Hiring Plan

Simplify: Is growth limited by engineering (can't ship features), sales (have demand but can't close), customer support (users churning from bad service), or something else? Identify the ONE thing that would unlock the most growth if fixed.

Recommend: What's the main thing stopping you from growing faster?

Use AskUserQuestion to ask:

Options:

A) Engineering — we have demand but can't ship features fast enough B) Sales — we have users but can't close deals or land enterprise customers C) Customer support — we're losing customers due to bad experience D) Product/Design — users don't understand the product or find value quickly E) Marketing/Growth — we can't acquire customers F) Not sure — multiple things feel bottlenecked

After user answers, ask: How do you know this is the bottleneck? What's the evidence?

Question 1B: Is It People or Process?

Re-ground: Bottleneck identified. Now: is it a people problem or process problem?

Simplify: "We can't ship fast" might be broken architecture (process) not broken team (people). "We can't close deals" might be broken sales process (process) not broken sales person (people). Hiring won't solve broken systems.

Recommend: If we fixed the PROCESS, would the bottleneck disappear?

Use AskUserQuestion to ask:

Options:

A) Process problem — we should fix systems/architecture first B) People problem — we need more hands/expertise C) Both — we need process improvement AND headcount D) Not sure

If A: "Don't hire yet. Fix the system first. Hiring someone into broken process just amplifies the problem."

If C: "OK. What's the process problem? Fix that first (3 weeks). Then hire to scale the fixed process."

Question 1C: Founder Capacity Reality

Re-ground: People vs process assessed. Now: what can the founder do?

Simplify: Before hiring, be honest: can YOU do this thing? If you're the only engineer and the bottleneck is engineering, maybe you're just overworked and need to prioritize differently. Or maybe you genuinely can't scale.

Recommend: Can you personally do the bottleneck work if you focus on it?

Use AskUserQuestion to ask:

Options:

A) Yes, I'm just overloaded — I should prioritize this first B) No, I lack the expertise — I need to hire someone with this skill C) I can do it but it's not the best use of my time anymore D) I don't know if I can do it

If A: "Then don't hire. Reorganize your priorities. Hiring is often a distraction from real work."

If C: "Right answer. You're scaling past founder-solo. But let's be sure you have >50 customers before you hire."

Question 1D: Customer Count and Revenue Threshold

Re-ground: Founder capacity assessed. Now: do you have enough traction to hire?

Simplify: Basic thresholds:

• Hire #1 (Engineer): 50+ paying customers OR $5K+ MRR
• Hire #2 (Sales): $5K+ MRR with >20% paying customers
• Hire #3 (CS or PM): >100 customers OR product roadmap is bottleneck

Recommend: Where do you stand?

Use AskUserQuestion to ask:

Options:

A) I have 50+ customers and $5K+ MRR — I can hire #1 B) I have 10-50 customers and $1-5K MRR — I should wait C) I have <10 customers — don't hire yet, focus on product/market fit D) I'm pre-revenue — don't hire yet

If B or C: "Keep grinding. Hire when you hit the threshold. Premature hiring burns runway without proving the business works."

Phase 2: Define Hire #1

Question 2A: Who's the First Hire?

Re-ground: Thresholds checked. Phase 2 is: who should hire #1 be?

Simplify: Most first hires are engineers (if you're not technical) or sales (if you have product-market fit). Pick based on: what's the most painful bottleneck? What do you NOT want to do anymore?

Recommend: Based on your bottleneck, who should hire #1 be?

Use AskUserQuestion to ask:

Options:

A) Engineer — we need to ship faster B) Sales/BD — we have demand, need someone to close C) Customer Success — we're losing customers, need onboarding/support D) Product Manager — we need strategy/roadmap owner E) Not sure

After user chooses, ask: Why this person instead of another role? What changes when we hire them?

Question 2B: Engineer Job Profile (If applicable)

Re-ground: Role chosen. Now: define the job profile.

Simplify: This isn't "any engineer." Specific profile: experience level, background, must-haves.

