Episodios
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I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.
Key topics:
Which PMs are secretly great founder materialRed flags: when founding isn't for youThe right time to start your companyKey skills that set you up for successThriving in ambiguityDebunking the "venture scale or bust" mindsetThe counterintuitive way to avoid burnoutMuch moreReferenced:
4 questions Shreyas wished heâd asked himself sooner: https://www.youtube.com/watch?v=atS060bNpE0&t=698sAvoiding burnout for high achievers: https://www.youtube.com/watch?v=5Iwymgai-ZMCrafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928sImproving your product sense: https://maven.com/shreyas-doshi/product-senseIs my next job at a startup or big tech?: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053sManaging your PM career in 2025 and beyond: https://maven.com/shreyas-doshi/product-management-career?utm_source=lennyNikhylâs career advice highlights at Lennyâs Summit: https://www.youtube.com/watch?v=rujK7HvD6es&t=124sStage of Company: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053sWhere to find Shreyas:
Twitter/XLinkedInYouTubeWhere to find Nikhyl:
Twitter/XLinkedInFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]
Timestamps
(00:00) Teaser: Why average PMs can make great founders
(01:17) Introduction
(02:34) The essential first step before founding
(06:21) Successful founder traits
(10:48) Managing at scale vs managing uncertainty
(18:25) Thriving in ambiguity
(21:29) Red flags: when founding isn't for you
(23:34) The surprising link between average PMs and founding success
(25:51) Building better product sense
(29:35) The right time to start your company
(37:03) Beyond venture scale: rethinking startup success
(44:26) A guide to avoiding burnout
(49:23) The real truth about big tech working hours
(52:27) Why taking a "demotion" might be a good move
(58:45) Learn more: Shreyas' Product Sense course
(63:15) Key takeaways
(65:22) Get in touch with Nikhyl
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Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss:
Rethinking retirementThe career-defining question every leader should askPower years versus foundational yearsLeveraging career storiesFinding peak rolesUnderstanding the shadow of your superpowerThe relationship between personal brand and reputationBreaking down burnoutBuilding your support network through Skip Communityâ
Referenced:
Mastering your 30s career resume4 secrets of career boosting companiesAvoiding burnout for high achieversBattling job search anxietyBill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive)Crafting a compelling career storyJZ: https://www.linkedin.com/in/jiaona/Shadows of your superpowers (Part 1)Shadows of your superpowers (Part 2)Shedding perceptions: Moving from lone wolf to team playerSix superpowers of product managersStage of company: A career unlockThe art of building your personal brandâ
Where to find Nikhyl:
TwitterLinkedInâ
Find The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokâ
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]
â
Timestamps:
(00:00) How to help the Skip community
(01:37) Lennyâs Summit
(04:10) Breaking your career into levels
(07:33) Crafting a compelling career story
(10:26) All elite PMs find âpeak rolesâ
(12:15) âThe reputation you build today is the brand youâll have tomorrowâ
(13:17) Avoiding burnout
(16:13) Knowing the shadow of your superpower
(18:13) Donât build a career alone
(18:53) Summary of advice
(20:19) Special announcement
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A great career story can accelerate growth, yet most struggle to craft one. Even top performers fall short, telling stories that are overly detailed, abstract, jargon-filled, or poorly structured â all of which can lose a listener's interest.
The first 30 seconds are crucial; you need to hook your audience quickly. Think of the beginning of your story as a movie trailer: highlight the most engaging aspects rather than chronologically detailing every event.
This episode focuses on crafting a captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of me coaching engineering and product leaders, demonstrating the transformation from initial attempts to polished and punchy narratives.
