While discussions around acquisitions often focus on technical diligence and deciding whether to make the acquisition, the integration that follows afterwards can be even more complex. There are few irreversible trapdoor decisions in engineering, but decisions made early in an integration tend to be surprisingly durable. This engineering strategy explores Stripe’s approach to integrating their 2018 acquisition of Index. While a business book would focus on the rationale for the acquisition itself, here that rationale is merely part of the diagnosis that defines the integration tradeoffs. The integration itself is the area of focus. Like most acquisitions, the team responsible for the integration has only learned about the project after the deal closed, which means early efforts are a scramble to apply strategy testing to distinguish between optimistic dates and technical realities. 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 As such, some of the links go to other draft chapters, both published drafts and very early, unpublished drafts.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 & Operation. To understand the thinking behind this strategy, read sections in reserve order, starting with Explore. More detail on this structure in Making a readable Engineering Strategy document. Policy & Operation We’re starting with little shared context between the acquired and acquiring engineering teams, and have a six month timeline to launch a joint product. So our starting policy is a mix of a commitment to joint refinment and several provisional architectural policies: Meet at least weekly until the initial release is complete: the involved leadership from Stripe and Index will hold a weekly sync meeting to refine our approach until we fulfill our intial release timeline. This meeting is jointly owned by Stripe’s Head of Traffic Engineering and Index’s Head of Engineering. Minimize changes to tokenization environment: because point-of-sale devices directly work with with customer payment details, the API that directly supports the point-of-sale device must live within our secured environment where payment details are stored. However, any other functionality must not be added to our tokenization environment. All other functionality must exist in standard environments: except for the minimum necessary functionality moving into the tokenization environment, everything else must be operated in our standard, non-tokenization environments. In particular, any software that requires frequent changes, or introduces complex external dependencies, should exist in the standard environments. 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. Escalations come to paired leads: given our limited shaed context across teams, all escalations must come to both Stripe’s Head of Traffic Engineering and Index’s Head of Engineering. Security review of changes impacting tokenization environment: we need to move quickly to launch the combined point-of-sale and payments product, but we must not cut corners on security to launch faster. Security must be included and explicitly sign off on any integration decisions that involve our tokenization environment Diagnose There are generally four categories of acquisitions: talent acquisitions to bring on a talented team, business acquisitions to buy a company’s revenue and product, technology acquisitions to add a differentiated capability that would be challenging to develop internally, and time-to-market acquisitions where you could develop the capability internally but can develop it meaningfully faster by acquiring a company. While most acquisitions have a flavor of several of these dimensions, this acquisition is primarily a time-to-market acquisition aimed to address these constraints: Several of our largest customers are pushing for us to provide a point-of-sale device integrated with our API-driven payments ecosystem. At least one has implied that we either provide this functionality on a committed timeline or they may churn to a competitor. We currently have no homegrown expertise in developing or integrating with hardware such as point-of-sale devices. Based on other zero-to-one efforts internally, we believe it would take about a year to hire the team, develop and launch a minimum-viable product for a point-of-sale device integrated into our platform. Where we’ve taken a horizontal approach to supporting web payments via an API, at least one of our competitors, Square, has taken a vertically integrated approach. While their API ecosystem is less developed than ours, they are a plausible destination for customers threatening to churn. We believe that at least one of our enterprise customers will churn if our best commitment is launching a point-of-sale solution 12 months from now. We’ve decided to acquire a small point-of-sale startup, which we will use to commit to a six month timeframe for supporting an integrated point-of-sale device with our API ecosystem. We will need to rapidly integrate the acquired startup to meet this timeline. We only know a small number of details about what this will entail. We do know that point-of-sale devices directly operate on payment details (e.g. the point-of-sale device knows the credit card details of the card it reads). Our compliance obligations restrict such activity to our “tokenization environment”, a highly secured and isolated environment with direct access to payment details. This environment converts payment details into a unique token that other environments can utilize to operate against payment details without the compliance overhead of having direct access to the underlying payment details. Going into this technical integration, we have few details about the acquired company’s technology stack. We do know that they are primarily a Java shop running on AWS, where we are primarily a Ruby (with some Go) shop running on AWS. Explore Prior to this acquisition, we have done several small acquisitions. None of those acquisitions had a meaningful product to integrate with ours, so we don’t have much of an internal playbook to anchor our approach in. We do have limited experience in integrating technical acquisitions from prior companies we’ve worked in, along with talking to peers at other companies to mine their experience. Synthesizing those experiences, the recurring patterns are: Usually deal teams have made certain commitments, or the acquired team has understood certain commitments, that will be challenging to facilitate. This is doubly true when you are unaware of what those commitments might be. If folks seem to be behaving oddly, it might be one such misunderstanding, and it’s worth engaging directly to debug the confusion. There should be an executive sponsor for the acquisition, and the sponsor is typically the best person ask about the company’s intentions. If you can’t find the executive sponsor, or they are not engaged, try to recruit a new executive sponsor rather than trying to make things work without one. Close the culture gap quickly where there’s little friction, and cautiously where there’s little trust. We do need to bring the acquired company into our culture, but we have years to do that. The most successful stories of doing this leaned on a mix of moving folks into and out of the acquired team rather than applying force. The long-term cost of supporting a new technology stack is high, and in conflict with our technology strategy of consolidating on as few programming languages as possible. This is not the place to be flexible, as each additional feature in the new stack will take you further from your desired outcome. Finally, find a way to derisk key departures. Things can go wrong quickly. One of the easiest starting points is consolidating infrastructure immediately, even if the product or software takes longer. Altogether, this was not the most reassuring exploration: it was a bit abstract, and much of our research returned strongly-held, conflicting perspectives. Perhaps acquisitions, like starting a new company, is one of those places where there’s simply no right way to do it well.

