Conversation 1: “Help Me Figure This Out”
How You’d Actually Say It:
“Hey, I’m thinking about starting an online course business, but honestly, I’m not sure if it’s a good idea. I know [your topic] really well, but there seem to be a lot of people already teaching this stuff. Can we just talk through whether this makes sense? I don’t want to waste six months building something nobody wants.”
Why This Works:
- Natural, conversational tone
- Admits uncertainty (which gets better advice)
- Asks for help thinking, not doing
- Shows you value your time
The Kind of Response You’ll Get:
Strategic discussion about market validation, positioning, and realistic assessment of your situation.
Conversation 2: “I’m Stuck on Something”
How You’d Actually Say It:
“I’ve been going back and forth on this and I can’t figure it out. Should I start with a course, or should I do coaching first? I keep reading different advice and I’m getting paralyzed. My situation is [describe your reality]. What would you do if you were me? And can you help me think through the pros and cons?”
Why This Works:
- Acknowledges you’re overthinking
- Asks for personalized advice
- Invites a back-and-forth discussion
- Shows you want guidance, not just information
Conversation 3: “Challenge My Thinking”
How You’d Actually Say It:
“I’ve been planning this course about [topic] for [audience], and I’m pretty excited about it. But before I dive in, can you poke some holes in this idea? What am I not seeing? What could go wrong? I’d rather you tell me the hard truths now than discover them after I’ve built everything.”
Why This Works:
- Invites honest feedback
- Shows you’re open to being wrong
- Prevents costly mistakes
- Gets strategic input, not validation
Conversation 4: “Walk Me Through This”
How You’d Actually Say It:
“I want to understand something better. Let’s say I do decide to create this course – what should the student experience actually look like? I mean, from the moment they first hear about me until they’re getting results. Can we map that out together? I want to make sure I’m thinking about this holistically.”
Why This Works:
- Asks for collaborative thinking
- Shows big-picture awareness
- Invites step-by-step discussion
- Focuses on student success
Conversation 5: “Give Me Your Honest Opinion”
How You’d Actually Say It:
“Okay, I need some straight talk. I’ve been creating content for [time period] and I have [audience size], but I’m not making the money I want. Looking at my situation honestly, what do you think the real problem is? Am I focusing on the wrong things? Be direct with me – what would you change if this was your business?”
Why This Works:
- Asks for honest assessment
- Shows willingness to face reality
- Invites constructive criticism
- Focuses on solutions
Conversation 6: “Reality Check My Numbers”
“I need someone to sanity-check my business projections. I’m thinking I can get to $10K/month within 6 months by selling a $500 course. Based on typical conversion rates and the fact that I currently have [your audience size] followers with [engagement level], does this seem realistic or am I being overly optimistic? Break down what would actually need to happen for me to hit that number.”
Why This Works:
- Provides specific metrics for analysis
- Asks for industry benchmarks, not just opinion
- Invites reality-based pushback on optimistic projections
- Forces you to understand the actual math behind your goals
Conversation 7: “Help Me Spot My Blind Spots”
“I’ve been in my industry for [X years] and sometimes I think I know what people need, but maybe I’m too close to it. Can you help me identify assumptions I might be making about my audience that could be wrong? What questions should I be asking my potential customers that I probably haven’t thought of? I want to make sure I’m not building something based on my own biases.”
Why This Works:
- Acknowledges expertise can create blind spots
- Asks for uncomfortable truths, not validation
- Shows self-awareness about potential biases
- Gets outside perspective on insider assumptions
Conversation 8: “Positioning Dilemma”
“I’m stuck between two different positioning strategies and I can’t decide. Option A is [describe approach] which feels safer but maybe more crowded. Option B is [describe approach] which feels riskier but more unique. Given what you know about market positioning and my situation, how would you think through this decision? What factors should I be weighing most heavily?”
