team-management

name	team-management
description	Hiring framework, contractor onboarding, 1:1 templates, performance reviews, delegation (RACI), capacity planning, communication protocols, and offboarding. Scales CC from solo to small team without losing operational quality.
tags	["skill","team","management","hiring"]
triggers	["team management","use team management","run team management","hiring framework"]

Team Management — Solo to Small Team Framework

Overview

This skill gives CC a repeatable system to hire, onboard, manage, and eventually offboard the right people — contractors first, full-time later. Every template is designed to be run quickly (CC's time is scarce) and to extract high signal at every stage.

When to load this skill: When CC is hiring, delegating to a contractor, doing a 1:1, or reviewing someone's performance.

---

1. Hiring Framework

Role Definition Template

Before writing a job post, complete this. Every field is required.

ROLE DEFINITION
───────────────
Role title:
Brand/team: (OASIS AI / PropFlow / Nostalgic / Cross-brand)
Weekly hours: (contract hours expected per week)
Duration: (Project-based / Ongoing / Trial 30 days)
Compensation range: ($X/hr or $X/month — never negotiate from zero)

Core responsibilities (3-5, each one specific and measurable):
1.
2.
3.

Required skills (deal-breakers — must have ALL of these):
-
-

Nice-to-haves (bonus signals, not filters):
-
-

NOT this role (what it explicitly isn't — prevents misaligned applicants):
-
-

Success in 30 days looks like:
Success in 90 days looks like:

Reporting to: CC directly
Tools used: (list every tool they'll need access to)

Job Description Generator Structure

Use this structure when posting on Upwork, LinkedIn, or referrals:

[HOOK — 1 sentence about why this role matters at this company]
[WHO WE ARE — 2-3 sentences about OASIS/PropFlow/the brand]
[THE ROLE — 3-4 sentences on what this person actually does day-to-day]
[WHAT YOU'LL DO — 4-6 bullets from the core responsibilities]
[WHAT WE NEED — 3-5 required skills as bullets]
[WHAT'S IN IT FOR YOU — compensation, schedule, remote, growth opportunity]
[HOW TO APPLY — specific instruction that filters lazy applicants
  e.g., "Start your application with the phrase 'I read the brief' and tell me about a similar project you've done"]

The application filter is non-negotiable. Anyone who skips it is auto-rejected.

Interview Question Bank

For Virtual Assistants / Ops roles:

• "Walk me through a week where you were managing tasks for 3 different people simultaneously. How did you prioritize and what broke down?"
• "Tell me about a time you caught a mistake before it became a problem. What was the mistake and how did you spot it?"
• "I'll send you a task with incomplete instructions. What do you do before you start it?" (Tests: ask-first vs. assume-and-fail behavior)
• "What does your ideal working relationship with a client look like?" (Tests: communication style, autonomy preference)
• "What tools are you currently fastest in and what would take you a week to get comfortable with?"

For Developers:

• "Show me the last feature you shipped. Walk me through the decision you made that you'd make differently now."
• "I have a bug in production affecting 10% of users. What's your first three moves?" (Tests: triage instinct, communication)
• "Describe how you estimate task complexity. What do you factor in that most developers forget?"
• "You disagree with a technical decision I've made. How do you handle it?"
• "What's the biggest technical debt in a project you've owned and why did you let it accumulate?"

For Marketers / Content:

• "Give me an example of a piece of content you created that performed significantly better than expected. What drove it?"
• "What's a content idea you'd pitch for OASIS AI's LinkedIn this week? Walk me through your reasoning."
• "How do you decide what NOT to create? What's your filter for content that isn't worth the time?"
• "You post something and it gets no engagement. What's your process for diagnosing why?"
• "Describe your relationship with data. What metrics do you actually check and on what cadence?"

For Sales / SDRs:

• "Walk me through your cold outreach process step by step. What's your open rate and how do you know if it's good?"
• "A lead ghosts after a solid discovery call. What's your sequence over the next 21 days?"
• "What's the hardest objection you've heard and what's the most honest response you've found?"
• "Tell me about a deal you should have won but didn't. What would you do differently?"
• "What does your personal CRM look like? How do you track follow-ups?"

Universal closing questions (ask every candidate):

• "What do you know about this company/project that makes you think you'd be good here?"
• "What questions do you have for me?" (Weak candidates have none or ask about salary immediately)
• "If you took this role, what would you want to accomplish in the first 30 days?"

Scoring Rubric

Rate each dimension 1-5 after the interview. Weighted score below.