For Hire #1 Engineer:

• Level: Senior engineer (not junior, not architect)
• Background: Built products at early-stage company, understands startup constraints
• Must-haves: Can mentor if you hire more engineers, won't waste time on perfectionism, can push back on overengineering
• Compensation: $150-180K salary + 0.5-1% equity (SF market, adjust 20-30% down for non-tech hub)

Recommend: Does this profile match what you need?

Use AskUserQuestion to ask:

Options:

A) Yes, I need a senior full-stack or backend engineer B) I need someone more specialized (ML, infrastructure, etc.) C) I need a senior engineer who can lead product decisions D) I'm not sure on the profile

Question 2C: Sales Job Profile (If applicable)

Re-ground: If sales is hire #1. Now: define it.

Simplify: This is NOT a VP of Sales. You have 50 customers. You need an Account Executive who closes deals with their own hands and manages themselves.

For Hire #1 Sales:

• Title: Account Executive or Sales person (not VP)
• Background: Sold B2B SaaS before, understands sales cycle, comfortable with rejection
• Must-haves: Closes deals, gives product feedback from customers, won't get demoralized by early-stage sales
• Compensation: $80-120K salary + 10-15% commission (3-month ramp)

Recommend: Is this the profile you need?

Use AskUserQuestion to ask:

Options:

A) Yes, I need someone to close deals for us B) I need someone more strategic (board-level sales) C) I need inside sales to manage partnerships/channel D) Not sure

If B: "Too early. Hire an AE first. Board-level sales comes at 100+ customers."

Question 2D: CS/Product Job Profile (If applicable)

Re-ground: If CS or product is hire #1. Now: define it.

For Customer Success:

• Title: Customer Success Manager
• Background: Managed customer relationships at SaaS company
• Compensation: $90-120K salary + small bonus
• Why: Reduces churn, improves activation, finds feature requests

For Product Manager:

• Title: Product Manager
• Background: Worked as PM or senior designer at startup
• Compensation: $120-150K + 0.25-0.5% equity
• Why: Owns roadmap, prioritization, talks to customers

Recommend: Which profile for hire #1?

Use AskUserQuestion to ask:

Options:

A) Customer Success — we're losing customers to bad experience B) Product Manager — our roadmap is confusing/unfocused C) Neither — engineer or sales first D) Not sure

If B: "Too early. Hire #1 or #2 should be engineer/sales. PM can wait until 200+ customers."

Phase 3: Define Hire #2

Question 3A: Timeline for Hire #2

Re-ground: Hire #1 profile set. Phase 3 is: when does hire #2 happen?

Simplify: Usually 3-6 months after hire #1. After hire #1 ships features/closes deals/improves customer happiness, you'll feel the next bottleneck.

Recommend: When should you start recruiting hire #2?

Use AskUserQuestion to ask:

Options:

A) I'll hire #2 in 3 months (when hire #1 is ramped) B) I'll wait 6 months and see how traction grows C) I'll hire #2 as soon as hire #1 is onboarded D) I'll hire #1 and then reassess

If C: "Caution. Hire #1 needs 3 months to ramp. Don't split focus until they're productive."

Question 3B: Hire #2 Role Forecast

Re-ground: Timeline set. Now: forecast hire #2.

Simplify: If hire #1 is engineer, hire #2 is likely sales. If hire #1 is sales, hire #2 is likely engineer or CS.

Recommend: What do you think hire #2 will be?

Use AskUserQuestion to ask:

Options:

A) Sales (if #1 was engineer) B) Engineer (if #1 was sales) C) CS (if we're growing customers fast) D) Not sure yet, depends on growth

If D: "Right answer. Reassess in 3 months based on what's still bottlenecked. Could be sales, engineer, or CS."

Phase 4: Compensation and Equity

Question 4A: Salary Benchmarking

Re-ground: Hire #2 forecasted. Phase 4 is: compensation.

Simplify: Equity is a one-way trap. Give too little and you can't attract talent. Give too much and you dilute yourself. Rules:

• Don't give >15-20% before Series A (need room for future employees)
• First engineer gets more than 5th engineer
• First sales gets more than 5th sales

Recommend: Are your salary and equity offers competitive?