We also discuss:
Common storytelling mistakes that everybody makesTechniques for weaving a theme into your storyEffective strategies that will hook listenersAdapting your story for various audiences and situationsBalancing between brevity and showcasing your unique valueReferenced:
Crafting a compelling career storyFounder Mode, done right with Shreyas DoshiWhere to find Nikhyl:
TwitterLinkedInFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]
Timestamps
(00:00) Episode teaser: Mastering your 30s resume
(01:15) Common mistakes everybody makes
(09:42) Why you need a 30s and 2m career story
(12:21) Showing the trailer, not the movie
(16:44) Example 1
(17:28) Thinking about story sequencing
(19:04) Example 2
(19:44) Avoiding detail
(21:21) Example 3 (before)
(21:54) Avoid abstract stories
(23:52) Example 3 (after)
(24:41) The art of thematic narratives
(28:29) Example 4 (before)
(29:18) Crafting a theme
(29:51) Example 4 (after)
(31:24) Avoiding jargon
(34:51) Tailoring communication tempo
(36:19) Example 5 (before and after)
(39:04) Example of a strong 30s resume
(41:13) Preparing multiple versions
(45:20) Nikhylâs strong but generic resume
(47:50) Nikhylâs deeper version
(50:57) How to submit your career story
(52:50) Get in touch with Nikhyl
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In this episode, Iâm joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why itâs appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.
We also discuss:
Why founder mode is a mindset, not a titleWhether founder mode is good or badBalancing detail and delegationThe importance of product sense and good judgmentMastering founder mode as a product leaderOperational insights from Meta and StripeReferenced:
Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=928sPaul Grahamâs "Founder Mode": https://paulgraham.com/foundermode.htmlShreyasâ Tweet on founder modeâ: https://x.com/shreyas/status/1830767630917214318Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-cShreyasâ previous appearance on the podcast: https://www.youtube.com/watch?v=y_TnXtnY3QM&t=23sThe 3 types of product leaders: https://x.com/shreyas/status/1375491623308550144Where to find Shreyas:
Twitter/XLinkedInYouTubeWhere to find Nikhyl:
Twitter/XLinkedInFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at [email protected]
Timestamps
(00:00) Teaser: Unpacking founder mode
(02:47) What Shreyas has been up to
(04:04) Shreyasâ take on founder mode
(08:59) Why judgment and product sense is critical
(13:04) Balancing detail and delegation
(20:57) The key question for founders about ownership
(23:01) Not every company needs a CPO or Head of Product
(28:07) When product people should prioritize detail
(31:32) What everyone gets wrong about Steve Jobs
(34:22) Shreyasâ observation about John and Patrick Collison
(38:17) Nikhylâs observation about Mark Zuckerberg
(40:05) Founder vs manager mode
(43:40) Should leaders avoid manager mode?
(48:17) Chase impact, not optics
(57:00) The 3 types of product leaders
(60:46) Aligning your environment, opinion, and superpower
(63:10) Shreyasâ non-consensus view on building product
(67:52) Mastering founder mode as a PM
(72:58) Getting in touch with Shreyas
(74:49) How to find Nikhyl
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Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or evaluating your current role, these insights will help you identify environments that truly foster career growth.
â
We also discuss:
Strong signals of a supercharged companyWhy shipping velocity is crucialLearning opportunities at immature companiesLooking for companies with strong talentWhat makes an excellent development cultureâ
Referenced:
Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=913sGreatest hits on career advice with Peter Yang: https://www.youtube.com/watch?v=-BcCHEXAVVkIs my next job at a startup or big tech?: https://www.youtube.com/watch?v=MiELOo4_XGg&t=9sShould I join or leave an ex-hypergrowth company: https://www.youtube.com/watch?v=5-rr1cYYfEUSix superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-cStage of Company: A career unlock: https://www.youtube.com/watch?v=H59CRHQ6va0&t=2053sâ
Where to find Nikhyl:
LinkedInTwitter/XThreadsFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]
â
Timestamps
(00:00) Episode Teaser: How to 10x your career
(01:10) Introducing the framework
(03:41) The callerâs question
(05:00) 1: Speed and execution
(08:43) 2: Market position
(11:47) 3: Quality of talent
(15:27) 4: Development culture
(20:22) How to get in touch
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In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere.
