10 Questions Every Leader Should Be Asking Now

This checklist is designed for legal, compliance, and executive leaders who are guiding AI adoption, risk management, and digital transformation. Use it to uncover hidden risks, clarify responsibilities, and strengthen your organization’s approach to AI governance, data strategy, and ethical innovation.

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1. Where is AI already in use across your organization?

  • We have identified both formal and informal AI tools across departments.
  • We track emerging tools introduced by vendors, staff, or internal teams.

2. Is accountability for each AI use case assigned and documented?

  • Each AI system has a named owner who is responsible for its use and outcomes.
  • Accountability is written into policy—not assumed or distributed informally.

3. Do we have a framework to explain how AI decisions are made?

  • Key decisions made by or with AI are traceable and explainable.
  • Higher-risk systems require more transparency and human oversight.

4. Is our data governance strong enough to support trustworthy AI?

  • Our training and operational data sources are clearly defined and regularly reviewed.
  • We evaluate data for bias, quality, access, and security controls.

5. Have we established ethical guardrails for high-risk AI use cases?

  • We have identified high-impact areas (e.g., HR, finance, healthcare, eligibility).
  • Guardrails and escalation procedures are clearly documented.

6. Are legal, risk, and compliance leaders included early in AI projects?

  • Legal and compliance teams are involved at the planning stage.
  • AI policy is driven by strategy—not retrofitted to innovation.

7. Are we monitoring AI systems with clear KPIs and red flags?

  • Performance, fairness, and error rates are tracked over time.
  • We have defined thresholds that trigger review or intervention.

8. Are we actively tracking AI regulations and policy developments?

  • We monitor local, national, and global regulations affecting our use of AI.
  • Our internal policies are updated regularly to stay aligned.

9. Can we show decision ownership and traceability to stakeholders?

  • We maintain a record of decisions made with or by AI systems.
  • We can demonstrate how those decisions align with our goals and values.

10. What is our process for human oversight of AI systems?

  • Human review is built into key workflows and outcomes.
  • Teams are trained on when and how to intervene.

Bonus Question

Are we building trust through transparency - or relying on blind faith in tech?

  • We communicate clearly with staff, clients, and stakeholders about AI use.
  • Our leaders can speak confidently and ethically about how AI supports our mission.

Let’s Take the Next Step

If you are guiding your organization through AI adoption, risk management, or digital transformation—this checklist is a practical starting point. Use it to uncover hidden risks, clarify responsibilities, and align your leadership approach with your mission, values, and long-term goals.

When you are ready to move from checklist to action, schedule a consult or strategy session at UpwardAction.com.

About TC Cooper

Tasha “TC” Cooper is President of UpwardAction® Advisory, where she partners with senior leaders to lead AI adoption and integration, identify and mitigate emerging risks, and manage organizational change with clarity and confidence. Her work centers on building human-first, values-driven, and efficient organizations that use digital tools—including AI and automation—not just to scale, but to lead with purpose and integrity.

With over two decades of experience in law, strategy, and data governance—including serving as a senior federal agency official for privacy and artificial intelligence—TC brings a practical, thoughtful lens to digital transformation. She has completed the coursework for the Certified AI Governance Professional (AIGP) credential through the International Association of Privacy Professionals and is an executive coach in ICF certification training.

At UpwardAction®, TC works with legal, compliance, operations, and innovation teams to:
– Develop responsible AI strategies rooted in business goals and organizational values
– Strengthen data governance and privacy frameworks to support trust and performance
– Clarify ownership, accountability, and risk across AI and automation initiatives
– Equip leaders to make strategic decisions with clarity in complex, evolving environments

Whether you are building your first AI strategy or scaling innovation across teams, UpwardAction® helps you use data and technology to grow—responsibly, effectively, and with confidence.

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