Why This Works:
- Presents real strategic choices with trade-offs
- Asks for decision-making framework, not just answers
- Shows understanding that positioning involves risk assessment
- Invites systematic thinking about complex choices
Conversation 9: “Scale vs Quality Trade-offs”
“I’m at a crossroads. I can keep doing what I’m doing and maintain high quality but limited reach, or I can systematize and scale but I’m worried about losing the personal touch that makes my students successful. How do other successful education businesses handle this transition? What would you prioritize if you were trying to grow without sacrificing results?”
Why This Works:
- Addresses real growth dilemma all successful educators face
- Asks for industry examples and proven approaches
- Shows you understand that scaling involves sacrifices
- Seeks strategic prioritization, not just growth tactics
Conversation 10: “Pricing Psychology Discussion”
“I’m struggling with pricing strategy and I think it’s more psychological than logical. I know my course delivers value, but I feel weird charging premium prices. At the same time, I don’t want to undervalue what I offer. Can we talk through the psychology of this? How do I get comfortable with charging what I’m worth while still feeling good about serving my audience?”
Why This Works:
- Admits psychological barriers, not just logical ones
- Asks for help with internal conflict, not just external strategy
- Shows awareness that pricing is emotional, not just mathematical
- Seeks mindset shifts along with tactical advice
Conversation 11: “Competitive Moves”
“Someone just launched a course that’s very similar to what I was planning. It’s got me second-guessing everything. Should I pivot, double down on what makes me different, or wait to see how their launch goes? How do you think about competitive moves in education businesses? What would be the smartest strategic response here?”
Why This Works:
- Presents real-time competitive pressure scenario
- Asks for strategic thinking, not emotional reassurance
- Shows understanding that competition requires strategic response
- Seeks principled approach to competitive decisions
Conversation 12: “Customer Success Optimization”
“My course completion rates are around [X%], which I think is typical, but I want to do better. Let’s think strategically about this – what are the real reasons people don’t finish courses, and how could I redesign my approach to address those issues? I’d rather have fewer students who get amazing results than more students who don’t finish.”
Why This Works:
- Focuses on student outcomes over revenue metrics
- Asks for root cause analysis, not quick fixes
- Shows willingness to sacrifice quantity for quality
- Invites systematic problem-solving approach
Conversation 13: “Business Model Evolution”
“I started with courses, but I’m wondering if I should add coaching, consulting, or maybe even a certification program. How do I think about evolving my business model without getting distracted or overcomplicating things? What would be the most logical next step given my current success and resources?”
Why This Works:
- Shows growth mindset while acknowledging complexity risks
- Asks for systematic expansion approach
- Seeks logic-based decisions, not opportunity-chasing
- Invites resource-aware strategic planning
Conversation 14: “Authority Building Strategy”
“I want to be known as THE expert in [your niche], not just another course creator. Beyond just creating good content, what would a strategic authority-building plan look like? How do the people who become recognized thought leaders actually make that happen? What would you focus on if establishing authority was the primary goal?”
Why This Works:
- Sets ambitious but specific positioning goal
- Asks for systematic approach beyond content creation
- Seeks understanding of actual thought leadership strategies
- Invites long-term strategic thinking
Conversation 15: “Exit Strategy Thinking”
“This might sound premature, but I want to build this business in a way that could eventually run without me or be valuable to someone else. How should that thinking influence the decisions I’m making now about systems, branding, and business model? What makes an education business sellable versus just a personal brand job?”
Why This Works:
- Shows sophisticated business building mindset
- Asks how future goals should influence current decisions
- Seeks understanding of business value creation
- Invites systems thinking over personal brand dependency
What Makes These “Advanced”:
- Strategic complexity – Multiple variables to consider
- Business sophistication – Real growth challenges
- Psychological depth – Internal barriers and mindset issues
- Long-term thinking – Beyond just immediate tactics
- Competitive awareness – Market dynamics and positioning
- Systems thinking – How decisions interconnect