Pilot2Service Workshop & Facilitation Design
Purpose
Designs the structure of a cross-functional workshop or design-thinking session.
Anchored in research
- Perplexity research — running workshops and design-thinking sessions
- Design Council (2004) — the Double Diamond (Discover, Define, Develop, Deliver): alternates divergent and convergent phases. A workshop meant to both explore a problem and converge on a decision needs to make that phase switch explicit to participants.
- Kaner et al., Facilitator's Guide to Participatory Decision-Making — the Diamond of Participation: a divergent zone (generating options), a "groan zone" (the necessary, uncomfortable phase where the group aligns on meaning before it can converge), and a convergent zone (narrowing to a decision). A workshop that skips the groan zone produces premature, brittle agreement.
Method
- Clarify the workshop's single deliverable and where it sits on the Double Diamond — is this a Discover/Define session (diverge on the problem, converge on a framing) or a Develop/Deliver session (diverge on solutions, converge on a decision)? Mixing both in one session without saying so confuses participants about when they're allowed to disagree.
- Design the divergent phase first — generate the widest reasonable set of inputs (problems, ideas, options) before any evaluation. Introduce evaluation criteria too early and the group anchors on the first idea.
- Budget explicit time for the groan zone (Kaner) — the point where diverse inputs collide and the group has to build shared understanding before it can converge. Rushing this step produces a decision that unravels once people leave the room.
- Design the convergent phase with an explicit decision rule — dot-voting, a scoring matrix, or a named decision-maker who breaks ties. A workshop that diverges well but never states how convergence will happen ends in a non-decision.
- Sequence the agenda in blocks with a facilitator role and timing per block, not just a topic list — who's driving, how long, and what artifact comes out of each block.
- Plan the close: decision, owner, and next step, captured before people leave the room. A workshop that "generated great discussion" but ends without a captured decision and owner hasn't produced a result.
- For fast-moving AI prototyping specifically, consider a real-time, cross-disciplinary working session instead of a staged workshop. When development, design, and business stakeholders review and adjust an AI prototype together, live, in the same physical or digital space, feedback is immediate and the discover/decide cycle above can compress into hours instead of a multi-day workshop cadence. This isn't a replacement for the structure above — it's a format choice for when the material under discussion (a working prototype that can be poked at directly) makes live, side-by-side reaction more valuable than a scheduled agenda with prepared materials. Use it for prototype review and refinement cycles specifically, not for the initial problem-framing work that still benefits from the Double Diamond structure in step 1.
What this skill does NOT do
- Doesn't make the final decision for you — it produces a structured draft to support a human decision.
- Doesn't confirm figures, market data, or competitor data from memory — it
uses the inputs you provide, or marks an assumption clearly
(
[assumption — verify]). - Doesn't facilitate the workshop for you — it designs the structure and timing for the facilitator.
Refinement notes
Areas to keep deepening with real practice:
- your own rules of thumb and heuristics for this technique
- concrete templates (into
../../references/) - reference cases / your own examples
- what this skill deliberately does not do (guardrails, common mistakes) — add to the list above
This is an internal working note, not a claim about the skill's current
usability. Track depth privately via the maturity field in
skills_index.json (see
../../../meta/maturity_levels.md).
Don't add new fields to the frontmatter — name and description are
the only ones allowed (see
../../../meta/frontmatter_schema.md).
Continue from here
- Next in this pack:
../executive-narrative-and-storyline/SKILL.md— Turns analysis into a narrative and storyline that serves executive decision-making. - A ready-made skill chain for this situation: see
../../../playbooks/ - This pack's shared guardrails:
../../CLAUDE.md
References
../../references/— the pack's shared background material- Step 7's real-time cross-disciplinary format is grounded in the general
underlying idea only (live, siloless collaboration beats staged
handoffs) rather than in a specific named model — a named model and its
attributed originators could not be independently verified, see
../../../human-ai-collaboration-design/references/hitl-partnership-heuristics-research.md ../../CLAUDE.md— the pack's shared guardrails