â
We also discuss:
Maximizing career potential without sacrificing familyReframing career decisions in the context of long-term growthHow to have it all, just not at onceThe value of wartime leadership experienceOvercoming job search anxietyâ
Referenced:
Avoiding burnout for high achieversâ
Where to find Nikhyl:
LinkedInTwitter/XThreadsâ
Find The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]
â
Timestamps
(00:07) Applying my career framework to the callerâs case
(02:13) Caller context
(02:52) Why one option is a âno-brainerâ
(03:58) The value of wartime leadership experience
(07:43) Why you wonât regret choosing family > career
(09:53) The wisdom in âplaying it safeâ
(11:11) Key takeaways
(11:44) How to get in touch
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Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage.
This episode reveals how a company's phase - from startup to market leader - shapes your work and career path. We explore the four key growth stages, how product management evolves, and how to align your strengths with the right stage.
Featuring insights from seasoned product leaders, learn to identify your ideal company stage and navigate transitions. This episode is your guide to making strategic career moves in product management by leveraging the often-overlooked power of company growth stages.
We also discuss:
The 4 stages of company growth: drunken walk, product market fit, hypergrowth, and established market leaderHow PM roles evolve across stagesMatching your skills to each stageIntentionally choosing your company stageThe value of diverse stage experience for successful PMsStrategies to gain multi-stage experienceReferenced:
Stage of company, not name of company: https://theskip.substack.com/p/stage-of-company-not-name-of-companyShadows of your superpowers (Part 1): https://www.youtube.com/watch?v=XZbjvymjabA&t=912sShadows of your superpowers (Part 2): https://www.youtube.com/watch?v=lcdb5enbDLEWhere to find Nikhyl:
LinkedInTwitter/XThreadsFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
Timestamps
(00:00) Intentionally choosing your company stage (episode teaser)
(01:25) The importance of company stage
(02:47) 3 common questions from PMs
(05:383) The link between PM and company stages
(07:48) The 4 company stages
(13:45) Whatâs unique about early-stage PMs
(15:24) How PM evolves when thereâs customer traction
(18:00) Product management at a hypergrowth company
(21:50) One example of what changes between the first three stages
(24:49) PM at an established leader
(30:04) How to know which stage is right for you
(37:03) Spotting when itâs time for something new
(38:36) Choose your stage of company wisely
(41:38) Why top product people have multi-stage experience
(43:28) How to get in touch
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Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship.
This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech executives, Annie Pearl of Microsoft and Iska Saric of Meta, we pull back the curtain on how industry leaders craft and wield their personal brands to open doors, land dream roles, and shape their legacies.
The episode provides actionable strategies to build an authentic and compelling brand that catapults your career forward.
We also discuss:
The critical distinction between reputation and brandWhy you donât need to become an influencerThe power of âpeak rolesâ in accelerating your careerTailoring your brand story to specific audiencesStrategies for expanding your professional networkNavigating gender dynamics in personal brandingThe 30-minute per week method to brand-buildingReferenced:
Annie Pearl, CVP at Microsoft: https://www.linkedin.com/in/anniepearl/Iska Saric, VP of Communications at Meta: https://www.linkedin.com/in/iska-saric-97210212/Crafting a compelling career story: https://www.youtube.com/watch?v=0Reh9wTUIYc&t=1078sWhere to find Nikhyl:
LinkedInTwitter/XThreadsFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
Timestamps
(00:00) Episode format
(02:14) Why brand matters
(04:47) Building a brand â becoming an influence
(08:14) Reputation versus brand
(10:28) How to establish a reputation
(13:55) Leveraging professional connections
(18:08) The role that will transform your career
(24:12) Crafting and communicating your brand
(30:09) The "30-minute per week" method
(30:49) Navigating
(35:36) Key takeaways from this episode
(35:56) How to get in touch
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Navigating job transitions in today's competitive tech landscape is difficult. Many people get stuck between roles, and an extended job search can dent your confidence. You might doubt your past achievements, question your current skills, and worry about what's next.
In todayâs episode, we tackle job hunting in todayâs tough market. I share insights from a real coaching session with a design leader who's struggling after being out of work for a few months.
