Appendix B: Question Templates for Common Situations

This appendix provides ready-to-use question sequences for common professional and personal scenarios. These templates can be used as starting points and customized to your specific context.

1. Problem-Solving Meeting Template

Use this sequence to guide a team through effective problem-solving.

Opening Questions (5-10 minutes)

• “What specific outcome do we want from today’s discussion?”
• “Who else should be involved in this conversation who isn’t here?”
• “What do we already know about this situation?”

Problem Definition Questions (10-15 minutes)

• “How would each of us describe the problem we’re trying to solve?”
• “Who is affected by this problem and how?”
• “What would success look like if this were solved completely?”
• “Is this a symptom of a deeper issue we should address instead?”

Root Cause Analysis Questions (15-20 minutes)

• “When did we first notice this issue, and what changed around that time?”
• “Why is this happening? And why is that happening?” (Continue at least 3-5 levels)
• “What systems or processes are contributing to this situation?”
• “What assumptions might we be making about the cause?”

Solution Generation Questions (15-20 minutes)

• “What are all the possible ways we could approach this?”
• “What would a completely different industry do with this challenge?”
• “What if resources weren’t a constraint—what would we do?”
• “What’s the simplest solution that might work?”

Solution Evaluation Questions (10-15 minutes)

• “What criteria should we use to evaluate these options?”
• “What are the potential unintended consequences of each approach?”
• “How might each solution affect different stakeholders?”
• “What’s the minimum viable version we could implement quickly?”

Decision and Next Steps Questions (5-10 minutes)

• “Based on our discussion, what approach makes the most sense to pursue?”
• “Who needs to do what by when to move this forward?”
• “How will we measure success?”
• “When should we check in on progress?”

2. One-on-One Coaching Conversation Template

Use this sequence for coaching team members, mentees, or colleagues.

Connection Questions (3-5 minutes)

• “What’s been going well since we last spoke?”
• “What’s on your mind today that you’d like to explore?”

Exploration Questions (10-15 minutes)

• “What aspect of this situation is most challenging for you?”
• “What have you tried so far, and what have you learned?”
• “What does your ideal outcome look like?”
• “What’s at stake here for you personally?”

Insight Questions (10-15 minutes)

• “What patterns do you notice in this situation?”
• “What might someone you respect advise you to do?”
• “What part of this situation is within your control?”
• “What unstated assumptions might be limiting your options?”

Action Questions (5-10 minutes)

• “What’s the smallest first step you could take?”
• “What resources or support would help you move forward?”
• “What might get in the way, and how will you address that?”
• “How confident are you in taking this action?”

Commitment Questions (3-5 minutes)

• “What specifically will you do by when?”
• “How will you hold yourself accountable?”
• “How would you like me to support you?”
• “When should we follow up on this?”

3. Strategic Planning Session Template

Use this sequence to guide strategic thinking and planning.

Context-Setting Questions (15-20 minutes)

• “What important changes are happening in our environment?”
• “What are our customers/stakeholders telling us through their behavior?”
• “What strengths can we build upon? What limitations must we acknowledge?”
• “What trends will most impact our future if they continue?”

Vision and Purpose Questions (20-30 minutes)

• “Why does our work matter? Who would be affected if we ceased to exist?”
• “What impact do we aspire to have in the long term?”
• “What unique value can we provide that others cannot?”
• “If we were wildly successful in 5-10 years, what would that look like?”

Strategic Options Questions (30-45 minutes)

• “What are the critical few priorities that would most move us toward our vision?”
• “What should we stop doing to free resources for these priorities?”
• “What capabilities must we develop or strengthen?”
• “What strategic options should we consider beyond the obvious ones?”

Decision Criteria Questions (15-20 minutes)

• “What criteria should guide our choices between options?”
• “How will we balance short-term results with long-term positioning?”
• “What trade-offs are we willing to make? What are we unwilling to compromise on?”
• “How will we know if our strategy is working?”

