Asking relevant questions - a template

Having joined a large retail organization six months ago as a senior engineer, I frequently found myself invited to brainstorming sessions and discussions without much prior context or background. This often involved topics outside my immediate area of expertise.

Initially, this posed a challenge in contributing effectively. However, adopting a structured approach of asking relevant, strategic questions helped me to clarify objectives, explore alternative viewpoints, and validate assumptions.

Following is a template I use to guide my questioning strategy in an unfamiliar discussions:

Establish Context and Objectives

Understanding the overall context and primary objectives is crucial for meaningful participation. The following questions can help to set the stage:

• Are we exploring a new opportunity, addressing a challenge, or optimizing an existing process?
• Can we briefly summarize the primary objective and its importance being discussed?
• What could go wrong if we don’t address this issue?
• How does this initiative align with our broader organizational goals?

Clarify Scope and Boundaries

Defining the scope and boundaries helps to focus the discussion and manage expectations. This avoids spiderwebbing into unrelated topics.

• Can we isolate the specific aspects or components of this initiative that we’re addressing today?
• What are the key deliverables or outcomes we aim to achieve through this discussion?
• How do we define success or completion criteria?
• Are there any known limitations or constraints we should consider upfront?
• Which technologies, resources, or teams are specifically involved or excluded?
• Are there any metrics or KPIs we should be mindful of during this discussion?
• What is the timeline or deadline for this initiative, and how does it impact our discussion today?

Tactical or Strategic Focus

Distinguishing between tactical and strategic focus helps to align the discussion with the desired outcomes and timeframes.

• Are we discussing immediate, tactical solutions or long-term, strategic implications?
• Is there a room to explore both tactical and strategic aspects in this discussion?
• For interim solutions, are we considering reusable components that can scale to a strategic solution?
• Are there any trade-offs between tactical and strategic approaches that we should be aware of?

Explore Existing Approaches and Considerations

Gathering insights on prior attempts or considerations can prevent redundant discussions. Additionally, it helps to build on existing knowledge and avoid reinventing the wheel.

• What has been previously attempted regarding this issue, and what were the outcomes?
• Have we already considered and discarded certain solutions? If so, why?
• Are there benchmarks, competitor examples, or industry standards that we can learn from?
• Are there any solutions or strategies from other departments or industries that could be adapted here?

Assess Risks and Validate Assumptions

Identifying risks and validating assumptions is critical for informed decision-making. This helps the team to understand risk appetite and contingency planning.

• What assumptions underpin our current approach?
• Have we identified major risks or uncertainties associated with this project?
• What contingency plans are in place if our initial assumptions prove inaccurate?
• Are there any changing market conditions or external factors that could impact our strategy?

Include Diverse Perspectives and Alternative Viewpoints

Encouraging diverse perspectives promotes creativity and innovation. It also helps to identify blind spots and consider alternative viewpoints.

• How might this initiative affect stakeholders or processes outside our immediate view?
• Could someone elaborate on the potential advantages or drawbacks of our current strategy?
• What alternative approaches or solutions have we not yet considered?
• Are there any off-the-shelf solutions available that could address our needs?
• Is there an opportunity to accomplish our goal more efficiently or cost-effectively?
• Are there best practices or innovations from other industries we could leverage?

Summarize and Validate Understanding

Periodic clarification demonstrates engagement and ensures collective alignment.

• Can I quickly summarize my understanding of what we’ve discussed to ensure alignment?
• Is my interpretation consistent with our intended direction?
• Are there any gaps or misunderstandings that need to be addressed before proceeding?
• Is there any documentation or follow-up required to capture our discussion outcomes?

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The above template is a starting point to guide your questioning strategy in unfamiliar discussions. It has helped me a lot and I hope it will be useful for you too. Feel free to customize it based on your specific needs and context.

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