Once you’ve written your strategy’s exploration, the next step is working on its diagnosis. Diagnosis is understanding the constraints and challenges your strategy needs to address. In particular, it’s about doing that understanding while slowing yourself down from deciding how to solve the problem at hand before you know the problem’s nuances and constraints. If you ever find yourself wanting to skip the diagnosis phase–let’s get to the solution already!–then maybe it’s worth acknowledging that every strategy that I’ve seen fail, did so due to a lazy or inaccurate diagnosis. It’s very challenging to fail with a proper diagnosis, and almost impossible to succeed without one. The topics this chapter will cover are: Why diagnosis is the foundation of effective strategy, on which effective policy depends. Conversely, how skipping the diagnosis phase consistently ruins strategies A step-by-step approach to diagnosing your strategy’s circumstances How to incorporate data into your diagnosis effectively, and where to focus on adding data Dealing with controversial elements of your diagnosis, such as pointing out that your own executive is one of the challenges to solve Why it’s more effective to view difficulties as part of the problem to be solved, rather than a blocking issue that prevents making forward progress The near impossibility of an effective diagnosis if you don’t bring humility and self-awareness to the process Into the details we go! 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. Diagnosis is strategy’s foundation One of the challenges in evaluating strategy is that, after the fact, many effective strategies are so obvious that they’re pretty boring. Similarly, most ineffective strategies are so clearly flawed that their authors look lazy. That’s because, as a strategy is operated, the reality around it becomes clear. When you’re writing your strategy, you don’t know if you can convince your colleagues to adopt a new approach to specifying APIs, but a year later you know very definitively whether it’s possible. Building your strategy’s diagnosis is your attempt to correctly recognize the context that the strategy needs to solve before deciding on the policies to address that context. Done well, the subsequent steps of writing strategy often feel like an afterthought, which is why I think of diagnosis as strategy’s foundation. Where exploration was an evaluation-free activity, diagnosis is all about evaluation. How do teams feel today? Why did that project fail? Why did the last strategy go poorly? What will be the distractions to overcome to make this new strategy successful? That said, not all evaluation is equal. If you state your judgment directly, it’s easy to dispute. An effective diagnosis is hard to argue against, because it’s a web of interconnected observations, facts, and data. Even for folks who dislike your conclusions, the weight of evidence should be hard to shift. Strategy testing, explored in the Refinement section, takes advantage of the reality that it’s easier to diagnose by doing than by speculating. It proposes a recursive diagnosis process until you have real-world evidence that the strategy is working. How to develop your diagnosis Your strategy is almost certain to fail unless you start from an effective diagnosis, but how to build a diagnosis is often left unspecified. That’s because, for most folks, building the diagnosis is indeed a dark art: unspecified, undiscussion, and uncontrollable. I’ve been guilty of this as well, with The Engineering Executive’s Primer’s chapter on strategy staying silent on the details of how to diagnose for your strategy. So, yes, there is some truth to the idea that forming your diagnosis is an emergent, organic process rather than a structured, mechanical one. However, over time I’ve come to adopt a fairly structured approach: Braindump, starting from a blank sheet of paper, write down your best understanding of the circumstances that inform your current strategy. Then set that piece of paper aside for the moment. Summarize exploration on a new piece of paper, review the contents of your exploration. Pull in every piece of diagnosis from similar situations that resonates with you. This is true for both internal and external works! For each diagnosis, tag whether it fits perfectly, or needs to be adjusted for your current circumstances. Then, once again, set the piece of paper aside. Mine for distinct perspectives on yet another blank page, talking to different stakeholders and colleagues who you know are likely to disagree with your early thinking. Your goal is not to agree with this feedback. Instead, it’s to understand their view. The Crux by Richard Rumelt anchors diagnosis in this approach, emphasizing the importance of “testing, adjusting, and changing the frame, or point of view.” Synthesize views into one internally consistent perspective. Sometimes the different perspectives you’ve gathered don’t mesh well. They might well explicitly differ in what they believe the underlying problem is, as is typical in tension between platform and product engineering teams. The goal is to competently represent each of these perspectives in the diagnosis, even the ones you disagree with, so that later on you can evaluate your proposed approach against each of them. When synthesizing feedback goes poorly, it tends to fail in one of two ways. First, the author’s opinion shines through so strongly that it renders the author suspect. Your goal is never to agree with every team’s perspective, just as your diagnosis should typically avoid crowning any perspective as correct: a reader should generally be appraised of the details and unaware of the author. The second common issue is when a group tries to jointly own the synthesis, but create a fractured perspective rather than a unified one. I generally find that having one author who is accountable for representing all views works best to address both of these issues. Test drafts across perspectives. Once you’ve written your initial diagnosis, you want to sit down with the people who you expect to disagree most fervently. Iterate with them until they agree that you’ve accurately captured their perspective. It might be that they disagree with some other view points, but they should be able to agree that others hold those views. They might argue that the data you’ve included doesn’t capture their full reality, in which case you can caveat the data by saying that their team disagrees that it’s a comprehensive lens. Don’t worry about getting the details perfectly right in your initial diagnosis. You’re trying to get the right crumbs to feed into the next phase, strategy refinement. Allowing yourself to be directionally correct, rather than perfectly correct, makes it possible to cover a broad territory quickly. Getting caught up in perfecting details is an easy way to anchor yourself into one perspective prematurely. At this point, I hope you’re starting to predict how I’ll conclude any recipe for strategy creation: if these steps feel overly mechanical to you, adjust them to something that feels more natural and authentic. There’s no perfect way to understand complex problems. That said, if you feel uncertain, or