A baseline, not a maturity score.
Most AI assessments rank organizations on a maturity scale and tell them where they should aspire to be. The implicit message is that there is a destination, and you are behind. That framing produces good slides and very little useful action.
The AI Baseline Workshop is built differently. It gives the leadership team a clear, evidence-grounded picture of what the organization has, what it’s already doing, what it actually wants, and what’s getting in the way. From that baseline the leadership team can make strategic decisions about AI that hold up in execution — without the implied judgment of a maturity scale and without the slide-deck theater that goes with it.
Leaders use it when they need to move quickly and confidently, with leadership aligned on what they’re actually working with.
Five dimensions, surfaced together.
The workshop is structured around the five dimensions that actually predict whether an AI strategy will land. Each is surfaced through evidence rather than self-report.
AI fluency across leadership and key teams
Where the leadership team and operational teams actually are with AI — what they understand, what they assume, where the gaps are. Surfaced through the survey and interviews, not self-reported.
What the org has already started doing with AI
Sanctioned and unsanctioned. The pilot in marketing nobody told IT about. The shadow tool the engineering team is already paying for. The proof-of-concept the CFO wants to know about. We map the actual surface area.
What you think you want AI to do — and whether that's the right ambition
Most stuck AI strategies fail at this step. What leadership says it wants from AI and what AI is actually well-suited to deliver are often different problems. We pressure-test the ambition against what AI is good at right now.
Organizational constraints that will help or hinder
The patterns underneath. Hero culture that will absorb AI capacity into existing bottlenecks. A governance posture that quietly blocks any AI tool with data implications. Incentives misaligned with the AI strategy you want to run. We name them.
How AI maps to existing business goals and strategy
AI is not a strategy. It supports a strategy. We map AI opportunities back to the business outcomes already on the leadership team’s plate, so the AI work compounds with what you’re already doing instead of competing with it.
Four steps over two to three weeks.
The format is deliberately short. Long enough to gather evidence and run a real working session with the leadership team. Short enough that it doesn’t become its own organizational event.
01Pre-engagement organizational survey
A short, structured survey that goes out to a defined slice of the organization before any conversation. It produces an evidence base instead of impressions, and it catches signals the leadership team would never volunteer in an interview.
025–8 stakeholder interviews
A targeted set of 30–45 minute conversations with leadership and a cross-section of the organization. The interviews surface the dynamics underneath the survey numbers — the politics, the history, the things people will say one-on-one but not in a group.
031-day findings + strategy workshop with leadership
The full leadership team in the room, walked through the findings and into the strategic decisions that follow. Not a slide review. A working session where we move from “what’s actually happening” to “what we’re going to do about it.”
04Synthesis and report
A clean written readout of what we found, what we recommend, and what the prioritized roadmap looks like. The artifact is built to survive the meeting — usable for board updates, sponsor conversations, and execution planning.
Four artifacts, built to be used.
The deliverables are the point — not a slide deck that gets archived after the readout. Each artifact is written to survive the meeting and stay useful as the organization executes against the roadmap.
AI Baseline Scorecard
A clear-eyed view of where the organization stands across the dimensions that matter for AI: fluency, infrastructure, data posture, organizational readiness, governance maturity, and strategy clarity. Used to align the leadership team on a shared starting line.
Prioritized AI Opportunity Roadmap
The set of AI opportunities ranked against your business goals and your organization’s ability to execute, sequenced for compound effect. Distinguishes the obvious-but-low-value opportunities from the underrated ones with real leverage.
90-day Quick Wins Plan
The two or three things worth doing in the next 90 days — small enough to execute, visible enough to build momentum, and chosen for what they teach the organization rather than just what they ship.
Constraints map
The organizational and structural friction that will help or hinder the roadmap. Useful for the leadership team because the constraints are what determine whether the roadmap actually gets executed — and they often live outside the technology function.
For leaders who want the baseline before the bigger move.
The AI Baseline Workshop is for leadership teams that want to understand where they stand on AI before committing to a larger investment, a bigger consulting engagement, or a strategic announcement they’ll have to live with for the next twelve months.
It’s the right size when the leadership team is reasonably aligned on the importance of AI but doesn’t yet agree on the ambition, the priorities, or the actual organizational readiness underneath. It produces the shared evidence base that aligns those conversations.
And it’s the right starting point when you suspect the AI strategy you’re running today isn’t the AI strategy your organization can actually execute — and you want to find that out in two weeks instead of two quarters.
The leaders who get AI right don’t guess. They get evidence first.
Three common paths.
Some clients use the AI Baseline Workshop as a standalone diagnostic. The roadmap and the quick-wins plan become the leadership team’s working artifact for the next quarter, and the work runs internally from there.
Some use it to scope a larger TRUST Assessment. The baseline surfaces organizational dynamics that warrant a deeper diagnostic — the kind of structural pattern work the full TRUST methodology is built for.
Some go straight to implementation. The roadmap points clearly enough at the next set of moves that the leadership team is ready to commission a Multi-Day Sprint, a Custom Agent Build, or a Fractional CTO engagement to execute. The baseline tells you which path makes sense.
Smart leaders let the workshop’s roadmap tell them which path fits — and don’t pre-commit to a direction before they have the evidence. The full Solutions hub shows what each next move looks like.
Talk to us about an AI Baseline Workshop.
A short conversation about what you’re dealing with — what you’ve tried, what feels stuck, what you’re trying to figure out. No pitch.
jason@drag6.com