gh-tenequm-claude-plugins-founder-playbook/skills/skill/references/question-banks.md

Coaching Question Banks

Categorized questions for every founder coaching scenario.

Opening Questions

Start Any Session

• "What's on your mind?"
• "What would you like to focus on today?"
• "What would make this conversation most useful for you?"
• "What's the most important thing we should discuss?"

After Any Response

• "And what else?" (The magic question - use 3-5 times)
• "What makes that feel important right now?"
• "Say more about that."

Getting to the Real Issue

• "What's the real challenge here for you?"
• "If you could only solve one thing today, what would it be?"
• "What's beneath that?"

Strategic Decisions

Clarifying the Decision

• "What are you actually deciding between?"
• "What would you need to know to make this decision confidently?"
• "What's the cost of not deciding?"
• "When does this decision need to be made by?"

Examining Options

• "What are all the options you see?"
• "What else?" (repeat 3-5 times)
• "If you couldn't fail, which would you choose?"
• "What would you advise a friend to do?"
• "What's the option you're afraid to consider?"

Testing Assumptions

• "What are you assuming about Option A?"
• "What would need to be true for Option B to work?"
• "What would change if that assumption were wrong?"
• "What evidence supports your current thinking?"
• "What would a skeptic say?"

Evaluating Trade-offs

• "What are you optimizing for?"
• "If you say yes to this, what are you saying no to?"
• "What's the best case? Worst case? Most likely case?"
• "What would you regret not trying?"
• "How would you explain this decision to yourself in a year?"

Building Confidence

• "What criteria matter most here?"
• "What information would help you decide?"
• "How will you know if it was the right call?"
• "What's the smallest version of this you could test?"

When Founder Is Stuck

Identifying the Block

• "What's stopping you?"
• "What are you avoiding?"
• "What feels heavy about this?"
• "Where do you feel most stuck?"
• "What would have to change for you to move forward?"

Shifting Perspective

• "What would you do if you had unlimited resources?"
• "What would [person they admire] do in this situation?"
• "If you knew you couldn't fail, what would you try?"
• "What's the simplest possible next step?"
• "What would you do if you only had one month left?"

Finding Past Solutions

• "When have you faced something similar? What did you do?"
• "Tell me about a time you overcame a similar challenge."
• "What's worked for you before in situations like this?"
• "What strengths do you have that could help here?"

Breaking the Pattern

• "What's one thing you could do differently this time?"
• "What's the smallest experiment you could run?"
• "What if you tried the opposite of what you've been doing?"
• "What would happen if you just did nothing?"

Prioritization

Identifying What Matters

• "If you could only accomplish one thing this week, what would it be?"
• "What would move the needle most?"
• "What's urgent vs. what's important?"
• "What would happen if you didn't do any of these things?"

Creating Focus

• "What are you saying yes to that you should say no to?"
• "What would a ruthless prioritizer do here?"
• "If your runway were halved, what would you cut?"
• "What's the one thing that, if you did it, would make everything else easier?"

Managing Trade-offs

• "What's the cost of doing everything?"
• "What balls can you let drop?"
• "What's good enough vs. what needs to be perfect?"
• "Who else could do this?"

Customer Development

Understanding the Problem

• "What problem are you solving?"
• "How do you know this is a real problem?"
• "Who has this problem most acutely?"
• "How are they solving it today?"

Validating with Users

• "How many users have you talked to this week?"
• "What did you learn?"
• "What surprised you?"
• "What did they say in their own words?"

Getting to Truth

• "What would prove you wrong?"
• "What would make someone pay for this?"
• "What are users actually doing vs. what they say they want?"
• "What's the strongest objection you've heard?"

Building Confidence

• "How many people would need to say yes for you to be confident?"
• "What's the smallest experiment to test this?"
• "What would 'enough' validation look like?"

Fundraising

Timing

• "Why raise money now?"
• "What would you do with the money specifically?"
• "How does this accelerate vs. bootstrap?"
• "What happens if you don't raise?"

Preparation

• "What's your story?"
• "Why you? Why now? Why this?"
• "What's the biggest risk, and how are you addressing it?"
• "What milestones would you hit with this round?"

Strategy

• "Who are the right investors for this stage?"
• "What's your target? What's your walk-away?"
• "How many conversations do you need to get one yes?"
• "What's your plan B if this round doesn't close?"

Alternatives

• "What would you do if you couldn't raise?"
• "How could you extend runway without dilution?"
• "What grants or non-dilutive options exist?"
• "Could you get to revenue faster instead?"

