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Seniority/Maturity

Moving towards seniority/maturity in work.

Resources​

  • Startup CTO Handbook
    • Targetting devs growing into CTO role. How to manage a tech team.
    • People: management, coaching, hiring, etc.; Tech: debt, roadmap, DX, DevOps, testing, security & compliance, etc.
  • Engineering Management | GitHub @charlax
    • List of resources related to (engineering) management (something like this Wiki)

Sites​

  • 3 Mistakes I made as an Engineer, but had to Become a Manager to See (HN)
    • People problems are important, hiring well saves time, and getting to know your coworkers
    • This feels like things to get right after getting the basics right, i.e. code is working
  • Stop Being a Junior | Kent C. Dodds
    • Tech is fast, take it as an opportunity to quickly catch up to the frontier
    • Try to be at the level of the seniors, and eventually will start to feel like one
    • Volunteer to participate and talk about accomplishments but do not overstep
  • On Being A Senior Engineer | Kitchen Soap
    • Mostly focused on software engineer role, but the skills and practices are transferable to any "senior" or "mature" role
    • These are observations, not rules. The goal is to internalize the principles. Some of the inspiring ones are:
      • The non-technical areas: self-awareness when it comes to communication. Be assertive, not passive or aggressive.
      • Anticipation of the outcome of a decision/design, how will things unfold in the future?
      • Sponsorship: provides opportunity and exposure for others, e.g.: suggesting someone to lead a project
      • Make trade-offs explicit: every project cuts corners, and mature engineers know how much is cut
      • Empathetic: the ability to view the decisions from others' perspective
      • No empty complaints: always provide at least 1 suggestion to improve before complaining
      • Aware of biases: confirmation, self-serving, fundamental attribution, hindsight, outcome, planning fallacy
      • Understand the importance of (sometimes irrational) feelings people have: objectively the best might not be subjectively the best for this group of people
  • An action plan for engineering career success | GitHub The ReadMe Project
    • Technical skills, connect the dots between engineering & revenue, demonstrate understanding of the business domain
    • Brag document: records of completed projects, professional development, feedback and recognition, etc
    • Communicate well, mentor others, write documentation, and continue to learn
  • The Curse of the Senior Software Engineer
    • The curse of staying too long at a senior role
    • Too senior to be considered as a senior but too inexperience for leadership role
    • Either play the corporate game and climb the ladder, or quit the game and do something that doesn't care about the titles

Managerial Role​

  • What you give up when moving into engineering management | Stackoverflow blog (HN)
    • Managers give up focus time, have to deal with longer feedback cycles, more conflicts and interpersonal issues, make fewer technical decisions, and less time acquiring tech skills
  • Promoted from Dev to Team Lead: 8 Things They Didn't Tell Me | Dev Interrupted
    • Quite an easy read with good examples
    • Skills don't translate: skill sets of a dev vs a team lead is different
    • Keep your instincts but change your behaviour: sometimes just asking the right question can unblock people
    • Communicate "why" more than "what and "how": let the team see the bigger picture
    • Culture is a real thing. Team leads are responsible for it
    • Clear a path for the team: unblock people. Generally three types of blockers: technical, dependencies and priorities
    • Spend 50% of the time on priority setting and estimation
    • Invest in the ecosystem: build relationships with other teams, sales, product owners, ops, etc
    • Translate engineering to executives with data: provide data and metrics
  • The way that Jensen Huang runs Nvidia is wild
    • Direct reports, no status reports, everyone has context, no formal planning cycles
  • What it's like to start a job as CEO?
    • E.g.: learn quick, be curious about the details but not micromanage, big decisions with bizarrely little context
  • The most important skill in a startup engineering leadership
    • Pacing, the leader pace and the member pace
    • Be honesty and transparent, constant measurement
    • Set goals, make incremental changes and carefully name the repercussions
  • What Your Job Ad Says About You
    • Competitive salary and years of experience means nothing
    • Instead of listing lengthy requirements, put what the candidate is expected to do in the first year
  • Mistakes as a new manager (HN)
    • Delegation: learn to delegate work and empower the team
    • Dopamine: changes from shipping to giving feedback, reports, etc.
    • Quality v.s. quantity: learn to build high quality team not a bigger team
    • Engagement: too much means micromanaging, too little means disengaging
    • Perception: how to show your work as a manager, clarity and visibility of effort
    • Success metric: Is the team shipping? Is the team happy?
  • How I've run major projects
    • Focus and set the project as the top priority
    • Maintain a detailed plan to success, observe and keep iterate quickly on the plan
    • Over-communicate, both 1-1 and broadcast updates to get everyone aware of what's happening around
    • Break off subproject and delegate to others to manage a goal
    • Project managers are laser focus and highly organized person, expect their IC ability to take a hit
  • Compensation as a Reflection of Values | Oxide (2021)
    • Also, Oxide's Compensation Mode: How is it Going? (2025)
    • Oxide pay almost everyone equal amount of salary, from founder to all employees, except some sales roles
    • Explained why they do this, how that reflect the values and benefit the company
  • Stuff I learned at Carta | Will Larson
    • 2 years as CTO of Carta
    • On strategy, culture, LLMs, managing seniors, managing costs, explaining eng costs to execs, etc.
    • Many links to previous blogs