are skeptical of your own track record, I do encourage you to start with the above approach as a launching point. Incorporating data into your diagnosis The strategy for Navigating Private Equity ownership’s diagnosis includes a number of details to help readers understand the status quo. For example the section on headcount growth explains headcount growth, how it compares to the prior year, and providing a mental model for readers to translate engineering headcount into engineering headcount costs: Our Engineering headcount costs have grown by 15% YoY this year, and 18% YoY the prior year. Headcount grew 7% and 9% respectively, with the difference between headcount and headcount costs explained by salary band adjustments (4%), a focus on hiring senior roles (3%), and increased hiring in higher cost geographic regions (1%). If everyone evaluating a strategy shares the same foundational data, then evaluating the strategy becomes vastly simpler. Data is also your mechanism for supporting or critiquing the various views that you’ve gathered when drafting your diagnosis; to an impartial reader, data will speak louder than passion. If you’re confident that a perspective is true, then include a data narrative that supports it. If you believe another perspective is overstated, then include data that the reader will require to come to the same conclusion. Do your best to include data analysis with a link out to the full data, rather than requiring readers to interpret the data themselves while they are reading. As your strategy document travels further, there will be inevitable requests for different cuts of data to help readers understand your thinking, and this is somewhat preventable by linking to your original sources. If much of the data you want doesn’t exist today, that’s a fairly common scenario for strategy work: if the data to make the decision easy already existed, you probably would have already made a decision rather than needing to run a structured thinking process. The next chapter on refining strategy covers a number of tools that are useful for building confidence in low-data environments. Whisper the controversial parts At one time, the company I worked at rolled out a bar raiser program styled after Amazon’s, where there was an interviewer from outside the team that had to approve every hire. I spent some time arguing against adding this additional step as I didn’t understand what we were solving for, and I was surprised at how disinterested management was about knowing if the new process actually improved outcomes. What I didn’t realize until much later was that most of the senior leadership distrusted one of their peers, and had rolled out the bar raiser program solely to create a mechanism to control that manager’s hiring bar when the CTO was disinterested holding that leader accountable. (I also learned that these leaders didn’t care much about implementing this policy, resulting in bar raiser rejections being frequently ignored, but that’s a discussion for the Operations for strategy chapter.) This is a good example of a strategy that does make sense with the full diagnosis, but makes little sense without it, and where stating part of the diagnosis out loud is nearly impossible. Even senior leaders are not generally allowed to write a document that says, “The Director of Product Engineering is a bad hiring manager.” 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 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. I think it’s helpful to discuss a few concrete examples of this, starting with the strategy for navigating private equity, whose diagnosis includes: 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. There are many things the authors of this strategy likely feel about their state of reality. First, they are probably upset about the fact that their new private equity ownership is likely to eliminate colleagues. Second, they are likely upset that there is no clear plan around what they need to do, so they are stuck preparing for a wide range of potential outcomes. However they feel, they don’t say any of that, they stick to precise, factual statements. For a second example, we can look to the Uber service migration strategy: Within infrastructure engineering, there is a team of four engineers responsible for service provisioning today. While our organization is growing at a similar rate as product engineering, none of that additional headcount is being allocated directly to the team working on service provisioning. We do not anticipate this changing. The team didn’t agree that their headcount should not be growing, but it was the reality they were operating in. They acknowledged their reality as a factual statement, without any additional commentary about that statement. In both of these examples, they found a professional, non-judgmental way to acknowledge the circumstances they were solving. The authors would have preferred that the leaders behind those decisions take explicit accountability for them, but it would have undermined the strategy work had they attempted to do it within their strategy writeup. Excluding critical parts of your diagnosis makes your strategies particularly hard to evaluate, copy or recreate. Find a way to say things politely to make the strategy effective. As always, strategies are much more about realities than ideals. Reframe blockers as part of diagnosis When I work on strategy with early-career leaders, an idea that comes up a lot is that an identified problem means that strategy is not possible. For example, they might argue that doing strategy work is impossible at their current company because the executive team changes their mind too often. That core insight is almost certainly true, but it’s much more powerful to reframe that as a diagnosis: if we don’t find a way to show concrete progress quickly, and use that to excite the executive team, our strategy is likely to fail. This transforms the thing preventing your strategy into a condition your strategy needs to address. Whenever you run into a reason why your strategy seems unlikely to work, or why strategy overall seems difficult, you’ve found an important piece of your diagnosis to include. There are never reasons why strategy simply cannot succeed, only diagnoses you’ve failed to recognize. For example, we knew in our work on Uber’s service provisioning strategy that we weren’t getting more headcount for the team, the product engineering team was going to continue growing rapidly, and that engineering leadership was unwilling to constrain how product engineering worked. Rather than preventing us from implementing a strategy, those components clarified what sort of approach could actually succeed. The role of self-awareness Every problem of today is partially rooted in the decisions of yesterday. If you’ve been with your organization for any duration at all, this means that you are directly or indirectly responsible for a portion of the problems that your diagnosis ought to recognize. This means that recognizing the impact of your prior actions in your diagnosis is a powerful demonstration of self-awareness. It also suggests that your next strategy’s success is rooted in your self-awareness about your prior choices. Don’t be afraid to recognize the failures in your past work. While changing your mind without new data is a sign of chaotic leadership, changing your mind with new data is a sign of thoughtful leadership. Summary Because diagnosis is the foundation of effective strategy, I’ve always found it the most intimidating phase of strategy work. While I think that’s a somewhat unavoidable reality, my hope is that this chapter has somewhat prepared you for that challenge. The four most important things to remember are simply: form your diagnosis before deciding how to solve it, try especially hard to capture perspectives you initially disagree with, supplement intuition with data where you can, and accept that sometimes you’re missing the data you need to fully understand. The last piece in particular, is why many good strategies never get shared, and the topic we’ll address in the next chapter on strategy refinement.

