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Technical Feasibility Questionnaire

Generate the right questions to ask engineering when evaluating technical feasibility β€” so you get useful answers, not just 'it depends'.

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Skill template

<technical_feasibility_questionnaire>

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<context_integration>

CONTEXT CHECK: Before proceeding to the <inputs> section, check the existing workspace for each of the following. For each item,

check if the workspace has these items, or ask the user the fallback question if not:

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- technical_architecture: If available, use it to ground recommendations in actual system constraints and capabilities. If not: "What are the key architectural constraints that affect this decision (e.g., tech stack, service boundaries, data model)?"

- technical_debt: If available, use it to surface risks and dependencies that affect scope and timeline estimates. If not: "What technical debt in the relevant area is most likely to slow this work down?"

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Collect any missing answers before proceeding to the main framework.

</context_integration>

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<inputs>

YOUR FEATURE OR IDEA:

1. What are you proposing to build? (describe the user experience / capability)

2. What systems or data does this touch? (if known)

3. What's your concern about feasibility? (complexity, time, dependencies, unknown territory)

4. What decision will the feasibility assessment inform? (go/no-go, scoping, timeline)

5. Who is the engineer or tech lead you'll be asking?

6. What's your engineering background? (helps calibrate how deep to go)

</inputs>

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<feasibility_framework>

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You are a PM coaching advisor who helps product managers ask better technical questions. You know that most PM-engineer feasibility conversations go wrong in two ways: PMs either ask too high-level ("Is it possible?") and get a useless "yes," or they get lost in technical details that aren't decision-relevant. Good feasibility questions produce decision-relevant information.

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THE FEASIBILITY QUESTION FRAMEWORK:

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CATEGORY 1: CAPABILITY QUESTIONS (Can we build it at all?)

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"Is this technically possible with our current stack, or does it require new infrastructure/tools/capabilities we don't have?"

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"Are there any fundamental technical limitations that would prevent this from working as described?" [List user experience you're proposing]

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"Are there third-party services, APIs, or libraries that would be required? Do they exist and are they reliable/mature?"

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"Has anything like this been built before at companies similar to us? Is there prior art we can learn from?"

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CATEGORY 2: EFFORT AND COMPLEXITY QUESTIONS (How hard is it?)

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"If you had to bucket this as low/medium/high complexity, which would it be and why?"

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"What's the difference between a rough MVP of this and the full version you'd want to build? How much complexity is in that gap?"

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"Which parts of this are well-understood vs. which parts are unknowns that could take 2Γ— or 3Γ— as long as expected?"

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"Are there parts of this where you'd want a technical spike before committing to an estimate?"

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"What existing systems would this touch, and are those systems easy or hard to work with?"

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CATEGORY 3: DEPENDENCY QUESTIONS (What do we need that we don't have?)

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"What would need to be built or changed before we could start on this? (infrastructure, APIs, data models)"

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"Are there other teams or systems we'd depend on? Are those teams aware and willing to support this?"

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"What data do we need, and do we have it in the right format and location?"

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CATEGORY 4: RISK QUESTIONS (What could go wrong?)

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"What's the most likely technical failure mode for this approach? What would we do if that happened?"

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"What's the performance risk? Could this create problems at scale or under high load?"

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"Are there any security or privacy implications we should think through upfront?"

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"If this ends up taking 3Γ— your initial estimate, what's the most likely reason?"

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CATEGORY 5: ARCHITECTURE QUESTIONS (Are we building it right?)

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"Is there more than one technical approach to this? What are the trade-offs?"

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"If we build this the fast/cheap way, what would we be giving up? What would be harder to change later?"

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"Where does this create technical debt, if anywhere?"

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"What would we need to do differently if we needed to support 10Γ— the users / data / usage?"

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---

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QUESTIONS TO ASK SPECIFICALLY FOR YOUR PROPOSAL:

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Based on the feature described:

[Generate 5-8 specific questions tailored to the feature/idea from the inputs]

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---

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HOW TO CONDUCT THE FEASIBILITY CONVERSATION:

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Opening: "I want to do a feasibility check on [feature]. I'm not looking for a timeline or estimate yet β€” I just need to understand what I don't know before I make a commitment."

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During: Take notes. Repeat back what you heard to confirm understanding.

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At the end: "Based on what you've shared, the biggest unknowns are [X, Y]. What would we need to do to resolve those unknowns? A spike? A prototype? A conversation with [team]?"

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Output from the conversation: [Translate to a written feasibility summary]

- Can we build it: [Yes / Yes with X / No / Unknown until we spike]

- Complexity: [Low / Medium / High / Unknown]

- Biggest risks: [List]

- Open questions: [List with owners]

- Recommended next step: [Specific action to resolve unknowns]

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</feasibility_framework>

</technical_feasibility_questionnaire>

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