How do I install the System Selection skill?

Run npx skillmds@latest add kaakati/system-selection in your terminal (requires Node.js), paste this page's agent-chat prompt into Claude, Cursor, or any MCP-connected agent, or download the SKILL.md file and copy it into your agent's skills directory.

What does the System Selection skill do?

Structured system and vendor selection methodology using weighted scoring with stakeholder-aligned criteria. USE THIS SKILL when the user asks about vendor evaluation, RFP creation, build vs buy decisions, system selection, ERP selection, CRM selection, platform evaluation, software procurement, or technology vendor comparison. Covers the full lifecycle from requirements gathering through contract negotiation with TCO modeling and decision presentation frameworks. It is listed under Product & Planning on SkillMD.

Is System Selection safe to use?

This skill has not completed SkillMD's automated safety review yet. SkillMD never runs a skill's scripts for you; review the SKILL.md before installing.

Which AI agents work with System Selection?

This skill is tagged as working with Claude Code, Claude.ai, OpenAI Codex. SKILL.md is an open format, so most agents that read a skills directory can load it too.

Is System Selection free to use?

Yes. Installing skills from SkillMD is free, and the skill stays under its author's original license.

Who published System Selection?

Kaakati (@kaakati) published this skill. Their other Agent Skills are listed on their SkillMD profile.

System Selection by kaakati — Agent Skill

Name: System Selection
Author: Kaakati

System Selection

Required Inputs

System Type: Category of system being selected (ERP, CRM, HRIS, data platform, etc.).
Business Context: Why this selection is happening (new implementation, replacement, consolidation).
Stakeholder Map: Key decision-makers, influencers, and end users.
Budget Range: Capital and operating budget constraints.
Timeline: Decision timeline and target go-live date.
Constraints: Mandatory requirements, regulatory needs, integration dependencies, preferred vendors.

Execution Steps

1. Requirements Gathering

Gather requirements across four categories. Each requirement is rated by priority and assigned a stakeholder owner.

Requirement Priority Classification:

Priority	Label	Definition	Scoring Impact
P1	Must Have	Non-negotiable; vendor fails without it	Eliminatory -- vendor disqualified if unmet
P2	Should Have	Important; significant impact on success	High weight in scoring (3x multiplier)
P3	Nice to Have	Desirable; adds value but not essential	Standard weight in scoring (1x multiplier)
P4	Future	Not needed now but anticipated within 2 years	Low weight (0.5x multiplier)

Functional Requirements Template:

ID	Requirement	Description	Priority	Stakeholder	Source
FR-001			P1/P2/P3/P4

Categories to cover:

Functional: Business capabilities, workflows, reporting, user experience
Technical: Architecture, APIs, security, performance, scalability, data model
Integration: Systems to connect, data flows, real-time vs batch, middleware
Non-Functional: Availability SLA, response time, data residency, accessibility, compliance

Requirements Discovery Methods:

Stakeholder interviews (1:1 with decision-makers and power users)
Process mapping workshops (current state and desired future state)
Pain point analysis (top 10 issues with current system)
Data flow analysis (what data moves between systems)
Regulatory review (compliance requirements that constrain selection)

2. Build vs. Buy vs. Configure Decision

Before evaluating vendors, determine if buying is the right approach.

Decision Scorecard:

Factor	Weight	Build (Custom)	Buy (SaaS/License)	Configure (Low-Code/Platform)
Strategic differentiation	15%	5: Full control, unique IP	1: Same as competitors	3: Moderate customization
Time to value	15%	1: 12-24 months	5: 1-6 months	4: 3-9 months
Total cost (5 year)	15%	Variable, often underestimated	Predictable licensing	Moderate, platform fees
Maintenance burden	10%	5: Full ownership	1: Vendor managed	3: Shared responsibility
Talent availability	10%	Specialized skills required	Lower barrier	Platform-specific skills
Vendor/platform risk	10%	None	Lock-in, viability risk	Platform dependency
Scalability	10%	Depends on architecture	Vendor-managed scaling	Platform-dependent
Integration flexibility	10%	Full control	API-dependent	Platform ecosystem
Regulatory compliance	5%	Full control	Vendor certification	Platform certification
Weighted Total	100%

Decision Threshold:

Build score > Buy by 20%+: Proceed with build (validate with CTO/CIO)
Scores within 20%: Default to buy unless strong strategic differentiation argument
Buy score > Build: Proceed with vendor evaluation (below)

3. Market Landscape Analysis

Vendor Universe Mapping:

Tier	Description	Example Criteria	Typical Count
Leaders	Established, broad capability, large customer base	Gartner MQ leaders, >$1B revenue	3-5
Challengers	Strong product, growing market share	Strong product reviews, fast growth	3-5
Niche Players	Specialized by industry, size, or function	Deep domain fit, innovative features	5-10
Emerging	New entrants, modern architecture, disruptive pricing	Cloud-native, AI-first, <3 years in market	3-5

Research Sources:

Analyst reports: Gartner Magic Quadrant, Forrester Wave, IDC MarketScape
Peer reviews: G2, Capterra, TrustRadius (filter for similar company size/industry)
Industry references: Peer company implementations, conference case studies
Vendor briefings: Analyst inquiry, vendor-provided materials

4. Long List to Short List Reduction

Stage Gate Process:

Stage	Input	Criteria	Output
Universe	All known vendors	Market presence in category	15-25 vendors
Long List	Universe filtered	Meets P1 requirements (desk research)	8-12 vendors
RFI Response	Long list vendors	Detailed capability match, pricing range	5-8 vendors
Short List	RFI respondents	Weighted scoring threshold (>70%)	3-5 vendors
Final Demo	Short list vendors	Full evaluation with stakeholders	2-3 vendors
Selection	Finalists	Final scoring, negotiation, reference checks	1 vendor

Long List Elimination Criteria (any = disqualify):

Does not meet any P1 requirement
No presence in target geography/market
Company size mismatch (too small = risk, too large = priority risk)
No relevant industry references
Technology architecture fundamentally incompatible
Pricing model misaligned with budget range

5. RFP/RFI Template Structure

RFP Document Outline:

Section	Content	Page Guidance
1. Company Overview	About the buying organization, strategic context	1-2 pages
2. Project Scope	System scope, users, geographies, timeline	2-3 pages
3. Current State	Existing systems, integrations, pain points	1-2 pages
4. Requirements	Functional, technical, integration, non-functional (reference matrix)	10-20 pages
5. Vendor Information	Company background, financials, references, roadmap	2-3 pages
6. Implementation Approach	Methodology, team, timeline, change management	3-5 pages
7. Pricing	License/subscription, implementation, ongoing costs (use TCO template)	2-3 pages
8. Security & Compliance	Certifications, data handling, audit reports	2-3 pages
9. SLA & Support	Uptime SLA, support tiers, escalation, maintenance windows	1-2 pages
10. Evaluation Criteria	Scoring methodology (transparent to vendors)	1 page
11. Response Instructions	Format, deadline, Q&A process, contact	1 page

RFP Requirements Response Format:

Req ID	Requirement	Priority	Response Options
FR-001	[Description]	P1	Fully Supported / Supported with Configuration / Supported with Customization / Roadmap (date) / Not Supported

6. Weighted Scoring Framework

Scoring Category Weights (adjustable by stakeholder priorities):

Category	Default Weight	Range	Key Stakeholder
Functional Fit	30%	25-40%	Business owners, end users
Technical Fit	20%	15-25%	IT/Engineering
Vendor Viability	15%	10-20%	Procurement, executive sponsor
Cost (TCO)	15%	10-20%	Finance, procurement
Implementation Risk	10%	5-15%	PMO, IT
Innovation & Roadmap	10%	5-15%	CTO/CIO, product
Total	100%

Detailed Scoring Rubric (apply consistently across all vendors):

Score	Label	Definition
5	Exceptional	Exceeds requirement; best-in-class capability demonstrated
4	Strong	Fully meets requirement with proven capability
3	Adequate	Meets requirement with minor gaps or workarounds
2	Partial	Partially meets requirement; significant customization needed
1	Weak	Barely addresses requirement; major gaps
0	Fail	Does not meet requirement (eliminatory for P1 items)

Scoring Matrix Template:

Category	Sub-Criteria	Weight	Vendor A	Vendor B	Vendor C
Functional Fit (30%)
	Core functionality coverage	10%
	Workflow/process alignment	8%
	Reporting & analytics	6%
	User experience	6%
Technical Fit (20%)
	Architecture & scalability	6%
	Security & compliance	6%
	Integration capabilities	5%
	Performance	3%
Vendor Viability (15%)
	Financial stability	5%
	Market position & trajectory	4%
	Customer references	3%
	Partner ecosystem	3%
Cost / TCO (15%)
	5-year TCO	10%
	Pricing model flexibility	5%
Implementation Risk (10%)
	Implementation complexity	4%
	Vendor implementation capability	3%
	Data migration risk	3%
Innovation (10%)
	Product roadmap alignment	5%
	AI/automation capabilities	3%
	Technology modernity	2%
TOTAL		100%	/5.0	/5.0	/5.0

7. Vendor Demo Evaluation Scorecard

Demo Structure (require from all vendors):

Segment	Duration	Content	Evaluators
Company & vision	15 min	Vendor strategy, roadmap, relevant experience	Executive sponsor
Core scenario 1	30 min	Primary business workflow (scripted)	Business users
Core scenario 2	30 min	Secondary business workflow (scripted)	Business users
Integration demo	15 min	Live integration with key systems	IT/Engineering
Administration	15 min	Configuration, security, user management	IT/Engineering
Q&A	15 min	Open questions from evaluation team	All

Demo Evaluation Form (per evaluator):

Criteria	Weight	Score (1-5)
Scenario completion (did it work?)	25%
Ease of use / UX quality	20%
Data handling and reporting	15%
Configurability (no custom code)	15%
Integration capability demonstrated	10%
Presenter knowledge and credibility	10%
Innovation / "wow factor"	5%
Weighted Score	100%	/5.0

8. Reference Check Methodology

Reference Selection Rules:

Require 3-5 references per short-listed vendor
At least 1 reference in same industry
At least 1 reference of similar company size
At least 1 reference that went live within last 18 months
Request references the vendor did NOT pre-select (ask for full customer list)

Reference Check Question Bank:

Category	Questions
Implementation	How long did implementation take vs. plan? What was the biggest surprise? Would you use the same implementation partner again?
Functionality	What works well? What are the top 3 gaps or workarounds? How does reporting meet your needs?
Performance	Any performance issues at scale? Uptime experience vs. SLA?
Support	How responsive is vendor support? How are bugs and enhancement requests handled?
Cost	Did total cost match proposal? Any unexpected costs? How have renewal negotiations gone?
Integration	How well does the system integrate? API quality and documentation?
Satisfaction	Net Promoter Score (0-10)? Would you choose this vendor again? What would you do differently?

9. Total Cost of Ownership (TCO) Model

5-Year TCO Template:

Cost Category	Year 0 (Impl)	Year 1	Year 2	Year 3	Year 4	Year 5	Total
Software Costs
License / subscription fees
User licenses (per seat)
Module / add-on fees
API / integration fees
Storage / compute overage
Implementation Costs
Vendor professional services
SI / implementation partner
Data migration
Custom development
Testing and QA
Internal Costs
Internal project team (FTE x months)
Business user time (training, UAT)
IT support team allocation
Change Management
Training development and delivery
Change management program
Productivity loss during transition
Ongoing Costs
Annual maintenance / support
Managed services / admin
Enhancements / releases
Infrastructure (if on-prem)
Risk Contingency (10-20%)
TOTAL							$[X]

TCO Comparison Normalization:

Convert all pricing to same term (monthly/annual)
Normalize user counts to same projected growth
Include contractual escalators (annual price increases)
NPV calculation at company's discount rate for multi-year comparison

NPV of TCO = Sum of (Annual Cost_t / (1 + discount_rate)^t) for t = 0 to 5
Cost per User per Month = 5-Year TCO / (Average User Count x 60 months)

10. Implementation Risk Assessment

Risk Assessment per Vendor:

Risk Factor	Weight	Assessment Criteria	Vendor A	Vendor B	Vendor C
Implementation complexity	20%	# of integrations, data migration volume, customizations
Vendor implementation track record	20%	On-time %, reference satisfaction, methodology maturity
Data migration risk	15%	Data volume, quality, mapping complexity, downtime tolerance
Organizational readiness	15%	Change magnitude, executive support, user buy-in
Integration risk	15%	API maturity, middleware needs, real-time requirements
Timeline feasibility	15%	Vendor capacity, internal resource availability, dependencies
Weighted Risk Score	100%	Lower = less risky	/5.0	/5.0	/5.0