Implementation Questions (20-30 minutes)

• “What milestones would indicate we’re on the right track?”
• “What resources will be required and how will we secure them?”
• “Who needs to be involved for this to succeed?”
• “What potential obstacles should we prepare for now?”

Alignment and Communication Questions (15-20 minutes)

• “How will we communicate this strategy to different stakeholders?”
• “What questions should we be prepared to answer?”
• “How will we maintain alignment as we implement?”
• “When and how will we review progress and make adjustments?”

4. Innovation Workshop Template

Use this sequence to stimulate creative thinking and innovation.

Challenge Framing Questions (15-20 minutes)

• “What challenge are we trying to address? How might we reframe it as an opportunity?”
• “Who experiences this problem most acutely, and what do they need?”
• “What would an ideal solution make possible?”
• “What constraints should we acknowledge? Which ones might we challenge?”

Divergent Thinking Questions (30-45 minutes)

• “How might we approach this challenge if we were [a completely different type of organization]?”
• “What if the opposite of our current assumptions were true?”
• “What analogous problems have been solved in other domains?”
• “If we had to solve this with only the resources in this room, what would we do?”

Convergent Thinking Questions (20-30 minutes)

• “Which ideas have the most potential to address our core challenge?”
• “How might we combine elements from different ideas?”
• “What would make these promising ideas even better?”
• “Which ideas could we prototype quickly with minimal resources?”

Concept Development Questions (30-45 minutes)

• “How would this solution work in practice?”
• “Who would need to be involved to make this successful?”
• “What assumptions are we making that we should test?”
• “What would be the first, smallest version we could create to learn from?”

Implementation Planning Questions (20-30 minutes)

• “What resources would we need to develop this concept further?”
• “What’s the first step we should take in the next 48 hours?”
• “What quick wins might build momentum?”
• “How will we measure progress and capture learning?”

5. Conflict Resolution Template

Use this sequence to navigate and resolve interpersonal or team conflicts.

Opening Questions (5-10 minutes)

• “Are we both/all open to finding a resolution that works for everyone?”
• “Can we agree on some ground rules for this conversation?”
• “What outcome would you like to see from this discussion?”

Understanding Different Perspectives (15-20 minutes)

• “Can you help me understand how you see this situation?”
• “What impact has this had on you?”
• “What needs or concerns are most important to you in this situation?”
• “Is there anything else I should know about your perspective?”

Finding Common Ground (10-15 minutes)

• “What goals or values do we share despite our differences?”
• “What parts of each other’s perspectives can we acknowledge as valid?”
• “What’s at stake for our relationship/team if we don’t resolve this?”
• “How might this look from a neutral third party’s perspective?”

Solution Exploration (15-20 minutes)

• “What possible approaches might address both our concerns?”
• “What would a compromise look like that honors what’s important to each of us?”
• “What are we each willing to contribute to a solution?”
• “What’s the smallest step we could take toward resolution?”

Agreement and Forward Path (10-15 minutes)

• “What specific agreements are we making today?”
• “How will we handle it if similar issues arise in the future?”
• “What have we learned from this conflict that could strengthen our relationship?”
• “When should we check in on how these agreements are working?”

6. Customer/User Interview Template

Use this sequence to gain deeper insights from customers or users.

Rapport Building Questions (3-5 minutes)

• “Tell me a bit about yourself and your role.”
• “How long have you been [using our product/working in this field]?”
• “What’s a typical day like for you?”

Context and Background Questions (5-10 minutes)

• “What were you trying to accomplish when you [used our product/encountered this situation]?”
• “What solutions had you tried before?”
• “How important is solving this particular challenge for you?”

Experience and Behavior Questions (10-15 minutes)

• “Could you walk me through exactly what you did step by step?”
• “What were you thinking at each stage of this process?”
• “What worked well? What was frustrating?”
• “Show me how you currently do this, if possible.”

Emotion and Value Questions (5-10 minutes)

• “How did that experience make you feel?”
• “What would have made this experience better for you?”
• “What impact does this issue have on your broader goals?”
• “What would an ideal solution make possible for you?”

