AI Tuesday · Deepen Your Craft w/ AI
Measuring Your
AI Collaboration Maturity
Dakota Fabro, M.Ed, M.Th (they/them)
Android @ TIDAL
June 30, 2026 · 15 min
What we'll cover
Session overview
The mismatch between tools and practice
Why having access to powerful AI tools doesn't automatically translate into deeper work
A framework for seeing your practice
Three dimensions that measure how you collaborate with AI: depth of thinking, tool maturity, and delegation trust
Self-assessment
Locate yourself on each dimension to establish a personal baseline
Growth zones and next steps
What your combination of scores reveals and how to use it going forward
01 · The Mismatch
Tooling is only one part of the equation.
Flamethrower + Candle
Overpowered tool, simple task
Formula One racecar at 25mph
Powerful tool, underskilled user
Chef + paring knife
Skilled user, underpowered tool
Hendrix vs. Hobbyist
Tool matches the practitioner, output varies
The relationship to the tool is where we find opportunities for growth.
02 · Three Dimensions
A framework for seeing your practice.
DOK
Depth of Knowledge
How deeply are you thinking alongside AI?
TM
Tool Maturity
How well do your tools match your skill set and work demands?
ADT
Agentic Delegation Trust
How much do you trust AI to produce what you intended?
02 · Three Dimensions
What each dimension measures
| Dimension | What it measures | Where growth happens |
|---|---|---|
| Depth of Knowledge | How deeply are you thinking alongside AI? | Moving from recall toward synthesis and strategic reasoning |
| Tool Maturity | How well do your tools match your skill set and work demands? | Expanding from single-tool chat toward orchestrated workflows |
| Agentic Delegation Trust | How much do you trust AI to produce what you intended? | Shifting from constant correction toward frontloaded collaboration |
03 · Self-Assessment
Where are you?
Depth of Knowledge
Think about your last 5 AI interactions. Were you mostly…
Asking for facts
'What is the syntax for X?'
Applying concepts
'Build this component using pattern Y'
Making strategic decisions
'What architecture handles these tradeoffs?'
Synthesizing something new
'Design a framework that bridges X and Y'
03 · Self-Assessment
Tool Maturity
How are you using AI in your workflow?
Single tool, occasional use, separate from main workflow
One tool integrated into daily workflow, back-and-forth collaboration
Multiple tools coordinated, beginning to delegate
Specialized tools for specialized tasks, parallel workstreams
Full orchestration across agents, tools, and workflows
03 · Self-Assessment
Agentic Delegation Trust
When you delegate work to AI, how much do you trust the output?
Check every line. The AI is a rough-draft machine at best.
Review key sections. Trust the routine parts.
Delegate sections. Inspect where pieces connect.
Frontload intent, trust execution. Intervene only on exceptions.
02 · Real Data
135 days of measured growth
January 28 → June 11, 2026
DOK
+29%
Tool Maturity
+ 3 tiers
Agentic Delegation Trust
The growth wasn't about switching tools. It was about changing my relationship to the tools I already had.
04 · Growth Zones
What the numbers mean
Thinking Ahead
Cognitive depth exceeds tool sophistication.
↳ Chef + paring knife
Growing
Approaching a match between tool sophistication and cognitive depth.
Frontier
TM and DOK matched and growing together. The productive edge.
↳ Hendrix vs. Hobbyist
Overpowered
Significant mismatch between tool complexity and task depth.
↳ Flamethrower + Candle
Expected
Tool usage and cognitive depth are appropriate for the current level.
Underutilizing
Powerful tools, simple questions. An opportunity to deepen.
↳ Formula One racecar at 25mph
Measuring your workflow allows you to analyze your process and make improvements to deepen your practice.
05 · Try It
Measure your baseline
If you use Goose
/rp-why currentAssesses the current Goose session
/rp-why baselineAssesses the last three months of Goose sessions
/rp-why compareAssesses the current session against the baseline measurement
Not a Goose user?
Copy this prompt into any LLM to assess your conversation history.
Note: This method has limitations compared to the full rp-why skill in Goose, which has access to session metadata, tool call logs, and historical baselines. Results will be approximate.
The point isn't the score. The growth is found in your awareness. Once you can see the pattern, you can change it.
Dakota Fabro, M.Ed, M.Th
they/them · Android @ TIDAL
Thank you for your time and attention.