The episode is packed with concrete tools, useful tips, and proven strategies to help you navigate a job transition.
â
We also discuss:
The mindset needed when in between jobsRebuilding your confidence from the ground upThe role of grit and hustle in an extended job searchHow to run an effective job searchMaking the most of your time between jobsTransforming your mental, physical, and social gameâ
Referenced:
Avoiding burnout for high achieversSteve Jobs 2005 Commencement speechâ
Where to find Nikhyl:
LinkedInTwitter/XThreadsâ
Find The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
â
Timestamps
(00:00) Episode teaser
(01:45) Navigating a job transition
(04:34) The callerâs crisis of confidence
(10:22) Nikhylâs advice
(16:24) Several strategies for effective job searches
(17:53) Pro Tip 1: Set realistic expectations
(21:41) Pro Tip 2: Work on yourself
(28:04) Pro Tip 3: Treat your craft like an athlete
(30:40) Pro Tip 4: Donât cut your search short
(34:50) Pro Tip 5: Run the process with grit and hustle
(41:33) Pro Tip 6: Take advantage of the US calendar
(43:55) Pro Tip 7: Donât try to find the âperfect roleâ
(47:55) Pro Tip 8: Bet on yourself
(48:59) Key takeaways from this episode
(51:02) How to get in touch
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Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies.
In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset.
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In today's episode, we discuss:
Why burnout is a deeply personal experienceInsights on burnout from real-world examplesWhy burnout is a side effect of successAdopting a long-term career viewThe importance of finding a hobbyAvoiding low-energy workâ
Referenced:
Balancing Work and Life: Insights from Nikhyl and the Skip CPO groupâ
Where to find Nikhyl:
Twitter/XLinkedInâ
Find The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokThis episode on YouTubeDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter/X.
â
Timestamps
(00:00) Why you resent your company
(01:35) People experience burnout differently
(04:52) Todayâs episode format
(05:36) The mindset needed to enforce boundaries
(07:25) Observation 1: High performing companies will always push their best people
(11:45) Observation 2: Family planning will require you to rework the timing of your career plan
(17:23) Observation 3: Ambitious, overworked people will eventually resent their job
(23:21) Pro tip 1: Changing your mindset toward burnout
(24:58) Pro tip 2: Finding a hobby forces joy on your calendar
(29:00) Pro tip 3: Recognizing what drives low energy at work
(31:04) Key takeaways from this episode
(32:39) How to get in touch
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After a three-month hiatus, The Skip returns with exciting news: April marked my departure from Meta, and I'm now fully focused on The Skip.
Though leaving was a difficult choice, the decision highlighted something important: effectively telling your career story matters more than ever in todayâs job market. Companies are concerned that some people may have been spectators to growth rather than contributors. Or worse yet, compelling successes at work are ignored or misunderstood due to an articulation skill gap.
In today's episode, learn to craft a compelling two-minute career story you can use for interviews, personal assessments, networking events, and LinkedIn. Good stories ensure clarity, showcasing your achievements and authenticity. We dissect a typical PM career story and walk through how to make it compelling.
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In today's episode we discuss the 6 steps of career storytelling:
Describe the projectDefine your roleFrame the challengeOutline what you built and whyHighlight what worked and what didnâtConcludeâ
Referenced:
Shedding perceptions: Moving from a lone wolf to a team playerIs my next job at a startup or big tech?Coaching grit, patience, and tenureWhere to find Nikhyl:
TwitterLinkedInFind The Skip:
WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokâ
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
â
Timestamps
(00:00) Why your career story is more important than ever
(01:25) Leaving Meta
(04:09) Episode format
(11:38) The case study
(15:04) The 6 steps
(16:44) Step 1: Project context
(16:40) Nikhylâs commentary
(18:09) Step 2: Role context
(18:43) Nikhylâs commentary
(21:12) Step 3: Frame the challenge
(22:15) Nikhylâs commentary
(25:14) Step 4: What you built and why
(25:19) Implementing step 4
(32:05) Step 5: What worked and what didnât
(31:58) Nikhylâs commentary
(37:08) Step 6: Conclusion
(37:30) Nikhylâs commentary
(38:39) Key takeaways from todayâs episode
(39:42) How to work on your career story with Nikhyl
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In my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.