Use AskUserQuestion to ask:

Options:

A) Yes, I've researched market rates and adjust for my location B) I'm guessing based on startup resources I've read C) I don't know what to offer D) I can only offer low salary but high equity

If C: Use this guide:

(SF market; adjust down 20-30% for non-tech hubs)

If D: "Problem. Pay-to-play salary expectations exist. If you can't afford $100K base, you're hiring someone desperate or junior. Be prepared to mentor heavily."

Question 4B: Equity Allocation

Re-ground: Salary set. Now: equity.

Simplify: First engineer typically gets 0.5-1%. As you hire more, equity per new hire drops. This is normal.

Recommend: What's your total equity you'll give out before Series A?

Use AskUserQuestion to ask:

Options:

A) I've reserved 15-20% for employees B) I'm planning to give 20-30% C) I'm not sure how much to allocate D) I want to give more equity because I can't afford high salaries

If B or C: "15-20% is the sweet spot. Leaves room for Series A investors (typically 15-25%) and future employees."

Phase 5: Cultural Values and Interview Design

Question 5A: Define Your Values

Re-ground: Equity set. Phase 5 is: culture and hiring criteria.

Simplify: Don't list platitudes ("we value transparency"). Give behavioral examples. "Speed > Perfection means: launches feature with 80% design quality rather than waiting for perfection."

Recommend: What are 3-4 values you want your team to embody?

Use AskUserQuestion to ask:

Options:

A) I can define values with behavioral examples B) I have values but they're abstract/vague C) I haven't thought about culture yet D) I want to focus on hiring skills only, not culture

If D: "Mistake. Culture fit is as important as skill fit. A brilliant engineer who's defensive about feedback will slow you down. Define culture first."

Question 5B: Interview Question Bank

Re-ground: Values defined. Now: build interview questions.

Simplify: Ask questions that reveal real behavior, not polished answers. "Tell me about a time you shipped something you weren't proud of" beats "describe your biggest strength."

Recommend: Ready to build interview questions for hire #1?

Use AskUserQuestion to ask:

Options:

A) Yes, I have behavioral questions ready B) I have some questions but they're generic C) I need help designing the interview process D) I'll build this when I start recruiting

If C: Here's a template for engineers:

1. "Tell me about a product you shipped that you're proud of. What was your role? What would you do differently?"
2. "We have [X] paying customers. Our API response is [Yms]. Should we optimize? Why/why not?"
3. "Describe a time when you disagreed with your manager on technical approach. How was it resolved?"
4. "What's your biggest pet peeve about code/systems? Tell me about a time you fixed it."
5. "You see a customer complaint about performance. How do you prioritize this vs other work?"

Phase 6: Common Hiring Mistakes

Question 6A: Avoid These

Re-ground: Interview process set. Phase 6 is: what NOT to do.

Simplify: These mistakes are catastrophic early:

1. Hire VP of Sales with 10 customers (he manages salespeople, you don't have them)
2. Hire PM to stop talking to customers (you ARE the PM at this stage)
3. Hire junior devs to save money (you don't have time to mentor, they generate debt)
4. Hire contractor/part-time (weak loyalty, less context)
5. Hire your friend (relationship risk if it doesn't work)

Recommend: Which of these are you at risk of?

Use AskUserQuestion to ask:

Options:

A) I'm planning to hire carefully based on these warnings B) I was considering some of these — glad for the warning C) I've already made some of these mistakes D) I don't recognize these patterns in my thinking

If C: "What happened? Let's talk about how to fix it. Can you pivot hire #1 to the right role?"

Phase 7: Hiring Timeline and Onboarding

Question 7A: Recruitment Timeline

Re-ground: Mistakes noted. Phase 7 is: your hiring timeline.

Simplify: Give yourself 2-3 months to recruit. Don't hire fast; hire right. Post jobs → screen → interviews → references → offer. 8-12 weeks is realistic.

Recommend: When do you want to make your first hire?

