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How can I tell if we’ve achieved true product-market fit? – Mentors can share signs they’ve seen when a startup really hits the mark (or conversely, warning signs it hasn’t) .What are we doing well in terms of understanding our customers, and what could we do better? – Reflecting on customer insight practices (user research, feedback loops) through your mentor’s lens may reveal gaps .Which metrics or KPIs do you recommend focusing on at this stage to gauge traction? – An experienced mentor can help you avoid vanity metrics and choose the numbers that matter .Have you seen a similar product or idea fail? If so, what went wrong? – Learning about comparable failures can highlight risks to mitigate (e.g. poor timing, distribution challenges, etc.).How would you critique our pricing or revenue model? – Money questions are tough; mentors might suggest pricing strategies or revenue streams you hadn’t considered .What’s one thing you’d improve about our product based on what you know? – This invites frank feedback. Even if your mentor isn’t a domain expert, a fresh set of eyes can yield valuable usability or value prop suggestions.In your experience, how do you balance building new features versus acquiring new customers in early stages? – Many founders struggle with product development vs. marketing trade-offs; mentors can share how they balanced “build it” and “sell it” .How did you gather and prioritize customer feedback when scaling up? – Tactics for customer development (interviews, surveys, beta tests) are useful to learn from someone who’s done it before.Who do you think is our ideal customer, and are we focusing on them enough? – Sometimes outsiders can spot a more lucrative niche or a segment that truly needs your solution, refining your ICP (Ideal Customer Profile) .If you were to stress-test our go-to-market strategy, what questions would you ask? – This meta-question encourages the mentor to poke holes in your sales/marketing approach (e.g. “Why will these channels work?”, “Do you have a plan B if CAC is too high?”).
How do you interpret our company’s mission and vision? – Gauge if your articulation is clear; a mentor’s feedback can show whether your “Why” resonates (à la Simon Sinek’s Start With Why ethos).What potential blind spots do you see in my business model or strategy? – Mentors with industry experience can often spot pitfalls or missing pieces that founders overlook.What would you do if you were in my shoes? – After explaining a challenge or decision you face, ask this to invite your mentor’s candid recommendations . It helps cut through theory to practical advice.Where do you see this industry or market heading in the next few years, and how can we prepare? (If your mentor is a domain expert) - Tapping your mentor’s strategic foresight can help you anticipate changes and stay ahead of the curve .If this were your company, what one thing would you prioritize right now? – Focus the mentor on identifying the most critical task or goal; their answer highlights what truly moves the needle.How did you approach strategic planning when you were at my stage? – Learning how an experienced entrepreneur set goals and adjusted strategy provides a template or at least reassurance that iteration is normal.What might winning look like for us in 5 years? – Have the mentor paint a picture of success from their perspective. This can clarify long-term objectives beyond the day-to-day grind and help you get and your mentor get aligned.Are there any strategic decisions you regret (or almost got wrong) in your own startup journey? What did you learn? – Lessons from mistakes are often the most memorable; mentors can impart wisdom by sharing war stories.Who else would you recommend I talk to? – Mentors often know specialists or other founders who can help. Asking for connections to other mentors or experts can exponentially expand your support network .If you could ask me one hard question about my strategy, what would it be? – Turn the tables. This invites the mentor to challenge you on an aspect you might be avoiding, surfacing valuable “unknown unknowns.”
What qualities should I look for in early hires or co-founders, based on your experience? – Hiring is critical and mentors can often pinpoint traits (resilience, learning ability, culture fit) that matter even more than hard skills at startup stage.How can I become a better leader for my team? – A humble but powerful question. Mentors might share leadership development tips or personal anecdotes about growing into the CEO role .Have you ever had to deal with co-founder conflict or team dysfunction? What did you do? – If you sense team tension, learning how mentors navigated conflict resolution can provide a playbook (or at least comfort that you’re not alone).How did you build and sustain your company culture early on? – Company culture often starts with the founder. A mentor’s stories of rituals or values they established can inspire ideas for your startup’s culture.What’s one mistake you see founders make in managing their teams? – Mentors who have observed many startups can usually list common management pitfalls (e.g. micromanaging, not communicating vision, delaying tough decisions on underperformers). Use this to self-check.When is the right time to delegate vs. stay hands-on? – Founders often struggle to let go. A mentor’s perspective on when they chose to hire or delegate (and how it worked out) can guide you in scaling your own role.How can I attract great mentors or advisors for specific needs (tech, sales, etc.)? – A bit meta, but mentors can advise you on bringing in additional expertise. They might suggest creating an advisory board or the best way to approach industry veterans.What are effective ways to motivate and retain the team when resources are tight? – Startups can’t always pay top dollar. Mentors may offer tips on using equity, mission, learning opportunities, and other creative motivators to keep morale high.How did you personally balance being decisive with being collaborative as a leader? – Being a strong decision-maker vs. seeking team input is a tricky balance. Hearing how an experienced founder earned trust and buy-in while still moving fast is instructive.If you were to hire for one key position for us right now, what role or profile would you prioritize? – Mentors might see a talent gap you’re overlooking (e.g. “You really need a product manager so you can focus on fundraising” or “Time to get a savvy CFO”).
