Hire, contract, or stretch the existing team
A piece of work has shown up. Three honest shapes for staffing it — and a default that's right more often than you'd think.
When to reach for this
The shape of the problem this playbook is for.
- A new initiative needs a skill the team doesn't have.
- A founder is the bottleneck on something they shouldn't be doing.
- A specific 6–12 week project is on the roadmap and nobody is owning it.
Signals you're ready
If these aren't true, you're not deciding yet — you're scoping.
- You can describe the work in concrete terms (deliverable + timeline + dependencies).
- You can describe what 'done' looks like in one paragraph.
- You know which skill is missing — and whether it's a skill or a generalist gap.
The rubric
Numbered, weighted, opinionated. Walk through them in order — the first decisive answer often ends the meeting.
- Decisive
Is the work bounded — a project — or unbounded — a domain?
Bounded with a clear end (3–6 months, well-scoped) → contract or stretch. Unbounded domain that will keep generating work for 12+ months → hire. Hiring for a project is how you get a permanent headcount you didn't budget for.
- Heavy
Will the skill matter to the team in 12 months, or only to this project?
Matters in 12 months → hire (or stretch + train). Only this project → contract; bring the skill in, ship the project, transfer the artifact, exit clean.
- Heavy
Is there an internal candidate who'd grow from owning this?
Yes → strong bias to stretch + back them with a contractor or staff-eng coach. Stretch assignments retain people; protected projects go to outsiders.
- Tiebreaker
What's the cost of getting this wrong — slipped timeline, churned headcount, or worse?
Critical-path with deadline → contract, accept the markup, get the skill in fast. Strategic but not deadline-driven → hire, take the time. Don't stretch the team on critical-path with a deadline; that's how good people leave.
Default pick
When the meeting is going in circles, ship this — and write down what would change your mind.
Red flags
Patterns that mean the playbook isn't your real problem.
- The role being hired for is shaped exactly like the project, not like a domain.
- Nobody on the existing team has been asked if they'd want to grow into it.
- The contractor is being asked to also onboard the next contractor.
Real applications
The playbook used in anger — context and outcome.
- ContextNeed a security engineer for an upcoming SOC 2 audit (3 months out).OutcomeContracted a fractional CISO + audit prep specialist. Cleared the audit, transferred the runbooks, exited the relationship. Hiring permanent at a 9-engineer company would have been the wrong shape.
- ContextNeed a data engineer to own the warehouse + dbt + analytics infra.OutcomeHired. The work was unbounded — every team would generate more. A contract would have produced an artifact nobody could maintain.