A surprising number of strategies are doomed from inception because their authors get attached to one particular approach without considering alternatives that would work better for their current circumstances. This happens when engineers want to pick tools solely because they are trending, and when executives insist on adopting the tech stack from their prior organization where they felt comfortable. Exploration is the antidote to early anchoring, forcing you to consider the problem widely before evaluating any of the paths forward. Exploration is about updating your priors before assuming the industry hasn’t evolved since you last worked on a given problem. Exploration is continuing to believe that things can get better when you’re not watching. This chapter covers: The goals of the exploration phase of strategy creation When to explore (always first!) and when it makes sense to stop exploring How to explore a topic, including discussion of the most common mechanisms: mining for internal precedent, reading industry papers and books, and leveraging your external network Why avoiding judgment is an essential part of exploration By the end of this chapter, you’ll be able to conduct an exploration for the current or next strategy that you work on. What is exploration? One of the frequent senior leadership anti-patterns I’ve encountered in my career is The Grand Migration, where a new leader declares that a massive migration to a new technology stack–typically the stack used by their former employer–will solve every pressing problem. What’s distinguishing about the Grand Migration is not the initially bad selection, but the single-minded ferocity with which the senior leader pushes for their approach, even when it becomes abundantly clear to others that it doesn’t solve the problem at hand. These senior leaders are very intelligent, but have allowed themselves to be framed in by their initial thinking from prior experiences. Accepting those early thoughts as the foundation of their strategy, they build the entire strategy on top of those ideas, and eventually there is so much weight standing on those early assumptions that it becomes impossible to acknowledge the errors. Exploration is the deliberate practice of searching through a strategy’s problem and solution spaces before allowing yourself to commit to a given approach. It’s understanding how others have approached the same problem recently and in the past. It’s doing this both in trendy companies you admire, and in practical companies that actually resemble yours. Most exploration will be external to your team, but depending on your company, much of your exploration might be internal to the company. If you’re in a massive engineering organization of 100,000, there are likely existing internal solutions to your problem that you’ve never heard of. Conversely, if you’re in an organization of 50 engineers, it’s likely that much of your exploration will be external. When to explore Exploration is the first step of good strategy work. Even when you want to skip it, you will always regret skipping it, because you’ll inadvertently frame yourself into whatever approach you focus on first. Especially when it comes to problems that you’ve solved previously, exploration is the only thing preventing you from over-indexing on your prior experiences. Try to continue exploration until you know how three similar teams within your company and three similar companies have recently solved the same problem. Further, make sure you are able to explain the thinking behind those decisions. At that point,you should be ready to stop exploring and move on to the diagnosis step of strategy creation. Exploration should always come with a minimum and maximum timeframe: less than a few hours is very suspicious, and more than a week is generally questionably as well. How to explore While the details of each exploration will differ a bit, the overarching approach tends to be pretty similar across strategies. After I open up the draft strategy document I’m working on, my general approach to exploration is: Start throwing in every resource I can think of related to that problem. For example, in the Uber service provisioning strategy, I started by collecting recent papers on Mesos, Kubernetes, and Aurora to understand the state of the industry on orchestration. Do some web searching, foundational model prompting, and checking with a few current and prior colleagues about what topics and resources I might be missing. For example, for the Calm engineering strategy, I focused on talking with industry peers on tools they’d used to focus a team with diffuse goals. Summarize the list of resources I’ve gathered, organizing them by which I want to explore, and which I won’t spend time on but are worth mentioning. For example, the Large Language Model adoption strategy’s exploration section documents the variety of resources the team explored before completing it. Work through the list one by one, continuing to collect notes in the strategy document. When you’re done, synthesize those into a concise, readable summary of what you’ve learned. For example, the monolith decomposition strategy synthesizes the exploration of a broad topic into four paragraphs, with links out to references. Stop once I generally understand how a handful of similar internal and external teams have recently approached this problem. Of all the steps in strategy creation, exploration is inherently open-ended, and you may find a different approach works better for you. If you’re not sure what to do, try following the above steps closely. If you have a different approach that you’re confident in–as long as it’s not skipping exploration!