An Elegant Puzzle: Systems of Engineering Management


This book starts with organizational design – it gets the right people in the right places, empowers them to make decisions, and then holds them accountable for their results. Next are some tools of management – from systems thinking to vision documents, metrics, reorgs, and career narratives. Approaches touches on how you might need to adjust how you manage as the organization scales. Culture is covered next and touches on how to nurture an inclusive team. Last is a focus on careers – interviewing hiring, and performance management

The Rabbit Hole is written by Blas Moros. To support, sign up for the newsletter, become a patron, and/or join The Latticework. Original Design by Thilo Konzok.

Key Takeaways


  1. When I want to solve a problem quickly and cheaply, I think about process design. If process is too weak a force, culture too slow, and there isn’t much time, then organizational design is a good option
  2. One of the fundamental challenges of organizational design is sizing teams
  3. Managers should support 6-8 engineers and managers-of-managers should support 4-6 managers
  4. A team is at least 4 people as this diversity helps attack and solve complex problems in a more efficient manner
  5. Keep innovation and maintenance together as this leads to higher morale and will avoid creating a two-tiered class system of innovators and maintainers
  6. 4 states of a team and the general solution. Teams want to climb from falling behind to innovating, while entropy drags them backward. Each
    1. Falling behind – add people
    2. Treading water – reduce WIP
    3. Repaying debt – add time
    4. Innovating – add slack
  7. Consolidate your efforts as a leader. Don’t “peanut butter” the situation by trying to evenly spread yourself out. Spend the most time on the teams that need the most help. Adding new individuals to teams disrupts that team’s gelling process, so have rapid growth periods followed by consolidation/gelling periods
  8. Do not separate high-performing teams. They can tackle new problems but should stay together. Shifting scope works better than moving people because it avoids re-gelling costs, and it preserves system behavior. You can also try rotating individuals for a fixed period into an area that needs help
    1. Campbell – Teams > Individuals > Problems
  9. You obviously don’t want to stop growth, but you can concentrate that growth such that your teams alternate between periods of gelling and consolidation
  10. Counterintuitively, you can slow a team down by shifting resources to it, because doing so creates new upstream constraints. Slack is a beautiful thing. It gives people and teams time to improve areas and do it with minimal coordination costs
  11. The real system killer is not system rewrites but the migrations that follow those rewrites
  12. You only get values from projects you finish. To make progress, above all else, you must ensure that some of your projects finish
  13. 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.
  14. Projects and tasks must have owners – “Who owns X?”
  15. Block out large chunks of time each week to focus. Telecommute, block out 8-11 each morning, experiment until you find something that works for you. The best solution is a culture of documentation – read documents, and a documentation reach that actually works. Try to get off the “critical path” – don’t be a gatekeeper. This is a significant implementation bug rather than a stability feature to be emulated (except for very important legal/financial/other matters that should have a gatekeeper.)
  16. Organizational debt – the sibling of technical debt and represents things like biased interview processes and inequitable compensation mechanisms, systemic problems which prevents your organization from reaching its potential. Responding to this is central to being an effective leader. A great way to attack this is to focus on a few areas you want to improve and if you’re making progress, feel good about it. You can slack off on the other areas (for now). You can’t do it all at once
  17. Succession planning is thinking through how the organization would function without you, documenting those gaps, and starting to fill them in. This is often overlooked but is vital for the long-term success of your team and organization. First step is to figure out what you do – write down what meetings you attend, what your role is in those meetings, recurring processes, individuals you support, emails you send, requests coming in, to-do lists, external relationships. Taking 2-3-week vacations is actually a beautiful thing – you can see what slips through the cracks and these items can be the start of next year’s list.


  1. Change is the catalyst of complexity and these tools are meant to help lead efficient change – systems thinking, metrics, and vision
  2. Creating an arena for quickly testing hypotheses about how things work, without having to do the underlying work beforehand, is the aspect of systems thinking that I appreciate most
  3. Problem discovery – problem selection – solution validation – execution – problem discovery…
  4. For problem discovery look at – users’ pain, users’ purpose, benchmark, cohorts, competitive advantages/moats
  5. Must align on strategy and vision in order to scale effectively. Strategies are grounded documents which explain the trade-offs and actions that twill be taken to address a specific challenge. Visions are aspirational documents that enable individuals who don’t work closely together to make decisions that fit together cleanly
  6. No extent of artistry can solve a problem that you’re unwilling to admit
  7. Vision – vision statement, value proposition, capabilities, solve constraints, future constraints, reference materials, narrative
  8. Define goals through a target, baseline, trend, time frame
    1. See John Doerr on OKRs
  9. Since value is gained when a project is completed, you must celebrate completions, no matter how small
  10. Rolling out the change can be difficult/awkward but here are 3 steps to help
    1. Explanation of reasoning driving the reorganization (particularly those who are heavily impacted)
    2. Documentation of how each person and team will be impacted
    3. Availability and empathy to help bleed off frustration from impacted individuals
  11. The 3 rules for speaking with the media
    1. Answer the question you’re being asked – reframe difficult questions
    2. Stay positive
    3. Speak in threes – three concise points, make them your refrain, and continue to refer back to your three speaking points
  12. Failure modes – domineering personalities, bottlenecks, status-oriented groups, inert groups
  13. Presenting to senior management
    1. Communication is company-specific
    1. Start with the conclusion
    2. Frame why the topic matters
    3. Everyone loves a narrative
    4. Prepare for detours
    5. Answer directly
    6. Dive deep into the data
    7. Derive actions from principles
    8. Discuss the details
    9. Prepare a lot, practice a little
    10. Make a clear ask
  14. Communicating with teams/peers
    1. Be a facilitator, not a lecturer
    2. Brief presentations, long discussions
    3. Small breakout groups
    4. Bring learnings to the full group
    5. Choose topics that people already know about
    6. Encourage tenured folks to attend
    7. Optional pre-reads
    8. Checking-in – your name, your team, one sentence about what’s on your mind
    9. Every quarter I spend a few hours categorizing my calendar from the past 3 months to figure out how I’ve invested my time. This is useful for me to reflect on the major projects I’ve done, and also to get a sense of my general allocation of time. I then use this analysis to shuffle my goal time allocation for the next quarter


