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
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?”).
Vision & Strategy
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.”
Team & Leadership
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”).
Growth & Finance
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 .
Personal Growth & Balance
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.
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
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).
Vision and Goals
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.
Strategy and Execution
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. Why do you believe this strategy is the right one? – Simply asking “Why?” – as Brad Feld notes, even in response to an answer – forces deeper reasoning . If a founder says, “We’re focusing on enterprise clients now,” a mentor asking “Why is that your focus?” can reveal whether the strategy is driven by real insight (e.g. inbound demand, higher LTV) or possibly a weak premise. It might expose gaps to address or reaffirm the logic once they explain. What would you do differently if you had an unlimited budget (or a smaller budget)? – A thought experiment that can reveal creative strategies. Sometimes constraints blind us to options; by toggling the scenario, mentors spur founders to think outside the box. The answers may contain seeds of an idea that’s actually feasible at some scale. Have you considered any alternative paths or pivots? What would trigger a pivot for you? – This assesses flexibility. A founder bent on one idea may not have thought through Plan B or signals for change. The mentor isn’t necessarily suggesting a pivot, but probing if the founder is aware of other options and what conditions might warrant them (new info, lack of traction after X time, etc.). It encourages a mindset of adaptability rather than stubbornness. How are you prioritizing what to do next? – Founders can be overwhelmed by to-do lists. A mentor asking this expects the founder to articulate their decision-making process for priorities. The mentor can then offer feedback: perhaps they see a critical task not on the list, or maybe the founder is spread too thin. It’s an opening to instill focus (e.g. using frameworks like OKRs or ICE scoring, if appropriate). What would happen if [assumption] turns out to be false? – Identify a key assumption and poke it. For instance, “What if users don’t behave the way you expect?” or “What if your sales cycle is twice as long?”. This question isn’t to induce pessimism, but to stress-test the plan. It teaches the founder to have contingency plans and not marry assumptions. Often it leads to “How can we test that assumption sooner?” – a very constructive outcome. What is your unfair advantage (or what do you wish it were)? – This makes the founder define or seek a competitive edge. If they struggle to name one, it’s a flag that their strategy might need sharpening. A mentor can follow up with brainstorming how to create an edge (unique tech, proprietary data, niche focus, etc.). If they have one, then the discussion shifts to how to capitalize on and defend it. How do you decide to say no to opportunities or ideas? – Strategy is often as much about what you don’t do. This question checks if the founder has criteria or the discipline to avoid shiny objects that distract from core goals. A mentor might share how they filtered opportunities and stayed on strategy, reinforcing the importance of a clear roadmap. If a much bigger competitor entered the scene tomorrow, what would you do? – A scenario planning question. It tests agility and strategic thinking under threat. The founder’s answer can lead to insight on their perceived strengths (e.g. “we’d double down on our niche/customers/community”) or weaknesses. The mentor can then discuss competitive strategy, differentiation, or defensive tactics. What’s your plan for the next 90 days, and how will you measure if it’s working? – This grounds the conversation in execution. A good mentor will often funnel high-level talk into an action plan. If the founder has a concrete 90-day plan, the mentor can critique or refine it. If not, they can help shape one with clear milestones or OKRs. This question ensures the mentorship translates to accountability and results, not just theory.
Learning and Reflection
What’s the biggest lesson you’ve learned from a customer or user recently? – Keeps the founder thinking outside-in. If they can quickly answer with something a customer taught them (good or bad), it shows a healthy learning loop. If not, the mentor might encourage more customer interactions or empathy work. It underscores that startups are ongoing experiments and the founder should be synthesizing learnings continuously. Can you tell me about a recent decision that didn’t turn out as expected? What did you learn from it? – This normalizes failure as learning . A founder might share a small failure (a marketing campaign flop) or larger one. The mentor listens for insight extraction – did the founder identify why it went wrong and how to adjust? If not, the mentor can guide a post-mortem discussion. This builds the founder’s ability to iterate and not fear mistakes. What do you know now that you wish you knew when you started this venture? – Encourages reflection on the journey so far. The answer could reveal how the founder has grown or how their perspective changed (e.g. “I wish I knew how important distribution is versus product”). Mentors can validate these insights and possibly share when they learned similar lessons in their own journey (creating a bonding moment and reinforcing the value of learning early). How do you personally learn new things relevant to your business (e.g. new skills, industry knowledge)? – A mentor asks this to assess the founder’s learning habits. Are they actively seeking knowledge (through books, courses, advisors) or just learning by brute force? If the latter, the mentor can recommend resources or more structured learning, stressing that continuously upgrading one’s skills is part of the job. When you encounter a problem you don’t know how to solve, what’s your approach? – This reveals whether the founder is resourceful and coachable. Maybe they say “I Google for answers or reach out to someone who might know” – good. Or “I try random things until something works” – potentially inefficient, an opportunity to suggest better problem-solving methods or using frameworks. The idea is to ensure the founder is not going it alone on tough problems when help exists. What’s an assumption you had about your business or the market that has changed as you’ve gained experience? – Highlights adaptive learning. Startups often pivot or refine assumptions (customer behavior, pricing, etc.). If a founder can identify such a shift, it shows flexibility and learning. If they insist all initial assumptions were right, that’s either great foresight or a red flag of being oblivious to new info. A mentor can gently challenge a lack of evolution. Do you actively seek feedback from your team, customers, or peers? What’s the most recent feedback that surprised you? – This checks if the founder has feedback loops. Surprising feedback indicates openness to listening and being proven wrong. A founder might share, “My lead engineer said our sprint planning was chaotic – I didn’t realize that.” A mentor would applaud the engineer’s candor and ask, “What will you change about it?”, reinforcing a culture of feedback. If the founder isn’t getting feedback, the mentor might stress creating opportunities for it (e.g. anonymous team retros, user surveys). If you could ask me (the mentor) one question that you’ve been hesitant to ask, what would it be? – Turning it around invites the founder to voice something they might be shy about – perhaps a sensitive topic like handling co-founder equity or even asking the mentor for more help. It builds trust. As Michael Skok often demonstrates, humility and approachability in a mentor encourages mentees to open up. This question signals, “No question is off-limits – I’m here to help.” How do you unwind or reflect outside of work? – Mentors know that constant hustle without reflection leads to burnout and shallow thinking. Asking this nudges the founder to articulate their reflection routine (journaling, talking with a peer, etc.) or lack thereof. If they don’t have one, the mentor might suggest they incorporate some reflection time. Often breakthroughs come away from the laptop – during a walk, in conversation – so a mentor might share how they did their best thinking while jogging or via a weekly “think hour,” encouraging the founder to give it a try. What are you hoping to learn in the next 6 months, and how can I (or others) help you with that? – This wraps up a reflective set by focusing on future learning goals. It shows the founder that mentorship is not just about firefighting current issues but also about growth and development. By explicitly asking how you or your network can assist, it reinforces the mentor’s role as a connector and coach for the founder’s continuous learning journey.
Support and Next Steps
What will you do differently tomorrow based on our conversation today? – Direct from the five questions framework , this prompts immediate action. It ensures the discussion translates into at least one concrete change or experiment. It could be as simple as “I’ll reach out to that customer we lost and ask for feedback” or “I’ll block time to finally fix our pricing page copy”. Following up on this next time provides accountability. Where do you need the most help right now? – A straightforward offer of support, mirroring Chopra’s final question . It allows the founder to explicitly identify an area to lean on the mentor (or others). Whether it’s opening a door to an investor, feedback on a pitch, or just encouragement, the mentor can then respond to that need. Importantly, asking this regularly helps the founder practice asking for help – something first-time founders may be reluctant to do, but which is vital (and 100% okay, as Michael would encourage). Can you outline your plan for the next month (or quarter)? – Similar to the 90-day plan earlier but ensuring the founder can articulate immediate next steps and goals. The mentor isn’t there to micromanage, but by having the founder speak the plan aloud, it becomes more real. The mentor can then say, “Great, let’s touch base on how these are going”, implicitly agreeing to hold them accountable. If the plan seems off, the mentor can advise adjustments. Who on your team (or among your advisors) do you lean on the most, and are you leveraging them enough?– This question encourages the founder to not be a lone wolf and to utilize their “tribe.” If they have co-founders or key employees, are they distributing responsibilities well? If they have other advisors, are they asking them for input? A mentor might follow up: “Maybe involve your product lead more in strategy – it will free you up” or “Could your investor help with that introduction?”. It’s about ensuring the founder realizes they have support around them besides just the mentor. What would disappoint you if we talk again in 6 months and it hasn’t happened? – This flips to the founder’s own expectations of progress, which can be revealing. Perhaps they’d be disappointed if they haven’t launched, or hit $X revenue, or resolved a certain issue. Knowing this, a mentor can calibrate advice (maybe the goal is unrealistic, or maybe it should indeed be a priority to avoid that disappointment). It also subtly asks the founder to set a goal without framing it as a goal – sometimes an emotional frame (“I’d be really bummed if…”) surfaces what they truly care about. Are there any questions I haven’t asked that you think I should? – A meta-question that empowers the founder to point out areas the mentor might be missing. It shows humility (“I don’t know what I don’t know about your situation”). The founder could respond with, “Well, we haven’t talked about our marketing, which I think is a big gap for me.” That gives the mentor a cue to dive into a new topic. It ensures the mentor’s questioning isn’t inadvertently neglecting something important to the mentee. How can I be most useful to you as a mentor? – An explicitly humble question that Michael himself might ask. It invites the founder to guide the mentorship. They may say, “Honestly, I just value your encouragement and big-picture perspective” or “I could really use more specific feedback on my sales approach”. This helps the mentor tailor their style to the founder’s needs (some need cheerleading, some need tough love, some need network access, etc.). It keeps the mentor in a stance of service, reinforcing that the mentee’s success is the measure of mentoring . What would you do if I (or another mentor) weren’t here to advise you? – This is a gentle challenge to bolster the founder’s self-reliance and decision-making. It’s not to make the mentor obsolete, but to push the founder to trust their own judgment. After they answer, a mentor might say, “That sounds like a solid approach – you had it in you all along!” or if the answer is way off, use it as a coaching moment: “Okay, let’s refine that approach so you’d be set even without advice.” It underlines the mentor’s goal: to make the founder capable of mentoring themselves in the long run. Can you teach me something you’ve learned about your business/market? – This flips roles and signals deep respect for the founder’s expertise. It embodies mutual mentorship – acknowledging that the mentor can learn from the mentee . Maybe the founder shares a trend or a technical insight the mentor wasn’t aware of. This not only boosts the founder’s confidence but also keeps the mentor humble and engaged. Michael often highlights learning with and from entrepreneurs – this question puts that into practice, creating a reciprocal exchange . What’s one question you think I should ask you in our next session? – Closing the loop, this gets the founder to actively think about their own accountability. If they say, “Ask me if I finished the prototype”, that’s a commitment. It turns into a to-do for them and a built-in follow-up for the mentor (“Next time, I will indeed ask if that prototype is done”). It empowers the founder to set the agenda and anticipate progress, aligning expectations for the next meeting.
