oldwinter Finding Mentors & Sponsors
Category: Career
Source: https://refoundai.com/lenny-skills/s/finding-mentors-sponsors
Finding Mentors & Sponsors | Refound AI
Lenny Skills Database SKILLS PLAYBOOKS GUESTS ABOUT SKILLS PLAYBOOKS GUESTS ABOUT Career 19 guests | 23 insights
Finding Mentors & Sponsors Career acceleration depends less on finding one perfect mentor and more on building a diverse network of advisors, sponsors, and peers who can provide different types of support. Mentors give advice; sponsors put their professional capital on the line to bet on you. Both matter, but sponsorship is often what unlocks the biggest opportunities.
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The Guide 6 key steps synthesized from 19 experts.
1 Build a stable of mentors, not a single oracle Don't wait for one perfect mentor who matches your exact path. Instead, create mental 'emulators' of multiple leaders whose specific strengths you can draw upon for different situations. Spread your meetings across the month so you always have someone to turn to. This approach provides more resilient support and diverse perspectives.
Featured guest perspectives
"It's actually better to have a stable of mentors. You want to have three or four. And ideally, what you do is you meet with each one of them once a month on a different Friday of the month."
— Bangaly Kaba "I had everything I needed, people were so kind and generous, but I didn't recognize it that way because we talk about it differently... Build 'emulators' of different leaders in your head to load their specific skillsets (e.g., 'What would Boz do here?')."
— Ami Vora "Get a personal board of directors... get people who will give you advice, give you social support, and hold you accountable."
— Jeffrey Pfeffer 2 Don't ask for mentorship directly—start small and offer value Formal mentorship requests feel like a burden. Instead, build relationships organically through tiny, specific asks that can be answered in under two minutes. Find ways to be helpful first. When you do reach out, come with a concrete problem rather than a vague request. Always follow up to show how you applied their advice.
Featured guest perspectives
"The first rule of thumb is, don't ask a person to be your mentor. That's really awkward. First, identify them. Say, this is a person I think that could be helpful to me. And then, find ways to be helpful. Everybody needs help."
— Gibson Biddle "Make the smallest ask possible... 'Hey, thanks so much for speaking today... Is there an example of product that you think was created with this approach?' Something he could answer in literally two minutes via email."
— Jules Walter "Never ask someone to be your mentor... the more it can be organic where you talk to somebody, you have actual advice that you want... reach out when you actually have a problem."
— Melissa Tan 3 Extract frameworks, not just answers When you get advice, don't just take it at face value. Be relentlessly curious about the 'why' behind the recommendation. Ask follow-up questions to understand the underlying mental model. This helps you apply their wisdom to situations they haven't anticipated, rather than misapplying specific anecdotes to different contexts.
Featured guest perspectives
"When you ask for advice, don't just ask what to do but why. Be an obnoxious two-year-old kid, why? Why? Why? Why? And really try to understand the framework that someone is using to give you advice."
— Bret Taylor "Brian would go to experts and say to the expert, 'I don't know what the hell I'm doing.' He did that with me when it came to hospitality. I appreciated that a guy who had a lot of hubris... could also have the humility to say, 'I want to learn more about this.'"
— Chip Conley 4 Distinguish between mentors and sponsors—and actively cultivate sponsors Mentors give you advice. Sponsors put their professional reputation on the line for you—recommending you for roles, giving you high-stakes opportunities, and advocating for you in rooms you're not in. Sponsors matter more for career acceleration. Build trust with potential sponsors by solving their hardest problems and demonstrating you're a high-ROI investment.
Featured guest perspectives
"When I think about the people in my life, who... the time that they donated to me... I would actually describe those folks as being sponsors and advocates, people who were willing to put up capital, whether that's professional, social capital to bet on you."
— Christopher Miller "I think of this as sponsorship, not mentorship... what I do have is a couple examples of people who deeply trusted me to solve big problems... it's about creating trust and knowing that you have a sponsor there, someone who's going to go to bat for you."
— Fareed Mosavat 5 Hire advisors and coaches for targeted skill acceleration Don't rely solely on organic relationships. Paid advisors and coaches provide structured, focused development. Interview multiple coaches to find the right fit. Use advisors for specific challenges like fundraising pitches, growth strategy, or navigating hyper-growth phases. Even one hour a week with the right expert can be transformative.
