150. Hiring Templates

Hiring is one of the first places where founder taste becomes company culture. These templates help you define the job, compare candidates fairly, and make the first months productive.

Do not use templates to create bureaucracy. Use them to remove ambiguity. Every hiring document should answer: what does success look like, how will we assess it, and how will we help the person win?

Offer letters, contractor agreements, ESOP terms, confidentiality clauses, and employment compliance should be reviewed with a lawyer, HR advisor, CA, or CS as relevant.

Job description

Write the job description for the work, not for a fantasy resume.

Section	Prompt
Role title	Use a title candidates understand. Avoid inflated titles too early.
Mission	In one paragraph, what problem will this person own?
Stage context	What is messy, changing, or undefined about the company right now?
Responsibilities	5-7 outcomes, not a laundry list of tasks.
First 90 days	What should be visibly better after three months?
Must-have skills	Skills required on day one. Keep this short.
Nice-to-have skills	Helpful but not required. Do not confuse these with must-haves.
Working style	Remote/hybrid/office, pace, communication norms, collaboration expectations.
Compensation range	Salary range, equity/ESOP philosophy if applicable, benefits.
Hiring process	Steps, estimated timeline, work test if any, who they will meet.

Good closing line:

If you have done similar work in a different context, tell us what you owned, what changed, and how you measured success.

Role urgency test

Before opening a role, test whether the company really needs a hire.

Question	Answer
What business bottleneck does this role remove?
What happens if we do not hire for 60 days?
Can the work be narrowed, automated, outsourced, or handled part-time?
Which founder responsibility will this role take over?
What metric or operating output should improve?
Who will manage this person weekly?
Can we afford salary, tools, onboarding, and management time?
What would make this hire a mistake?

Hire when the role has a clear owner, clear work, and a clear success standard. Do not hire because the founder feels busy and wants relief.

Hiring scorecard

Use a scorecard before interviews begin. Otherwise every interviewer will judge a different imaginary candidate.

Competency	Why it matters	Evidence to look for	Score 1-5	Notes
Role craft	Can they do the core work?	Shipped work, examples, portfolio, work test, deep answers.
Judgment	Can they make good tradeoffs without supervision?	Past decisions, failure stories, prioritization logic.
Customer/user sense	Do they understand who the work is for?	Customer examples, empathy, field learning, practical questions.
Ownership	Will they push work through ambiguity?	Examples of taking responsibility end to end.
Communication	Can they write/speak clearly and disagree well?	Structured answers, thoughtful questions, concise follow-up.
Startup fit	Can they operate with constraints?	Comfort with speed, uncertainty, limited resources.
Values fit	Do they strengthen the culture you want?	Integrity, respect, learning speed, no ego-driven behavior.

Decision rule:

Outcome	Meaning
Strong yes	Clear evidence, high confidence, likely to raise the bar.
Yes	Meets the bar, risk is understood and manageable.
Hold	Need one more specific signal; do not drift.
No	Evidence is weak or risk is too high for this stage.

Interview plan

Interviews should reduce uncertainty, not repeat the same conversation five times.

Step	Purpose	Questions or tasks	Owner
Screen	Check motivation, communication, basic fit, salary/timing.	Why this role? What are you looking for next? What have you owned?	Founder/recruiter
Craft interview	Assess role-specific depth.	Walk through a past project. What tradeoffs did you make? What failed?	Functional lead
Work test	See how they solve a relevant problem.	Time-boxed practical task with clear evaluation criteria.	Functional lead
Founder interview	Test ownership, judgment, values, and company-stage fit.	Tell me about a hard decision. What do you do when goals are unclear?	Founder
Reference check	Validate patterns from past managers/peers.	Strengths, risks, collaboration, integrity, rehiring question.	Founder/recruiter

End every interview with:

Interviewer note	Prompt
Evidence	What did we directly observe?
Concern	What risk remains?
Recommendation	Strong yes, yes, hold, or no.
Follow-up	What question should the next interviewer answer?

Interview evidence matrix

Use this after interviews to keep the decision evidence-based.

Candidate	Role craft	Judgment	Ownership	Communication	Startup fit	Risk	Decision
	Evidence, not vibe	Evidence, not vibe	Evidence, not vibe	Evidence, not vibe	Evidence, not vibe	What could fail?	Hire / hold / no

Common weak evidence:

Weak evidence	Better evidence
”I liked them.”	Which past work or answer proves they can do this job?
”They worked at a good company.”	What did they personally own, ship, improve, or decide?
”They seem smart.”	How did they reason through a relevant problem?
”They are affordable.”	Can they raise execution quality, or will they create management load?
”They can join immediately.”	Why are they available, and is the fit real?

