One of the most memorable quotes in Arthur Miller’s The Death of a Salesman comes from Uncle Ben, who describes his path to becoming wealthy as, “When I was seventeen, I walked into the jungle, and when I was twenty-one I walked out. And by God I was rich.” I wish I could describe the path to learning engineering strategy in similar terms, but by all accounts it’s a much slower path. Two decades in, I am still learning more from each project I work on. This book has aimed to accelerate your learning path, but my experience is that there’s still a great deal left to learn, despite what this book has hoped to accomplish. This final chapter is focused on the remaining advice I have to give on how you can continue to improve at strategy long after reading this book’s final page. Inescapably, this chapter has become advice on writing your own strategy for improving at strategy. You are already familiar with my general suggestions on creating strategy, so this chapter provides focused advice on creating your own plan to get better at strategy. It covers: Exploring strategy creation to find strategies you can learn from via public and private resources, and through creating learning communities How to diagnose the strategies you’ve found, to ensure you learn the right lessons from each one Policies that will help you find ways to perform and practice strategy within your organization, whether or not you have organizational authority Operational mechanisms to hold yourself accountable to developing a strategy practice My final benediction to you as a strategy practitioner who has finished reading this book With that preamble, let’s write this book’s final strategy: your personal strategy for developing your strategy practice. 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 As such, some of the links go to other draft chapters, both published drafts and very early, unpublished drafts. Exploring strategy creation Ideally, we’d start our exploration of how to improve at engineering strategy by reading broadly from the many publicly available examples. Unfortunately, there simply aren’t many easily available works to learn from others’ experience. Nonetheless, resources do exist, and we’ll discuss the three categories that I’ve found most useful: Public resources on engineering strategy, such as companies’ engineering blogs Private and undocumented strategies available through your professional network Learning communities that you build together, including ongoing learning circles Each of these is explored in its own section below. Public resources While there aren’t as many public engineering strategy resources as I’d like, I’ve found that there are still a reasonable number available. This book collects a number of such resources in the appendix of engineering strategy resources. That appendix also includes some individuals’ blog posts that are adjacent to this topic. You can go a long way by searching and prompting your way into these resources. As you read them, it’s important to recognize that public strategies are often misleading, as discussed previously in evaluating strategies. Everyone writing in public has an agenda, and that agenda often means that they’ll omit important details to make themselves, or their company, come off well. Make sure you read through the lines rather than taking things too literally. Private resources Ironically, where public resources are hard to find, I’ve found it much easier to find privately held strategy resources. While private recollections are still prone to inaccuracies, the incentives to massage the truth are less pronounced. The most useful sources I’ve found are: peers’ stories – strategies are often oral histories, and they are shared freely among peers within and across companies. As you build out your professional network, you can usually get access to any company’s engineering strategy on any topic by just asking. There are brief exceptions. Even a close peer won’t share a sensitive strategy before its existence becomes obvious externally, but they’ll be glad to after it does. People tend to over-estimate how much information companies can keep private anyway: even reading recent job postings can usually expose a surprising amount about a company. internal strategy archaeologists – while surprisingly few companies formally collect their strategies into a repository, the stories are informally collected by the tenured members of the organization. These folks are the company’s strategy archaeologists, and you can learn a great deal by explicitly consulting them becoming a strategy archaeologist yourself – whether or not you’re a tenured member of your company, you can learn a tremendous amount by starting to build your own strategy repository. As you start collecting them, you’ll interest others in contributing their strategies as well. As discussed in Staff Engineer’s section on the Write five then synthesize approach to strategy, over time you can foster a culture of documentation where one didn’t exist before. Even better, building that culture doesn’t require any explicit authority, just an ongoing show of excitement. There are other sources as well, ranging from attending the hallway track in conferences to organizing dinners where stories are shared with a commitment to privacy. Working in community My final suggestion for seeing how others work on strategy is to form a learning circle. I formed a learning circle when I first moved into an executive role, and at this point have been running it for more than five years. What’s surprised me the most is how much I’ve learned from it. There are a few reasons why ongoing learning circles are exceptional for sharing strategy: Bi-directional discussion allows so much more learning and understanding than mono-directional communication like conference talks or documents. Groups allow you to learn from others’ experiences and others’ questions, rather than having to guide the entire learning yourself. Continuity allows you to see the strategy at inception, during the rollout, and after it’s been in practice for some time. Trust is built slowly, and you only get the full details about a problem when you’ve already successfully held trust about smaller things. An ongoing group makes this sort of sharing feasible where a transient group does not. Although putting one of these communities together requires a commitment, they are the best mechanism I’ve found. As a final secret, many people get stuck on how they can get invited to an existing learning circle, but that’s almost always the wrong question to be asking. If you want to join a learning circle, make one. That’s how I got invited to mine. Diagnosing your prior and current strategy work Collecting strategies to learn from is a valuable part of learning. You also have to determine what lessons to learn from each strategy. For example, you have to determine whether Calm’s approach to resourcing Engineering-driven projects is something to copy or something to avoid. What I’ve found effective is to apply the strategy rubric we developed in the “Is this strategy any good?” chapter to each of the strategies you’ve collected. Even by splitting a strategy into its various phases, you’ll learn a lot. Applying the rubric to each phase will teach you more. Each time you do this to another strategy, you’ll get a bit faster at applying the rubric, and you’ll start to see interesting, recurring patterns. As you dig into a strategy that you’ve split into phases and applied the evaluation rubric to, here are a handful of questions that I’ve found interesting to ask myself: How long did it take to determine a strategy’s initial phase could be improved? How high was the cost to fund that initial phase’s discovery? Why did the strategy reach its final stage and get repealed or replaced? How long did that take to get there? If you had to pick only one, did this strategy fail in its approach to exploration, diagnosis, policy or operations? To what extent did the strategy outlive the tenure of its primary author? Did it get repealed quickly after their departure, did it endure, or was it perhaps replaced during their tenure? Would you generally repeat this strategy, or would you strive to avoid repeating it? If you did repeat it, what conditions seem necessary to make it a success? How might you apply this strategy to your current opportunities and challenges? It’s not necessary to work through all of these questions for every strategy you’re learning from. I often try to pick the two that I think might be most interesting for a given strategy. Policy for improving at strategy At a high level, there are just a few key policies to consider for improving your strategic abilities. The first is implementing strategy, and the second is practicing implementing strategy. While those are indeed the starting points, there are a few more detailed options worth consideration: If your company has existing strategies that are not working, debug one and work to fix it. If you lack the authority to work at the company scope, then decrease altitude until you find an altitude you can work at. Perhaps setting Engineering organizational strategies is beyond your circumstances, but strategy for your team is entirely accessible. If your company has no documented strategies, document one to make it debuggable. Again, if operating at a high altitude isn’t attainable for some reason, operate at a lower altitude that is within reach. If your company’s or team’s strategies are effective but have low adoption, see if you can iterate on operational mechanisms to increase adoption. Many such mechanisms require no authority at all, such as low-noise nudges or the model-document-share approach. If existing strategies are effective and have high adoption, see if you can build excitement for a new strategy. Start by mining for which problems Staff-plus engineers and senior managers believe are important. Once you find one, you have a valuable strategy vein to start mining. If you don’t feel comfortable sharing your work internally, then try writing proposals while only sharing them to a few trusted peers. You can even go further to only share proposals with trusted external peers, perhaps within a learning circle that you create or join. Trying all of these at once would be overwhelming, so I recommend picking one in any given phase. If you aren’t able to make traction, then try another until something works. It’s particularly important to recognize in your diagnosis where things are not working–perhaps you simply don’t have the sponsorship you need to enforce strategy so you need to switch towards suggesting strategies instead–and you’ll find something that works. What if you’re not allowed to do strategy? If you’re looking to find one, you’ll always unearth a reason why it’s not possible to do strategy in your current environment. If you’ve convinced yourself that there’s simply no policy that would allow you to do strategy in your current role, then the two most useful levers I’ve found are: Lower your altitude – there’s always a scale where you can perform strategy, even if it’s just your team or even just yourself. Only you can forbid yourself from developing personal strategies. Practice rather than perform – organizations can only absorb so much strategy development at a given time, so sometimes they won’t be open to you doing more strategy. In that case, you should focus on practicing strategy work rather than directly performing it. Only you can stop yourself from practice. Don’t believe the hype: you can always do strategy work. Operating your strategy improvement policies As the refrain goes, even the best policies don’t accomplish much if they aren’t paired with operational mechanisms to ensure the policies actually happen, and debug why they aren’t happening. Although it’s tempting to ignore operations when it comes to our personal habits, I think that would be a mistake: our personal habits have the most significant long-term impact on ourselves, and are the easiest habits to ignore since others generally won’t ask about them. The mechanisms I’d recommend: Explicitly track the strategies that you’ve implemented, refined, documented, or read. This should be in a document, spreadsheet or folder where you can explicitly see if you have or haven’t done the work. Review your tracked strategies every quarter: are you working on the expected number and in the expected way? If not, why not? Ideally, your review should be done in community with a peer or a learning circle. It’s too easy to deceive yourself, it’s much harder to trick someone else. If your periodic review ever discovers that you’re simply not doing the work you expected, sit down for an hour with someone that you trust–ideally someone equally or more experienced than you–and debug what’s going wrong. Commit to doing this before your next periodic review. Tracking your personal habits can feel a bit odd, but it’s something I highly recommend. I’ve been setting and tracking personal