Featured guest perspectives
"Not hiring advisors is something that I do not recommend for you to do. You can get access to anybody for one hour a week. Yeah, you'll have to pay them... but hiring advisors is the biggest career amplification and your business amplification can possibly do."
— Elena Verna "The equivalent of that in your life is an executive coach... Number one, make space to ask yourself the big questions in life about your career, your relationships, your health... And then part two is that person can hold you accountable."
— Graham Weaver "If you're thinking about getting a coach... talk to two or three different coaches. And really get a sense of their vibe and how well you get to know them... half of people that founder their coach literally went with the first coach that they talked to."
— Ada Chen Rekhi 6 Leverage peer communities and 'dead or distant mentors' Join coaching circles with peers at similar career stages for shared learning and validation. Also study historical leaders through their original talks, letters, and interviews to build 'distant mentors' who inform your decisions. You don't need to meet someone to learn from their specific approach to challenges.
Featured guest perspectives
"I'm in a lean-in group and we are just like, we support each other. I'm in a coaching circle in YPO, so that's a group of CEOs... which give you an opportunity to learn from each other and to get pure coaching."
— Deb Liu "One of the ways that everyone listening to this podcast today can get a mentor, you can get what I call a dead or distant mentor. Warren Buffett is my mentor, he just doesn't know it... if you really study that moment and study what Jobs did, it can inform your decisions and actions."
— Phyl Terry "I think community as a way of creating safety, having authentic conversations, feeling that you're not alone, that others are going through the same thing, and then sharing best practices is so powerful."
— Nikhyl Singhal
✗ Common Mistakes
Waiting to find one perfect mentor who matches your exact life pathAsking 'Will you be my mentor?' instead of starting with a specific, low-effort questionTaking advice at face value without understanding the underlying frameworkFocusing only on mentors (advice-givers) while ignoring sponsors (opportunity-creators)Not following up to show how you applied their guidance ✓ Signs You're Doing It Well
You have 3-4 people you can reach out to for different types of guidanceMentors proactively send you opportunities without being askedSomeone advocates for you in a room you weren't inYou can quickly explain the decision-making framework of your mentors, not just their adviceYour outreach messages get high response rates because they're specific and easy to answer
All Guest Perspectives
Deep dive into what all 19 guests shared about finding mentors & sponsors.
Ada Chen Rekhi 1 quote
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"If you're thinking about getting a coach... talk to two or three different coaches. And really get a sense of their vibe and how well you get to know them... half of people that founder their coach literally went with the first coach that they talked to." Tactical: Interview multiple coaches before committing to one.Use coaches for hyper-growth phases, sensitive interpersonal conflicts, or specific skill acceleration.Consider 'niche' coaches for short-term goals like fundraising pitches or writing.
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Ami Vora 1 quote
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"I think we tell women things like, you need to find a mentor and you need to find a sponsor, and that's just another set of hoops... I had the extreme generosity of so many wonderful leaders who helped me on my way, but I didn't feel like I had this mentor... I had everything I needed, people were so kind and generous, but I didn't recognize it that way because we talk about it differently." Tactical: Build 'emulators' of different leaders in your head to load their specific skillsets (e.g., 'What would Boz do here?').Don't feel pressured to find one perfect mentor who matches your exact life path.
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Bangaly Kaba 1 quote
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"It's actually better to have a stable of mentors. You want to have three or four. And ideally, what you do is you meet with each one of them once a month on a different Friday of the month." Tactical: Schedule meetings with different mentors on different Fridays of the month.Ask for mentors by describing a specific challenge you are trying to solve rather than asking for general mentorship.