Work test

A good work test resembles the actual job and respects the candidate’s time.

Field	Prompt
Role	Which role is this for?
Scenario	What realistic company/customer situation will the candidate solve?
Task	What must they produce?
Time box	How much time should it take? Keep it reasonable.
Inputs	What data, context, customer notes, or constraints will you provide?
Evaluation criteria	What makes an answer strong, average, or weak?
Discussion	What questions will you ask after reviewing the work?
Candidate respect	Will you pay for a large assignment or keep it short enough to be fair?

Evaluation:

Criterion	Strong signal
Clarity	The answer is easy to follow and does not hide assumptions.
Prioritization	The candidate makes tradeoffs instead of trying everything.
Customer sense	The answer considers the user, buyer, or internal stakeholder.
Practicality	The solution can actually be executed with startup constraints.
Learning	The candidate responds well to questions and feedback.

Reference check

References are not a formality. They reveal patterns.

Ask for at least one manager-style reference and one peer/cross-functional reference where possible.

Question	What it reveals
What was your working relationship with the candidate?	Context and credibility of reference.
What were they responsible for?	Scope and ownership.
What are they unusually good at?	Strengths to amplify.
Where did they need support or coaching?	Risks to manage.
How did they handle pressure or ambiguity?	Startup fit.
How did they disagree or receive feedback?	Collaboration.
Would you hire or work with them again? Why?	Bottom-line trust signal.
What should we know to help them succeed here?	Onboarding insight.

Record:

Field	Notes
Reference name and relationship
Dates/context
Strength patterns
Risk patterns
Hiring decision impact

Offer letter checklist

Use this as a checklist before sending an offer. Do not treat it as legal language.

Item	Check
Candidate name and role title	Correct spelling and designation.
Start date and location	Office, remote, hybrid, reporting location.
Reporting manager	Clear reporting line.
Compensation	Salary, variable pay if any, payment frequency, benefits.
Equity/ESOP	Grant philosophy, vesting summary if applicable, formal plan reference.
Probation/notice	Terms reviewed by advisor and aligned with company policy.
Confidentiality/IP	Proper agreement prepared, especially for product/tech roles.
Background/reference checks	Any conditions clearly stated if applicable.
Acceptance deadline	Date and next steps.
Onboarding owner	Who will prepare laptop, tools, accounts, first-week plan.

Before sending:

Check	Why
Salary internally approved	Prevents awkward renegotiation.
Role expectations documented	Avoids hiring for one job and managing another.
Legal/HR review complete	Reduces avoidable compliance risk.

Onboarding plan

The first two weeks decide whether a new hire feels useful or lost.

Time	Founder/manager responsibility	New hire outcome
Before joining	Laptop, accounts, reading list, calendar invites, buddy, first task.	Arrives with context and working tools.
Day 1	Company story, team intros, role expectations, product/customer walkthrough.	Understands mission, people, and immediate priorities.
Week 1	Shadow calls, review docs, small useful task, daily check-ins.	Learns how work moves and ships something small.
Week 2	Owns a defined task, meets stakeholders, clarifies success metrics.	Starts contributing independently.
Days 30-60	Feedback loop, role calibration, remove blockers.	Builds momentum and trust.
Days 60-90	Larger ownership area, performance conversation, next goals.	Has a clear operating lane.

30/60/90 plan

Use this for key early employees and leadership hires.

Period	Focus	Outputs	Manager support
First 30 days	Learn customers, product, team, metrics, and constraints.	Diagnosis memo, stakeholder map, quick wins, questions list.	Context, access, frequent feedback.
Days 31-60	Own a meaningful project or operating rhythm.	Project shipped, process improved, metric movement or learning.	Decision clarity, prioritization help, introductions.
Days 61-90	Increase scope and improve repeatability.	Roadmap, hiring needs, system/process, measurable outcomes.	Performance feedback and scope agreement.

Add this bottom line:

At the end of 90 days, this hire is successful if [specific business/customer/team outcome] is true.

Onboarding risk register

Early hires fail when the company assumes context transfers automatically. Track risks before the person joins.