goals for some time now—for example, in my 2024 year in review—and have benefited greatly from it. Too busy for strategy Many companies convince themselves that they’re too much in a rush to make good decisions. I’ve certainly gotten stuck in this view at times myself, although at this point in my career I find it increasingly difficult to not recognize that I have a number of tools to create time for strategy, and an obligation to do strategy rather than inflict poor decisions on the organizations I work in. Here’s my advice for creating time: If you’re not tracking how often you’re creating strategies, then start there. If you’ve not worked on a single strategy in the past six months, then start with one. If implementing a strategy has been prohibitively time consuming, then focus on practicing a strategy instead. If you do try all those things and still aren’t making progress, then accept your reality: you don’t view doing strategy as particularly important. Spend some time thinking about why that is, and if you’re comfortable with your answer, then maybe this is a practice you should come back to later. Final words At this point, you’ve read everything I have to offer on drafting engineering strategy. I hope this has refined your view on what strategy can be in your organization, and has given you the tools to draft a more thoughtful future for your corner of the software engineering industry. What I’d never ask is for you to wholly agree with my ideas here. They are my best thinking on this topic, but strategy is a topic where I’m certain Hegel’s world view is the correct one: even the best ideas here are wrong in interesting ways, and will be surpassed by better ones.

In Uber’s 2014 service migration strategy, we explore how to navigate the move from a Python monolith to a services-oriented architecture while also scaling with user traffic that doubled every six months. This Wardley map explores how orchestration frameworks were evolving during that period, to be used as an input into determining the most effective path forward for Uber’s Infrastructure Engineering team. 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. Reading this map To quickly understand this Wardley Map, read from top to bottom. If you want to review how this map was written, then you should read section by section from the bottom up, starting with Users, then Value Chains, and so on. More detail on this structure in Refining strategy with Wardley Mapping. How things work today There are three primary internal teams involved in service provisioning. The Service Provisioning Team abstracts applications developed by Product Engineering from servers managed by the Server Operations Team. As more servers are added to support application scaling, this is invisible to the applications themselves, freeing Product Engineers to focus on what the company values the most: developing more application functionality. The challenges within the current value chain are cost-efficient scaling, reliable deployment, and fast deployment. All three of those problems anchor on the same underlying problem of resource scheduling. We want to make a significant investment into improving our resource scheduling, and believe that understanding the industry’s trend for resource scheduling underpins making an effective choice. Transition to future state Most interesting cluster orchestration problems are anchored in cluster metadata and resource scheduling. Routing requests, whether through DNS entries or allocated ports, depends on cluster metadata. Mapping services to a fleet of servers depends on resource scheduling managing cluster metadata. Deployment and autoscaling both depend on cluster metadata. This is also an area where we see significant changes occurring in 2014. Uber initially solved this problem using Clusto, an open-source tool released by Digg with goals similar to Hashicorp’s Consul but with limited adoption. We also used Puppet for configuring servers, alongside custom scripting. This has worked, but has required custom, ongoing support for scheduling. The key question we’re confronted with is whether to build our own scheduling algorithms (e.g. bin packing) or adopt a different approach. It seems clear that the industry intends to directly solve this problem via two paths: relying on Cloud providers for orchestration (Amazon Web Services, Google Cloud Platform, etc) and through open-source scheduling frameworks such as Mesos and Kubernetes. Our industry peers with over five years of technical infrastructure are almost unanimously adopting open-source scheduling frameworks to better support their physical infrastructure. This will give them a tool to perform a bridged migration from physical infrastructure to cloud infrastructure. Newer companies with less existing infrastructure are moving directly to the cloud, and avoiding solving the orchestration problem entirely. The only companies not adopting one of these two approaches are extraordinarily large and complex (think Google or Microsoft) or allergic to making any technical change at all. From this analysis, it’s clear that continuing our reliance on Clusto and Puppet is going to be an expensive investment that’s not particularly aligned with the industry’s evolution. User & Value Chains This map focuses on the orchestration ecosystem within a single company, with a focus on what did, and did not, stay the same from roughly 2008 to 2014. It focuses in particular on three users: Product Engineers are focused on provisioning new services, and then deploying new versions of that service as they make changes. They are wholly focused on their own service, and entirely unaware of anything beneath the orchestration layer (including any servers). Service Provisioning Team focuses on provisioning new services, orchestrating resources for those services, and routing traffic to those services. This team acts as the bridge between the Product Engineers and the Server Operations Team. Server Operations Team is focused on adding server capacity to be used for orchestration. They work closely with the Service Provisioning Team, and have no contact with the Product Engineers. It’s worth acknowledging that, in practice, these are artificial aggregates of multiple underlying teams. For example, routing traffic between services and servers is typically handled by a Traffic or Service Networking team. However, these omissions are intended to clarify the distinctions relevant to the evolution of orchestration tooling.

