The AI Design Org Playbook

12 leadership moves to make a small design team feel 3x bigger in an AI-native world.

LeadershipDecember 202520 min read
The AI Design Org Playbook

AI didn't just break your features; it broke your org chart and your rituals.

So, we need some new ones. Here are 12 leadership moves, each with when to use it, what it actually looks like in your team, guardrails so you don't wreck trust or quality, and a concrete exercise you can run with your team this week.

1. Upgrade "Design as Service" to "Design as System Stewardship"

The anti-pattern: Design is a request queue. PMs file tickets. Designers ship screens. Nobody owns how the AI in your product actually behaves.

The move: Define design's job as owning system behavior, not just interfaces. Each designer co-owns a problem space and its AI behavior, not just a backlog. Their remit explicitly includes prompts, failure modes, guardrails, and explainability patterns—not just Figma.

2. Swap Phase Gates for a Single, Shared Loop

The anti-pattern: You still present neat Double Diamonds while AI is rewriting problems mid-sprint. Your process deck and your reality live on different planets.

The move: Give the whole org one loop and kill the illusion of phases: Discover continuously, Define and re-define problems, Design behavior and UI, Deploy with telemetry and guardrails, Interpret & tune models + UX in production.

3. Build a Capability Map Before You Touch Headcount

The anti-pattern: You react to every pain with a hire. Suddenly you have more people and the same problems.

The move: Define capabilities, then decide who covers them: System behavior design, Prompt/model stewardship, Continuous AI-native discovery, Ethics & explainability, DesignOps for AI.

4. Architect Tiny, Durable Squads Instead of Borrowed Designers

The anti-pattern: Designers are loaned out to projects like office chairs. They never stay long enough with one area to understand users, models, or real outcomes.

The move: Create small, stable squads that own problem spaces: 1 designer, 1 PM, 2–3 engineers, 1 data/ML partner (fractional is fine). Each squad owns a clear slice of the product, the loop for that slice, and the model and UX behavior for that slice.

5. Install Three Org-Level AI Rituals (and Kill Two Old Ones)

The anti-pattern: You bolted AI demos onto your existing meetings. Everyone is exhausted and nothing really changed.

The move: Anchor AI-native work in three non-negotiable rituals:

  1. Rolling AI Design Review (weekly) – Squad shows live work: flows, prompts, outputs, telemetry.
  2. Model Behavior Review (bi-weekly) – Walk specific scenarios, failure modes, and edge cases.
  3. Ethics & Risk Checkpoint (per major release) – 30 minutes with design, PM, legal, and data.

6. Demand Behavior Briefs for Every Agent and Copilot

The anti-pattern: Teams are quietly shipping "agents" defined by who shouted loudest, not by any clear rules.

The move: Before any agent/copilot ships, require a 1-page Behavior Brief: Purpose and audience, Inputs, Capabilities, Constraints, Decision rules, Logs & user controls.

7. Make Telemetry and Logs a Leadership, Not Just Data, Concern

The anti-pattern: You talk about "data-driven design" but only see a pie chart in QBRs.

The move: Treat AI + UX telemetry and logs as leadership artifacts. For each AI surface, track Adoption, Effectiveness, and Trust/control metrics.

8. Redefine "Shipped" So It Includes Tuning

The anti-pattern: Launch is still treated as the finish line.

The move: In your org, "shipped" = start of a feedback loop. Every AI-related feature gets at least one dedicated post-launch sprint for tuning.

9. Build AI Literacy Into Performance and Promotions

The anti-pattern: Your ladder still rewards stakeholders being happy with Figma, while your real leverage is in how your team shapes AI behavior.

The move: Bake AI-native skills into reviews and promotions. Can this person design and document system behavior? Do they use logs and research to iteratively improve AI flows?

10. Train PM and Engineering to Shoulder Design Work—Without Lowering the Bar

The anti-pattern: You are the bottleneck because only "design" is allowed to touch flows and copy.

The move: Teach PMs and engineers enough design and AI UX to contribute safely. Run internal labs on Writing Behavior Briefs, Designing uncertainty states and kill switches, and Turning user problems into Prompt Blocks.

11. Decide What You Will Stop Doing—In Writing

The anti-pattern: You keep adding AI responsibilities to your team's plate without removing anything.

The move: Create an explicit "Stop Doing" list tied to your AI-native shift. Tie each stop to a start: "We stop X so we can do Y."

12. Run a 90-Day Transformation as a Product, Not a Project

The anti-pattern: You treat org change as an amorphous "transformation," then wonder why nothing sticks.

The move: Run your AI-native org redesign like a product launch:

Month 1 – Discover & Design: Capability mapping, Loop definition, Squad chartering, Ritual prototypes.

Month 2 – Pilot & Tune: One or two squads fully on the new loop and rituals, Behavior Briefs + telemetry for their AI features.

Month 3 – Rollout & Codify: Roll patterns to remaining squads, Update ladders and review templates, Publish a short internal playbook.

Run even half of these moves and your design team stops being the group that "makes it pretty" after AI features appear. It becomes the group that owns how AI behaves—with a small, sharp, purpose-driven team that feels, to the rest of the company, like it's three times the size.

Let's talk about your product, team, or idea.

Whether you're a company looking for design consultation, a team wanting to improve craft, or just want to collaborate—I'm interested.

Get in Touch
Newsletter

Weekly design insights

Weekly observations on design, AI, leadership, and the craft of building. What I'm reading, thinking about, and making.