derisk-measurement-advisor skill

Purpose

Guide product managers through identifying the most important things to measure, test, or track across 10 risk dimensions — 4 internal and 6 external — then triage each into act on immediately or start tracking. The output is a prioritized risk register that tells you what to do first, not just what could go wrong.

This is not a generic risk list. It's a guided scan tied to your specific product, customer, and market context. The question it answers: is the orange worth the squeeze?

Input

Works best with: The product or AI idea you want to stress-test. Also useful: Its stage (concept, prototype, in-market), what you've already validated, and any dimensions you already know are risky.

Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re-ask.

Arriving empty-handed? That works too. The advisor opens by asking for the idea in a sentence or two, then scans the 10 risk dimensions against it.

Example invocation: De-risk this: an AI agent that auto-drafts insurance claim responses for adjusters — prototype stage, no compliance review yet.

Key Concepts

Two Lenses, One Question

Every product idea carries two kinds of risk. Most PMs check one and ignore the other.

Internal risks ask whether the product itself will work:

• Product Outcome Metrics (Desirability + Usability) = "What's in it for the customer/user?"
• Business Outcome Metrics (Feasibility + Viability) = "What's in it for our business/organization?"

External risks ask whether the world will let it work:

• PESTEL forces (Political, Economic, Social, Technological, Environmental, Legal) = "What could blindside us?"

The single triage question that applies to both sides: Do I act on this now, or start tracking it?

The Internal Risk Framework (DUFV)

Adapted from Marty Cagan's four product risks, split into two measurement categories:

Product Outcome Metrics answer: What's in it for the customer/user? They measure whether the product is solving meaningful problems and delivering value to its intended users.

Business Outcome Metrics answer: What's in it for our business/organization? They measure how effectively and reliably the product supports a seamless customer experience while remaining feasible to deliver.

The connection to positioning: Product Outcome Metrics validate your Problem Positioning Statement (the customer promise). Business Outcome Metrics validate your Problem Framing Statement (the business case).

The External Risk Framework (PESTEL)

Six categories of forces outside your organization that can reshape, delay, or kill your product plans:

Key insight from the classroom: Market conditions don't just change — they potentially change us, our business, and our products. PESTEL helps PMs categorize and respond to that change, not just observe it.

The Act/Watch Triage

Every surfaced risk gets one of two labels:

• Act on immediately: This risk is present, material, and requires a response now — run a test, change a plan, mitigate a gap.
• Start tracking: This risk is real but not yet urgent — monitor it, set a trigger threshold, revisit on a cadence.

The triage applies equally to internal and external risks. A desirability gap you can't answer is an "act now" just as much as a regulatory deadline. A demographic trend you see coming is a "watch" just like a feasibility concern you've already partially mitigated.

Anti-pattern: Labeling everything "act now." If every risk is urgent, none of them are prioritized. Force yourself to split roughly 40/60 act/watch.

When to Use This Skill

Use this when:

• You have a product or AI idea and need to decide whether to commit
• You're about to put something on the roadmap and want a structured risk check
• You've been focused on internal risks and haven't scanned external forces (or vice versa)
• Leadership asks "what could go wrong?" and you want a better answer than "nothing, we're good"

Don't use this when:

• You don't have a specific product idea yet (use problem-framing-canvas first)
• You need a deep PESTEL analysis with data and citations (use pestel-analysis component skill)
• You've already validated the idea and need to pick a validation method (use pol-probe-advisor)
• The idea is already in production and you're optimizing, not de-risking

Facilitation Source of Truth

Use workshop-facilitation as the default interaction protocol for this skill.

It defines:

• session heads-up + entry mode (Guided, Context dump, Best guess)
• one-question turns with plain-language prompts
• progress labels (for example, Context Qx/4 and Risk Scan Qx/6)
• interruption handling and pause/resume behavior
• numbered recommendations at decision points
• quick-select numbered response options for regular questions (include Other (specify) when useful)

This file defines the domain-specific assessment content. If there is a conflict, follow this file's domain logic.

Application

This interactive skill uses adaptive questioning to scan your product idea across 10 risk dimensions (4 internal + 6 external), triage each surfaced risk into act/watch, and produce a prioritized risk register.

Session Start: Heads-Up + Entry Mode (Mandatory)

Agent opening prompt:

"Quick heads-up before we start: this usually takes about 15-20 minutes. We'll cover 4 context questions, then scan 10 risk dimensions — 4 internal (will customers want it, can they use it, can we build it, does the business work) and 6 external (political, economic, social, technological, environmental, legal). For each risk that surfaces, we'll triage it: act now or track.

How do you want to do this?

1. Guided mode: I'll walk through each dimension one at a time.
2. Context dump: Paste what you know about the idea and I'll skip what's covered.
3. Best guess mode: Give me the idea in a sentence and I'll make reasonable assumptions, labeled."

Step 0: Gather Context

Agent asks the following questions, one per turn:

Context Q1/4: "What's the product or AI idea you're evaluating? Describe it in 1-2 sentences — what it does and who it's for."

Context Q2/4: "What stage is this idea at?"

1. Concept — we're still exploring whether to pursue it
2. Prototype — we have something testable but uncommitted
3. Building — we've committed and are developing it
4. Scaling — it's live and we're growing it

Context Q3/4: "What's your primary concern right now?"

1. Will anyone actually want this? (demand/desirability risk)
2. Can users figure out how to use it? (usability risk)
3. Can we actually build and sustain this? (technical/feasibility risk)
4. Will this work as a business? (viability/business model risk)
5. Something external could disrupt our plans (regulatory, market, competitive)

Context Q4/4: "Who is the customer — the person who would use or buy this product? Give me a job title or role, not a company name."

After Q4, agent summarizes:

"Here's what I'm working with:

• Idea: [summary]
• Stage: [stage]
• Primary concern: [concern]
• Customer: [role]

Let's scan for risks. We'll start with internal risks (Product Outcome Metrics and Business Outcome Metrics), then move to external forces (PESTEL)."

Step 1: Internal Risk Scan — Product Outcome Metrics (Desirability + Usability)

Agent introduces: