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Ask Precise Engineering Questions Every Time
Created by Shaunak Ghosh
Learn a repeatable, structured way to ask non-vague questions in software engineering so others can respond with clear next steps. You’ll learn how to surface hidden goals, tailor questions to the right audience, structure context without noise, and probe for the missing information that makes debugging and requirements unambiguous.
Requirements
- Basic software engineering workflow (tickets, pull requests, standups, Slack/email)
- Basic debugging literacy (errors, logs, reproduction steps)
- Comfort explaining what you’re trying to achieve in plain language
What you'll learn
- Diagnose why a question is vague and rewrite it into an answerable ask with the minimum necessary context.
- Detect and correct the XY problem by surfacing hidden assumptions and reframing toward the underlying goal.
- Tailor question framing and detail level to different audiences (peer, senior, leader) without losing precision.
- Use a repeatable structure (top-line ask + organized supporting details) that makes questions scannable in async channels.
- Probe systematically to close information gaps using meaning/reasons/alternatives rather than random follow-ups.
- Ask debugging questions that narrow the search space and request discriminating evidence and reproducible steps.
- Turn ambiguous product requests into scoped requirements, including functional and non-functional constraints, and align on what “done” means.
- Improve response quality and collaboration through better async packaging and active listening-driven follow-ups.
Learning path
9 modules • Each builds on the previous one
1
Vague versus actionable work questions
Differentiate vague questions from actionable ones by focusing on answerability: can someone respond with a concrete next step using the information provided? Learn what “complete information” means in engineering contexts (decision, diagnosis, or alignment).
1 video5 min
2
Avoiding the XY problem at work
Learn to detect when you’re asking about a chosen solution (Y) instead of the real problem or goal (X). Practice converting solution-framed questions into goal-framed questions to get complete information and better options.
1 video5 min
3
Clarify your intent and audience
Decide what you need (decision, approval, data, diagnosis, alignment) and who can provide it. Tailor the question’s structure and level of detail to the audience’s role (peer engineer, senior, manager, stakeholder).
1 video4 min
4
Structured question: context, constraints, ask
Use a consistent payload that reduces ambiguity: brief context, problem/goal, relevant constraints, what you already tried, and a specific ask. Learn what counts as “relevant” context vs noise.
1 video6 min
5
Probing with 5W1H question ladders
Use 5W1H (who/what/when/where/why/how) and “question ladders” to systematically close information gaps. Learn to start broad, then narrow, and avoid random follow-ups that feel vague.
1 video9 min
6
Debugging questions: hypotheses and evidence
In technical diagnosis, good questions are tied to testable hypotheses. Learn to ask for the minimum evidence that differentiates likely causes (logs, error messages, recent changes) and to phrase questions that reduce search space.
1 video7 min
7
Ask for minimal reproducible information
Learn the concept of a minimal reproducible example (MRE) and the “environment checklist” (versions, config, data shape, dependencies). This ensures completeness without vagueness when asking for help or escalating bugs.
2 videos8 min
8
Requirements questions and acceptance criteria
For feature work, structured questions reduce ambiguity by turning vague requirements into testable acceptance criteria. Learn to ask about users, scope boundaries, success metrics, non-functional requirements, and edge cases.
2 videos8 min
9
Tone, channel, follow-up question checklist
Improve answer quality by optimizing delivery: respectful tone, clear assumptions, and explicit follow-ups. Use a short pre-send checklist to ensure your question is specific, complete, and easy to respond to (especially async).
2 videos12 min
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Begin your learning journey
Modules9
Duration59 min
Science-backed learning
In-video quizzes and scaffolded content to maximize retention.
Key concepts
Actionable Vs Vague Engineering QuestionsSurfacing Hidden Assumptions To Avoid Solution Fixation (XY Problem)Audience-Aware Questioning (Exec Vs Implementer)Top-Down Message Structure For Scannable QuestionsSystematic Probing: Clarify Meaning, Reasons, AlternativesDebugging By Isolation, Reproduction, And Scope ReductionRequesting Reproducible Evidence (Steps, Logs, Environment)Writing Clear Bug Reports (Expected Vs Actual)Functional Vs Non-Functional Requirements VocabularyScoping Ambiguous Feature Requests Through ClarificationAsync Question Delivery: Subject Lines, Calls-To-Action, ThreadsActive Listening Behaviors That Improve Follow-Ups