Dimension	Weight	1 (Bad)	3 (Ok)	5 (Strong)
Relevant experience	30%	Minimal overlap with the actual work	Some overlap, needs coaching	Deep overlap, has done this exact thing
Communication clarity	20%	Vague, needs repeated prompting	Adequate but not precise	Crisp answers, asks smart follow-ups
Ownership mindset	20%	Waits to be told, passes blame	Moderate autonomy	Runs toward problems, owns outcomes
Speed/efficiency signals	15%	No evidence of speed	Average pace	Fast, systematic, tools-first thinker
Culture/values fit	15%	Doesn't read as authentic or hungry	Neutral	Clearly driven, aligns with CC's energy

Minimum hiring bar: Weighted average ≥ 3.5. Never hire below 3.0.

Veto rule: A score of 1 on Ownership Mindset OR Communication Clarity is an automatic no regardless of total score.

Red Flags During Interviews

Stop the process if you see these:

• Can't give specific examples — everything is "we did X" (not "I did X")
• Blames former employers in detail — signals pattern, not isolated incident
• Hasn't researched the company at all — signals low interest or high entitlement
• Negotiates aggressively before seeing the offer — signals misaligned priorities
• Can't explain why they left their last role clearly — often hiding performance issues
• Answers questions with questions to buy time repeatedly — signals gaps they're masking
• Talks exclusively about what they want from the role, not what they'll deliver

Green Flags During Interviews

Strong signals to weight heavily:

• Mentions a specific problem they identified in your company before the interview
• Uses numbers and outcomes unprompted ("I reduced turnaround from 3 days to same-day")
• Asks about your challenges, not just the role's perks
• Admits what they don't know and explains how they'd close the gap
• Has a portfolio, work sample, or case study ready without being asked
• Pushes back on a weak assumption you make — thoughtfully and respectfully

Reference Check Template

Ask three questions. These are the ones that actually reveal signal.

Reference Check — [Candidate Name]
Speaking with: [Name, role, relationship to candidate]

1. "On a scale of 1-10, how strongly would you rehire [Name] if you had an open role they were suited for? What would need to be true for that number to be higher?"
   (Forces honesty — anything below 8 is a red flag. The "what would need to be true" part surfaces real weaknesses.)

2. "What type of manager brings out the best in [Name]? And what type of working environment is NOT a good fit?"
   (Reveals how much management the person needs — critical for a lean team where CC has limited bandwidth.)

3. "Is there anything about how [Name] operates that took you a while to figure out, that you wish someone had told you upfront?"
   (Open-ended and non-threatening. Often surfaces the one real issue no one else asked about.)

---

2. Contractor Onboarding Protocol

Day 0: Legal and Payment

• NDA signed via DocuSign or equivalent (use scripts/contract_generator/generator.py if OASIS)
• Contractor agreement signed (scope, rate, payment terms, IP assignment)
• Payment method confirmed (Wise, PayPal, Stripe, e-transfer)
• Payment schedule confirmed (weekly, bi-weekly, or milestone-based)
• Invoice format agreed (they submit → CC approves within 48h → paid within 72h)

Day 1: Access Provisioning

• Email added to relevant Google Workspace or given CC's shared credentials via 1Password
• GitHub repo access granted (minimum permissions required)
• Slack/Discord added to relevant channels (not every channel)
• Project management tool access (Notion, Linear, or Asana if applicable)
• Loom account access or record a 10-min welcome walkthrough (saves 3 async Q&A threads)

Day 1: Context Download

• Brand guide sent (CC's voice, values, visual identity)
• Relevant SOPs sent (only what applies to their role — don't overwhelm)
• Key contacts introduced (CC, Adon if PropFlow, any current clients they'll interact with)
• Stated outcome for their first 30 days in writing

Day 3: First Task Assignment

• Task has a clear title, deliverable, success criteria, and deadline
• Resources needed are provided upfront (no scavenger hunts)
• Preferred communication channel confirmed (Slack DM vs. email for each type of question)
• Explicitly stated: "Ask before assuming. Wrong direction for 2 hours costs more than a 5-min question."

Day 7: First Deliverable Check-In

• Review the first deliverable against the success criteria (not subjective feel)
• Give specific feedback (not "good job" — "section 2 needs X because Y")
• Adjust scope, timeline, or communication frequency if needed
• Ask: "Is there anything about how we're working together that's slowing you down?"

Day 14: First Performance Snapshot

Snapshot (internal, not shared unless issues):

• Deliverable quality: 1-5
• Communication quality: 1-5
• Speed vs. expectations: 1-5
• Proactiveness (flags issues before they escalate): 1-5
• Overall: continue / adjust / end

Day 30: Full Review

Formal conversation:

1. Review deliverables produced vs. committed deliverables
2. Performance snapshot scores across the month
3. Feedback exchange: CC gives feedback, then asks "What's one thing I could do better as a client?"
4. Decision: Continue at same terms / Adjust scope or rate / End engagement
5. If continuing: set next 30-day goals explicitly

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3. 1:1 Framework

Weekly 1:1 Template (15-30 min)

Run this every week with any contractor working >10 hrs/week. Keep notes.