These mentor questions echo the principles of Socratic inquiry and Michael Skok’s “gift of mutual mentorship” approach: they are open-ended, thought-provoking, and aimed at helping the founder arrive at their own insights and decisions . A mentor who utilizes questions like these isn’t just giving answers – they’re building the founder’s capacity to think critically and independently, which is the ultimate goal of mentorship.
Acknowledging the Voices That Inspire Better Mentorship
In the spirit of shared learning and mutual mentorship, Startup Secrets humbly acknowledges and thanks the following authors, thinkers, entrepreneurs, and organizations whose insights have shaped and enriched our understanding of startup mentorship. These resources complement our own materials and reflect the wisdom of a much broader community committed to supporting founders on their journey.
Articles, Essays, and Frameworks
David Cohen & Brad Feld – The Mentor Manifesto (Techstars)
A foundational set of principles from the Techstars community reminding us to be Socratic, give-first, and always mentor with humility.
Anthony Tjan – Five Questions Every Mentor Must Ask (Harvard Business Review)
An elegant framework encouraging mentors to guide founders through reflection and self-awareness.
Whitnie Low Narcisse – We Studied 100 Mentor–Mentee Matches—Here’s What Makes Mentorship Work (First Round Review)
A data-driven perspective on what makes mentoring relationships thrive, including thoughtful structure and mutual accountability.
Jessica Stillman – What Socrates Can Teach You About Mentorship (Inc. Magazine)
Featuring Brad Feld’s reflections, this article applies Socratic thinking to startup mentoring with humility and curiosity.
Foti Panagiotakopoulos – Why You (Probably) Shouldn’t Be a Startup Mentor (GrowthMentor Blog)
A provocative but essential reminder that great mentorship starts with self-awareness and a genuine give-first mindset.
Angelina Graumann – Should Your Startup Have Mentors? (Visible.vc)
A founder-friendly guide exploring the benefits, expectations, and boundaries of startup mentorship.
Natalie Clarkson – Richard Branson: How to Find a Mentor (Virgin.com)
Practical, down-to-earth guidance from Richard Branson on how to approach and build authentic mentoring relationships.
First Round Review Editors – How to Be a Career-Changing Mentor: 25 Tips from the Best Mentors We Know
A collection of tactical and reflective practices from seasoned mentors across the startup ecosystem.
Micah McGuire – 98 Must-Ask Questions for Your Startup Mentor (GrowthMentor Blog)
A highly practical resource offering founders a ready-to-use playbook of mentoring questions across startup domains.
Books & Long-Form Wisdom 📖
Eric Schmidt, Jonathan Rosenberg & Alan Eagle – Trillion Dollar Coach: The Leadership Playbook of Silicon Valley’s Bill Campbell
I was lucky enough to attend the tribute to Bill upon his passing when I lived in Silicon Valley. It deeply touched me. This book is a wonderful gift passed down from the late Bill Campbell, whose mentorship of tech legends shows that leading with heart, honesty, and humility can scale not just companies, but people.
A Word of Thanks
These voices, frameworks, and stories complement the Startup Secrets approach to mentorship by echoing our belief that mentoring is not about having the answers—it’s about asking the right questions, walking alongside founders, and growing together. We share these not as the definitive list, but as a starting point for anyone seeking to learn the art of mentorship in service to others.
A personal request
If you’ve benefited from these resources, I encourage you to pay it forward—and consider becoming a mentor yourself. The startup journey is never walked alone, and my hope for startup mutual mentorship is that no entrepreneur ever feels alone and no mentor goes unrewarded.
Thank you for even reading all this!
Happy venturing, Michael
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