After last week’s article about good questions, the “Is It Worth Your T.E.A.M.” community had some good questions for me! I’m sharing them, along with examples, for the good of the group.
Common Question Concerns
How do you ask a technical question without sounding naive?
Focus on what you need to learn, not what you think you should already know.
- “I’m still getting familiar with this. Will you please walk me through how it connects to X?”
- “What’s the best resource to understand how this works?”
How do I ask my manager better questions during one-on-ones?
Ask about expectations, priorities, and growth. Avoid general “How am I doing?” questions. Be specific.
- “What’s one area you think I could improve in this quarter?”
- “Are there upcoming projects where I can take more ownership?”
How can I ask questions in a meeting without sounding like I’m showing off?
Focus on curiosity, not performance. Keep it brief, stay on topic, and avoid jargon.
- “Will you please share the process of how you weighed the options before landing on this approach?”
How do I ask questions without putting someone on the spot?
Use softer language and offer space to think. This shows respect and lowers pressure.
- “Would you be open to breaking down how you landed on this course of action?”
- “Whenever you have a moment, I’d love your take on how this decision came together.”
How do I push back or ask challenging questions tactfully?
Lead with respect and aim for understanding, not debate.
- “I see the benefits of this plan. What would you say are the trade-offs we should keep in mind?”
- “Is there a reason we ruled out Option B? I just want to understand the full picture.”
What if I asked a question and it didn’t land well?
It happens. Don’t over-apologize. Clarify or follow up later.
- “I realized I may not have been clear earlier. What I meant to ask was how the timeline impacts our testing phase.”
How do I ask better questions in time-pressured situations?
Be direct and results-focused. You don’t need context, just the information you need to act.
- “Can I get a quick yes/no on whether we’re moving forward with the update today?”
- “Is this blocking anything else on your end?”
How do I know when to stop asking questions?
Watch for signs like:
- You’re getting short answers
- The person repeats themselves
- The person says, “Let me follow up later”
- You’re starting to ask things you could find yourself
At that point, pause, thank them, and pivot:
- “Thanks, that’s helpful. I’ll take a look at what’s documented and come back if needed.”
Practice
Asking good questions helps you make better use of your time, understand your work more clearly, and build stronger relationships. Like any skill, it improves with practice. Here are a few things you can do right away:
- Rewrite one vague question you ask often. Make it clearer and more specific
- During your next meeting, ask one thoughtful follow-up
- Practice active listening: Summarize what you heard before asking a follow-up
- Ask one question at a time
- After a presentation, ask a “what’s next” question to keep things moving
Do you have a good follow-up question for the community? Please share it in the comments.