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Scale an Engineering Team from 5 to 20

24 weeks · 5 milestones

Scale an engineering team from 5 to 20 people — the hardest management transition in software. The skills that made you effective at 5 will actively harm you at 20. Every milestone here is about replacing personal relationships with systems, and replacing your presence with documented authority.

Milestone map

Milestone map

5 milestones

Find what breaks as you grow

2–3 weeks. The interviews take one week. Writing the document takes another. The most important bottleneck is usually the one that takes longest to name — build in time to sit with the findings before writing.

Before hiring anyone, find what will break when the team doubles. Interview every team member alone. Ask what slows them down, what they can't find, and which decisions they wait for. Write a scaling risk document naming the top five bottlenecks, ranked by severity. It becomes your hiring and process roadmap.

Proof required

Share the risk document, at least 500 words. For each of five bottlenecks, give the current state and the fix. Say what breaks at double size. Share anonymised interview notes with at least one direct quote per person. Write 200 words on the bottleneck that surprised you most.

What gets checked

  • Bottlenecks are specific. 'I sign off all API design and block two squads' is specific.
  • Each person has at least one direct quote. Paraphrases don't count.
  • Each fix is a system, not an event. An ADR process beats 'improve communication'.

Common mistakes

  • Skipping the interviews. Managers miss their own bottlenecks because they're inside them.
  • Ranking by ease of fixing, not severity. The hardest one is usually the most important.

Resources

Foundationstart here

Depthgo deeper

Masteryfor the dedicated

What a verifier looks for

  • Could each bottleneck brief a new hire? 'Process needs work' can't; a named failure can.
  • Ask them to read one quote that surprised them. No surprising quote means they ran a survey.
  • Ask which bottleneck is their own fault. A good audit names one.
  • Check each fix is a system. A fix that needs the manager ongoing isn't a fix.

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Design the team for 20 engineers

2–3 weeks. The design takes a week. The team presentation and incorporating feedback takes another. The design will change based on the presentation — budget time for a second draft.

Design your team structure for 20 engineers before hiring anyone. Decide how many sub-teams there are and what each owns. Decide how they communicate and make decisions together. Set the manager-to-engineer ratio at each level. Write it up as a design document. Present it to the current team and record their reactions. Their concerns now are your problems at scale.

Proof required

Share the design document with diagrams, at least 600 words. Include the org chart by role and what each sub-team owns. Show how they decide together and how often they meet. Share anonymised notes with at least three concerns the team raised. Write 200 words on how you'll resolve the most serious one.

What gets checked

  • The org chart shows roles, not names. It must work for people who haven't joined yet.
  • Each sub-team owns named systems or domains. Overlaps are named, with a way to resolve them.
  • The three concerns are specific, like shared infrastructure falling between two sub-teams.

Common mistakes

  • Designing around current people, not current systems. It breaks when anyone leaves.
  • Finalising without showing the team. Their known concerns become your future incidents.

Resources

Foundationstart here

Depthgo deeper

Masteryfor the dedicated

What a verifier looks for

  • Can you tell what each sub-team owns from the document alone? If not, there are gaps.
  • Ask who owns the deployment pipeline. 'Shared' with no process means nobody.
  • Ask what happened in the room when the biggest concern came up.
  • Ask what they'd do if a new VP wanted a different structure in six months.

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Hire five engineers without lowering the bar

12–20 weeks depending on the hiring market and role. Five hires at an average 4-week process each. Running processes in parallel is required — sequential hiring takes too long at this stage.

Run five engineering hires from job description to signed offer. Log every final-round candidate with the decision and a specific reason. For each offer, record anything you compromised on and why. For each declined or rejected candidate, record the deciding factor. The log proves you held the bar.

Proof required

Share the anonymised hiring log, Candidate A onwards. Show every final-round candidate, the decision and a one-sentence reason. For the five offers, show the deciding factor. Write 250 words on whether your idea of a strong candidate drifted, and when.