11. Contract Negotiation Key Terms

Critical Contract Terms Checklist:

Term	What to Negotiate	Acceptable / Watch Out
Pricing protections	Annual increase cap, volume discount tiers, MFN clause	Cap at 3-5%; avoid uncapped CPI adjustments
SLA and penalties	Uptime guarantee, response times, credit mechanism	99.9%+ uptime; meaningful credits (5-10% of monthly fee)
Data ownership	Data portability, export formats, deletion on termination	You own all data; vendor provides full export at no cost
Termination rights	Convenience termination, cause termination, transition period	90-day notice; 6-12 month transition assistance
Liability cap	Vendor liability for data breach, downtime, errors	Minimum 2x annual fees; carve-outs for IP infringement, data breach
Implementation guarantees	Fixed price or cap, milestone payments, warranty period	Milestone-based payments; 90-day warranty post go-live
IP rights	Ownership of customizations, configurations, integrations	You own all custom code; vendor retains core product IP
Escrow	Source code escrow for vendor insolvency	Required for critical systems; annual verification
Compliance	Audit rights, certification maintenance, breach notification	Annual SOC 2; 24-hour breach notification
Renewal terms	Auto-renewal notice period, renewal pricing	90-day opt-out; renewal at current published rates or negotiated cap

12. Decision Presentation Template

Steering Committee Decision Pack Structure:

Section	Content	Slides
Executive Summary	Recommendation, key rationale, investment required	1
Process Overview	Methodology, timeline, participants, vendors evaluated	1
Requirements Summary	Key requirements, prioritization, stakeholder alignment	1
Vendor Comparison	Scoring summary, strengths/weaknesses, key differentiators	2-3
TCO Comparison	5-year cost comparison, NPV, cost per user	1
Risk Assessment	Implementation risk by vendor, mitigation plans	1
Reference Insights	Key findings from reference checks	1
Recommendation	Recommended vendor with top 3 reasons, second choice	1
Implementation Plan	High-level timeline, resource needs, key milestones	1
Decision Required	Specific ask, approval needed, next steps	1

Output Template

# System Selection: [System Type] for [Organization]

**Prepared for**: [Steering Committee] | **Date**: [Date] | **Decision Required By**: [Date]

## Executive Summary

**Recommendation**: [Vendor Name]
**Confidence Level**: [High / Medium / Low]

[3-5 sentence summary: why this system is being selected, the recommended vendor,
key differentiators, and total investment required.]

### Selection at a Glance
| Criterion | Vendor A | Vendor B | Vendor C |
|---|---|---|---|
| Weighted Score | X.X/5.0 | X.X/5.0 | X.X/5.0 |
| 5-Year TCO | $[X]M | $[X]M | $[X]M |
| Implementation Risk | Low/Med/High | Low/Med/High | Low/Med/High |
| Go-Live Timeline | X months | X months | X months |

## 1. Requirements Summary
**Total Requirements**: [X] (P1: [X] | P2: [X] | P3: [X] | P4: [X])
[Key requirements highlights]

## 2. Build vs. Buy Decision
**Decision**: [Build / Buy / Configure]
[Scoring summary and rationale]

## 3. Market Landscape
[Vendor universe, long list, and short list progression]

## 4. Detailed Vendor Scoring

### Scoring Summary
| Category (Weight) | Vendor A | Vendor B | Vendor C |
|---|---|---|---|
| Functional Fit (30%) | X.X | X.X | X.X |
| Technical Fit (20%) | X.X | X.X | X.X |
| Vendor Viability (15%) | X.X | X.X | X.X |
| Cost / TCO (15%) | X.X | X.X | X.X |
| Implementation Risk (10%) | X.X | X.X | X.X |
| Innovation (10%) | X.X | X.X | X.X |
| **Weighted Total** | **X.X** | **X.X** | **X.X** |

### Vendor Profiles
**[Vendor A]**: [2-3 sentence summary of strengths and weaknesses]
**[Vendor B]**: [2-3 sentence summary of strengths and weaknesses]
**[Vendor C]**: [2-3 sentence summary of strengths and weaknesses]