As part of my work on #eng-strategy-book, I’ve been editing a bunch of stuff. This morning I wanted to work on two editing problems. First, I wanted to ensure I was referencing strategies evenly across chapters (and not relying too heavily on any given strategy). Second, I wanted to make sure I was making references to other chapters in a consistent, standardized way, Both of these are collecting Markdown links from files, grouping those links by either file or url, and then outputting the grouped content in a useful way. I decided to experiment with writing a one-shot prompt to write the script for me rather than writing it myself. The prompt and output (from ChatGPT 4.5) are available in this gist. That worked correctly! The output was a bit ugly, so I tweaked the output slightly by hand, and also adjusted the regular expression to capture less preceding content, which resulted in this script. Although I did it by hand, I’m sure it would have been faster to just ask ChatGPT to fix the script itself, but either way these are very minor tweaks. Now I can call the script in either standard of --grouped mode. Example of ./scripts/links.py "content/posts/strategy-book/*.md" output: Example of ./scripts/links.py "content/posts/strategy-book/*.md" --grouped output: Altogether, this is a super simple script that I could have written in thirty minutes or so, but this allowed me to write it in less than ten minutes, and get back to actually editing with the remaining twenty.

One of the recurring challenges in any organization is how to split your attention across long-term and short-term problems. Your software might be struggling to scale with ramping user load while also knowing that you have a series of meaningful security vulnerabilities that need to be closed sooner than later. How do you balance across them? These sorts of balance questions occur at every level of an organization. A particularly frequent format is the debate between Product and Engineering about how much time goes towards developing new functionality versus improving what’s already been implemented. In 2020, Calm was growing rapidly as we navigated the COVID-19 pandemic, and the team was struggling to make improvements, as they felt saturated by incoming new requests. This strategy for resourcing Engineering-driven projects was our attempt to solve that problem. 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. Reading this document To apply this strategy, start at the top with Policy. To understand the thinking behind this strategy, read sections in reverse order, starting with Explore. More detail on this structure in Making a readable Engineering Strategy document. Policy & Operation Our policies for resourcing Engineering-driven projects are: We will protect one Eng-driven project per product engineering team, per quarter. These projects should represent a maximum of 20% of the team’s bandwidth. Each project must advance a measurable metric, and execution must be designed to show progress on that metric within 4 weeks. These projects must adhere to Calm’s existing Engineering strategies. We resource these projects first in the team’s planning, rather than last. However, only concrete projects are resourced. If there’s no concrete proposal, then the team won’t have time budgeted for Engineering-driven work. Team’s engineering manager is responsible for deciding on the project, ensuring the project is valuable, and pushing back on attempts to defund the project. Project selection does not require CTO approval, but you should escalate to the CTO if there’s friction or disagreement. CTO will review Engineering-driven projects each quarter to summarize their impact and provide feedback to teams’ engineering managers on project selection and execution. They will also review teams that did not perform a project to understand why not. As we’ve communicated this strategy, we’ve frequently gotten conceptual alignment that this sounds reasonable, coupled with uncertainty about what sort of projects should actually be selected. At some level, this ambiguity is an acknowledgment that we believe teams will identify the best opportunities bottoms-up, we also wanted to give two concrete examples of projects we’re greenlighting in the first batch: Code-free media release: historically, we’ve needed to make a number of pull requests to add, organize, and release new pieces of media. This is high urgency work, but Engineering doesn’t exercise much judgment while doing it, and manual steps often create errors. We aim to track and eliminate these pull requests, while also increasing the number of releases that can be facilitated without scaling the content release team. Machine-learning content placement: developing new pieces of media is often a multi-week or month process. After content is ready to release, there’s generally a debate on where to place the content. This matters for the company, as this drives engagement with our users, but it matters even more to the content creator, who is generally evaluated in terms of their content’s performance. This often leads to Product and Engineering getting caught up in debates about how to surface particular pieces of content. This project aims to improve user engagement by surfacing the best content for their interests, while also giving the Content team several explicit positions to highlight content without Product and Engineering involvement. Although these projects are similar, it’s not intended that all Engineering-driven projects are of this variety. Instead it’s happenstance based on what the teams view as their biggest opportunities today. Diagnosis Our assessment of the current situation at Calm is: We are spending a high percentage of our time on urgent but low engineering value tasks. Most significantly, about one-third of our time is going into launching, debugging, and changing content that we release into our product. Engineering is involved due to limitations in our implementation, not because there is any inherent value in Engineering’s involvement. (We mostly just make releases slowly and inadvertently introduce bugs of our own.) We have a bunch of fairly clear ideas around improving the platform to empower the Content team to speed up releases, and to eliminate the Engineering involvement. However, we’ve struggled to find time to implement them, or to validate that these ideas will work. If we don’t find a way to prioritize, and succeed at implementing, a project to reduce Engineering involvement in Content releases, we will struggle to support our goals to release more content and to develop more product functionality this year Our Infrastructure team has been able to plan and make these kinds of investments stick. However, when we attempt these projects within our Product Engineering teams, things don’t go that well. We are good at getting them onto the initial roadmap, but then they get deprioritized due to pressure to complete other projects. Engineering team is not very fungible due to its small size (20 engineers), and because we have many specializations within the team: iOS, Android, Backend, Frontend, Infrastructure, and QA. We would like to staff these kinds of projects onto the Infrastructure team, but in practice that team does not have the product development experience to implement theis kind of project. We’ve discussed spinning up a Platform team, or moving product engineers onto Infrastructure, but that would either (1) break our goal to maintain joint pairs between Product Managers and Engineering Managers, or (2) be indistinguishable from prioritizing within the existing team because it would still have the same Product Manager and Engineering Manager pair. Company planning is organic, occurring in many discussions and limited structured process. If we make a decision to invest in one project, it’s easy for that project to get deprioritized in a side discussion missing context on why the project is important. These reprioritization discussions happen both in executive forums and in team-specific forums. There’s imperfect awareness across these two sorts of forums. Explore Prioritization is a deep topic with a wide variety of popular solutions. For example, many software companies rely on “RICE” scoring, calculating priority as (Reach times Impact times Confidence) divided by Effort. At the other extreme are complex methodologies like [Scaled Agile Framework)(https://en.wikipedia.org/wiki/Scaled_agile_framework). In addition to generalized planning solutions, many companies carve out special mechanisms to solve for particular prioritization gaps. Google historically offered 20% time to allow individuals to work on experimental projects that didn’t align directly with top-down priorities. Stripe’s Foundation Engineering organization developed the concept of Foundational Initiatives to prioritize cross-pillar projects with long-term implications, which otherwise struggled to get prioritized within the team-led planning process. All these methods have clear examples of succeeding, and equally clear examples of struggling. Where these initiatives have succeeded, they had an engaged executive sponsoring the practice’s rollout, including triaging escalations when the rollout inconvenienced supporters of the prior method. Where they lacked a sponsor, or were misaligned with the company’s culture, these methods have consistently failed despite the fact that they’ve previously succeeded elsewhere.