–then go ahead and try that instead. While not discussed in this chapter, you can also use some techniques like Wardley mapping, covered in the Refinement chapter, to support your exploration phase. Wardley mapping is a strategy tool designed within a different strategy tradition, and consequently categorizing it as either solely an exploration tool or a refinement tool ignores some of its potential uses. There’s no perfect way to do strategy: take what works for you and use it. Mine internal precedent One of the most powerful forms of strategy is simply documenting how similar decisions have been made internally: often this is enough to steer how similar future decisions are made within your organization. This approach, documented in Staff Engineer’s Write five, then synthesize, is also the most valuable step of exploration for those working in established companies. If you are a tenured engineer within your organization, then it’s somewhat safe to assume that you are aware of the typical internal approaches. Even then, it’s worth poking around to see if there are any related skunkworks projects happening internally. This is doubly true if you’ve joined the organization recently, or are distant from the codebase itself. In that case, it’s almost always worth poking around to see what already exists. Sometimes the internal approach isn’t ideal, but it’s still superior because it’s already been implemented and there’s someone else maintaining it. In the long-run, your strategy can ride along as someone else addresses the issues that aren’t perfect fits. Using your network How should we control access to user data’s exploration section begins with: Our experience is that best practices around managing internal access to user data are widely available through our networks, and otherwise hard to find. The exact rationale for this is hard to determine, While there are many topics with significant public writing out there, my experience is that there are many topics where there’s very little you can learn without talking directly to practitioners. This is especially true for security, compliance, operating at truly large scale, and competitive processes like optimizing advertising spend. Further, it’s surprisingly common to find that how people publicly describe solving a problem and how they actually approach the problem are largely divorced. This is why having a broad personal network is exceptionally powerful, and makes it possible to quickly understand the breadth of possible solutions. It also provides access to the practical downsides to various approaches, which are often omitted when talking to public proponents. In a recent strategy session, a proposal came up that seemed off to me, and I was able to text–and get answers to those texts–industry peers before the meeting ended, which invalidated the room’s assumptions about what was and was not possible. A disagreement that might have taken weeks to resolve was instead resolved in a few minutes, and we were able to figure out next steps in that meeting rather than waiting a week for the next meeting when we’d realized our mistake. Of course, it’s also important to hold information from your network with skepticism. I’ve certainly had my network be wrong, and your network never knows how your current circumstances differ from theirs, so blindly accepting guidance from your network is never the right decision either. If you’re looking for a more detailed coverage on building your network, this topic has also come up in Staff Engineer’s chapter on Build a network of peers, and The Engineering Executive’s Primer’s chapter on Building your executive network. It feels silly to cover the same topic a third time, but it’s a foundational technique for effective decision making. Read widely; read narrowly Reading has always been an important part of my strategy work. There are two distinct motions to this approach: read widely on an ongoing basis to broaden your thinking, and read narrowly on the specific topic you’re working on. Starting with reading widely, I make an effort each year to read ten to twenty industry-relevant works. These are not necessarily new releases, but are new releases for me. Importantly, I try to read things that I don’t know much about or that I initially disagree with. Some of my recent reads were Chip War, Building Green Software, Tidy First?, and How Big Things Get Done. From each of these books, I learned something, and over time they’ve built a series of bookmarks in my head about ideas that might apply to new problems. On the other end of things is reading narrowly. When I recently started working on an AI agents strategy, the first thing I did was read through Chip Huyen’s AI Engineering, which was an exceptionally helpful survey. Similarly, when we started thinking about Uber’s service migration, we read a number of industry papers, including Large-scale cluster management at Google with Borg and Mesos: A Platform for Fine-Grained Resource Sharing in the Data Center. None of these readings had all the answers to the problems I was working on, but they did an excellent job at helping me understand the range of options, as well as identifying other references to consult in my exploration. I’ll mention two nuances that will help a lot here. First, I highly encourage getting comfortable with skimming books. Even tightly edited books will have a lot of content that isn’t particularly relevant to your current goals, and you should skip that content liberally. Second, what you read doesn’t have to be books. It can be blog posts, essays, interview transcripts, or certainly it can be books. In this context, “reading” doesn’t event have to actually be reading. There are conference talks that contain just as much as a blog post, and conferences that cover as much breadth as a book. There are also conference talks without a written equivalent, such as Dan Na’s excellent Pushing Through Friction. Each job is an education Experience is frequently disregarded in the technology industry, and there are ways to misuse experience by copying too liberally the solutions that worked in different circumstances, but the most effective, and the slowest, mechanism for exploring is continuing to work in the details of meaningful problems. You probably won’t choose every job to optimize for learning, but allowing you to instantly explore more complex problems over time–recognizing that a bit of your data will have become stale each time–is uniquely valuable. Save judgment for later As I’ve mentioned several times, the point of exploration is to go broad with the goal of understanding approaches you might not have considered, and invalidating things you initially think are true. Both of those things are only possible if you save judgment for later: if you’re passing judgment about whether approaches are “good” or “bad”, then your exploration is probably going astray. As a soft rule, I’d argue that if no one involved in a strategy has changed their mind about something they believed when you started the exploration step, then you’re not done exploring. This is especially true when it comes to strategy work by senior leaders. Their beliefs are often well-justified by years of experience, but it’s unclear which parts of their experience have become stale over time. Summary At this point, I hope you feel comfortable exploring as the first step of your strategy work, and understand the likely consequences of skipping this step. It’s not an overstatement to say that every one of the worst strategic failures I’ve encountered would have been prevented by its primary author taking a few days to explore the space before anchoring on a particular approach. A few days of feeling slow are always worth avoiding years of misguided efforts.