Do you think we should bootstrap longer or consider fundraising sooner? Why? – A mentor who’s raised capital (or not) can weigh the pros and cons with you. This can clarify your financing strategy and ensure it aligns with your goals .What’s your read on our pitch or value proposition from an investor’s perspective? – If your mentor has investor insight, their feedback here is gold. Even if not, they might pinpoint jargon or assumptions that are unclear.What are the most common questions or concerns investors or partners might have about our business? – Seasoned mentors have sat through many pitches; they can play devil’s advocate so you can prepare answers (much like practicing with Y Combinator’s 250 question list!).Have you ever scaled a team or product too quickly or too slowly? What did you learn? – Timing growth is tricky. A mentor’s hindsight on hyper-growth pains or missed opportunities can help you calibrate your pace.How can we make our business more attractive to investors or strategic partners? – Beyond the pitch deck, mentors might suggest strengthening certain metrics, finding a lead customer, or de-risking some aspect to improve your bargaining position.What are some creative growth strategies you’ve seen work on a tight budget? – Mentors might share non-traditional hacks (viral loops, strategic partnerships, community-building) that you can try when resources are limited.What KPIs mattered most to you when convincing others to invest or join your company? – This can reveal which metrics or proof points you should focus on (e.g. user retention, revenue growth rate, LTV/CAC ratio) to show you’re on a winning track .At what point did you decide to scale operations or expand to new markets, and how did you know it was time? – Learning the signals that prompted a mentor to scale (or the mistakes if they jumped too early) can inform your own expansion plans.How would you approach our biggest growth challenge right now (e.g. low user acquisition, high churn, etc.)? – This invites your mentor to problem-solve on a specific issue, potentially drawing on analogous problems they’ve solved.What’s one thing not to do when pitching or seeking growth? – Sometimes knowing what to avoid (common faux pas or “red flags”) is as valuable as knowing what to do. Mentors might warn you against certain buzzwords, aggressive projections with no backing, or other mistakes they’ve seen founders make in growth mode .
Was there a time you felt you failed or hit rock-bottom as an entrepreneur? How did you bounce back? – Almost every founder faces dark moments. Hearing your mentor’s comeback story provides perspective and coping strategies (and reminds you failure is often a learning rite of passage) .How do you manage stress and avoid burnout? – Startup life is intense. Mentors can share their habits for self-care, time management, or maintaining mental health, which is crucial for long-term success .What’s the best career or life advice you ever received? – This often elicits a mentor’s guiding principle or mantra. For example, they might echo Bill Campbell’s focus on people, or a motto like “No failure, only learning”.How have your priorities or definition of success changed from when you were a first-time founder to now? – This invites reflection and can help you define success on your own terms, not just chasing what others chase.What do you do to keep learning and improving as a leader? – Great mentors are lifelong learners. They might recommend books, courses, or peer groups (even Plato and Socrates show up – e.g. practicing the Socratic method to sharpen thinking ). Take notes on resources that help you grow.How do you balance work with family or personal life? – Many founders struggle with this. A mentor’s honest discussion of how they juggled responsibilities or what they wish they’d done differently can offer guidance (or at least solidarity).In what ways should I get out of my comfort zone to grow faster? – Mentors might challenge you with something like: “Go talk to 10 customers face-to-face” or “Start writing publicly about your journey”. These stretch goals can catalyze personal and professional development.What are my strengths as you see them? And what’s a blind spot I should work on? – A mentor’s external view can validate what you’re great at (so you double down on it) and gently point out a weakness you might not realize (so you can address it). Self-awareness is key, and a good mentor will be honest here .How can I be a better mentee for you or others? – This humble question shows you value the relationship. Mentors might suggest being more proactive, following up on advice given, or other ways to improve the mentor/mentee dynamic. It demonstrates the mutual respect Michael champions.Is there anything you wish your younger entrepreneurial self had asked your mentors? – This meta-question can surface issues that mentees often neglect. Your mentor might say, “I wish I had asked for more feedback on my leadership style” or “…understood finance earlier”, which in turn might prompt you to explore those areas now.