The caller reveals both their superpower and its shadow. They are an opinionated product manager, blessed with exceptional taste and intuition. However, these traits also lead them to resist compromise. We confront the callerâs shadow, and explore frameworks and strategies essential for effective collaboration.
Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
â
In today's episode, we discuss:
How to shed poor perceptions in the workplaceNavigating organizational power dynamicsThe up/down/across model of collaborationWhen and how to compromiseWhy 0 to 1 doesnât exist in big techHow to use the founder mindset in a large orgâ
Timestamps:
(00:00) Introduction
(01:56) Caller context
(05:02) Callerâs reputation as a ârebel leaderâ
(07:11) How can I change peopleâs perception of me?
(08:37) Nikhylâs response
(12:05) What the caller wants to avoid
(13:09) Nikhyl outlines two choices
(15:12) Should I optimize for short or long-term career wins?
[00:15:41] Nikhylâs advice on risk and reward
(17:38) Should I leave big tech and become a founder?
(19:25) Nikhylâs notes on compromise
(20:57) Should I play organizational Game of Thrones?
(21:45) Nikhylâs recommendation
(25:39) Key takeaways from todayâs episode
(33:03) Key links for this podcast
â
Where to find Nikhyl:
TwitterLinkedInâ
Where to find The Skip Podcast:
WebsiteYouTubeTikTokSpotifyApple Podcastsâ
Don't forget to subscribe to The Skip to hear Nikhyl teach unique and timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
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In my third episode of live coaching sessions, this caller was feeling dissatisfied with their narrow scope of role and lack of cultural fit in their current company.
The caller wanted guidance on what their next role should be, given their personal situation and professional ambition. Their situation captures a difficult choice facing many superstars: seeking a sizable impact rarely found outside of startups, while also craving the compensation only late-stage companies can afford. We discuss the frameworks and strategies required to approach this career choice wisely.
Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
Aligning the stage of company to your specific situationCompensation expectationsRisk tolerance in making career movesThe risks and benefits of joining big techWhy top product executives do tour duties at big companiesHow to break a big tech tenure into two rolesWhy some big tech projects are more data-driven than othersWhy experienced managers should consider IC roles
â
In today's episode, we discuss:â
Where to find Nikhyl:
TwitterLinkedIn
WebsiteYouTubeTikTokSpotifyApple Podcasts
Where to find The Skip Podcast:â
Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. If youâre interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
â
Timestamps:
[00:00:00] Introduction and caller context
[00:02:17] Callerâs question
[00:07:40] Nikhylâs follow-up questions
[00:10:15] Matching the stage of company to the callerâs situation
[00:11:03] Nikhylâs recommendation
[00:16:56] Should I join a big tech company?
[00:18:03] Nikhylâs response
[00:22:08] How do big tech product teams operate?
[00:22:55] Nikhylâs response
[00:25:58] Why managers should consider IC roles at late-stage companies
[00:29:44] Key takeaways from todayâs episode
[00:32:27] Key links for this podcast -
This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes Iâm often asked about by listeners.
This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the traits and strategies required to approach these problems wisely.
Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
In today's episode, we discuss:
Why the callerâs difficult scenario could be their greatest opportunityHow to think about a current role in the context of future goalsThe nature of tough leadership problemsThe value of patience and long tenuresHow to align on performance and timeframe expectations with higher-upsAdvice for solving contentious problems with multiple stakeholdersTimestamps
[00:00:00] Introduction and context on caller
[00:02:43] Callerâs question
[00:06:35] Nikhylâs initial reaction
[00:09:11] Could she solve this problem if she wanted to?