We’ve read a lot of strategy at this point in the book. We can judge a strategy’s format, and its construction: both are useful things. However, format is a predictor of quality, not quality itself. The remaining question is, how should we assess whether a strategy is any good? Uber’s service migration strategy unlocked the entire organization to make rapid progress. It also led to a sprawling architecture problem down the line. Was it a great strategy or a terrible one? Folks can reasonably disagree, but it’s worthwhile developing our point of view why we should prefer one interpretation or the other. This chapter will focus on: The various ways that are frequently suggested for evaluating strategies, such as input-only evaluation, output-only evaluation, and so on A rubric for evaluating strategies, and why a useful rubric has to recognize that strategies have to be evaluated in phases rather than as a unified construct Why ending a strategy is often a sign of a good strategist, and sometimes the natural reaction to a new phase in a strategy, rather than a judgment on prior phases How missing context is an unpierceable veil for evaluating other companies' strategies with high-conviction, and why you’ll end up attempting to evaluate them anyway Why you can learn just as much from bad strategies as from good ones, even in circumstances where you are missing much of the underlying context Time to refine our judgment about strategy quality a bit. 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. How are strategies graded? Before suggesting my own rubric, I want to explore how the industry appears to grade strategies in practice. That’s not because I particularly agree with them–I generally find each approach is missing an important nuance–understanding their flaws is a foundation to build on. Grading strategy on its outputs is by far the most prevalent approach I’ve found in industry. This is an appealing approach, because it does make sense that a strategy’s results are more important than anything else. However, this line of thinking can go awry. We saw massive companies like Google move to service architectures, and we copied them because if it worked for Google, it would likely work for us. As discussed in the monolith decomposition strategy, it did not work particularly well for most adopters. The challenge with grading outputs is that it doesn’t distinguish between “alpha”, how much better your results are because of your strategy, and “beta”, the expected outcome if you hadn’t used the strategy. For example, the acquisition of Index allowed Stripe to build a point-of-sale business line, but they were also on track to internally build that business. Looking only at outputs can’t distinguish whether it would have been better to build the business via acquisition or internally. But one of those paths must have been the better strategy. Similarly, there are also strategies that succeed, but do so at unreasonably high costs. Stripe’s API deprecation strategy is a good example of a strategy that was extremely well worth the cost for the company’s first decade, but eventually became too expensive to maintain as the evolving regulatory environment created more overhead. Fortunately, Stripe modified their strategy to allow some deprecations, but you can imagine an alternate scenario where they attempted to maintain their original strategy, which would have likely failed due to its accumulating costs. Confronting these problems with judging on outputs, it’s compelling to switch to the opposite lens and evaluate strategy purely on its inputs. In that approach, as long as the sum of the strategy’s parts make sense, it’s a good strategy, even if it didn’t accomplish its goals. This approach is very appealing, because it appears to focus purely on the strategy’s alpha. Unfortunately I find this view similarly deficient. For example, the strategy for adopting LLMs offers a cautious approach to adopting LLMs. If that company is outcompleted by competitors in the incorporation of LLMs, to the loss of significant revenue, I would argue that strategy isn’t a great one, even if it’s rooted in a proper diagnosis and effective policies. Doing good strategy requires reconciling the theoretical with the practical, so we can’t argue that inputs alone are enough to evaluate strategy work. If a strategy is conceptually sound, but struggling to make an impact, then its authors should continue to refine it. If its authors take a single pass and ignore subsequent information that it’s not working, then it’s a failed strategy, regardless of how thoughtful the first pass was. While I find these mechanisms to be incomplete, they’re still instructive. By incorporating bits of each of these observations, we’re surprisingly close to a rubric that avoids each of these particular downfalls. Rubric for strategy Balancing the strengths and flaws of the previous section’s ideas, the rubric I’ve found effective for evaluating strategy is: How quickly is the strategy refined? If a strategy starts out bad, but improves quickly, that’s a better strategy than a mostly right strategy that never evolves. Strategy thrives when its practitioners understand it is a living endeavour. How expensive is the strategy’s refinement for implementing and impacted teams? Just as culture eats strategy for breakfast, good policy loses to poor operational mechanisms every time. Especially early on, good strategy is validated cheaply. Expensive strategies are discarded before they can be validated, let alone improved. How well does the current iteration solve its diagnosis? Ultimately, strategy does have to address the diagnosis it starts from. Even if you’re learning quickly and at a low cost, at some point you do have to actually get to impact. Strategy must eventually be graded on its impact. With this rubric in hand, we can finally assess the Uber’s service migration strategy. It refined rapidly as we