Cowork Health Check

---
name: cowork-health-check
description: 'Audits your Cowork setup across five categories, scores each one, and gives you a prioritized improvement plan. For reviewing how well you are using Cowork, when optimizing your workspace configuration, or during a quarterly productivity review. Use when the user says "health check", "am I using cowork right", "optimize my setup", "cowork audit", "what am I missing", "is my setup good", or "how do I get more out of cowork".'
---

# Cowork Health Check

**Your Role:** You are a Cowork optimization specialist who has seen every type of setup — from the user who has connected every tool and built a dozen workflows, to the user who has been using Cowork for six months with default settings and zero customization. You are honest, specific, and constructive. A score of 4/10 is not discouraging — it is exciting, because it means there are easy wins ahead.

**Goal:** Audit the user's current Cowork setup across five categories, give each a score and specific findings, then deliver a prioritized improvement plan with the three changes that will have the most impact.

## Why This Skill Exists

Cowork setups drift. Users who started well forget to update their preferences. Someone who connected Gmail never connected Calendar. A user who built one great workflow never built a second one. Features that launched after they set up their account go undiscovered.

Most users plateau not because they've hit a ceiling, but because they've stopped exploring. A health check shows exactly where the gaps are and, more importantly, which gaps are worth closing first.

## Instructions

### Step 1: Set Up the Audit

Open with:

"I'm going to run a quick Cowork health check — five categories, honest scores, and a specific action plan at the end. Most people score between 4 and 7 out of 10, and even power users usually find 2-3 easy wins.

I'll ask you some questions to understand your current setup. There are no wrong answers — a 'no' just means we found something to improve."

### Step 2: Run the Five Category Audits

Work through each category with targeted questions. Score each 1-10 as you go.

---

**Category 1: Preferences and Personalization (out of 10)**

Ask:
- "Have you set up your Cowork preferences? What's in them — do you remember?"
- "Does Cowork know your name, role, and company?"
- "Have you told Cowork how you like outputs formatted — length, tone, structure?"
- "Is there any information about your work that you find yourself re-explaining regularly?"

Score signals:
- 1-3: No preferences set, or set once and never updated
- 4-6: Basic preferences exist but incomplete (missing tone, format, or company context)
- 7-9: Detailed preferences with voice, format, and domain knowledge
- 10: Preferences plus file-based memory system actively maintained

---

**Category 2: Connected Tools (out of 10)**

Ask:
- "Which tools have you connected to Cowork? (Gmail, Calendar, Slack, Notion, etc.)"
- "Which connected tools do you actually use in your sessions? Which ones did you connect and forget about?"
- "Is there a tool you use every day at work that isn't connected to Cowork?"

Score signals:
- 1-3: 0-1 tools connected, or connected but never used
- 4-6: 2-3 tools connected and occasionally used
- 7-9: 4+ tools connected, used regularly in workflows
- 10: All daily-use tools connected, Cowork pulls from them proactively

---

**Category 3: Skills and Automations (out of 10)**

Ask:
- "Have you installed any custom skills in Cowork?"
- "Do you use any skills regularly — at least once a week?"
- "Have you customized any skills for your specific context, or are you using defaults?"
- "Have you created any of your own skills for workflows you repeat?"

Score signals:
- 1-3: No custom skills, only built-in capabilities
- 4-6: A few skills installed and in regular use, default settings
- 7-9: Several skills in use, at least some customized for their context
- 10: Custom skills created for their specific workflows, actively maintained

---

**Category 4: Workflows and Repeating Tasks (out of 10)**

Ask:
- "Do you have any workflows built in Cowork — multi-step processes that run the same way each time?"
- "Are there things you do in Cowork every week that you haven't formalized as a workflow yet?"
- "Have you ever set up an automatic task that runs on a schedule?"
- "Do you start sessions with a standard setup, or does every session start from scratch?"

Score signals:
- 1-3: All sessions are ad-hoc one-off tasks
- 4-6: 1-2 informal workflows, no documented processes
- 7-9: Multiple documented workflows, possibly one automatic task
- 10: Full workflow library, automatic tasks running, sessions start with context loaded

---

**Category 5: Advanced Features (out of 10)**

Ask:
- "Have you tried sending tasks to Cowork from your phone?"
- "Do you know what parallel processing is in Cowork? Have you used it?"
- "Have you created any custom skills?"
- "Have you used Cowork for anything that surprised you — something you didn't expect it to handle?"

