Intelligent Leadership® AI Fitness Assessment
Is Your Organization Positioned to Realize the Full Value of AI?
Assess whether your leadership, strategy, culture, people, execution, and governance are aligned to turn AI investment into business results, and identify the critical gaps that could be limiting the return.
Why Assess AI Fitness?
Many organizations measure AI activity: tools deployed, pilots launched, employees trained, or use cases identified.
Those indicators do not reveal whether the enterprise can turn that activity into results, or where it is likely to stall.
The Intelligent Leadership® AI Fitness Assessment examines the human and organizational conditions that determine whether AI ambition can become measurable enterprise value.
It gives the CEO, the executive team, and the board an objective view of strengths, vulnerabilities, misalignment, and the leadership priorities requiring attention.
What We Assess
- Leadership
- Strategy
- Culture
- People
- Execution
- Governance
Leadership
- Executive courage, agility, judgment, and accountability
- Willingness to challenge assumptions and role-model change
- Capacity to lead through uncertainty without creating unnecessary fear
- Alignment between stated priorities and visible leadership behavior
Strategy
- Clarity of AI ambition and connection to enterprise strategy
- Prioritization of value-creating opportunities
- Shared understanding of risk, opportunity, and tradeoffs
- Alignment across business, technology, people, risk, and operations
Culture
- Learning, experimentation, speed, candor, and intelligent risk-taking
- Cross-functional collaboration and the strength of organizational silos
- Psychological safety and how responsible failure is treated
- Alignment between the current culture and the culture required for AI
People
- Workforce trust, clarity, and confidence
- Capability and reskilling priorities
- Leadership communication and change readiness
- Talent implications, role evolution, and human + AI performance
Execution
- Operational ownership and decision flow
- Accountability, priorities, measures, and review cadence
- Ability to convert pilots into scaled enterprise adoption
- Discipline to intervene, learn, and adapt when results fall short
Governance
- Responsible AI principles that guide real decisions, not only policy documents
- Risk, compliance, and control practices matched to each use case
- Decision rights and meaningful human oversight for AI-shaped decisions
- Transparency to the board, and a real way for people to raise concerns and trigger correction
How the Assessment Works
The scope is tailored to the organization and may include:
- 1
Executive discovery
Clarify strategy, transformation ambition, business context, and critical concerns.
- 2
Leadership interviews
Surface where the senior team agrees and where it differs, and the assumptions and risks behind each view.
- 3
The AI Fitness Index™
A structured survey of the organization, from senior leaders to the front line, read alongside interviews and organizational evidence.
- 4
Fitness synthesis
Identify strengths, vulnerabilities, gaps, and transformation priorities across the six dimensions, including where business units and leadership tiers differ.
- 5
Executive readout
Present the findings to the executive team and lead the working session that turns them into agreed priorities.
The Intelligent Leadership® AI Fitness Index™
At the center of the diagnosis: a structured measure of the conditions that decide whether AI creates value, taken across the organization, not only at the top.
Who takes part
Board
A separate governance protocol, never averaged with employee results.
Senior leaders and C-suite
The full 72 statements, with interviews and documentary evidence.
Managers
The core survey plus a leader module: whether AI direction becomes team practice.
All employees
The enterprise core: how the change is actually experienced.
How true is this of our organization today?
All 72 statements put the same question, each about an observable condition rather than an opinion about AI. Answers run from Not at all true to Completely true, and Not enough visibility means no one has to guess.
What the executive team sees
Eighteen facets roll up into six dimensions, each placed in one of four bands.
- LeadershipEstablished fitness across the enterprise
- StrategyEstablished fitness across the enterprise
- CultureDeveloping fitness across the enterprise
- PeopleDeveloping fitness across the enterprise
- ExecutionEstablished fitness across the enterprise; one tier at Material vulnerability
- GovernanceMaterial vulnerability across the enterprise
- Material vulnerability
- Developing fitness
- Established fitness
- Transformation strength
EnterpriseOne business unit or tier
A high enterprise average can conceal the weak point where implementation will fail. The profile shows where business units and leadership tiers differ.
Illustrative. Bands are working ranges for the conversation, not norms or benchmarks.
Built to diagnose the organization, not to judge individuals.
Results are reported for groups, never for a single person, and are never used to select, promote, or rank anyone. Any coaching that follows stays confidential and separate from enterprise reporting.
Scores help locate the gaps. The discussion behind them explains what to change.
What Leaders Receive
AI Fitness Profile
Across the six dimensions, showing where business units and leadership tiers differ.
Executive Alignment Findings
Highlighting agreement, tension, and unresolved questions.
Leadership & Culture Risk Map
Identifying conditions that may accelerate or obstruct transformation.
Priority Recommendations
Defining what should happen now, next, and later.
Executive Readout & Working Session
Where the executive team turns the findings into decisions.
Recommended Transformation Roadmap
When the findings call for work beyond the assessment.
The SILA™ Leader Assessment
The AI Fitness Index™ reads the organization. SILA™, the Synthetic Intelligence Leadership Assessment, reads the leaders: whether each senior leader's judgment holds up when the input in front of them is AI-generated.
A leader can be strong on every conventional leadership measure and still make poor calls once AI enters the room: mistaking a fluent answer for a correct one, or backing AI builds and uses that have not been stress-tested. AI has also removed the time and friction that used to catch a weak call before it compounded. The barrier to AI value at scale is often the leader's own judgment, not the technology.
