Tooling Decisions
AI development tools are evolving rapidly, with new entrants, features, and pricing models emerging monthly. As a development manager, you need a structured approach to evaluating, piloting, adopting, and sunsetting AI tools that balances innovation with stability. This section provides that framework, aligned with Pillar 3: Governance & Oversight and the technology strategy set by your CTO per Technology Strategy & Tool Selection.
Evaluation Rubric
Use this rubric to assess any AI development tool before piloting it with your team. Score each criterion from 1 (poor) to 5 (excellent).
| Criterion | Weight | What to Evaluate | Scoring Guide |
|---|---|---|---|
| Code Quality | 25% | Accuracy, correctness, and adherence to patterns | 5: Consistently high quality; 3: Acceptable with review; 1: Frequently incorrect |
| Security Posture | 20% | Data handling, privacy controls, vulnerability introduction rate | 5: Enterprise-grade controls; 3: Adequate with configuration; 1: Unacceptable data practices |
| Developer Experience | 15% | IDE integration, latency, context understanding, workflow fit | 5: Seamless integration; 3: Usable with workarounds; 1: Disruptive to workflow |
| Organizational Fit | 15% | Compatibility with tech stack, language support, policy compliance | 5: Full stack coverage; 3: Covers primary languages; 1: Poor fit for our needs |
| Cost Effectiveness | 10% | Per-seat pricing, usage-based costs, total cost vs. value delivered | 5: Clear ROI; 3: Reasonable cost; 1: Expensive relative to value |
| Vendor Stability | 10% | Company viability, product roadmap, support quality, SLAs | 5: Established vendor; 3: Growing but credible; 1: Risky or unstable |
| Configurability | 5% | Ability to customize behavior, enforce policies, integrate with CI/CD | 5: Highly configurable; 3: Basic configuration; 1: No customization |
Minimum threshold for pilot: Weighted score of 3.0 or higher with no criterion scoring 1 in Security Posture.
Evaluation Process
- Identify candidate. Tool surfaces through team request, CTO recommendation, or market research.
- Initial screening. Review against PRD-STD-001 approved tool criteria and security requirements. Disqualify tools that cannot meet security baselines.
- Structured evaluation. Two developers (one senior, one mid-level) evaluate the tool for 5 business days using prepared exercises that cover code generation, debugging, refactoring, and test writing.
- Score and compare. Apply the rubric above. Compare to current tools.
- Pilot decision. If the score exceeds threshold and offers meaningful improvement over current tools, proceed to pilot.
Pilot Criteria
A pilot is a time-boxed, controlled evaluation with a subset of the team working on real (non-critical) projects.
Pilot Design
| Parameter | Recommendation |
|---|---|
| Duration | 4-6 weeks (at least 2 full sprints) |
| Team size | 3-5 developers representing different skill levels |
| Project scope | Non-critical project or well-understood feature area |
| Success criteria | Define before pilot begins (see below) |
| Data collection | Track all metrics from Metrics That Matter plus tool-specific measures |
| Comparison method | Compare pilot team metrics against their own recent baselines, not against non-pilot team members |
Pilot Success Criteria
Define these before the pilot begins and share them with the pilot team:
- Code quality scores are at or above team baseline
- No security incidents or data leakage events
- Developer satisfaction score > 3.5/5
- Measurable productivity improvement in at least one metric
- No significant workflow disruption after week 2
- Licensing and infrastructure costs are within budget projections
Pilot Failure Criteria (Stop Conditions)
- Security incident or data leakage of any severity
- Tool unavailability exceeding 4 hours during business hours
- Consistent developer dissatisfaction (score < 2.5/5 after 2 weeks)
- Code quality degradation exceeding 20% above baseline defect rate
- Vendor changes terms of service or data handling practices during pilot
Vendor Management
Ongoing Vendor Assessment
For adopted tools, maintain an ongoing vendor relationship:
| Activity | Frequency | Owner |
|---|---|---|
| Review vendor security posture and certifications | Quarterly | Security team + manager |
| Assess product roadmap alignment | Quarterly | Manager + CTO |
| Review usage metrics and license utilization | Monthly | Manager |
| Monitor vendor stability (funding, leadership, market position) | Quarterly | CTO |
| Renegotiate pricing based on usage patterns | Annually | Procurement + manager |
| Review data handling agreement and privacy terms | Annually or on change | Legal + security |
Vendor Risk Indicators
Watch for these signs that a vendor relationship needs attention:
- Significant price increases without corresponding value increases
- Degradation in tool quality or reliability over time
- Changes to data handling or privacy policies
- Key personnel departures or signs of financial instability
- Failure to address reported bugs or feature requests
- Acquisition by a company with conflicting interests
See Technical Risk Management for deeper analysis of vendor lock-in risks.
Multi-Tool Strategy
Most teams benefit from more than one AI tool. Design your tool portfolio deliberately:
| Tool Category | Purpose | Example Selection Criteria |
|---|---|---|
| Primary coding assistant | Day-to-day code generation, completion, and editing | Best IDE integration, fastest for your primary language |
| Conversational AI | Architecture design, debugging complex issues, documentation | Best at long-context reasoning and explanation |
| Specialized tools | Security analysis, test generation, code review assistance | Best in specific domain |
Limit your team to 2-3 AI tools maximum. Each additional tool increases cognitive load, training requirements, and vendor management overhead. Choose depth over breadth.
Sunset Procedures
When a tool needs to be replaced or removed, follow a structured sunset process:
Phase 1: Decision (2 weeks)
- Document the reason for sunsetting (cost, quality, replacement, policy change)
- Identify all dependencies on the tool (prompt libraries, workflows, integrations)
- Communicate the decision with the rationale to the full team
- Set the sunset timeline
Phase 2: Migration (2-4 weeks)
- Migrate reusable assets (prompt templates, configurations) to the replacement tool
- Retrain team on the replacement tool if applicable
- Run both tools in parallel to ensure the replacement meets needs
- Update all documentation and workflows
Phase 3: Decommission (1 week)
- Revoke licenses for the sunset tool
- Remove IDE integrations and configurations
- Archive any tool-specific data per retention policies
- Update PRD-STD-001 approved tool list
- Confirm with each team member that the transition is complete
Phase 4: Review (2 weeks post-sunset)
- Collect team feedback on the transition
- Verify that metrics are stable or improved
- Document lessons learned for future tool transitions
For the organizational perspective on build-vs-buy and tool strategy, see Build vs. Buy and Technology Strategy in the CTO Guide.