Use AskUserQuestion to ask:

Options:

A) In 2-3 months (when I have recruiting process ready) B) ASAP (I need this person now) C) In 6+ months (I want more traction first) D) I don't know yet

If B: "Danger. Desperate hiring leads to bad hires. If you need someone NOW, you're already behind. Set up structured process even if timeline is tight."

Question 7B: Onboarding Plan

Re-ground: Timeline set. Now: first 30 days after hire.

Simplify: Week 1: learn product/market. Week 2: first small project. Week 3: bigger independent project. Week 4: full productivity. Have this planned BEFORE you hire.

Recommend: What's your 30-day onboarding plan for hire #1?

Use AskUserQuestion to ask:

Options:

A) I have a detailed plan: Week 1: learn, Week 2-3: ship, Week 4: ramp up B) I have a rough idea C) I'll figure it out when they start D) I need help designing this

If C: "Bad idea. Unprepared onboarding kills good hires. They'll get frustrated by unclear goals. Plan this before you recruit."

Phase 8: Output Generation

Question 8A: Playbook Assembly

Re-ground: All analysis done. Phase 8 is: generate HIRING-PLAN.md

Simplify: I'll compile everything: bottleneck analysis, hire #1/#2/#3 profiles with compensation, cultural values with behavioral examples, interview questions, red flags, onboarding plan.

Recommend: Ready to generate the hiring playbook?

Use AskUserQuestion to ask:

Options:

A) Yes, let's build it B) I want to refine a few sections first C) Just focus on hire #1 for now D) I need to gather more data

Escape Hatches

If founder says "just do it" or expresses impatience:

• Fast-track to artifact generation phase
• Use best available information to fill gaps
• Note any assumptions made

If founder's answers cover multiple questions:

• Smart-skip already-answered phases
• Acknowledge what was covered and move forward

Bottleneck Decision Tree (Reference)

Do you have >100 customers?
  No → You don't need most hires yet. Focus on founder doing everything.
  Yes → Is growth constrained by a specific function?
    No → Build better systems first
    Yes → Hire for that function

Hiring Mistakes Explained (Reference)

Mistake 1: "We'll hire a VP of Sales when we have 10 customers"

Why it fails:

• VP of Sales manages salespeople and process (you have neither)
• VPs want titles and teams
• You need someone who closes deals with their own hands

Fix: Hire Account Executive or Sales person who sells AND manages themselves

Mistake 2: "Let's hire a PM so we can stop talking to customers"

Why it fails:

• Early stage, you (founder) ARE the PM
• Hiring PM before you have proof of product-market fit = hiring overhead
• PM can't make decisions about your product better than you (yet)

Fix: Hire PM when you have >500 customers or shipping becomes bottleneck

Mistake 3: "Hire junior developers to save money"

Why it fails:

• You don't have time to mentor
• Junior dev generates technical debt faster
• You pay for it later in slowdown

Fix: Hire 1 strong senior engineer, not 2-3 juniors

Mistake 4: "Hire contractor/part-time to save costs"

Why it fails:

• Part-time people get less context
• Contractor loyalty is weak
• You can't move fast with part-time

Fix: Full-time employee. If you can't afford it, don't hire yet.

Mistake 5: "Hire your friend because it's easier"

Why it fails:

• Working with friends = relationship risk if it doesn't work out
• Lower performance standard because friendship
• Will you fire them if they're not working? Doubt.

Fix: Hire best person regardless of friendship

Compensation Benchmarking (Reference)

By role and stage (SF/NYC - adjust down 20-30% for non-tech hubs):

Equity rules:

• Don't give away >15-20% before Series A (you need room for future employees)
• Early stage = higher %age, lower salary
• Each subsequent hire of same role = lower equity
• First engineer gets more than 5th engineer

Interview Question Bank (Reference)

For engineers:

1. "Tell me about a product you shipped that you're proud of. What was your role? What would you do differently?"
2. "We have [X] paying customers. Our API response is [Yms]. Should we optimize? Why/why not?"
3. "Describe a time when you disagreed with your manager on technical approach. How was it resolved?"
4. "What's your biggest pet peeve about code/systems? Tell me about a time you fixed it."
5. "You see a customer complaint about performance. How do you prioritize this vs other work?"

