Asking insightful questions involves a combination of preparation, active listening, critical thinking, and curiosity. Here are some tips:
Do your research
If you know in advance the topic of discussion on which you may have questions, having some background knowledge can help you ask more specific and relevant questions. This doesn’t mean being an expert, but a quick Google search, reviewing notes or familiarizing yourself with the topic can go a long way.
Listen actively
Pay close attention to what others are saying. Avoid forming a response in your head before they complete. Listen not just to the words, but also to the underlying meaning and nuances. Paraphrase what they say to confirm your understanding.
Ask open-ended questions
Instead of questions that can be answered with a simple yes or no, try to ask questions that encourage deeper reflection and discussion. E.g. “What were the main challenges you faced, and how did you overcome them?”. “Team X has attempted this before. What are the differences this time?”
Probe for specifics
If something isn’t clear or you want more details, ask follow-up questions. For example, if someone mentions a strategy or decision, you could ask, “Can you give me an example of how that strategy address this specific situation?”
Avoid assumptions
Approach the conversation with an open mind and avoid making assumptions. Don’t be afraid to question your own assumptions or seek clarification if something doesn’t align with your understanding.
Reflect on the answers
After asking a question, take time to reflect on the response and consider how it fits into the broader context. This can help you deepen your understanding and identify additional questions to ask.
Framing is critical
Framing refers to the way you present a question. It subtly influences the direction of the answer and the overall tone of the conversation. Instead of “Why did the project fail?” try “What can we learn from the challenges faced during the project?” This encourages a more constructive response. More on this in the next post.
Examples
Ask yourself what do you hope to learn by asking the question?
This isn’t an exhaustive list, but it’ll hopefully give you an idea.
Do you want to gain a deeper understanding?
- Can you tell me more about this step / use case / scenario?
- What are the underlying assumptions?
Do you want to spark discussion
- Is this applicable to another situation / team?
- How does this work in a different context, e.g. internationalization?
Do you want to challenge an assumption?
- How do we handle this if the assumptions turn out to be incorrect?
- What makes us believe that we are making the right trade offs?
Keep in mind:
- Ask questions but not for the sake of asking.
- Avoid repeating question unless what they explain is not clear.
- Maintain respectful tone. The question “How’s this going to work in this situation” could sound very differently depending on your tone. Try not to appear confrontational.
Remember, asking insightful questions demonstrates curiosity, critical thinking, and a commitment to learning. By honing this skill, you can enhance your effectiveness in communication, problem-solving, and collaboration.
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