# 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?"