AI projects don’t fail because models are weak. They fail when implementation ignores the business: data realities, compliance, workflow fit, security, user trust, and total cost. That’s why many CIOs lean on outside partners to accelerate delivery—especially where data quality and skills are bottlenecks, as highlighted by a recent CIO report on AI implementation strategies. The right partner delivers outcomes and leaves your team stronger. The wrong one creates rework, risk, and dependency.
Below is a direct playbook: the pains to watch for, how to test a partner’s real capabilities, and concrete moves tied to recognized standards so you can verify, not just trust.
Pain 1: “They know models, not my industry”
- Risk: Compliance problems, rework, failed go-lives.
- How to test:
- Ask for references and case studies in your vertical with similar regulatory and data sensitivity.
- Review artifacts from past work: data lineage, audit logs, model documentation, compliance mappings.
- Check fluency with NIST AI Risk Management Framework (AI RMF 1.0), ISO/IEC 23894 (AI risk management), and ISO/IEC 42001 (AI management systems). They should show how these shaped design choices.
- Moves:
- Make “compliance by design” contractual: traceability, accountability, and documentation aligned to NIST AI RMF functions (Govern/Map/Measure/Manage).
- Enforce data protection principles such as GDPR data minimization and purpose limitation where applicable.
- Require model cards, data sheets, decision logs, and change control.
Pain 2: “Great demo; broken workflow”
- Risk: Disruption, low adoption, shadow IT.
- How to test:
- Require mapping of “as-is” workflows, systems, and data pipelines before solutioning; look for identity and access alignment, secrets management, and observability.
- Assess MLOps maturity: dataset/model versioning, CI/CD for ML, drift monitoring, rollback strategies, and operational SLOs (latency/uptime).
- Demand phased deployment: staged rollouts, feature flags, and human-in-the-loop checkpoints.
- Moves:
- Make integration the first deliverable: architecture, data flows, and compatibility with your cloud, Kubernetes, IAM, logging, and data platforms.
- Tie payments to a production-ready slice that proves value without disrupting critical processes.
Pain 3: “AI is being inflicted on people”
- Risk: Quiet resistance, low adoption, reputational harm.
- How to test:
- Request a role-based enablement plan for engineers, product, risk/compliance, and front-line users; look for workshops, pairing, runbooks.
- Review human-in-the-loop design and escalation paths; align to human-centered principles like the OECD AI Principles.
- Ask for examples of how they built user trust with explainability, calibrated confidence, and contestability.
- Moves:
- Require a change plan with communications, training milestones, and adoption metrics (active users, override rates, satisfaction).
- Define what your team can operate independently at 90 days and 12 months; incentivize knowledge transfer.
Pain 4: “Security and privacy are an afterthought”
- Risk: Data leakage, prompt injection, model poisoning, compliance exposure.
- How to test:
- Map controls to the OWASP Top 10 for Large Language Model Applications (prompt injection, data leakage, insecure output handling, etc.).
- Validate secure SDLC practices mapped to NIST SP 800-218 (SSDF): threat modeling, code review, dependency hygiene, release controls.
- Inspect privacy by design: data minimization, encryption, retention/deletion, redaction, and mechanisms to honor data subject rights (GDPR).
- Review third-party risk: SOC 2 Type II or equivalent, subprocessor transparency, and incident response SLAs.
- Moves:
- Require a documented threat model and mitigations before build; include red-team testing pre–go-live.
- Enforce least-privilege IAM, environment segregation, key rotation, and secrets management integration.
- Log prompts/outputs with privacy safeguards; monitor for anomalies, drift, and abuse.
Pain 5: “We can’t prove business value”
- Risk: Perpetual pilots, lost sponsorship, sunk cost.
- How to test:
- Ask for a value hypothesis with quantifiable KPIs that tie to your goals: cycle time, cost-to-serve, revenue lift, quality, or risk reduction.
- Establish baselines and controls where feasible; set SLOs for latency, uptime, and resilience.
- Track trust and quality metrics: adoption, override/appeal rates, incident counts, error propagation.
- Moves:
- Pilot a bounded use case with a 60–90 day measurement window; publish the dashboard—good or bad.
- Tie milestone payments to business outcomes and operational readiness, not just code delivery.
Pain 6: “We bought a black box”
- Risk: Vendor lock-in, rising costs, stalled roadmap.
- How to test:
- Demand documentation: architecture, model cards, data sheets, evaluation protocols, operational runbooks.
- Prefer deployment in your environment; avoid bespoke stacks that bypass your standards.
- Clarify IP, data rights, and model portability upfront.