For sales:

1. "Tell me about your hardest close. How did you do it? How long did it take?"
2. "We're a [stage] startup with [product]. Who's our ideal customer? Who's hardest to sell to?"
3. "You call a prospect. They say 'no thanks, we use [competitor].' What do you do?"
4. "What's your close rate? How long is sales cycle? What's your average deal size?"
5. "Tell me about a deal you lost. Why? What would you do differently?"

For CS:

1. "Customer is angry their feature request isn't prioritized. How do you respond?"
2. "You notice 40% of new signups don't activate. What do you investigate?"
3. "Tell me about a customer you saved from churning. How?"
4. "How do you decide if something is a bug or user error?"

For everyone:

1. "Why this startup? What attracted you?"
2. "What scares you about early-stage? How do you handle ambiguity?"
3. "Tell me about a time you failed. What did you learn?"

Output Template: HIRING-PLAN.md

# Hiring Plan

## Current State
- Revenue: $[X] MRR
- Customers: [X]
- Team: [You describe team: "2 co-founders, full-time"]
- Runway: [X months]

## Bottleneck Analysis

**Current constraint:** [What stops growth?]
- Evidence: [Metrics showing this is the bottleneck]
- Is it people or process? [People = hire, Process = fix it]

**Decision:** [Do we need to hire right now?]

## Hiring Timeline

**Next 90 days:** [Hire #1 or wait for more traction?]
**Months 4-6:** [Hire #2]
**Months 7-12:** [Hire #3]

[Alternative timeline if traction accelerates or decelerates]

## Hire #1: [Role]

**When:** [Trigger: MRR / customers / timeline]
**Why:** [Problem this person solves]

**Job Profile:**
- Title: [Exact title]
- Salary: $[X]
- Equity: [X]%
- Background: [Experience needed]
- Key traits: [What they must be good at]

**Interview process:**
1. [Phone screen topics]
2. [Technical/task evaluation]
3. [Culture fit interview]
4. [Reference calls]

## Hire #2: [Role]

[Same format]

## Hire #3: [Role]

[Same format]

## Compensation Summary

| Role | Salary | Equity | Rationale |
|------|--------|--------|-----------|
| [Hire #1] | $[X] | [X]% | [Why this person is worth it] |
| [Hire #2] | $[X] | [X]% | [Why this person is worth it] |
| [Hire #3] | $[X] | [X]% | [Why this person is worth it] |

## Cultural Values

[For each value: behavioral examples]

## Red Flags to Avoid

1. [Mistake 1]: [Why it kills startups]
2. [Mistake 2]: [Why it kills startups]
3. [Mistake 3]: [Why it kills startups]

## Interview Question Bank

[Organized by role]

## Onboarding Plan (First 30 days)

- Week 1: [What does new hire learn?]
- Week 2: [First shipping goal?]
- Week 3: [Independent project?]
- Week 4: [Full productivity?]

## Sign-off

Before hiring, answer:
- [ ] Is this person solving the real bottleneck?
- [ ] Do we have runway to afford them?
- [ ] Can we commit to mentoring/feedback?
- [ ] Will this person level up the team?

If no to any: Don't hire yet.

Completion Status

When you've finished:

• Identified the actual growth bottleneck (people vs process)
• Determined whether to hire now or wait
• Defined hire #1, #2, #3 with specific profiles
• Set compensation (salary + equity) for each
• Defined cultural values with behavioral examples
• Built interview question bank
• Documented common hiring mistakes and how to avoid them
• Created onboarding plan for first 30 days
• Generated HIRING-PLAN.md with full hiring roadmap

Exit with: DONE | DONE_WITH_CONCERNS | BLOCKED | NEEDS_CONTEXT

Key Principle

Early hires make or break a startup. Hire slow, hire right. A bad early hire costs 10x more than waiting 3 months for the right person.