AI Strategy
Nov 20, 2025
The Board's Blind Spot: Why the AI Oversight Questions Now Demand Measurement

Joelle Kaufman
From Larridin
The conversation around Artificial Intelligence has moved decisively past "if" and into "how." For corporate boards, AI is no longer a technology initiative for the CIO to manage; it is a fiduciary responsibility.
The urgency of this shift is being called out at the highest levels. A recent Forbes piece highlighted the Ten AI Questions Every Board Should Be Asking—a necessary focus that underscores a critical governance gap.
What most directors don't realize is that asking the right questions is only the first step. Without measurement, those ten questions are unanswerable.
Enterprises are flying blind through history's most significant business transformation. They are spending billions—projected to reach $644 billion in 2025—yet they lack the basic infrastructure to measure what's working. That's the symptom of zero measurement.
Inspired by this necessary board focus, I’ve synthesized the most critical oversight questions and paired them with the Measurement Imperative that Larridin is solving for every executive.
10 Board Questions That Demand Independent Measurement
A director’s duty is to oversee strategy and manage enterprise risk. Here is where those duties intersect with AI and why Larridin Scout provides the only objective answer:
I. Strategy and Value Creation (Turning Spend into Impact)
1. Strategic Alignment & Value: How is our AI strategy integrated into the core business strategy, and what are the specific KPIs for measuring AI’s impact and ROI?
The Measurement Imperative: Most companies can't answer this. You need Productivity Correlation. Larridin Scout shows which AI applications drive measurable productivity gains and provides evidence-based insights on AI ROI by department. This replaces guesswork with evidence.
2. Organizational Proficiency & Competitive Positioning: What is our current organizational AI maturity, and how does our proficiency compare to key competitors?
The Measurement Imperative: This requires Proficiency Benchmarking. Larridin quantifies organizational AI maturity 16and identifies high-performing vs. struggling teams. Without independent benchmarks, you cannot know if you’re winning or losing.
II. Risk, Governance, and Liability (Closing the Visibility Gap)
3. The Shadow AI Reality: What is the complete inventory of all AI tools and agents actually in use, including unapproved applications and personal accounts?
The Measurement Imperative: Without detection, you cannot govern what you cannot see. Our data shows that two-thirds of employees use personal accounts for AI tools. Scout’s AI Discovery & Detection provides real-time visibility into sanctioned tools and shadow AI.
4. D&O Liability and Coverage: What is our specific D&O insurance exposure related to AI, and can we provide carriers with the audit trail and governance evidence they require?
The Measurement Imperative: Insurers will demand a complete, up-to-date AI inventory and monitoring of its usage. Larridin Scout creates a continuous audit trail for insurance documentation, which is crucial for fighting claims and policy rescission.
5. Regulatory and Compliance Posture: How are we ensuring our AI usage is compliant with emerging regulations when we lack a complete understanding of where AI is embedded across the organization?
The Measurement Imperative: Governance failures—like inadequate board oversight or insufficient monitoring—create D&O liability. Larridin provides the objective measurement required for data-driven AI governance. You get the real-time usage intelligence needed to block, warn, or permit detected AI applications.
III. People and Adoption (Optimizing the Human+AI Workforce)
6. Talent and Upskilling: Which teams are becoming AI-proficient, and where are the specific skill gaps that require targeted training and enablement?
The Measurement Imperative: Proficiency scoring quantifies organizational AI maturity. It’s how you systematically develop capabilities. Larridin’s Proficiency Benchmarking provides skill gap analysis, identifying enablement opportunities based on what’s actually happening across the Human+AI workforce.
7. Adoption Momentum: Are our AI investments actually being adopted, and is the usage scaling quickly enough to avoid falling behind AI-native competitors?
The Measurement Imperative: We are in a race; 85% of leaders believe they have less than 18 months before falling behind permanently. Larridin provides deep analytics on adoption patterns, trend analysis, and usage evolution. You move from running AI experiments to leading a systematic transformation.
8. Vendor and Investment Optimization: Which AI investments are driving measurable productivity gains, and where should we cut spending versus doubling down?
The Measurement Imperative: 72% of AI investments are destroying value through waste. You can't manage what you don't measure. Larridin provides evidence-based insights to optimize investments and leverage objective usage intelligence for strategic vendor negotiations.
The Window is Closing. Act Now.
Every transformative technology—from TV (Nielsen) to the Internet (comScore)—required an independent measurement standard to unlock its value. AI is the biggest transformation yet.
The 18-month window is open right now. Organizations making blind AI investments are building a strategic disadvantage.
You cannot afford to navigate blind. Larridin Scout is the independent measurement platform for enterprise AI transformation that provides the intelligence that turns billions in AI investment into a measurable competitive advantage.
Answer the Board’s Questions. Deploy Measurement.
Ready to stop making blind bets?
Begin Measurement Today: Deploy Scout in 30 minutes and discover your complete AI landscape—with independent measurement of adoption, proficiency, and productivity impact.
Click here to see how Larridin Scout gives you the objective, board-ready intelligence you need.