WEEKLY 1:1 — [Name] — [Date]
─────────────────────────────
1. How are you doing? (Genuine check-in — not just work)
   Notes:

2. What went well this week?
   Notes:

3. What's blocked or frustrating?
   Notes:
   Action items:

4. Priorities for next week (agree on top 3 together)
   1.
   2.
   3.

5. Anything you need from me? (Resources, decisions, unblocking)
   Notes:

Duration: ___   Format: Slack huddle / Loom / Zoom

Rule: CC speaks <40% of the time in a 1:1. This is for the contractor to talk.

Monthly 1:1 Template (45-60 min)

Run once per month in addition to weeklies. More strategic.

MONTHLY 1:1 — [Name] — [Date]
──────────────────────────────
1. Career growth discussion
   "Where do you want to be in 12 months? Is this engagement helping you get there?"
   Notes:

2. Skill development opportunities
   "Is there anything you want to learn that we could incorporate into the work?"
   Notes:

3. Process improvements
   "What's one thing about how we work together that, if we fixed it, would make your work 20% better?"
   Notes:
   Action items:

4. Compensation and role alignment (if applicable)
   Review: market rates, performance, scope changes
   Decision: maintain / increase / renegotiate
   Notes:

Follow-up actions (with deadlines):

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4. Performance Review Framework

Quarterly Review Template

Run this every 90 days for any contractor working >15 hrs/week.

QUARTERLY REVIEW — [Name] — [Quarter: Q1/Q2/Q3/Q4 YYYY]
──────────────────────────────────────────────────────────
Role:
Review period:

GOALS ACHIEVED
Goal 1: [stated goal] → [outcome with evidence]
Goal 2: [stated goal] → [outcome with evidence]
Goal 3: [stated goal] → [outcome with evidence]
Overall goal achievement: X/3 goals fully met

AREAS OF STRENGTH (be specific — name actual deliverables)
-
-

AREAS FOR IMPROVEMENT (specific and actionable — not vague)
Improvement area:
Why it matters:
Specific action to take:
By when:

GOALS FOR NEXT QUARTER
1. [Specific, measurable goal with deadline]
2.
3.

COMPENSATION REVIEW
Current rate: $X
Market check: [comparable rate range]
Performance rating: [1-5 — see scale below]
Recommendation: Maintain / Increase by X% / Renegotiate scope
New rate (if changed): $X effective [date]

OVERALL RATING: ___/5

Rating Scale:

• 5 — Exceeds: consistently delivers beyond scope, proactively improves processes
• 4 — Meets+: meets all goals and frequently goes beyond on quality or speed
• 3 — Meets: delivers what was agreed, rarely more, rarely less
• 2 — Below: missing goals or quality issues requiring repeated correction
• 1 — Critical: performance gap threatening project outcomes; PIP required or end engagement

Rule: A 1 rating requires immediate intervention, not a quarterly review. Address within the week it's identified.

---

5. Delegation Framework (RACI-Based)

RACI Definitions

• R — Responsible: Does the actual work
• A — Accountable: Owns the outcome; the one CC asks "did it happen?"
• C — Consulted: Input needed before decision is finalized
• I — Informed: Kept in the loop but not required for decision

Task Delegation Template

TASK DELEGATION BRIEF
─────────────────────
Task name:
Project/context:
Deadline: (hard deadline vs. soft target)

WHAT: (specific deliverable — what does done look like in 1 sentence?)

WHY: (why this task matters — context that changes how they approach it)

WHO (RACI):
  Responsible:    [name]
  Accountable:    [almost always CC for now]
  Consulted:      [who they need to check with, if anyone]
  Informed:       [who gets notified when done]

HOW (success criteria):
  - [Measurable criterion 1]
  - [Measurable criterion 2]
  - [Format/channel for delivery]

RESOURCES AVAILABLE:
  - [Relevant doc, template, or credential they'll need]
  - [Example of a similar completed task for reference]

CONSTRAINTS:
  - [Budget limit if applicable]
  - [Tools they must or must not use]
  - [Anything that's out of scope for this task]

CHECK-IN POINT: [Midpoint check before final delivery, if task is >2 days]

Rule: Never delegate a task without completing this brief. "Figure it out" is not a success criterion.