SILA is used with the senior leaders carrying the transformation, as part of the C-Level AI Transformation Retreat and the AI Transformation Accelerator.
Two instruments, two lenses
| The AI Fitness Index™ | SILA™ | |
|---|---|---|
| Reads | The organization | Each senior leader |
| Across | Six dimensions of AI fitness | Six areas of judgment |
| Asks | How true is this of our organization today? | What would you actually do? |
| Reported | For groups, never for a single person | To the leader, for development only |
| Used in | The AI Fitness Assessment | The Retreat and the Accelerator |
The two meet on judgment. The Index asks the organization whether its leaders show judgment and meaningful human oversight, in its Leadership and Governance dimensions. SILA tests that judgment in each senior leader, one decision at a time. The six dimensions
A decision, not a self‑rating
SILA does not ask leaders to rate themselves. It puts a realistic leadership decision in front of them and asks what they would do, the method known as situational judgment. That matters on AI: the leaders who rate themselves highest are often the ones who question model output least.
12situations, two for each area
Situations are built from a documented corpus of 65 real AI leadership incidents, drawn from regulatory findings, court filings, accident investigations, executive interviews, and investigative journalism.
What the leader sees
Each area is scored out of six and placed in one of four bands, so the report shows where a leader's judgment is already sound and which habits to work on next.
L2Aware
SILA-AI Leadership Index, five levels
- Avoiding
- Aware
- Active
- Capable
- Leading
AI Mindset. What happens inside the leader.
Disruption Response
Treating AI as part of how the function works, and leading the redesign.
Practicing · 4/6Disruption Response: 4 of 6, PracticingIndependence of Thought
Noticing where a model has shaped their view.
Developing · 1/6Independence of Thought: 1 of 6, DevelopingJudgment Quality
Checking AI output against its sources before it informs a decision.
Emerging · 3/6Judgment Quality: 3 of 6, EmergingDevelopment edge
For any conclusion that matters, verify two of the figures behind it and ask the team for the strongest counter-case before you present.
AI Leadership. What the leader does about it.
Responsible Use
Owning a governance concern, not only flagging it.
Emerging · 2/6Responsible Use: 2 of 6, EmergingOversight Judgment
Matching human review to the risk and the consequence.
Emerging · 2/6Oversight Judgment: 2 of 6, EmergingTeam Enablement
Building AI capability around real tasks, person by person.
Emerging · 2/6Team Enablement: 2 of 6, Emerging
- Developing 0–1
- Emerging 2–3
- Practicing 4–5
- Leading 6
From a sample SILA report: one leader's result, shown to illustrate the report format.
For development only.
SILA results inform coaching and development. They are never used for selection, promotion, or performance decisions.
SILA is at an early version, with two situations per area. That is enough to show a direction of development and to open a coaching conversation, not to draw a fixed conclusion about a leader. The result is a starting point, not a verdict.
The MLEI® and STLI-360® show who a leader is and how they lead. SILA™ adds what neither was built to test: whether that judgment holds when the input in front of them is AI-generated.
SILA™ was developed by Ryan Flanagan, Global Managing Partner, AI & Enterprise Transformation.
What the Assessment Is, and Is Not
It is
- A diagnostic of leadership, strategy, culture, people, execution, and governance across the enterprise
- A fact-based starting point for executive decisions
- A way to reduce transformation risk before scaling activity
- A foundation for leadership alignment and development
It is not
- A technical audit of AI platforms or infrastructure
- A cybersecurity, data-management, or regulatory compliance review
- A generic engagement survey: its statements describe observable conditions, not opinions about AI
- Another AI-tools training course
Who It Is For
- CEOs and C-level teams preparing for enterprise AI transformation
- Boards seeking confidence that the organization can turn AI investment into results
- CHROs and transformation leaders responsible for the people side of AI
- Organizations with multiple pilots but limited enterprise adoption
- Leadership teams experiencing misalignment, resistance, or unclear accountability
If one of these describes your organization, the assessment is the place to start.
Request an AI Transformation ConversationFrom Insight to Action
The assessment can stand alone. It can also establish the baseline for a C-Level AI Transformation Retreat or the broader Intelligent Leadership® AI Transformation Accelerator.
- AssessThis assessment
- AlignThe C-Level AI Transformation Retreat
- TransformThe AI Transformation Accelerator
Enterprise engagements are customized to organizational scope and typically begin at $125,000.
In practice
In an integrated engagement, the diagnostic is what exposes the leadership, culture, and execution gaps an organization cannot see while AI is treated as a technology program. It decides where the rest of the work is aimed.
See the full example engagement- Countries
- 55+
- Organizations consulted
- 250+
- Leaders reached
- 1M+
Trusted by leaders in global enterprises, governments, financial institutions, and high-growth organizations across 55+ countries.
Intelligent Leadership® was created by John Mattone, ranked the world's #1 Executive Coach six times by Global Gurus (2019 to 2026).
Do Not Guess Whether Your Organization Is Fit for AI.
Establish the truth before you commit the next AI investment.
For CEOs, executive teams, boards, and CHROs leading enterprise-wide AI transformation.
What happens next
- 1.Your inquiry goes directly to the John Mattone Global team. We reply within one business day.
- 2.We arrange a confidential conversation about your organization and its AI ambition.
- 3.If there is a fit, we propose the scope that matches where you stand.
Not ready for a conversation yet? Read the white paper first.