At some point in a startup’s lifecycle, they decide that they need to be ready to go public in 18 months, and a flurry of IPO-readiness activity kicks off. This strategy focuses on a company working on IPO readiness, which has identified a gap in their internal controls for managing access to their users’ data. It’s a company that wants to meaningfully improve their security posture around user data access, but which has had a number of failed security initiatives over the years. Most of those initiatives have failed because they significantly degraded internal workflows for teams like customer support, such that the initial progress was reverted and subverted over time, to little long-term effect. This strategy represents the Chief Information Security Officer’s (CISO) attempt to acknowledge and overcome those historical challenges while meeting their IPO readiness obligations, and–most importantly–doing right by their users. 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, then Diagnose and so on. Relative to the default structure, this document has been refactored in two ways to improve readability: first, Operation has been folded into Policy; second, Refine has been embedded in Diagnose. More detail on this structure in Making a readable Engineering Strategy document. Policy & Operations Our new policies, and the mechanisms to operate them are: Controls for accessing user data must be significantly stronger prior to our IPO. Senior leadership, legal, compliance and security have decided that we are not comfortable accepting the status quo of our user data access controls as a public company, and must meaningfully improve the quality of resource-level access controls as part of our pre-IPO readiness efforts. Our Security team is accountable for the exact mechanisms and approach to addressing this risk. We will continue to prioritize a hybrid solution to resource-access controls. This has been our approach thus far, and the fastest available option. Directly expose the log of our resource-level accesses to our users. We will build towards a user-accessible log of all company accesses of user data, and ensure we are comfortable explaining each and every access. In addition, it means that each rationale for access must be comprehensible and reasonable from a user perspective. This is important because it aligns our approach with our users’ perspectives. They will be able to evaluate how we access their data, and make decisions about continuing to use our product based on whether they agree with our use. Good security discussions don’t frame decisions as a compromise between security and usability. We will pursue multi-dimensional tradeoffs to simultaneously improve security and efficiency. Whenever we frame a discussion on trading off between security and utility, it’s a sign that we are having the wrong discussion, and that we should rethink our approach. We will prioritize mechanisms that can both automatically authorize and automatically document the rationale for accesses to customer data. The most obvious example of this is automatically granting access to a customer support agent for users who have an open support ticket assigned to that agent. (And removing that access when that ticket is reassigned or resolved.) Measure progress on percentage of customer data access requests justified by a user-comprehensible, automated rationale. This will anchor our approach on simultaneously improving the security of user data and the usability of our colleagues’ internal tools. If we only expand requirements for accessing customer data, we won’t view this as progress because it’s not automated (and consequently is likely to encourage workarounds as teams try to solve problems quickly). Similarly, if we only improve usability, charts won’t represent this as progress, because we won’t have increased the number of supported requests. As part of this effort, we will create a private channel where the security and compliance team has visibility into all manual rationales for user-data access, and will directly message the manager of any individual who relies on a manual justification for accessing user data. Expire unused roles to move towards principle of least privilege. Today we have a number of roles granted in our role-based access control (RBAC) system to users who do not use the granted permissions. To address that issue, we will automatically remove roles from colleagues after 90 days of not using the role’s permissions. Engineers in an active on-call rotation are the exception to this automated permission pruning. Weekly reviews until we see progress; monthly access reviews in perpetuity. Starting now, there will be a weekly sync between the security engineering team, teams working on customer data access initiatives, and the CISO. This meeting will focus on rapid iteration and problem solving. This is explicitly a forum for ongoing strategy testing, with CISO serving as the meeting’s sponsor, and their Principal Security Engineer serving as the meeting’s guide. It will continue until we have clarity on the path to 100% coverage of user-comprehensible, automated rationales for access to customer data. Separately, we are also starting a monthly review of sampled accesses to customer data to ensure the proper usage and function of the rationale-creation mechanisms we build. This meeting’s goal is to review access rationales for quality and appropriateness, both by reviewing sampled rationales in the short-term, and identifying more automated mechanisms for identifying high-risk accesses to review in the future. Exceptions must be granted in writing by CISO. While our overarching Engineering Strategy states that we follow an advisory architecture process as described in Facilitating Software Architecture, the customer data access policy is an exception and must be explicitly approved, with documentation, by the CISO. Start that process in the #ciso channel. Diagnose We have a strong baseline of role-based access controls (RBAC) and audit logging. However, we have limited mechanisms for ensuring assigned roles follow the principle of least privilege. This is particularly true in cases where individuals change teams or roles over the course of their tenure at the company: some individuals have collected numerous unused roles over five-plus years at the company. Similarly, our audit logs are durable