View all skills from Bangaly Kaba →
Bret Taylor 1 quote
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"When you ask for advice, don't just ask what to do but why. Be an obnoxious two-year-old kid, why? Why? Why? Why? And really try to understand the framework that someone is using to give you advice." Tactical: Ask 'why' repeatedly to uncover the first principles behind a mentor's suggestionAsk 'who should I talk to get good advice?' to find consensus among experts
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Christian Idiodi 1 quote
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"You're going to find the loudest, most influential person in your organization, the person that everybody knows, knows everything, is in every meeting and stuff, and you're going to ask them to teach you. You're going to challenge them. And if they don't have the time to teach you, you're going to volunteer to help them." Tactical: Ask to sit in on a leader's meetings for a week just to observe.Offer to help a mentor with their tasks in exchange for the opportunity to learn their decision-making process.
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Chip Conley 3 quotes
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"Brian would go to experts and say to the expert, 'I don't know what the hell I'm doing.' He did that with me when it came to hospitality. I appreciated that a guy who had a lot of hubris... could also have the humility to say, 'I want to learn more about this.'" Tactical: Approach experts with a growth mindset and radical honesty about your knowledge gaps "Maybe that's what a mentor can be is a confidant, someone who gives you confidence and helps by asking questions, helps you as the younger mentee find your roadmap to success." Tactical: Act as a 'confidant' by building the mentee's confidence through inquiry "One of the things I loved at Airbnb... where I had something to teach them and they had something to teach me... mutual mentorships." Tactical: Seek 'mutual mentorships' where you trade skills with someone from a different generation or background
View all skills from Chip Conley →
Christopher Miller 2 quotes
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"Mentors are great, don't get me wrong... but when I think about the people in my life, who... the time that they donated to me... I would actually describe those folks as being sponsors and advocates, people who were willing to put up capital, whether that's professional, social capital to bet on you." Tactical: Differentiate between mentors (advice-givers) and sponsors (opportunity-creators)Build trust with potential sponsors by being coachable and delivering results on their behalf "putting ego aside and embracing not knowing stuff and embracing not being good at stuff, and not feeling self-conscious about that and letting the desire to be the best at something or at least be great at something overpower the fear of being inadequate at something." Tactical: Explicitly ask for hard feedback and respond with gratitude rather than defensivenessShow sponsors that you are a high-ROI investment by quickly applying their feedback
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Deb Liu 1 quote
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"I'm in a lean-in group and we are just like, we support each other. I'm in a coaching circle in YPO, so that's a group of CEOs. And I'm in a number of these coaching circles, which give you an opportunity to learn from each other and to get pure coaching. And I think that's a great place to start, especially early in your career when you're seeing the same people making the same mistakes." Tactical: Join or form a 'coaching circle' with peers at a similar career stage to share challengesUse peer groups to validate whether a challenge is personal or situational
View all skills from Deb Liu →
Elena Verna 2 quotes
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"Don't think that you have unique problems. You don't... Your problem has been solved by somebody. Or at least that there's a lot of failures on the problem that you should be learning from. And number one thing that whenever you have an initiative or whenever you have a metric that you need to go and move, to not start from scratch, ever." Tactical: Reach out to peers at other companies via LinkedIn or X to ask how they solved specific growth challenges.Hire advisors to provide structural frameworks for new initiatives (e.g., community building). "Not hiring advisors is something that I do not recommend for you to do. You can get access to anybody for one hour a week. Yeah, you'll have to pay them... but hiring advisors is the biggest career amplification and your business amplification can possibly do." Tactical: Conduct a paid workshop with a potential advisor to see their problem-solving style before committing to a retainer.Evaluate advisor value on a monthly basis rather than assuming a long-term fixed engagement.Hire advisors as contractors to gain access to specific expertise for just one hour a week.