What are you doing really well that is helping you get closer to your goal? – A positive reinforcement question from the Chopra/Tjan framework . It makes the founder inventory their strengths and recent wins. A mentor might follow up with “How can you double down on those strengths?” to leverage what’s working.What are you not doing well that is preventing you from getting there? – The flip side, directly from Tjan’s five questions . This encourages honest self-assessment of weaknesses or obstacles. If the founder struggles to answer, the mentor might gently share observations (“From our talks, I sense time management has been an issue – would you agree?”). Identifying these gaps is crucial for improvement.What is the single biggest challenge you’re facing right now? – A mentor classic. Founders often have a laundry list of issues; forcing a choice of the top challenge helps focus the discussion (and the founder’s energy). Once identified, the mentor can drill deeper or help prioritize tackling it.Why is this challenge so challenging – what have you tried so far? – A follow-up to get context. By explaining their attempts and why they think something is hard, the founder often uncovers assumptions or insights. The mentor can identify if perhaps a different approach or mindset is needed.What’s one thing in your business that you know you need to fix or improve, but haven’t gotten around to yet? – This surfaces procrastinated issues (technical debt, a difficult conversation, etc.). A mentor can help probe why it’s been avoided and how to address it. Often, that “one thing” is a source of stress that once tackled, frees up momentum.How do you handle the things you’re not good at? – The reality check on delegation and self-awareness. Founders often try to do everything. If a founder admits, for example, “I’m bad at finance and kind of ignoring it,” the mentor can strongly advise a remedy (find a part-time CFO or bone up on basics). This question nudges founders toward leveraging strengths and getting help on weaknesses – a hallmark of mature leadership .Are there any decisions or areas where you feel out of your depth? – A safe way for a founder to admit they’re unsure or inexperienced. It could be hiring, marketing strategy, technical scaling – whatever it is, acknowledging it lets the mentor step in with targeted guidance or suggest resources. It builds trust, as the mentor is implicitly saying “It’s okay not to know everything – let’s figure it out.”What have you learned about yourself in the last 6 months running this startup? – A variant of a question Bert Gervais calls a “whopper” for revealing self-awareness . Insightful founders will share personal growth points or newly discovered limits. If they struggle to answer, that itself is telling – it might prompt a conversation about reflection and learning practices.Who on your team (or in your support network) is your go-to person to compensate for your weaknesses? – Checks if the founder has surrounded themselves with complementary strengths or advisors. If they haven’t, it leads to discussing how to fill that gap (maybe the mentor themselves can fill one, or introduce someone who can). If they have, it affirms they know how to leverage others and the mentor can encourage more of it.If I asked your co-founder or team to name a challenge in how you lead or work, what might they say? – This indirect approach encourages empathy and awareness of how others see the founder. It might surface issues in communication, delegation, or work style that the founder knows at some level but hasn’t addressed. A mentor can then explore those in a constructive way (sometimes suggesting the founder actually ask their team for feedback as an action item).