  1. Work the policy, not the exceptions – consistency is a precondition of fairness so cultures which allow frequent exceptions are not only susceptible to bias, but also inefficient
  2. Collect every escalation as a test case for reconsidering your constraints. This approach is powerful because it creates a release valve for folks who are frustrated with edge cases in your current policies – they’re still welcome to escalate – while also ensuring that everyone is operating in a consistent, fair environment; escalations will only be used as inputs for updated policy, not handled in a one-off fashion. The approach also maintains working on policy as a leveraged operation for leadership, avoiding the onerous robes of an exceptional judge
  3. Velocity – when folks want you to commit to more work than you believe you can deliver; your goal is to provide a compelling explanation for how your team finishes work. Finishes is particularly important, as opposed to does, because partial work has no value, and your team’s defining constraints are often in the finishing stages.
  4. Management, at its core, is an ethical profession. To see ourselves, we don’t look at the mirror, but rather at how we treat a member of the team who is not succeeding. Not at the mirror, but at our compensation policy. Not at the mirror, but at how we pitch the roles to candidates
  5. Strong relationships > any problem. Start debugging problems from the relationship angle before anything else. With the right people, any process works, and with the wrong people, no process works
  6. Instead of avoiding the hardest parts, double down on them
  7. Do the right thing for the company, the right thing for the team, and the right thing for yourself, in that order
  8. The best management philosophy never stands still, but – in the model of the Hegelian dialectic – continues to evolve as it comes into contact with reality. The worst theory of management is to not have one at all, but the second worst is one that doesn’t change.
  9. Long bones have growth plates at their ends, which is where the growth happens, and the middle doesn’t grow. This is a pretty apt metaphor for rapidly growing companies, and a useful mental model to understand why your behaviors might not be resonating in a new role. Execution is the primary currency in the growth plates because you typically have a surplus of fairly obvious ideas to try and there is constrained bandwidth for evaluating those ideas. What folks in the growth plates need is help reducing and executing the existing backlog of ideas, not adding more ideas that must be evaluated. Teams in these scenarios are missing the concrete resources necessary to execute, and supplying those resources is the only way to help. Giving more ideas feels helpful, but it isn’t. Away from the growth plates you’re mostly working on problems with known solutions. Known solutions are amenable to iterative improvement, so it would make sense for execution to be highly valued, but I find that, in practice, ideas – especially ideas that are new within your company – are most highly prized.
  10. Leadership is matching appropriate action to your current context
  11. As managers looking to grow ourselves, we should really be pursuing scope: not enumerating people but taking responsibility for the success of increasingly important and complex factors of the organization and company. This is where advancing a career can veer away from a zero-sum competition to have the largest team and evolve into a virtuous cycle of empowering the organization and taking on more responsibility. There is a lot less competition for hard work. Aim to grow scope through broad, complex projects
  12. You need to learn how to set your own direction – talk to peers and see what they’re thinking about, read technical papers, cast the widest net possible so that you understand the problem space
  13. For every problem that comes your way – close out, solve, or delegate


  1. An inclusive organization is one in which individuals have access to opportunity and membership
  2. Useful metrics – retention, usage rate, level distribution, time at level
  3. Useful programs – recurring weekly events, employee resource groups, team offsites, coffee chats, team lunches,
  4. Ingredients for a great ream – awareness of each other’s work, evolution from character to person, refereeing defection, avoiding zero-sum culture
  5. The best learning doesn’t always come from your manager – create a community of learning with your peers
  6. Humans are prone to interpreting events as causal, but it may be more appropriate to see problems in terms of a series of stockpiles that grow and shrink based on incoming and outgoing flows


  1. Interviewing tips
    1. Be kind to the candidate
    2. Ensure that all interviewers agree on the role’s requirements
    3. Understand the signal your interview is checking for
    4. Come to your interview prepared to interview
    5. Deliberately express interest in candidates
    6. Create feedback loops for interviewers and the loop’s designer
    7. Instrument and optimize as you would any conversion funnel
  2. If you like an interviewee and will extend an offer, have everyone who interviewed them send them an email or letter saying how much they enjoyed meeting them
  3. Have interviewers write up their feedback on candidates individually
  4. The most sacred responsibilities of management are selecting your company’s role model, identifying who to promote, and deciding who needs to leave
  5. If hiring from within, some necessary ingredients are: an executive sponsor, a recruiting partner, self-sustaining mission, a clear career ladder, role models, dedicated calibrations (performance reviews)


  1. Teams have a limited appetite for new processes: try to roll out one change at a time and don’t roll out the next change until the previous change has enthusiastic compliance
  2. Process needs to be adapted to its environment, and success comes from blending it with your particular context

What I got out of it

  1. Some great tools, ideas, perspective on how to manage a quickly scaling organization

In the Latticework, we've distilled, curated, and interconnected the 750+book summaries from The Rabbit Hole. If you're looking to make the ideas from these books actionable in your day-to-day life and join a global tribe of lifelong learners, you'll love The Latticework. Join us today.