---

6. Team Capacity Planning

Capacity Snapshot Template

CAPACITY SNAPSHOT — [Week of DATE]
────────────────────────────────────
Name          | Role        | Hrs/week | Projects          | Utilization
[Contractor]  | [VA/Dev/etc] | 15       | [Project A, B]   | 85%
[Contractor]  | [...]        | 20       | [Project C]      | 70%

Total capacity: X hrs/week
Total allocated: Y hrs/week
Overall utilization: Z%

Utilization Targets

Work Type	Target Utilization	Why
Creative / strategic work	70-80%	Creative output needs slack; over-utilization kills quality
Execution / ops work	80-90%	Predictable tasks can run tighter
Any role	>90% for 4+ consecutive weeks	Hire signal — add headcount or reduce scope

When to Hire Next

Hire indicator is met when ANY of these are true for 4+ consecutive weeks:

1. Your own utilization (CC's hours on delegatable work) is >90%
2. A contractor's utilization is >90% and the work is still growing
3. A critical skill is routinely absent (e.g., no one owns design and it's blocking launches)
4. Client onboarding speed is limited by team capacity, not sales pipeline

CC's non-delegable hours (never hire to replace these):

• Sales calls and client relationship decisions
• Strategic decisions (pricing, partnerships, pivots)
• Content creation (personal brand requires CC's voice)
• Final approval on anything that ships to a client or the public

---

7. Communication Protocols

Channel Routing

Type of Message	Channel	Expected Response
Urgent blocker (>2hr impact)	Phone call or voice message	Within 1 hour
Task question or decision needed	Slack DM	Within 4 business hours
Status update or FYI	Slack DM or project tool	No response required
Formal feedback or review	Email or written doc	Within 24 hours
Billing / contracts	Email only	Within 48 hours

Async-first rule: Default to async. Call only when a back-and-forth would take >5 messages to resolve.

Status Update Format

When a contractor gives CC a status update (request this weekly at minimum):

STATUS — [Name] — [Date]
✅ DONE: [What was completed this week — 2-4 items]
🔄 DOING: [What's in progress right now]
🚫 BLOCKED: [Anything that's stuck and what it's waiting on]
📅 NEXT: [Top priority for next 3-5 days]

Meeting Cadence

Meeting	Frequency	Duration	Participants
Async status update	Weekly (Thursday)	Written	All contractors
1:1 check-in	Weekly (for >10 hrs/wk contractors)	15-30 min	CC + individual
Monthly deep 1:1	Monthly	45-60 min	CC + individual
Quarterly review	Every 90 days	60 min	CC + individual
Team sync (when team > 2)	Bi-weekly	30 min	All

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8. Offboarding Protocol

Knowledge Transfer Checklist

Before last day, contractor must complete:

• All work-in-progress documented (status, next steps, where files live)
• All credentials they created or modified updated in 1Password / .env.agents
• All ongoing automations documented (n8n, cron jobs, scheduled tasks they owned)
• Client-facing work handed off to CC or next person with context note
• All project files organized in the agreed folder structure
• Loom walkthrough recorded for complex processes they owned

Access Revocation Checklist

Revoke on or before last day:

• Remove from GitHub org / repos
• Revoke Supabase access (check all projects they had access to)
• Remove from Slack workspace
• Remove from any project management tool
• Change shared passwords they had access to
• Revoke any API keys issued specifically to them
• Remove from email lists or forwarding rules

Final Deliverables Handoff

OFFBOARDING HANDOFF — [Name] — [Date]
──────────────────────────────────────
Projects handed off:
  - [Project]: [handoff doc or Loom link]

Work in progress at time of exit:
  - [Item]: [status + next step + location]

Open items still needing resolution:
  - [Item]: [owner going forward]

Outstanding payments:
  Final invoice received: Y/N
  Invoice amount: $
  Payment due: [date]

Notes for future reference (would we rehire?):

Exit Interview Questions

Ask these on the final call (5-10 min max):

1. "What was the most valuable thing you worked on here?"
2. "What was the most frustrating part of working with us? What could we do better?"
3. "Is there anyone in your network who might be a great fit for the work you did?"

---

Integration Points

• Hiring decisions → log to memory/DECISIONS.md
• Performance issues → log to memory/MISTAKES.md with root cause and prevention
• Onboarding tasks → add to memory/ACTIVE_TASKS.md
• New team member → trigger workflow .agents/workflows/onboard-team-member.md
• Capacity data → update brain/STATE.md (team section)

Obsidian Links

• [[brain/USER]] | [[brain/STATE]] | [[memory/ACTIVE_TASKS]] | [[brain/CAPABILITIES]]
• [[skills/ceo-dashboard/SKILL]] | [[skills/project-management/SKILL]]
• /onboard-team-member