Team & Hiring Playbook

Core Rule

Hire slow. Fire fast. The first 5 hires define your culture permanently.

When to Hire

Hire when:

• A specific role is blocking revenue or product — and you can name the blocker
• You've validated the need for 3+ months (not just 1 busy week)
• You can clearly define what "good" looks like in the role
• You have runway to cover 12+ months of their salary

Don't hire when:

• You're avoiding a hard problem by adding headcount
• You don't have time to onboard them properly
• The role is undefined ("we just need more help")
• You could solve it with a tool, automation, or contractor first

The Hiring Ladder

Before making a full-time hire, exhaust cheaper options:

1. CAN YOU AUTOMATE IT?     → Use a tool (Zapier, templates, AI)
2. CAN YOU OUTSOURCE IT?    → Use a freelancer or agency for a project
3. CAN YOU CONTRACT IT?     → Hire a part-time contractor for 3 months
4. IS IT STILL A BOTTLENECK? → Now hire full-time

This saves months of salary and lets you test the role before committing.

First 5 Hires Priority Order

For most startups:

1. First engineer (if founders aren't technical) — can build the product
2. First salesperson (if founders aren't selling) — can close revenue
3. Customer success / support — reduces churn, captures feedback
4. Second engineer or designer — product velocity
5. Marketing / growth — only after you have repeatable GTM

Do not hire for ops, finance, or HR until you have real scale (20+ people).

Contractor-to-FTE Conversion

The safest hiring pattern for early-stage:

Step 1 — Paid trial project (1-2 weeks)

• Give them a real project with a clear deliverable
• Pay market rate — don't ask for free work
• Evaluate: quality, speed, communication, independence

Step 2 — Part-time contract (1-3 months)

• 10-20 hours/week on ongoing work
• Treat them like a team member (standups, Slack, context)
• Evaluate: consistency, culture fit, self-direction

Step 3 — Full-time offer (if it's working)

• Convert with a proper offer letter, equity, and onboarding
• Use the trial period data to set expectations

Why this works: You've de-risked the hire before committing salary + equity. The candidate has also de-risked YOU — they know what they're joining.

Remote Hiring

Most early-stage startups hire remote. Do it well:

What to look for in remote hires:

• Strong written communication (this IS the work in remote)
• Self-directed — doesn't need to be told what to do next
• Proactive updater — shares progress without being asked
• Timezone overlap of at least 4 hours with core team

Remote interview additions:

• Ask: "Walk me through how you structure a work-from-home day"
• Give a take-home project instead of a whiteboard — better signal for async work
• Do one interview via async video (Loom) — tests their written/async communication

Remote onboarding extras:

• Virtual coffee chat with every team member in week 1
• Buddy system — pair them with someone for the first 30 days
• Daily 15-min check-in for the first 2 weeks, then taper

Job Description Template

Title: [Specific — "Head of Sales" not "Growth Person"]

We're looking for: [2 sentences — what they'll do and why it matters]

You'll be great if you:
- [Required: specific, observable skill]
- [Required: mindset or working style]
- [Nice to have: bonus experience]

What you'll own in the first 90 days:
- [Concrete deliverable 1]
- [Concrete deliverable 2]
- [Concrete deliverable 3]

Compensation:
- Salary: $X–$X
- Equity: X% (4yr / 1yr cliff)
- [Benefits if any]

This is NOT a fit if you:
- [Anti-pattern 1]
- [Anti-pattern 2]

Equity Ranges by Stage

Source: Holloway Guide to Equity Compensation, AngelList benchmarks.

Cash vs. equity tradeoff: Early employees accept lower cash for higher equity. As you raise more, cash goes up and equity percentages go down. Always be transparent about the tradeoff.

Interview Process (Early Stage, Lean)

Keep it to 3 rounds max. Respect candidate time.

Round 1 (30 min): Founder screen — culture, motivation, basics Round 2 (60 min): Skills assessment — relevant work sample or case Round 3 (30 min): Reference check + offer conversation

Work sample examples:

• Engineer: Code review or take-home challenge (<2 hours, paid)
• Salesperson: Mock cold call or discovery call roleplay
• Designer: Portfolio review + design critique
• Marketer: Critique your current website or write a sample post

Pay for take-home work. Even $200 shows respect and gets better candidates.

Reference Check Questions

Call references — don't just email.

• "How would you describe [candidate]'s greatest strength?"
• "What's the area where they most need to grow?"
• "On a scale of 1-10, how likely are you to hire them again? Why not a 10?"
• "How did they handle a significant failure or setback?"
• "What type of environment brings out their best work?"

A lukewarm reference is a red flag. A great candidate has enthusiastic references.

Onboarding (First 90 Days)

Before Day 1:

• Accounts, tools, access set up before they arrive
• Welcome message from founder
• First week schedule shared

Day 1:

• Meet the whole team (even if it's 2 people)
• Read company docs: mission, strategy, product overview
• First task assigned — something small they can ship today

Week 1:

• Shadow all key workflows
• Customer calls (even if not their role — everyone should hear customers)
• 1:1 with founder — learn context, ask anything

30 / 60 / 90 Day Check-Ins:

• What's going well?
• What's unclear or blocking you?
• What do you need from me to be successful?

Success metric: Can they operate independently in their role by day 90?

Culture (Define It Early)

Culture is what you tolerate and what you reward — not what you write on the wall.

Define 3-5 cultural values with specific behavioral examples:

Value: [Name]
What it looks like: [Specific behavior we reward]
What violates it: [Specific behavior we don't tolerate]

Hire and fire according to these. Inconsistency kills culture.

When to Fire

Fire when:

• Performance hasn't improved after clear feedback and a plan (30-60 day PIP)
• Culture violations (dishonesty, toxicity, harassment) — immediately
• The role no longer exists (be honest about this)

How to fire well: Direct, compassionate, final. Don't drag it out. Offer severance if you can. Be honest with the team about what happened (without oversharing).

See also: crisis-difficult-templates.md for separation communication templates.

> Disclaimer: This playbook provides educational frameworks for hiring and team building. Employment law varies by jurisdiction — consult an employment attorney for compliance questions. This is not legal or HR advice.