A written version of the interactive roadmap above — every station, what you'll learn, and a small thing to build — laid out for reading, reference and search.
The Transition Start here
F1. From IC to Manager
Beginner · 50 min
The skills that made you a great engineer are not the ones that make you a good manager. Learn the fundamental shift — your output is now the team’s output — the trap of staying the best coder in the room, and why letting go of the keyboard feels like losing your identity before it feels like a promotion.
Skills: The output shift · Letting go of the code · Player vs coach · Redefining your value
Build it: Name three things you were rewarded for as an IC that would now make you a worse manager. What replaces each?
✓ Checkpoint: Name what you shipped last month. If everything on the list is something you personally typed, your output has not shifted yet.
F2. 1:1s That Matter
Beginner · 45 min
The 1:1 is a manager’s highest-leverage recurring meeting — and the first one people cancel. Learn to run 1:1s that belong to the report not the status update: building trust, surfacing problems while they’re small, and listening more than you talk. Skipping them is how you find out about resignations too late.
Skills: Their agenda, not yours · Building trust · Surfacing problems early · Listening > talking
Build it: Your report says "everything’s fine" every week. Write three questions that get past the reflex answer.
✓ Checkpoint: Explain why a 1:1 where you did most of the talking was a status meeting wearing a costume.
F3. Feedback & Coaching
Beginner · 50 min
Feedback is a gift most managers withhold until review season, when it’s useless. Learn to give specific, timely, kind-not-nice feedback — praise in the moment, correct in private, always about behavior not character — and to coach by asking questions instead of handing out answers that keep people dependent on you.
Skills: Specific & timely · Kind, not nice · Behavior not character · Coaching questions
Build it: Turn "your PRs are sloppy" into feedback someone can actually act on tomorrow. What made the original useless?
✓ Checkpoint: Give a piece of feedback out loud that is kind rather than nice — aimed at a behaviour, not at who someone is.
F4. Delegation
Intermediate · 45 min
Delegation is how a manager scales, and doing it badly is how they burn out. Learn to delegate outcomes not tasks, match the work to the person’s growth edge, and sit with the discomfort of watching someone do it differently — and slower — than you would, because that’s where they grow and you get your time back.
Skills: Outcomes, not tasks · Match to growth edge · Tolerating "not how I’d do it" · Delegation vs abdication
Build it: You keep taking back a task because "it’s faster to do it myself." Explain the compounding cost of that choice over a quarter.
✓ Checkpoint: Describe something you delegated that came back done differently than you would have done it, and whether you let that stand.
F5. Running the Work
Intermediate · 50 min
A team needs a legible way to turn priorities into shipped work. Learn just enough process — planning, standups, retros, backlog health — to create clarity without ceremony, spot when a project is quietly slipping, and know the difference between process that serves the team and process the team serves.
Skills: Lightweight planning · Standups & retros · Spotting slippage · Process that serves the team
Build it: A project is "80% done" three weeks running. What questions expose where the real risk is hiding?
✓ Checkpoint: Name one ritual your team runs that you would defend, and one you keep only because stopping feels awkward.
F6. Hiring & Interviewing
Intermediate · 55 min
The team you build is the biggest decision you make. Learn to write a real role, run a fair and consistent interview loop, read signal past nerves and pedigree, sell the role honestly, and know that a rushed bad hire costs far more than a slow-filled seat — especially the one you have to manage out later.
Skills: Defining the role · Consistent loops · Signal vs noise · Selling honestly
Build it: Two candidates: one polished and average, one rough and exceptional. Design the loop that reliably tells them apart.
✓ Checkpoint: Explain the difference between signal and a candidate who reminds you of yourself.
Leading People The craft
T1. Performance Management
Intermediate · 55 min
Nothing tests a manager like a performance problem. Learn to set clear expectations before they’re missed, diagnose whether it’s a skill, will or fit issue, run a fair improvement plan, and act early — because a low performer you tolerate is a tax you charge every other person on the team.
Skills: Clear expectations · Skill vs will vs fit · Fair improvement plans · Acting early
Build it: A senior engineer is technically strong but toxic in reviews. Is this a performance problem? Explain how you’d frame it.
✓ Checkpoint: Take an underperformance case and say whether it is skill, will or fit — and explain why the response differs for each.
T2. Growth & Careers
Intermediate · 50 min
People stay where they grow. Learn to use the career ladder as a map not a weapon, have real growth conversations, sponsor people into stretch work and visible wins, and understand that promotion is recognition of a level someone already operates at — not a reward you dangle for more effort.
Skills: Reading the ladder · Growth conversations · Sponsorship vs mentorship · Promotion as recognition
Build it: A strong mid-level wants to make senior. Describe the stretch work you’d sponsor and the evidence a promo committee needs.
✓ Checkpoint: Explain the difference between mentoring someone and sponsoring them, and which one you have actually done recently.
T3. Difficult Conversations
Advanced · 50 min
The conversations you avoid are the ones that most need having. Learn to prepare for and hold the hard ones — underperformance, conflict, comp disappointment, letting someone go — with candor and care, leading with the hard thing instead of burying it under ten minutes of small talk that fools no one.
Skills: Preparing the message · Candor with care · Leading with the hard part · Staying present
Build it: You have to deny a promotion someone expected. Write your opening two sentences — no cushioning that hides the answer.
✓ Checkpoint: Explain why burying the hard part at the end of a difficult conversation is unkind rather than gentle.
