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team-onboarding-playbook

Design a structured onboarding experience that gets new team members productive in 30, 60, and 90 days. Use when a new hire is joining, when contractors or agency partners need to ramp up, when an existing team is restructuring and members are switching focus, or when current onboarding feels chaotic and slow. Also triggers when one person owns all the tribal knowledge and you need to capture it, when you keep losing people in their first 90 days, or when a new project has many fresh members joining at once. Useful for engineering, design, product, marketing, and operations roles.

60

Quality

70%

Does it follow best practices?

Impact

No eval scenarios have been run

SecuritybySnyk

Passed

No known issues

Optimize this skill with Tessl

npx tessl skill review --optimize ./skills/team-onboarding-playbook/SKILL.md
SKILL.md
Quality
Evals
Security

Quality

Content

50%

Reviews the quality of instructions and guidance provided to agents. Good implementation is clear, handles edge cases, and produces reliable results.

This is a well-structured onboarding framework skill with good coverage of roles, milestones, and anti-patterns. Its main weaknesses are verbosity (explanatory prose that doesn't add actionable value for Claude), lack of concrete templates or examples of the deliverables it asks Claude to produce, and a monolithic structure that could benefit from splitting detailed content into reference files. The content is solid but reads more like a blog post or handbook than a lean, actionable skill file.

Suggestions

Add a concrete example of at least one deliverable (e.g., a sample pre-day-1 checklist or a 30/60/90 milestone table) so Claude knows the exact format expected in output.

Move role-specific overlays and failure patterns into separate reference files to reduce the main SKILL.md length and improve progressive disclosure.

Trim motivational and explanatory prose (e.g., 'The first week is mostly about belonging, not productivity') that Claude doesn't need to follow the instructions.

Add explicit validation steps in the workflow, such as 'Review the checklist with the hiring manager before day 1' or 'At 30-day check-in, compare against milestones and flag gaps explicitly.'

DimensionReasoningScore

Conciseness

The content is well-organized but verbose for an AI skill. Sections like 'When to use' and 'When NOT to use' largely repeat what Claude can infer. The Layer descriptions include motivational/explanatory prose ('The first week is mostly about belonging, not productivity. Get this right and everything else accelerates.') that doesn't add actionable value. The failure patterns section, while useful, is lengthy. Overall, there's meaningful content but it could be tightened by ~30%.

2 / 3

Actionability

The skill provides structured guidance with role-specific overlays and concrete milestones, which is good. However, it's an instruction-only skill that remains at a fairly high level of abstraction—it describes what a good onboarding plan contains rather than providing fill-in templates, specific scripts for welcome messages, or concrete checklist formats. The output format section lists deliverables but doesn't show what they look like. The referenced checklist file could help but isn't provided.

2 / 3

Workflow Clarity

The 9-step workflow section provides a clear sequence, and the 30/60/90 milestones serve as checkpoints. However, there are no explicit validation or feedback loops within the workflow steps themselves—step 7 mentions 'formal 30/60/90 check-ins' but doesn't specify what to validate or how to course-correct. Step 8-9 (retrospective and update) are good but come only at the end. For a process that spans 90 days with many potential failure points, more intermediate validation would strengthen this.

2 / 3

Progressive Disclosure

The skill references one external file (references/onboarding-checklist.md) which is appropriate, but the bundle doesn't include it, making it impossible to verify. The main SKILL.md is quite long (~200+ lines) and could benefit from splitting the role-specific overlays and failure patterns into separate reference files. The structure within the file is good with clear headers, but the content density suggests it would benefit from more aggressive splitting.

2 / 3

Total

8

/

12

Passed

Description

89%

Based on the skill's description, can an agent find and select it at the right time? Clear, specific descriptions lead to better discovery.

This is a strong description with excellent trigger coverage and completeness, clearly articulating when the skill should be used across many realistic scenarios. Its main weakness is that the 'what' portion could be more specific about the concrete deliverables and actions the skill performs beyond 'design a structured onboarding experience.' However, the second-person voice ('you need to capture it', 'you keep losing people') should be noted as a minor style issue per the rubric guidelines.

Suggestions

Add more specific concrete actions/deliverables, e.g., 'Creates milestone checklists, mentor pairing guides, knowledge transfer documents, and progress review templates' to strengthen specificity.

Rewrite second-person phrases like 'you need to capture it' and 'you keep losing people' to third-person voice, e.g., 'when one person owns all tribal knowledge and it needs to be captured' to align with rubric style expectations.

DimensionReasoningScore

Specificity

It names the domain (onboarding) and a key structural element (30/60/90 day plan), but doesn't list multiple concrete actions like 'create checklists, assign mentors, schedule check-ins, document tribal knowledge.' The description is more about the outcome than specific actions performed.

2 / 3

Completeness

Clearly answers both 'what' (design a structured onboarding experience with 30/60/90 day milestones) and 'when' with extensive explicit trigger scenarios covering new hires, contractors, restructuring, knowledge capture, retention issues, and new project staffing.

3 / 3

Trigger Term Quality

Excellent coverage of natural trigger terms: 'new hire', 'onboarding', 'ramp up', 'contractors', 'agency partners', 'restructuring', 'tribal knowledge', 'first 90 days', 'new project'. These are phrases users would naturally use when seeking onboarding help.

3 / 3

Distinctiveness Conflict Risk

The focus on structured onboarding with 30/60/90 day timelines is a clear niche. The specific trigger scenarios (tribal knowledge capture, first-90-day retention, ramp-up) make it highly distinguishable from general HR, project management, or documentation skills.

3 / 3

Total

11

/

12

Passed

Validation

90%

Checks the skill against the spec for correct structure and formatting. All validation checks must pass before discovery and implementation can be scored.

Validation10 / 11 Passed

Validation for skill structure

CriteriaDescriptionResult

frontmatter_unknown_keys

Unknown frontmatter key(s) found; consider removing or moving to metadata

Warning

Total

10

/

11

Passed

Repository
rampstackco/claude-skills
Reviewed

Table of Contents

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