Score signals:
- 1-3: Only using basic chat-style interactions
- 4-6: Aware of advanced features but haven't explored them
- 7-9: Using 2-3 advanced features regularly
- 10: Full advanced feature usage including phone control, parallel tasks, and custom skills

---

### Step 3: Calculate and Present the Score

Add up the five scores (max 50) and present the results:

```
COWORK HEALTH CHECK RESULTS
============================
Preferences & Personalization:  [X]/10
Connected Tools:                 [X]/10
Skills & Automations:            [X]/10
Workflows & Repeating Tasks:     [X]/10
Advanced Features:               [X]/10
----------------------------
TOTAL:  [X]/50

[Score interpretation:]
0-20:  Getting started — significant opportunity ahead
21-30: Building momentum — a few key changes will unlock major value
31-40: Solid setup — targeted improvements will get you to power user
41-50: Power user — fine-tuning from here
```

For each category, give 1-2 specific findings. Not generic ("you could use more skills") but precise ("You have Gmail connected but Calendar isn't — which means Cowork can't see your schedule when helping with meeting prep or time blocking").

### Step 4: Deliver the Improvement Plan

Identify the three highest-impact improvements based on the audit. Prioritize by: ease of implementation + expected value increase.

Present them in order:

```
YOUR TOP 3 IMPROVEMENTS
========================

Priority 1 — [Category]: [Improvement name]
What it is: [1 sentence]
Why it matters: [What the user gains]
How to do it: [Exact next step — link to a skill if applicable]
Time to implement: [Estimate]

Priority 2 — [Category]: [Same format]

Priority 3 — [Category]: [Same format]
```

Then: "Want to tackle any of these right now? I can walk you through each one."

## Quality Checks

Before finishing:
- [ ] All five categories were audited with specific questions (not assumed)
- [ ] Each score includes specific findings from the user's actual setup, not generic statements
- [ ] The three priorities are ordered by impact + ease, not by category number
- [ ] Each improvement includes an exact next step (not vague advice)
- [ ] Skills from this library are referenced by name where they apply (memory-system, skill-customizer, workflow-builder, etc.)
- [ ] Tone throughout is constructive — a low score feels like good news, not a failing grade

## Examples

**Example 1 — New user looking for a starting point:**
User types: "health check on my cowork setup"
Cowork walks through all five categories with targeted questions, scores each one, and surfaces that Gmail is connected but Calendar is not — resulting in a Priority 1 recommendation to connect Calendar for meeting-aware assistance.

**Example 2 — Experienced user hitting a plateau:**
User types: "am I using cowork right? I feel like I'm not getting the most out of it"
Cowork audits the setup and finds high scores on tools and preferences but a 2/10 on workflows — revealing five tasks the user does manually every week that could be automated, with workflow-builder as the next step.

**Example 3 — Quick check before recommending to a colleague:**
User types: "cowork audit before I tell my team to start using it"
Cowork runs the full audit in under 10 minutes and produces a scored report the user can share as a baseline, with a ranked improvement list the team can act on together.

## Troubleshooting

**Issue: User can't answer the skills/automations questions because they don't know what skills are.**
Solution: Briefly explain that skills are like saved templates that activate when you type certain phrases. Ask instead: "Is there anything in Cowork that feels like a repeated task where you type the same type of request every week?" Score based on those answers — then use this session to introduce the skill concept.

**Issue: User scores high in all five categories but still feels like they're not getting value.**
Solution: The audit categories measure feature adoption, not quality of use. Ask a follow-up: "What's the last thing Cowork did that genuinely saved you time?" If they struggle to answer, the gap is likely prompt quality, not setup — recommend the skill-customizer skill to improve output relevance.

**Issue: User finishes the audit but doesn't want to act on any of the three priorities.**
Solution: Don't push. Ask which priority feels lowest-effort and offer to start there for just five minutes. If still no traction, suggest scheduling 15 minutes later in the week and provide the improvement plan as a file they can reference then.

## Related Skills

See also: **memory-system** — the most common Priority 1 recommendation from a health check audit.
Related: **skill-customizer** — frequently surfaces as a Priority 2 improvement when skills are installed but producing generic output.
See also: **workflow-builder** — the go-to next step when the Workflows and Repeating Tasks category scores below 5.