’t agree with you, it’s because you are wrong. When I’ve been obviously wrong about things I understand well, it’s usually because I’ve fallen into viewing a situation through the Karpman Drama Triangle, where all parties are mapped as the persecutor, the rescuer, or the victim. Poor-judgment environment Even when you do an excellent job diagnosing challenges, it can be difficult to drive agreement within the organization about how to address them. Sometimes this is due to genuinely complex tradeoffs, for example in Stripe’s acquisition of Index, there was debate about how to deal with Index’s Java-based technology stack, which culminated in a compromise that didn’t make anyone particularly happy: Defer making a decision regarding the introduction of Java to a later date: the introduction of Java is incompatible with our existing engineering strategy, but at this point we’ve also been unable to align stakeholders on how to address this decision. Further, we see attempting to address this issue as a distraction from our timely goal of launching a joint product within six months. We will take up this discussion after launching the initial release. That compromise is a good example of a difficult tradeoff: although parties disagreed with the approach, everyone understood the conflicting priorities that had to be addressed. In other cases, though, there are policy choices that simply don’t make much sense, generally driven by poor judgment in your organization. Sometimes it’s not poor technical judgment, but poor judgment in choosing to prioritize one’s personal interests at the expense of the company’s needs. Calm’s strategy to focus on being a product-engineering organization dealt with some aspects of that, acknowledged in its diagnosis: We’re arguing a particularly large amount about adopting new technologies and rewrites. Most of our disagreements stem around adopting new technologies or rewriting existing components into new technology stacks. For example, can we extend this feature or do we have to migrate it to a service before extending it? Can we add this to our database or should we move it into a new Redis cache instead? Is JavaScript a sufficient programming language, or do we need to rewrite this functionality in Go? In that situation, your strategy is an attempt to educate your colleagues about the tradeoffs they are making, but ultimately sometimes folks will disagree with your strategy. In that case, remember that most interesting problems require iterative solutions. Writing your strategy and sharing it will start to change the organization’s mind. Don’t get discouraged even if that change is initially slow. Dealing with missing strategies The strategy for dealing with new private equity ownership introduces a common problem: lack of clarity about what other parts of your own company want. In that case, it seems likely there will be a layoff, but it’s unclear how large that layoff will be: Based on general practice, it seems likely that our new Private Equity ownership will expect us to reduce R&D headcount costs through a reduction. However, we don’t have any concrete details to make a structured decision on this, and our approach would vary significantly depending on the size of the reduction. Many leaders encounter that sort of ambiguity and decide that they cannot move forward with a strategy of their own until that decision is made. While it’s true that it’s inconvenient not to know the details, getting blocked by ambiguity is always the wrong decision. Instead you should do what the private equity strategy does: accept that ambiguity as a fact to be worked around. Rather than giving up, it adopts a series of new policies to start reducing cost growth by changing their organization’s seniority mix, and recognizes that once there is clarity on reduction targets that there will be additional actions to be taken. Whenever you’re doing something challenging, there are an infinite number of reasonable rationales for why you shouldn’t or can’t make progress. Leadership is finding a way to move forward despite those issues. A missing strategy is always part of your diagnosis, but never a reason that you can’t do strategy. Who shouldn’t do strategy In my experience, there’s almost never a reason why you cannot do strategy, but there are two particular scenarios where doing strategy probably doesn’t make sense. The first is not a who, but a when problem: sometimes there is so much strategy already happening, that doing more is a distraction. If another part of your organization is already working on the same problem, do your best to work with them directly rather than generating competing work. The other time to avoid strategy is when you’re trying to satisfy an emotional need to make a direct, immediate impact. Sharing a thoughtful strategy always makes progress, but it’s often the slow, incremental progress of changing your organization’s beliefs. Even definitive, top-down strategies from executives are often ignored in pockets of an organization, and bottoms-up strategy spread slowly as they are modeled, documented and shared. Embarking on strategy work requires a tolerance for winning in the long-run, even when there’s little progress this week or this quarter. Summary As you finish reading this chapter, my hope is that you also believe that you can work on strategy in your organization, whether you’re an engineer or an executive. I also hope that you appreciate that the tools you use vary greatly depending on who you are within your organization and the culture in which you work. Whether you need to model or can mandate, there’s a mechanism that will work for you.