## 5. TCO Comparison (5-Year)
| Cost Category | Vendor A | Vendor B | Vendor C |
|---|---|---|---|
| Software | $[X] | $[X] | $[X] |
| Implementation | $[X] | $[X] | $[X] |
| Ongoing (annual) | $[X] | $[X] | $[X] |
| Internal costs | $[X] | $[X] | $[X] |
| **5-Year Total** | **$[X]** | **$[X]** | **$[X]** |
| NPV @ [X]% | $[X] | $[X] | $[X] |
| Cost/user/month | $[X] | $[X] | $[X] |

## 6. Reference Check Summary
| Vendor | NPS (avg) | On-Time Implementation | Top Concern |
|---|---|---|---|
| [Vendor A] | [X]/10 | [X]% | [Concern] |

## 7. Implementation Risk Assessment
[Risk comparison by vendor with mitigation strategies]

## 8. Recommendation and Rationale

**Recommended**: [Vendor Name]
**Second Choice**: [Vendor Name] (if primary negotiation fails)

**Top 3 Reasons:**
1. [Reason with supporting evidence]
2. [Reason with supporting evidence]
3. [Reason with supporting evidence]

**Key Risks of Recommended Vendor:**
1. [Risk with mitigation plan]

## 9. Implementation Plan (High Level)
| Phase | Timeline | Key Activities | Investment |
|---|---|---|---|
| Contract & Kickoff | Weeks 1-4 | Contract signing, project setup, team mobilization | $[X] |
| Design & Configure | Weeks 5-16 | Requirements validation, configuration, integrations | $[X] |
| Test & Train | Weeks 17-24 | UAT, performance testing, training delivery | $[X] |
| Go-Live & Stabilize | Weeks 25-30 | Cutover, hypercare, issue resolution | $[X] |

## 10. Decision Required
- [ ] Approve recommended vendor: [Vendor Name]
- [ ] Approve budget: $[X]M (implementation) + $[X]M/year (ongoing)
- [ ] Authorize contract negotiation to proceed
- [ ] Confirm go-live target: [Date]

Quality Checks

Requirements gathered across all four categories (functional, technical, integration, non-functional).
Build vs. buy analysis completed before vendor evaluation.
All vendors scored using identical weighted criteria with consistent rubric.
Category weights validated with stakeholders before scoring begins.
At least 3 vendors on final short list for meaningful comparison.
Demo evaluation uses scripted scenarios consistent across all vendors.
Reference checks completed with at least 3 references per finalist.
5-year TCO model includes all cost categories with consistent assumptions.
NPV calculation applied for multi-year cost comparison.
Implementation risk assessed per vendor with mitigation strategies.
Contract negotiation checklist covers all critical terms.
Decision presentation structured for steering committee approval.
Scoring methodology is transparent and defensible.
All estimates carry confidence levels (High/Medium/Low).

System Selection

File contents

System Selection

Required Inputs

Execution Steps

1. Requirements Gathering

2. Build vs. Buy vs. Configure Decision

3. Market Landscape Analysis

4. Long List to Short List Reduction

5. RFP/RFI Template Structure

6. Weighted Scoring Framework

7. Vendor Demo Evaluation Scorecard

8. Reference Check Methodology

9. Total Cost of Ownership (TCO) Model

10. Implementation Risk Assessment

11. Contract Negotiation Key Terms

12. Decision Presentation Template

Output Template

Quality Checks

Frequently asked questions

System Selection

File contents

System Selection

Required Inputs

Execution Steps

1. Requirements Gathering

2. Build vs. Buy vs. Configure Decision

3. Market Landscape Analysis

4. Long List to Short List Reduction

5. RFP/RFI Template Structure

6. Weighted Scoring Framework

7. Vendor Demo Evaluation Scorecard

8. Reference Check Methodology

9. Total Cost of Ownership (TCO) Model

10. Implementation Risk Assessment

11. Contract Negotiation Key Terms

12. Decision Presentation Template

Output Template

Quality Checks

Related skills

Frequently asked questions

How do I install the System Selection skill?

What does the System Selection skill do?

Is System Selection safe to use?

Which AI agents work with System Selection?

Is System Selection free to use?

Who published System Selection?