and pervasive, but we have limited proactive mechanisms for identifying anomalous usage. Instead they are typically used to understand what occurred after an incident is identified by other mechanisms. For resource-level access controls, we rely on a hybrid approach between a 3rd-party platform for incoming user requests, and approval mechanisms within our own product. Providing a rationale for access across these two systems requires manual work, and those rationales are later manually reviewed for appropriateness in a batch fashion. There are two major ongoing problems with our current approach to resource-level access controls. First, the teams making requests view them as a burdensome obligation without much benefit to them or on behalf of the user. Second, because the rationale review steps are manual, there is no verifiable evidence of the quality of the review. We’ve found no evidence of misuse of user data. When colleagues do access user data, we have uniformly and consistently found that there is a clear, and reasonable rationale for that access. For example, a ticket in the user support system where the user has raised an issue. However, the quality of our documented rationales is consistently low because it depends on busy people manually copying over significant information many times a day. Because the rationales are of low quality, the verification of these rationales is somewhat arbitrary. From a literal compliance perspective, we do provide rationales and auditing of these rationales, but it’s unclear if the majority of these audits increase the security of our users’ data. Historically, we’ve made significant security investments that caused temporary spikes in our security posture. However, looking at those initiatives a year later, in many cases we see a pattern of increased scrutiny, followed by a gradual repeal or avoidance of the new mechanisms. We have found that most of them involved increased friction for essential work performed by other internal teams. In the natural order of performing work, those teams would subtly subvert the improvements because it interfered with their immediate goals (e.g. supporting customer requests). As such, we have high conviction from our track record that our historical approach can create optical wins internally. We have limited conviction that it can create long-term improvements outside of significant, unlikely internal changes (e.g. colleagues are markedly less busy a year from now than they are today). It seems likely we need a new approach to meaningfully shift our stance on these kinds of problems. Explore Our experience is that best practices around managing internal access to user data are widely available through our networks, and otherwise hard to find. The exact rationale for this is hard to determine, but it seems possible that it’s a topic that folks are generally uncomfortable discussing in public on account of potential future liability and compliance issues. In our exploration, we found two standardized dimensions (role-based access controls, audit logs), and one highly divergent dimension (resource-specific access controls): Role-based access controls (RBAC) are a highly standardized approach at this point. The core premise is that users are mapped to one or more roles, and each role is granted a certain set of permissions. For example, a role representing the customer support agent might be granted permission to deactivate an account, whereas a role representing the sales engineer might be able to configure a new account. Audit logs are similarly standardized. All access and mutation of resources should be tied in a durable log to the human who performed the action. These logs should be accumulated in a centralized, queryable solution. One of the core challenges is determining how to utilize these logs proactively to detect issues rather than reactively when an issue has already been flagged. Resource-level access controls are significantly less standardized than RBAC or audit logs. We found three distinct patterns adopted by companies, with little consistency across companies on which is adopted. Those three patterns for resource-level access control were: 3rd-party enrichment where access to resources is managed in a 3rd-party system such as Zendesk. This requires enriching objects within those systems with data and metadata from the product(s) where those objects live. It also requires implementing actions on the platform, such as archiving or configuration, allowing them to live entirely in that platform’s permission structure. The downside of this approach is tight coupling with the platform vendor, any limitations inherent to that platform, and the overhead of maintaining engineering teams familiar with both your internal technology stack and the platform vendor’s technology stack. 1st-party tool implementation where all activity, including creation and management of user issues, is managed within the core product itself. This pattern is most common in earlier stage companies or companies whose customer support leadership “grew up” within the organization without much exposure to the approach taken by peer companies. The advantage of this approach is that there is a single, tightly integrated and infinitely extensible platform for managing interactions. The downside is that you have to build and maintain all of that work internally rather than pushing it to a vendor that ought to be able to invest more heavily into their tooling. Hybrid solutions where a 3rd-party platform is used for most actions, and is further used to permit resource-level access within the 1st-party system. For example, you might be able to access a user’s data only while there is an open ticket created by that user, and assigned to you, in the 3rd-party platform. The advantage of this approach is that it allows supporting complex workflows that don’t fit within the platform’s limitations, and allows you to avoid complex coupling between your product and the vendor platform. Generally, our experience is that all companies implement RBAC, audit logs, and one of the resource-level access control mechanisms. Most companies pursue either 3rd-party enrichment with a sizable, long-standing team owning the platform implementation, or rely on a hybrid solution where they are able to avoid a long-standing dedicated team by lumping that work into existing teams.