Risk	Example	Prevention
Role ambiguity	Founder expects strategy; hire expects execution.	Written 30/60/90 and weekly manager check-in.
Tool/access delay	New hire spends week one waiting.	Prepare accounts, docs, laptop, permissions, and first task before joining.
Culture mismatch	Hire expects corporate process; startup needs ownership.	Explain stage reality during hiring and onboarding.
Founder bottleneck	Every decision waits for founder.	Define decision rights and escalation rules.
No customer context	Hire works from internal assumptions.	Shadow sales/support/customer calls in week one.
Weak feedback loop	Problems surface after probation.	Weekly feedback in first month, then biweekly.

The first employee is not only a capacity decision. It is a management test for the founder.

Hiring packet by role stage

Do not start sourcing because “we need someone.” Start sourcing only after the hiring packet is clear enough that a good candidate can understand the work and a founder can reject a wrong candidate without guilt.

Stage	Packet to prepare	Founder decision
Role idea	Role urgency test, bottleneck statement, budget range, manager owner.	Is this really a hire, or should we narrow, outsource, automate, or wait?
Role opened	Job description, scorecard, interview plan, sourcing list.	Are we judging all candidates against the same success standard?
Candidate shortlist	Interview evidence matrix, work test, salary expectations, risk notes.	Which candidate has evidence for the job, not just a good story?
Offer	Reference notes, offer checklist, closing plan, onboarding owner.	Are we ready to make the person successful from day one?
First 90 days	Onboarding plan, 30/60/90 plan, risk register, weekly feedback cadence.	Is the hire becoming productive, or are we discovering a role mismatch?

For very early teams, the role packet should fit on a few pages. If it takes a 40-page process to explain the job, the job is probably not defined. If it fits in three vague lines, the founder is probably hiding uncertainty from the candidate.

Use the packet to make tradeoffs visible:

• Senior generalist or narrow specialist
• Full-time hire or contractor
• Local, remote, or hybrid
• Salary-heavy or ESOP-heavy
• Immediate execution or long-term leadership potential
• Founder-managed or manager-managed

The strongest early hires usually know what is messy before they join. Tell them the truth: what is working, what is broken, what decisions are still open, and what pressure the company is under.

Hiring decision gate

Before sending an offer, force the decision through a red-yellow-green gate.

Signal	Green	Yellow	Red
Role clarity	The business outcome and first 90-day output are clear.	The role is useful but scope is still broad.	The role exists mainly because founders feel overloaded.
Evidence	Candidate has directly relevant examples or strong work-test evidence.	Candidate has adjacent experience and learning speed.	Candidate has brand-name credentials but weak evidence for this job.
Management	There is a clear manager and feedback cadence.	Founder will manage but needs discipline.	Nobody has time to manage the hire.
Budget	Salary and onboarding cost fit runway and plan.	Affordable only if revenue or funding arrives on time.	Hire materially shortens runway without a clear milestone.
Culture	Candidate understands startup constraints and communicates cleanly.	Some adjustment needed, but risks are explicit.	Entitlement, blame, unclear ownership, or poor integrity signals.

Decision rule:

• If two or more signals are red, do not hire yet.
• If role clarity is red, fix the role before interviewing more people.
• If management is red, the hire will likely fail even if the candidate is good.
• If budget is yellow, write down what must become true in the next 90 days.
• If the candidate is green but the company is not ready, slow down and prepare onboarding.

Hiring well is not only choosing the right person. It is building a small system where the right person can produce visible progress quickly.

Copy-paste hiring scorecard

Use this before interviewing. A scorecard protects the founder from hiring the person they like most instead of the person the company needs.

Role:

Primary business outcome:

Why now:

What the founder will stop doing:

First 30-day win:

Must-have skills:

Must-have behaviours:

Nice-to-have skills:

Deal breakers:

Work sample:

Reference questions:

Compensation range:

Start date:

Interview scoring:

Dimension	Evidence	Score 1-5
Role skill
Judgment
Ownership
Learning speed
Communication
Customer empathy
Ambiguity handling
Values / trust
Founder load reduction

Decision rule:

Pattern	Decision
Strong score, strong work sample, strong references	Make offer if role is still urgent.
Strong interview, weak work sample	Do not hire yet. Re-test or pass.
Strong skill, weak ownership	Risky for early team.
Strong person, vague role	Pause and rewrite role.
Founder is hiring to feel less alone	Re-check whether a contractor/advisor/process solves it.

Hiring gets easier when the role has a job to do. The scorecard is not bureaucracy. It is protection against emotional hiring.

Copy-paste reference check sheet

Use references to verify risks, not to collect praise.

Candidate:
Role:
Reference:
Relationship:
Dates worked together:

What we are trying to verify:
1.
2.
3.