improved our tooling, minimized costs because we had to rely on voluntary adoption, and solved its diagnosis extremely well. So this was a great strategy, but how do we think about the fact that its diagnosis missed out on the consequences of a wide-spread service architecture on developer productivity? This brings me to the final component of the strategy quality rubric: the recognition that strategy exists across multiple phases. Each phase is defined by new information–whether or not this information is known by the strategy’s authors–that render the diagnosis incomplete. The Uber strategy can be thought of as existing across two phases: Phase 1 used service provisioning to address developer productivity challenges in the monolith. Phase 2 was engaging with consequences of a sprawling service architecture. All the good grades I gave the strategy are appropriate to the first phase. However, the second phase was ushered in by the negative impacts to developer productivity exposed by the initial rollout. The second phase’s grades on the rate of iteration, the cost, and the outcomes were reasonable, but a bit lower than first phase. In the subsequent years, the second phase was succeeded by a third phase that aimed to address the second’s challenges. Does stopping mean a strategy’s bad? Now that we have a rubric, we can use it to evaluate one of the important questions of strategy: does giving up on a strategy mean that the strategy is a bad one? The vocabulary of strategy phases helps us here, and I think it’s uncontroversial to say that a new phase’s evolution of your prior diagnosis might make it appropriate to abandon a strategy. For example, Digg owned our own servers in 2010, but would certainly not buy their own servers if they started ten years later. Circumstances change. Sometimes I also think that aborting a strategy in its first phase is a good sign. That’s generally true when the rate of learning is outpaced by the cost of learning. I recently sponsored a developer productivity strategy that had some impact, but less than we’d intended. We immortalized a few of the smaller pieces, and returned further exploration to a lower altitude strategy owned by the teams rather than the high altitude strategy that I owned as an executive. Essentially all strategies are competing with strategies at other altitudes, so I think giving up on strategies, especially high altitude strategies, is almost always a good idea. The unpierceable veil Working within our industry, we are often called upon to evaluate strategies from afar. As other companies rolled out LLMs in their products or microservices for their architectures, our companies pushed us on why we weren’t making these changes as well. The exploration step of strategy helps determine where a strategy might be useful for you, but even that doesn’t really help you evaluate whether the strategy or the strategists. There are simply too many dimensions of the rubric that you cannot evaluate when you’re far away. For example, how many phases occurred before the idea that became the external representation of the strategy came into existence? How much did those early stages cost to implement? Is the real mastery in the operational mechanisms that are never reported on? Did the external representation of the strategy ever happen at all, or is it the logical next phase that solves the reality of the internal implementation? With all that in mind, I find that it’s generally impossible to accurately evaluate strategies happening in other companies with much conviction. Even if you want to, the missing context is an impenetrable veil. That’s not to say that you shouldn’t try to evalute their strategies, that’s something that you’ll be forced to do in your own strategy work. Instead, it’s a reminder to keep a low confidence score in those appraisals: you’re guaranteed to be missing something. Learning despite quality issues Although I believe it’s quite valuable for us to judge the quality of strategies, I want to caution against going a step further and making the conclusion that you can’t learn from poor strategies. As long as you are aware of a strategy’s quality, I believe you can learn just as much from failed strategy as from great strategy. Part of this is because often even failed strategies have early phases that work extremely well. Another part is because strategies tend to fail for interesting reasons. I learned just as much from Stripe’s failed rollout of agile which struggled due to missing operational mechanisms. as I did from Calm’s successful transition to focus primarily on product engineering. Without a clear point of view on which of these worked, you’d be at risk of learning the wrong lessons, but with forewarning you don’t have run that risk. Once you’ve determined a strategy was unsuccessful, I find it particularly valuable to determine the strategy’s phases and understand which phase and where in the strategy steps things went wrong. Was it a lack of operational mechanisms? Was the policy itself a poor match for the diagnosis? Was the diagnosis willfully ignoring a truculent executive? Answering these questions will teach you more about strategy than only studying successful strategies, because you’ll develop an intuition for which parts truly matter. Summary Finishing this chapter, you now have a structured rubric for evaluating a strategy, moving beyond “good strategy” and “bad strategy” to a nuanced assessment. This assessment is not just useful for grading strategy, but makes it possible to specifically improve your strategy work. Maybe your approach is sound, but your operational mechanisms are too costly for the rate of learning they facilitate. Maybe you’ve treated strategy as a single iteration exercise, rather than recognizing that even excellent strategy goes stale over time. Keep those ideas in mind as we head into the final chapter on how you personally can get better at strategy work.