Notes on ‘An Elegant Puzzle: Systems of Engineering Management’ by Will Larson (2019)

Read in May 2023

Organizations

• “A team is falling behind if each week their backlog is longer than it was the week before. Typically, people are working extremely hard but not making much progress, morale is low, and your users are vocally dissatisfied”
• “A team is treading water if they’re able to get their critical work done…and your users may seem happier because they’ve learned that asking for help won’t go anywhere”
• “A team is innovating when their technical debt is sustainably low, morale is high, and the majority of work is satisfying new user needs”
• When the team is falling behind (when backlog growing), focusing on easy wins makes ton of sense
• “When the team is treading water … limit work in progress … transition from personal view of productivity to team view”
• “adding new individuals to a team disrupts that team’s gelling process, so I’ve found it much easier to have rapid growth periods for any given team, followed by consolidation/gelling periods during which the team gels. The organization will never stop growing, but each team will.” 
• “The expected time to complete a new task approaches infinity as a team’s utilization approaches 100 percent” 
• “strategy here is to funnel interruptions into an increasingly small area, and then automate that area as much as possible. Ask people to file tickets, create chatbots that automate filing tickets, create a service cookbook, and so on. With that setup in place, create a rotation for people who are available to answer questions, and train your team not to answer other forms of interruptions. This is remarkably uncomfortable because we want to be helpful humans, but it becomes necessary as the number of interruptions climbs higher”
• “Take a look at your calendar and write down your role in meetings”
• “Look back over the past six months for recurring processes, like roadmap planning, performance calibrations, or head count decisions, and document your role in those processes”
• “For each of the individuals you support, in which areas are your skills and actions most complementary to theirs? How do you help them? What do they rely on you for?”