Feature/Solution Testing Questions (10-15 minutes)

• “What’s your reaction to [specific feature or concept]?”
• “How might this fit into your current workflow?”
• “What questions or concerns do you have about this approach?”
• “What would make you choose this solution over alternatives?”

Closing Questions (3-5 minutes)

• “Is there anything else you think I should know?”
• “Who else should I speak with to learn more about this?”
• “Would you be open to testing future iterations of this solution?”
• “What’s the best way to stay in touch as we develop this further?”

7. Personal Decision-Making Template

Use this sequence for important personal or career decisions.

Clarification Questions (Self-Reflection)

• “What exactly am I trying to decide?”
• “By when does this decision need to be made?”
• “Who else will be affected by this decision?”
• “What are the actual options I’m considering?”

Values Alignment Questions (Self-Reflection)

• “What matters most to me in this situation?”
• “Which option best aligns with my core values?”
• “What does my intuition tell me, and why might it be saying that?”
• “How will I feel about this decision a year from now? Five years from now?”

Information Gathering Questions (Research/Ask Others)

• “What information am I missing to make this decision confidently?”
• “Who has expertise or experience I could learn from?”
• “What are the long-term implications of each option?”
• “What risks or opportunities am I not seeing?”

Option Evaluation Questions (Self-Reflection/Discussion)

• “What are the pros and cons of each option?”
• “Which option has the best alignment of benefits vs. costs?”
• “What would I advise someone else to do in my situation?”
• “What’s the worst that could happen with each option? Could I handle that?”

Testing and Validation Questions (Action)

• “Is there a way to test this decision on a smaller scale first?”
• “How can I remain open to changing course if new information emerges?”
• “What specifically will I do to implement this decision?”
• “How will I know if this was the right decision?”

8. Learning Reflection Template

Use this sequence to extract maximum learning from experiences.

Description Questions (5-10 minutes)

• “What actually happened in this situation? Just the facts.”
• “Who was involved and what did each person do?”
• “What was the sequence of events?”
• “What was the outcome or result?”

Reaction Questions (5-10 minutes)

• “How did I feel during this experience?”
• “What was surprising or unexpected?”
• “Which parts were most challenging or uncomfortable?”
• “What was energizing or satisfying?”

Analysis Questions (10-15 minutes)

• “What went well and why?”
• “What didn’t go as expected and why?”
• “What patterns do I notice from previous experiences?”
• “What assumptions did I make that proved true or false?”

Insight Questions (10-15 minutes)

• “What have I learned about myself from this experience?”
• “What have I learned about others or the situation?”
• “What principles or lessons can I extract?”
• “How does this experience change my understanding?”

Application Questions (5-10 minutes)

• “How can I apply these insights to future situations?”
• “What will I do differently next time?”
• “What additional skills or knowledge would help me?”
• “What’s the most important thing to remember from this experience?”

How to Use These Templates

These templates are structured as conversation guides, not rigid scripts. To use them effectively:

1. Customize to your context:
   • Add or remove questions based on your specific situation
   • Adjust the suggested timing to fit your available time
   • Modify language to match your natural communication style
2. Remain flexible:
   • Be willing to go “off-script” when an unexpected but valuable direction emerges
   • Circle back to skipped questions if they become relevant later
   • Adapt the sequence based on how the conversation unfolds
3. Focus on quality over completion:
   • It’s better to explore fewer questions deeply than to rush through all of them
   • Allow for silence after asking powerful questions
   • Be comfortable with not using every question in the template
4. Prepare in advance:
   • Review the relevant template before your meeting or conversation
   • Highlight the questions that seem most important for your specific situation
   • Consider sending key questions to participants beforehand for reflection
5. Capture insights:
   • Take notes or designate someone to document key insights
   • Record especially powerful questions that emerge during the conversation
   • Schedule follow-up actions based on the discoveries made

Remember that these templates provide structure and inspiration, but the most powerful questions often emerge organically from genuine curiosity and attentive listening.

Next Page: Appendix C: Question Journal Templates