- Moves:
- Define exit criteria and knowledge transfer deliverables; reserve audit rights for artifacts and pipelines.
- Require portability: containerized components, infrastructure as code, and the ability to swap models and providers.
Pain 7: “TCO keeps creeping”
- Risk: Budget overruns, executive fatigue.
- How to test:
- Request a 12–24 month TCO model covering compute, storage, observability, evaluation/red-teaming, retraining, and licenses.
- Review capacity planning, autoscaling, cost controls, and rate limiting.
- Ask how they handle periodic re-evaluation as data, models, and regulations change.
- Moves:
- Set cost SLOs and alerts; instrument usage and unit economics by user/team.
- Fund evaluation and monitoring as first-class budget items.
How to structure the engagement
1. Start with discovery and design
- Deliverables: current-state maps, risk register, threat model, value hypothesis, architecture and data flows, governance plan (privacy and audit artifacts), and an evaluation/red-team test plan.
- Gate: executive review that validates feasibility, risks, and success metrics before build.
2. Pilot a bounded, high-leverage use case
- Criteria: meaningful value, limited blast radius, clear baseline.
- Include human review and logging from day one.
- Test robustness, bias, and prompt-injection defenses before end-user exposure.
3. Harden and scale deliberately
- Instrument everything: prompts, outputs, versions, features, latency, costs.
- Establish SLOs and dashboards for business and engineering.
- Schedule periodic re-evaluation for model/data drift, fairness, and security posture.
4. Govern for auditability
- Maintain artifacts: model cards, data sheets, evaluation reports, access logs, policy mappings.
- Align processes and documentation to NIST AI RMF and ISO/IEC 23894 for predictable audits.
5. Exit on your terms
- Tie final payments to operational readiness: trained staff, runbooks, code and infrastructure handover, and a successful incident response drill.
- Retain rights to metrics, artifacts, and data regardless of model provider.
A fast due-diligence checklist
- Industry and compliance: vertical references; governance artifacts aligned to NIST AI RMF; fluency with ISO/IEC 23894 and ISO/IEC 42001; GDPR-aligned privacy by design where relevant.
- Security and privacy: controls mapped to OWASP LLM Top 10; secure SDLC mapped to NIST SP 800-218; encryption, retention/deletion, redaction; SOC 2 (or equivalent), subprocessor transparency, incident SLAs.
- MLOps and integration: CI/CD for ML; dataset/model versioning; canary/staged rollouts; rollback plans; drift/performance monitoring; integration with your IAM, secrets, observability, and data platforms.
- Responsible AI and oversight: bias/fairness evaluation; model documentation; human-in-the-loop checkpoints and escalation paths.
- Enablement and change: role-based training; co-building; operational playbooks; knowledge transfer milestones; adoption targets.
- Outcomes and economics: KPIs tied to business value; trust and quality metrics; 12–24 month TCO including evaluation and monitoring.
Red flags
- Demo-first, discovery-later.
- Vague “bank-grade security” claims without mappings to OWASP/NIST/ISO.
- No model/data documentation.
- Proprietary black boxes that can’t run in your environment.
- Dismissing domain constraints as “policy we can work around.”
What good looks like. A credible partner starts with your workflows, not their demo; designs to recognized frameworks (NIST AI RMF, ISO/IEC 23894/42001, OWASP LLM Top 10, GDPR); builds for observability and governance from day one; treats privacy, safety, and ethics as requirements; shares risk on outcomes; and leaves your team capable of operating and improving the system without ongoing vendor dependence.
Bottom Line: speed and safety aren’t opposites. The fastest path to durable AI value is a verifiable path—one grounded in integration with your reality, measurable outcomes, and responsible engineering. Anchor partner selection to evidence and artifacts, not promises. That’s how you avoid costly missteps and build AI capabilities that compound.
References
- CIO. “What to look for in an AI implementation partner.” https://www.cio.com/article/4089704/what-to-look-for-in-an-ai-implementation-partner.html
- NIST. AI Risk Management Framework (AI RMF 1.0), 2023. https://www.nist.gov/itl/ai-risk-management-framework
- ISO/IEC 23894:2023. https://www.iso.org/standard/77304.html
- ISO/IEC 42001:2023. https://www.iso.org/standard/81230.html
- OWASP Top 10 for Large Language Model Applications. https://owasp.org/www-project-top-10-for-large-language-model-applications/
- NIST SP 800-218 (SSDF). https://csrc.nist.gov/publications/detail/sp/800-218/final
- GDPR Article 5. https://eur-lex.europa.eu/eli/reg/2016/679/oj
- OECD AI Principles. https://oecd.ai/en/ai-principles