Tools

• “key tools for leading efficient change are systems thinking, metrics, and vision”
• stocks = stuff. “might be the number of trained managers at your company”
• flows = “changes to stocks”. “inflows or outflows. Training a new manager is an inflow”
• information link “indicates that the value of a stock is a factor in the size of a flow. The link [shown in the first useful diagram] shows that the time available for developing features depends on the number of trained managers.”
• “every flow is a rate, every stock is a quantity”
• “a stock outside of a diagram’s scope will be represented as a cloud, indicating that something complex happened there that we’re not currently exploring”
• Accelerate: The Science of Lean Software and DevOp four measures:
  1. Delivery lead time is the time from teh creation of code to its use in production
  2. Deployment frequency is how often you deploy code
  3. Change fail rate is how frequency changes fail
  4. Time to restore service is the time spent recovering from defects
• “Problem discovery”
  • First phase of planning cycle: explore different problems you could pick to solve. Use these themes to populate problem space:
    • Users’ pain
    • Users’ purpose
    • Benchmark
    • Cohorts
    • Competitive advantages
    • Competitive moats
    • Compounding leverages
• “Problem selection”
  • Once identified possible problems, narrow down to specific problem portfolio. Consider:
    • Surviving the round
    • Surviving the next round
    • Winning rounds
    • Consider different time frames
    • Industry trends
    • Return on investment
    • Experiments to learn
• “Solution validation”
  • have explicit solution validation phase rather than jumping in w/ most difficult approach
    • Write customer letter
    • Identify prior art
    • Find reference users
    • Prefer experimentation over analysis
    • Find path more quickly traveled (expensive to build in entirety)
    • Justify switching costs
• “Strategies are grounded documents which explain the trade-offs and action that will be taken to address a specific challenge”
  • vs vision, strategy is approach to specific challenge (vs gentle aligning pressure), practical (vs aspirational), variable time frame (vs long-term), accurate and detailed (vs illustrative and directional), and can be written as often as useful (vs as few as possible)
  • start off w/ diagnosis: theory describing the challenge at hand
    • call out factors and constraints that define challenge
    • have thorough problem statement
  • second step: identify policies that will apply to address challenge. describes general approach that you’ll take, are often trade-offs between two competing goals
  • when apply guiding principles to diagnosis, get actions. “this is going to be uncomfortable, but I think it can work” is ideal outcome
• “visions describe a future in which [the tradeoffs described in strategy docs] are no longer mutually exclusive. An effective vision helps folks think beyond the constraints of their local maxima”
  • “details are used to illustrate the dream vividly, not to prescriptively constrain its possibilities”
  • composed of:
    • one-to-two sentence aspirational statement
    • value prop: how will you be valuable to your users and to your company?
    • what capabilities will the product, platform, or team need in order to deliver on your value prop?
  • will know vision is succeeding when people reference the doc to make their own decisions
• Metrics and baselines
  • “There is a moment in every company’s growth when top-level planning shifts from discussing specific projects to talking about goals. This happens recursively across each scope of leadership, as areas of accountability become too broad or complex for their leaders to consistently understand every project’s details.”
  • Good goals have:
    • Target: where want to reach
    • Baseline: where you are today
    • Trend (current velocity)
    • Time frame (bounds change)
  • Helpful to have baseline (counter) metrics. Identify when should pause pursuing goals and instead invest in platform quality
• on migrations: “The fact that something stops working at significantly increased scale is a sign that it was designed appropriately to the previous constraints rather than being over-designed”
• Defining teams and groups. Consider:
  • Can you write a crisp mission statement for each team?
  • Would you personally be excited to be a member of each of the teams as well as to be the manager of each of those teams?
  • Put teams that work together (especially poorly) as close together as possible
  • Can you define clear interfaces for each team?
  • Can you list the areas of ownership for each team?
• When rolling out changes, “if necessary, hold an organization all-hands, but probably try not to. People don’t process well in large groups, and the best discussions take place in small rooms”. 
• Controls (the mechanisms you use to align with other leaders you work with)
  • Metrics align on outcomes (while leaving flexibility for how outcomes achieved)
  • Visions ensure you agree on long-term direction while preserving short-term flexibility
  • Strategies confirm you have shared understanding of current constraints and how you will address them
  • others include org design, headcount and transfers, roadmaps, performance reviews
  • Degree of alignment (apply to each control):
    • I’ll do it Best used sparingly, but when do, be explicit that you will handle something
    • Preview “I’d like to be involved early and often”. An area where aren’t on same page, will avoid redoing work
    • Review “I’d like to weigh in before it gets published or rolled out, but we’re probably aligned on the topic”
    • Notes “I’d like to follow but don’t have much I can add to” Likely aligned, and likely far-reaching initiative, where want to be able to represent their work
    • No surprises We’re aligned, but need updates to keep mental model in tact. I’m evaluated on my ability to stay on top of new problems
    • Let me know “We’re well aligned on this, since my colleagues have done it efore and done it well. I want them to let me know if something comes up that I can help with, but otherwise I’m totally confident it’ll go well, so we don’t need to talk about this much”
  • Controls + Alignment = Interface between you and folks you support
  • use to identify if micromanaging. If can’t imagine world where you don’t preview everyone’s work, probably time to reflect on what’s holding you back from letting the team thrive
• Career narratives
  • “most folks are always at the furthest point in their career, each change a step into the unknown, with limited visibilty into the upcoming opportunities that their company can provide”
  • identify the skills needed to do the job you want (e.g. head of engineering) and find ways to apply those in current role. Don’t need to wait to get there. E.g. org design, process design, business strategy, recruiting, mentoring, coaching, public speaking, written communication, broad personal network, broad foundation from product eng to infrastructure eng. Find opportunities in current role to practice these
• Three rules for speaking to the media
  • Answer the question you want to be asked. Don’t accept a question’s implicit frame; (re-)frame it yourself
  • Stay positive. Find positive framing and stick to it
  • Speak in threes. Find three concise points, make them your refrain, refer back to them repeatedly