What gets checked

  • The log covers every final-round candidate, not just the hires.
  • Each reason is specific, like 'strong design, couldn't explain debugging trade-offs'. Not 'not the right fit'.
  • The reflection is honest. If time pressure lowered the bar, call it drift.

Common mistakes

  • Hiring for 'culture fit' without defining it. Write the reason before the offer goes out.
  • Letting urgency lower the bar. The fifth hire is the riskiest; address it in the reflection.

Resources

Foundationstart here

What a verifier looks for

  • Count final-round candidates who didn't get offers. Zero means the log is incomplete.
  • Could someone else apply each reason? 'Not quite right' can't be replicated.
  • Ask what they'd change if they ran it again tomorrow.
  • Ask whether hire five was as strong as hire one. The honest answer tells you most.

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Build a team that works without you

2 weeks of absence plus 1 week of preparation and 1 week of documentation on return. The preparation week is not optional — a team that is not briefed on the authority matrix before you leave will default to waiting for you regardless of what the document says.

Take two weeks in a row fully off: no Slack, email, code reviews or decisions. Before you go, list every regular decision type and who can make it without you. When you're back, list the decisions made, the ones delayed for you, and any incidents. Decisions made versus decisions delayed is your delegation score.

Proof required

Share your decision table: decision type, who decides, and the fallback if they're away too. Share your return notes. List decisions made and by whom, and decisions delayed and why. Add any incidents with how long they took. Write 200 words on your delegation score and what the delays show.

What gets checked

  • Two weeks in a row. Most gaps appear in week two.
  • At least ten decision types, named, like 'approve a vendor contract under $X'.
  • Every delayed decision has a reason. Uncertainty about authority is a gap in the table.

Common mistakes

  • Checking in while away. One message tells the team you're still available.
  • Delegating everything vaguely. Each decision type needs a named person or role.

Resources

Foundationstart here

Depthgo deeper

What a verifier looks for

  • Confirm two weeks in a row. Evidence can be an out-of-office, a status or a teammate.
  • Count decision types. Under ten is too coarse. Ask who merges a breaking change at 5pm Friday.
  • For each delay, ask why it waited. It should point to a gap in the table.
  • Ask what they'd change before the next absence. 'It worked fine' is a warning sign.

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Deliver a project through two sub-teams

8–16 weeks depending on project scope. This milestone cannot be manufactured — it requires a real project with real cross-team complexity. If no such project exists in your current roadmap, that is information about whether your team structure is working.

Pick a project that needs at least two sub-teams, and ship it to production. Don't run the day-to-day yourself. Set the goal and success criteria at the start. Remove blockers that cross sub-team lines. Review the outcome at the end. The rest belongs to your sub-team leads. Log each time you got pulled in, why, and what would prevent it.

Proof required

Write a 500–700 word retrospective. Cover the goal and success criteria, and what each sub-team owned. Cover the three biggest cross-team blockers and how they were solved. List each time you got pulled in and the fix you made. Say whether you hit the criteria. A sub-team lead must verify this proof on Powstik.

What gets checked

  • Each pull-in names the fix that followed. Example: a data contract both teams now sign.
  • A sub-team lead verifies it on Powstik before you submit. Your own account isn't enough.
  • Success criteria were set at the start, as the retrospective's opening shows.

Common mistakes

  • Calling a one-team project cross-team. Answering questions for another team doesn't count.
  • Writing the pull-in log at the end from memory. Write it as it happens.

Resources

Foundationstart here

Masteryfor the dedicated

What a verifier looks for

  • Does each pull-in have a fix? Without fixes, it's a list of times they managed.
  • Ask the verifying lead whether the manager stayed out of execution. It should match the log.
  • Were the criteria measurable? 'p95 under 200ms for 30 days' is measurable; 'ship it' isn't.
  • Ask what they'd change next time. 'Communicate better' isn't an answer.

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