View all skills from Elena Verna →
Fareed Mosavat 1 quote
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"I think of this as sponsorship, not mentorship. I don't necessarily find that in my career. I've had a lot of managers where I'm like, "Wow, their day-to-day help was super awesome at helping me be a better leader." ... But what I do have is a couple examples of people who deeply trusted me to solve big problems... it's about creating trust and knowing that you have a sponsor there, someone who's going to go to bat for you." Tactical: Focus on building deep trust with leaders by solving their most important problemsCommunicate your work in a way that demonstrates you are ready for the next level of responsibilityIdentify leaders who have the influence to 'go to bat' for you in organizational decisions
View all skills from Fareed Mosavat →
Gibson Biddle 1 quote
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"The first rule of thumb is, don't ask a person to be your mentor. That's really awkward. First, identify them. Say, this is a person I think that could be helpful to me. And then, find ways to be helpful. Everybody needs help." Tactical: Identify mentors who can help you 'see around corners'Offer specific help to potential mentors (e.g., explaining new tech like Discord or building a simple website)Build a 'Personal Board of Directors' consisting of both peers and senior mentors
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Graham Weaver 1 quote
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"The equivalent of that in your life is an executive coach... Number one, make space to ask yourself the big questions in life about your career, your relationships, your health... And then part two is that person can hold you accountable." Tactical: Hire a coach to act as a 'personal trainer' for your life and careerUse a structured weekly form to report on goals, past actions, and intended outcomes before every meetingIf a coach is unaffordable, find a like-minded peer for mutual weekly accountability walks
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Jeffrey Pfeffer 1 quote
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"get a personal board of directors like they talk about in the Wall Street Journal. In other words, get people who will give you advice, give you social support, and hold you accountable." Tactical: Assemble a 'personal board of directors' to provide diverse perspectives and hold you accountable to your development goals.
View all skills from Jeffrey Pfeffer →
Jules Walter 1 quote
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"make the smallest ask possible, which is the opposite of what 95% of people do. 95% of people is like, 'Hey, I've never met you... Can we set up a call?' That's like a big ask. What I do... reached out in the evening and I was like, 'Hey, thanks so much for speaking today... Is there an example of product that you think was created with this approach?' Something he could answer in literally two minutes via email?" Tactical: Start with a specific question that can be answered in under two minutes via email.Always circle back to the mentor to show exactly how you applied their advice and what the result was.Look for mentors who are not only experts but also possess the ability to explain their process clearly.Reciprocate by asking mentors what problems they are currently facing and offering your help.
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Manik Gupta 1 quote
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"The first one is really about people. It's about surrounding yourself with the best people you can find... The important thing when you look back is how much luck played a big part, and of course the risk that somebody took played a big part... If you're create enough opportunities, especially early on in your career as you asked, around hanging around people who are doing interesting things and they're doing things which really are different, or they're doing things in a different manner and it's exciting, the right things will happen." Tactical: Identify 'A plus' people early in your career and find ways to work in their orbit.Play the long game by sticking with talented individuals across multiple career moves to build shared trust.
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Melissa Tan 1 quote
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"Never ask someone to be your mentor... the more it can be organic where you talk to somebody, you have actual advice that you want... reach out when you actually have a problem. People that want to help others are just going to, if they have the time, they'll say yes." Tactical: Reach out with a specific, actionable problem rather than a general requestAvoid using the word 'mentor' in early interactions to reduce pressureNurture relationships by following up on how their advice was implemented
View all skills from Melissa Tan →
Nikhyl Singhal 1 quote
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"I think that learning is changing... there's community, which I think whether it's within your company or outside of company, I think is the answer that we'll see more and more. I think community as a way of creating safety, having authentic conversations, feeling that you're not alone, that others are going through the same thing, and then sharing best practices is so powerful." Tactical: Join or build a small, high-trust community of peers in similar rolesUse community to validate that your challenges are systemic rather than personal failures
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Paul Millerd 1 quote
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"Reach out to somebody, sort of like a podcast, that's ahead of you on a similar path, and just send them a message and say, really thoughtful message. Say, 'Hey, you're on a path a few years ahead of me. I'm really curious about this. I don't have people in my life that have done things like this. Can I just pick your brain? If we can't jump on a call, can I send you a list of questions?'" Tactical: Identify people 2-3 years ahead of you on your desired pathOffer to send written questions instead of requesting a live call to increase response rates
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Phyl Terry 1 quote
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"One of the ways that everyone listening to this podcast today can get a mentor, you can get what I call a dead or distant mentor. Warren Buffett is my mentor, he just doesn't know it... I mean really study. If you really study Jobs, you have to come to 1997... if you really study that moment and study what Jobs did, it can inform your decisions and actions." Tactical: Select a leader you respect and study their specific actions during critical career moments.Read primary sources (talks, letters, original interviews) rather than just biographies.Apply their frameworks to your current professional challenges as if they were advising you.
View all skills from Phyl Terry →
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