What is it that you really want to be and do? – The ultimate vision question . This helps the founder articulate their true north: not just what the business does, but what kind of entrepreneur (and person) they aspire to become.Why are you pursuing this venture – what drives you? – A purposeful “why” can sustain founders through tough times. Asking this uncovers their core motivation (passion, a problem they can’t ignore, a vision of impact) and reconnects them to their mission when things get chaotic.How do you define success for yourself and for the company? – Mentors use this to check if the founder has clear and realistic goals. It may reveal mismatches (e.g. chasing vanity metrics vs. sustainable growth) and allows a discussion on aligning personal fulfillment with business outcomes.If everything went perfectly, where do you see the company in 5 years? – This encourages the founder to articulate a long-term vision. A mentor can then gauge if the strategy and short-term actions align with that vision, or gently challenge any inconsistencies.What keeps you up at night when you think about your business? – A way to get the founder to voice their deepest anxieties or biggest unknowns. It surfaces the nagging issues they might not volunteer otherwise, opening the door to address those directly (or put them in perspective).Who are your role models or mentors (past or present)? – Understanding who the founder admires can tell a mentor a lot about their values and perhaps their leadership style aspirations. It can also segue into discussing traits of successful founders and how to cultivate them.What do you not want your startup to become? – An unusual question that flips perspective to negatives or cautionary outcomes. Founders often have lines they don’t want to cross (e.g. “I don’t want us to sacrifice quality for growth”). Knowing these can guide the mentor in framing advice consistent with the founder’s values.If you had to pitch your vision in one sentence, what would it be? – A test of clarity. If the founder struggles, that signals an opportunity to refine the vision/story (which the mentor can assist with). If they succeed, it reinforces focus.What personal goals or growth areas are you hoping this startup journey will help you achieve? – This reminds both mentor and founder that the founder’s personal development is part of the equation. Maybe they want to become a better leader, or learn a specific skill. The mentor can then tailor guidance to those personal aims as well.How will you know when it’s time to declare victory (or time to walk away)? – This can be provocative, but it’s important. Founders seldom think about exit criteria for success or failure. Discussing this encourages strategic thinking: what milestones justify doubling down versus reconsidering the path. It frames the journey as one of learning, not just an endless grind.
What hypothesis are you testing right now in your business? – A very Socratic question. It gets the founder to articulate the assumptions they are currently validating (e.g. “We believe customers will prefer X feature enough to pay for it”). If they aren’t sure, the mentor can emphasize the importance of always having a hypothesis to test (lean startup style), to keep learning fast.
Startup Secrets Sandbox
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Mentorship Resources for Startups
Fifty fifty!
Below you’ll find 50 hopefully great questions for founders to ask mentors and fifty for mentors to ask founders. They're only great if they work for you so please just use them as starting points for your needs. Given mentorship deserves to be mutual hopefully both sets of questions will serve you in your mentorship journey Enjoy and please comment and share your learning so we can share your experience!
50 Great Questions for Founders to Ask Mentors
One of the best ways for founders to extract value from mentors is by asking excellent, specific questions. As Michael often says, the right question can unlock a breakthrough. Below are 50 curated questions a founder can ask a mentor, grouped by topic. These cover strategic, operational, and personal domains – helping you tap into your mentor’s experience and insight. Please adapt them to your own context.
(Tips: Don’t try to ask all of these at once! Pick a few relevant ones per meeting, and always listen deeply to the answers. But as Michael would say, also question the answers. Make sure they are appropriate for YOU. And even then, take them as input and form your own answers. )
Remember the Startup Secrets principle:
Startup Secret: Ultimately the best advice is your own.
Product & Market
Vision & Strategy
Team & Leadership
Growth & Finance
Personal Growth & Balance
These questions will help ensure your mentor meetings are productive and engaging. Remember Michael Skok’s guidance: approach mentorship with curiosity, openness, and the confidence to ask even the “dumb” questions. Often, the questions you ask determine the quality of the answers – and the quality of the mentorship.
50 Great Questions Mentors Can Ask Founders
Just as founders should come prepared with questions, great mentors know that asking the right questions is one of the most powerful tools to guide a founder’s learning. Rather than handing out solutions, adept mentors use questions to prompt reflection, test assumptions, and help entrepreneurs discover answers for themselves .
(Mentor Tips: We wouldn’t recommend that you rapid-fire these; pick judiciously based on context. And listen intently – often the founder’s answers will lead to the next question. And remember you don’t have the answers! Encourage the mentees to find their own answers. Follow the Startup Secrets principle that the best advice is the advice the mentees form as their own advice.)
Here are 50 questions (grouped by theme) that mentors can use to unlock insight and “teach founders to fish,” inspired by frameworks like the 5 Deepak Chopra questions and the Socratic method. These assume a trusting mentor–mentee relationship where frank, caring inquiry is welcome.
Strengths, Weaknesses, and Challenges
Vision and Goals
Strategy and Execution
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