Runway & Cash

Understanding the Situation

• "What's your current runway?"
• "What's your monthly burn?"
• "What's driving the burn?"
• "When did you last calculate this?"

Creating Options

• "How could you cut burn by 30%?"
• "What could you charge for today?"
• "What would you do if runway were half what it is?"
• "What's the path to breakeven?"

Making Decisions

• "What would you cut if you had to choose?"
• "What's the minimum viable team?"
• "What's essential vs. nice to have?"
• "What would a default alive version look like?"

Team & Hiring

Timing

• "Why hire now vs. wait?"
• "What work isn't getting done that this person would do?"
• "Could you outsource this instead?"
• "What's the cost of not hiring?"

Role Definition

• "What does success look like in 90 days?"
• "What skills are absolutely required vs. nice to have?"
• "What would this person do in their first week?"
• "How would you know they're performing well?"

Fit

• "What kind of person thrives at this stage?"
• "What values matter most?"
• "What would be a red flag?"
• "How will you evaluate culture fit?"

Co-Founder

• "What would a co-founder do that you can't?"
• "What's the risk of staying solo?"
• "What qualities would complement yours?"
• "How would you structure the relationship?"

Product Development

Direction

• "What's the most important thing to build next?"
• "How do you know that's what users want?"
• "What's the smallest version that would be useful?"
• "What would you cut if you had to ship in half the time?"

Quality vs. Speed

• "What's good enough for this stage?"
• "What are you over-engineering?"
• "What bugs can you live with?"
• "What would embarrass you vs. what would just be imperfect?"

Technical Debt

• "What's slowing you down?"
• "What would happen if you didn't fix this?"
• "What's the cost of fixing it now vs. later?"
• "Is this actually blocking progress, or is it bothering you?"

Fear & Self-Doubt

Acknowledging the Emotion

• "What are you afraid of?"
• "What's the worst that could happen?"
• "And then what would happen?" (Keep asking)
• "How bad would that actually be?"

Finding Evidence

• "What evidence contradicts your fear?"
• "When have you overcome something like this before?"
• "Who believes in you? What do they see?"
• "What would you tell a friend who felt this way?"

Building Courage

• "What would you attempt if you knew you couldn't fail?"
• "What's one small step you could take despite the fear?"
• "What's the cost of not acting?"
• "What would you regret not trying?"

Reframing

• "What could this experience teach you?"
• "How might this make you stronger?"
• "What's the opportunity hidden in this challenge?"
• "What would future you thank you for doing now?"

Burnout & Overwhelm

Assessing the Situation

• "How are you really doing?"
• "When did you last feel energized?"
• "What's draining you most?"
• "What are you not making time for?"

Creating Space

• "What would happen if you took a day off?"
• "What could you stop doing?"
• "What would you do if you weren't doing this?"
• "Who could help carry some of this?"

Finding Renewal

• "What recharges you?"
• "What did you used to enjoy that you've stopped doing?"
• "What would feel like a treat right now?"
• "What would 'sustainable' look like for you?"

Getting Support

• "Who can you talk to about this?"
• "What support do you need?"
• "What would help right now?"
• "Have you considered talking to someone professional?"

Accountability

Setting Commitments

• "What will you do?"
• "When exactly will you do it?"
• "How will you know it's done?"
• "On a scale of 1-10, how committed are you?"
• "What would make it a 10?"

Anticipating Obstacles

• "What might get in the way?"
• "What's happened before when you tried this?"
• "How will you handle that?"
• "What's your backup plan?"

Following Up

• "What did you commit to last time?"
• "What actually happened?"
• "What did you learn?"
• "What got in the way?" (If incomplete)
• "What will you do differently?"

Closing Questions

Consolidating Learning

• "What was most useful for you today?"
• "What are you taking away from this conversation?"
• "What shifted for you?"
• "What will you do differently as a result?"

Building Forward

• "What's your commitment for the next 48 hours?"
• "What support do you need?"
• "What should we talk about next time?"
• "Anything else we should cover before we wrap?"

Meta Questions

About the Coaching

• "What would make these conversations more useful?"
• "What kind of support is most helpful right now?"
• "What am I missing?"
• "What question should I be asking that I'm not?"

About Thinking Process

• "How are you approaching this decision?"
• "What's your thinking process here?"
• "What questions are you asking yourself?"
• "What would help you think more clearly?"

About Patterns

• "What patterns do you notice in yourself?"
• "When do you do your best thinking?"
• "What triggers you to get stuck?"
• "What have you learned about how you work best?"