Questions:

Area	Question	Notes
Context	What was the company/team situation when you worked together?
Scope	What did this person own directly?
Ambiguity	How did they handle unclear goals or messy environments?
Ownership	What would you trust them to own without supervision?
Weakness	Where did they need support?
Feedback	How did they respond when challenged?
Pressure	What happened under stress?
Startup fit	Would you hire them into an early-stage startup? Why or why not?
Rehire	Would you work with them again?

Reference interpretation:

Signal	Meaning
Specific stories	Stronger than generic praise.
Careful hesitation	Investigate the risk.
”Great when…”	Conditions matter.
No ownership examples	Risky for early teams.
Strong skill but weak collaboration	Dangerous in small teams.

Copy-paste offer checklist

Before sending an offer, confirm:

Item	Checked
Role title and reporting line are clear.
90-day outcome is written.
Compensation, bonus, ESOP/equity, vesting, and review cycle are clear.
Start date and location/remote expectations are clear.
Probation or trial period expectations are clear, where applicable.
Offer has legal/HR review as needed.
Candidate understands runway, stage, risk, and role ambiguity.
Founder knows what management support the hire needs.
Onboarding owner is assigned.
Access, equipment, and first-week plan are ready.

Do not use the offer to hide uncertainty. Use it to make the working relationship clear.

Copy-paste onboarding plan

Early onboarding should reduce confusion quickly.

Period	Founder/company responsibility	New hire output
Before start	Share mission, context, role, tools, people, first-week calendar.	Reads context and asks early questions.
Day 1	Explain company, customer, product, stage, runway, current priorities.	Understands why role exists.
Week 1	Introductions, tool access, customer/product exposure, first small task.	Ships or completes a small useful output.
Days 8-30	Weekly manager check-in, role clarity, feedback, customer context.	Owns first 30-day win.
Days 31-60	Increase ownership, clarify decision rights, inspect collaboration.	Runs a meaningful project or workflow.
Days 61-90	Review role fit, performance, energy, and scope.	Demonstrates repeatable contribution.

30/60/90 template:

Role:
Manager:
Why this role exists:

First 30 days:
- Outcome:
- Support needed:
- Risks:

First 60 days:
- Outcome:
- Support needed:
- Risks:

First 90 days:
- Outcome:
- Support needed:
- Risks:

Review date:

Hiring is not complete when the offer is accepted. It is complete when the person is producing trusted work in the real company.

Copy-paste candidate closing plan

Use this when you want to make an offer to a strong candidate.

Candidate:
Role:
Why we want them:
Why they might say yes:
Why they might say no:
Compensation range:
ESOP/equity explanation needed:
Stage/risk explanation needed:
Who should speak with them:
Offer deadline:
Start date:
Fallback candidate or plan:

Closing conversation checklist:

Topic	Covered?
Role outcome and first 90 days
Company stage, runway, and uncertainty
Compensation, benefits, ESOP/equity basics
Work mode and operating rhythm
Manager and feedback style
Why this role matters now
Candidate’s personal decision criteria
Questions from family/partner/advisors if relevant

Do not oversell. A candidate who joins with a realistic view of the company is more likely to stay through hard weeks.

Copy-paste first one-on-one

Use this in the first week with a new hire.

What is clearer after joining?

What is more confusing than expected?

Which customer/user context do you need?

Which tools, access, or documents are blocking you?

What should the founder/manager explain better?

What small win can you own this week?

What decision can you make without asking?

What should you escalate immediately?

Manager notes:

Area	Notes
Context gaps
Role clarity gaps
Access blockers
Feedback given
Next task
Review date

The first one-on-one sets the tone: direct, practical, and supportive. If the founder is vague in week one, the hire learns that ambiguity is normal and feedback is optional.

Copy-paste no-hire memo

Write a no-hire memo for strong candidates you choose not to hire. This improves hiring judgment over time.

Candidate:
Role:
Stage reached:
Main strengths:
Main concerns:
Evidence reviewed:
Reason for no:
Would we reconsider later? Under what conditions?
What this teaches us about the role:

Common no-hire reasons:

Reason	What to do next
Strong person, vague role	Rewrite the role before more interviews.
Good skill, weak startup ownership	Look for stronger ambiguity evidence.
Great seniority, too expensive for runway	Change level, scope, or timing.
Culture risk	Do not rationalize it because skill is strong.
Candidate wants a later-stage environment	Keep relationship warm for future stage.

A good no-hire decision is not wasted effort. It teaches the founder what the company actually needs.

Related chapters

• Early Hiring
• Recruiting
• Culture