Approaches

• “consistency is a precondition of fairness”
• rather than writing policies, write norms, “which provide nonbinding recommendations that] don’t require escalations to address ambiguities or edge cases”
• “Folks who communicate a “no” effectively are not the firmest speakers, nor do they make frequent use of the word itself. They are able to convincingly explain their team’s constraints and articulate why the proposed path is either unattainable or undesirable”
• Most frequent topics for disagreement:
  • velocity – why is this taking so long?
    • response: provide compelling explanation of how team finishes work
    • partial work has no value, and the team’s defining constraints are often in the finishing stages
    • one solution is to build kanban board to display constraints (need not maintain)
    • this allows to focus on core constraint
    • then need to describe what’s preventing you from solving for it
  • prioritization – why can’t you work on this, more important project?
    • document all incoming asks (roadmap, migrations, complaints, surprise opportunities), develop guiding principles for how work is selected
    • need to accept that plans will change, and have clear point in time when that’s on the table (e.g. sprint planning meeting, quarterly okr review)
• “with the right people, any process works, and with the wrong people, no process works”
• in midsize, rapidly growing company, parts are growing quickly, with emphasis on execution, other parts largely stabilized, with ideas becoming more valued currency. Metaphor: growth plates (middle part of bone doesn’t grow, plate does)
  • small startup or at growth plate of any company, dealing with new problems
    • not necessarily novel, but problems company has never prioritized long enough to get usable solution out the door
    • execution is focus. surplus of fairly obvious ideas, but constrained bandwidth for evaluating them
    • adding more ideas is counter-productive
    • hard to consistently do the basics well, b/c won’t have enough time to do them well. have to get comfortable doing as well as time constraints allow, sometimes that will lead to being mediocre at things you’re passionate about
  • outside growth plates, working on problems with known solutions
    • slow-growth environments used to be high-growth environments, “which means they were once run by someone who was a sufficiently effective executor to evolve them into slow-growth”
    • can do basics as manager very well (build relationships, gel team, work w/ them on career development)
• pursue scope, not growing headcount; take responsibility for success of increasingly important and complex facets of the organization and company. Lot less competition for hard work than headcount
• project-managing an initiative working w/ 50 EMs is far better learning opportunity than managing an org of 50, and builds same skills

Culture

• most effective way to provide opportunity (to those in org) is through structured application of good process; as lightweight as possible, rigorous enough to consistently work
• “The more fully you embrace optimizing for your collective peers, the closer your priorities will mirror your manager’s”
• hiring manager-of-managers
  • Partnership have they been effective partners to their peers, and to the team that they’ve managed?
  • Execution can they support the team in operational excellence?
  • Vision Can they present a compelling, energizing vision of the future state of their team and scope?
  • Strategy Can they identify the necessary steps to transform the present into their vision?
  • Spoken and written communication Can they convey complicated topics in both written and verbal communication? Can they do all this while being engaging and tuning the level of detail to their audience?
  • Stakeholder management Can they make others, especially executives, feel heard? Can they make these stakeholders feel confident that they’ll address any concerns?

Careers

• build map of past year. write down each transition (meaningful change in how you work, e.g. manager changed, team’s mission redefined, major reorg). What skills did you rely on to navigate the transition? What skills did the transition give you an opportunity to develop?
• interview suggestion: do prepared presentation instead of impromptu
• career ladders
  • rule of thumb: any ladder w/ more than 10 individuals should be fully fleshed out, smaller functions can survive w/ something rough
  • open invitation to folks in role to improve their ladder
  • establish template for shared themes across every ladder

Appendix

• Measuring effective sprint process

  • team knows what they should work on
  • team knows why work is valuable
  • team can determine if work is complete
  • team knows how to figure out what to do next
  • stakeholders can learn what team is working on
  • stakeholders can learn what team plans to work on next
  • stakeholders know how to influence team’s plans