T4. Culture & Psychological Safety
Advanced · 55 min
Teams don’t rise to your standards; they fall to their culture. Learn what psychological safety actually is — the belief you can take a risk without being punished — how a manager’s reaction to the first mistake or dumb question sets it, and why safe teams ship faster because they surface problems instead of hiding them.
Skills: Psychological safety · Reaction to mistakes · Norms & rituals · Culture as behavior
Build it: Someone ships a bug that causes an outage. Describe your first public reaction and what it teaches everyone watching.
✓ Checkpoint: Describe what your team saw happen the last time someone broke production — and what that taught them about reporting the next one.
T5. Motivation & Retention
Advanced · 45 min
Regretted attrition is expensive and quiet until it isn’t. Learn what actually motivates engineers — autonomy, mastery, purpose over ping-pong tables — how to spot the disengagement that precedes a resignation, and why the stay conversation beats the exit interview every time: one keeps people, the other explains why you didn’t.
Skills: Autonomy, mastery, purpose · Spotting disengagement · Stay conversations · Regretted attrition
Build it: Your best engineer just went quiet in meetings. List the signals you’d watch and the conversation you’d start this week.
✓ Checkpoint: Name one person on your team who is quietly disengaging, and what you would ask them before they resign rather than after.
T6. Managing Yourself
Advanced · 45 min
You can’t pour from an empty cup, and management is a job with no natural stopping point. Learn to manage your own time and energy, resist becoming the bottleneck, find peers and a manager-of-managers to vent to, and separate your self-worth from a team’s outcomes you only partly control.
Skills: Time & energy · Avoiding the bottleneck · Peer support · Identity vs outcomes
Build it: Every decision routes through you and you’re drowning. Name the three you should never have kept — and who gets them.
✓ Checkpoint: Identify the decision your team currently cannot make without you, and say whether that is necessary or a bottleneck you built.
Leading the Org Scale beyond one team
P1. Strategy & Roadmaps
Advanced · 55 min
A manager translates fuzzy company goals into work a team can do and believe in. Learn to build a roadmap that’s a bet not a promise, say no to good ideas to protect great ones, connect daily tasks to why they matter, and keep the plan honest when reality — as it always does — disagrees with the quarter’s plan.
Skills: Goals → work · Roadmap as a bet · Saying no · Connecting to the why
Build it: Leadership hands you three "top priorities." Explain why three top priorities means zero, and how you’d force the ranking.
✓ Checkpoint: State a roadmap item as a bet: what you believe, what would prove you wrong, and what you gave up to fund it.
P2. Stakeholder Management
Advanced · 50 min
Your team’s work is judged through other people’s eyes. Learn to manage stakeholders — product, other eng teams, execs — by building trust before you need it, communicating status honestly (including bad news early), and turning a room of competing agendas into aligned support instead of a source of thrash.
Skills: Trust before you need it · Honest status · Bad news early · Managing competing agendas
Build it: A dependency team is about to make you miss a deadline. Draft the message you send up before it becomes a surprise.
✓ Checkpoint: Explain why bad news early buys you credibility while bad news late spends it, even when the outcome is identical.
P3. Cross-Functional Work
Advanced · 45 min
Real impact happens across team boundaries, where no one is in charge. Learn to lead through influence not authority — with product, design, data and other eng teams — clarify who owns what with a light RACI, and drive shared outcomes when the people you depend on don’t report to you and never will.
Skills: Influence without authority · Clarifying ownership · Shared outcomes · Working across boundaries
Build it: A project spans three teams with no clear owner and it’s stalling. What’s the first artifact you create to unstick it?
✓ Checkpoint: Name a piece of cross-functional work with genuinely unclear ownership, and how you would resolve it without a reorg.
P4. Managing Up & Influence
Advanced · 50 min
Managing up isn’t politics; it’s making sure your team’s work is understood and resourced. Learn to give your own manager the context they need, disagree well and commit, bring solutions with problems, and represent your team’s reality upward so decisions above you are made with the facts, not despite them.
Skills: Giving context up · Disagree & commit · Solutions with problems · Representing the team
Build it: You think a top-down deadline is unrealistic. Describe how you push back in a way that gets heard, then either wins or commits.
✓ Checkpoint: Explain what your manager needs to know that they cannot see from where they sit — and how much of it you actually pass up.
P5. Org Design & Scaling
Advanced · 50 min
As you grow, the shape of the org becomes the shape of the software (Conway’s Law). Learn to split and form teams around clear ownership, manage the handoffs a split creates, weigh the cost of every dependency you draw between teams, and re-org for a reason — not because someone above you got bored.
Skills: Conway’s Law · Team boundaries · Managing dependencies · Re-orgs with a reason
Build it: One team owns a service three other teams constantly wait on. Sketch two org fixes and the trade-off each makes.
✓ Checkpoint: Explain Conway's Law in one sentence, then name a system boundary at your company that exists because of an org chart.
P6. Managing Managers
Advanced · 50 min
The next step multiplies the distance from the code. Learn to manage managers — coaching leadership instead of doing the work, running a team through skip-levels without undermining, holding a consistent bar across teams you don’t see daily, and deciding whether the director path or a return to deep IC work is actually the life you want.
Skills: Coaching leaders · Skip-levels · A consistent bar · Director vs staff+ path
Build it: A skip-level reveals a manager on your team is the problem. How do you act without going around them or ignoring it?
✓ Checkpoint: Explain what changes about feedback when the person receiving it manages people themselves.