Entering 2025, I decided to spend some time exploring the topic of agents. I started reading Anthropic’s Building effective agents, followed by Chip Huyen’s AI Engineering. I kicked off a major workstream at work on using agents, and I also decided to do a personal experiment of sorts. This is a general commentary on building that project. What I wanted to build was a simple chat interface where I could write prompts, select models, and have the model use tools as appropriate. My side goal was to build this using Cursor and generally avoid writing code directly as much as possible, but I found that generally slower than writing code in emacs while relying on 4o-mini to provide working examples to pull from. Similarly, while I initially envisioned building this in fullstack TypeScript via Cursor, I ultimately bailed into a stack that I’m more comfortable, and ended up using Python3, FastAPI, PostgreSQL, and SQLAlchemy with the async psycopg3 driver. It’s been a… while… since I started a brand new Python project, and used this project as an opportunity to get comfortable with Python3’s async/await mechanisms along with Python3’s typing along with mypy. Finally, I also wanted to experiment with Tailwind, and ended up using TailwindUI’s components to build the site. The working version supports everything I wanted: creating chats with models, and allowing those models to use function calling to use tools that I provide. The models are allowed to call any number of tools in pursuit of the problem they are solving. The tool usage is the most interesting part here for sure. The simplest tool I created was a get_temperature tool that provided a fake temperature for your location. This allowed me to ask questions like “What should I wear tomorrow in San Francisco, CA?” and get a useful respond. The code to add this function to my project was pretty straightforward, just three lines of Python and 25 lines of metadata to pass to the OpenAI API. def tool_get_current_weather(location: str|None=None, format: str|None=None) -> str: "Simple proof of concept tool." temp = random.randint(40, 90) if format == 'fahrenheit' else random.randint(10, 25) return f"It's going to be {temp} degrees {format} tomorrow." FUNCTION_REGISTRY['get_current_weather'] = tool_get_current_weather TOOL_USAGE_REGISTRY['get_current_weather'] = { "type": "function", "function": { "name": "get_current_weather", "description": "Get the current weather", "parameters": { "type": "object", "properties": { "location": { "type": "string", "description": "The city and state, e.g. San Francisco, CA", }, "format": { "type": "string", "enum": ["celsius", "fahrenheit"], "description": "The temperature unit to use. Infer this from the users location.", }, }, "required": ["location", "format"], }, } } After getting this tool, the next tool I added was a simple URL retriever tool, which allowed the agent to grab a URL and use the content of that URL in its prompt. The implementation for this tool was similarly quite simple. def tool_get_url(url: str|None=None) -> str: if url is None: return '' url = str(url) response = requests.get(url) soup = BeautifulSoup(response.content, 'html.parser') content = soup.find('main') or soup.find('article') or soup.body if not content: return str(response.content) markdown = markdownify(str(content), heading_style="ATX").strip() return str(markdown) FUNCTION_REGISTRY['get_url'] = tool_get_url TOOL_USAGE_REGISTRY['get_url'] = { "type": "function", "function": { "name": "get_url", "description": "Retrieve the contents of a website via its URL.", "parameters": { "type": "object", "properties": { "url": { "type": "string", "description": "The complete URL, including protocol to retrieve. For example: \"https://lethain.com\"", } }, "required": ["url"], }, } } What’s pretty amazing is how much power you can add to your agent by adding such a trivial tool as retrieving a URL. You can similarly imagine adding tools for retrieving and commenting on Github pull requests and so, which could allow a very simple agent tool like this to become quite useful. Working on this project gave me a moderately compelling view of a near-term future where most engineers have simple application like this running that they can pipe events into from various systems (email, text, Github pull requests, calendars, etc), create triggers that map events to templates that feed into prompts, and execute those prompts with tool-aware agents. Combine that with ability for other agents to register themselves with you and expose the tools that they have access to (e.g. schedule an event with tool’s owner), and a bunch of interesting things become very accessible with a very modest amount of effort: You could schedule events between two busy people’s calendars, as if both of them had an assistant managing their calendar Reply to your own pull requests with new blog posts, providing feedback on typos and grammatical issues Crawl websites you care about and identify posts you might be interested in Ask the model to generate a system model using lethain:systems, run that model, then chart the responses Add a “planning tool” which allows the model to generate a plan to guide subsequent steps in a complex task. (e.g. getting my calendar, getting a friend’s calendar, suggesting a time we could meet) None of these are exactly lifesaving, but each is somewhat useful, and I imagine there are many more fairly obvious ideas that become easy once you have the necessary scaffolding to make this sort of thing easy. Altogether, I think that I am convinced at this points that agents, using current foundational models, are going to create a number of very interesting experiences that improve our day to day lives in small ways that are, in aggregate, pretty transformational. I’m less convinced that this is the way all software should work going forward though, but more thoughts on that over time. (A bunch of fun experiments happening at work, but early days on those.)