[00:10:48] The relevance of patience/impatience
[00:12:40] The relationship between tenure and solving hard problems
[00:15:20] Earning trust as a leader
[00:16:30] Understanding the companyâs expectations and timelines
[00:18:05] The advice discussed so far
[00:22:54] Why this matters for future opportunities at startups
[00:27:10] Advice for approaching this challenging leadership scenario
[00:31:08] Nikhyl's closing reflections
[00:33:45] Key links for this podcastWhere to find Nikhyl:
TwitterLinkedInWhere to find The Skip Podcast:
WebsiteYouTubeTikTokSpotifyApple PodcastsDon't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.
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Welcome back to The Skip; this episode is a little bit special as Iâm experimenting with a new format: live coaching sessions. This idea came from the realization that the coaching queries I receive from listeners often have common themes.
My hope is that recording and sharing a coaching call like this demonstrates how the frameworks are applied in real conversations and possibly helps others with similar situations. Naturally, privacy is paramount, so weâve anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
In today's episode, we discuss:
Strategies for presenting your individual contributor (IC) experience during career advancement interviews.How to map the complexities you are solving in your current role into specific phrases that hook a recruiter or a future hiring managerAvoiding over selling your experience and landing in a sub-optimal role, focused on org-building vs. product-buildingExploring how far an IC can travel within a company, and how to ultimately become an executiveTimestamps:
(00:00) Introduction and welcome to the podcast
(00:57) Introducing the format of this episode
(04:08) Context ahead of the coaching call
(06:40) How to frame your experience as an IC when interviewing for the next step in your career.
(08:25) Nikhyl's follow-up questions
(09:11) Why the caller left Microsoft
(11:17) Nikhyl's thoughts and initial reaction to the caller's situation
(12:22) Identifying if you have a product ambiguity or team ambiguity problem
(15:10) Nikhyl's thoughts on how to frame the caller's experience when interviewing
(16:08) Nikhyl's thoughts on the types of companies suitable for the caller
(19:34) How to find suitable companies based on your management experience
(23:13) How to navigate questions around your management experience when your current role is an IC
(28:19) How to navigate people managing anxiety
(29:52) Can ICs build a lasting career?
(33:17) Conversation conclusion and final thoughts
(36:06) Episode conclusion
Where to find Nikhyl:
TwitterLinkedInWhere to find The Skip Podcast:
WebsiteYouTubeTikTokSpotifyApple PodcastsDon't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.
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Much of the career advice out there is for aspiring PMs. But what about those who have one foot on the ladder and are looking to climb the next rung? This episode is about advancing mid to late-stage product management careers. I'm joined by Peter Yang, Product Lead at Roblox, and product newsletter writer, to discuss how established PMs can avoid getting stuck. From pursuing growth over promotion to knowing when to change companies, we discuss a wide range of strategies to help you continue building the career you want based on your individual goals.
Todayâs discussion covers:
⢠Wisdom for mid and late-stage product managers looking to advance their careers
⢠Why you should focus on growth, not promotion
⢠Optimizing for company stage instead of company name
⢠Signs you should leave a company
⢠The under-discussed trade-offs between compensation and tenure
⢠Why top companies offer such high compensationCreator Economy by Peter Yang:
⢠Nikhyl Singhal (VP Meta): How to Advance Your Product Management Career (Part 1)
⢠Nikhyl Singhal (VP Meta): How to Advance Your Product Management Career (Part 2)Referenced in this episode:
⢠Blog post "Stage of company, not name of company"
⢠Six Superpowers of Product Managers
⢠Shadows of your Superpowers (Part 1)
⢠Shadows of your Superpowers (Part 2)Timestamps:
(00:00) Introduction
(01:27) Advancing mid or late-stage careers
(04:38) Promotions matter less than you think
(08:36) The different end goals for PM careers
(13:56) How to find the right company to elevate your career
(19:07) The best and worst reasons to change companies
(23:28) The impact of short tenures on someoneâs resume
(27:19) Why top companies offer such high compensation
(31:31) The relationship between title and compensation
(34:52) Advice for negotiating compensation
(37:21) The under-discussed tradeoff between compensation and tenure
(39:07) Recapping the "shadows of your superpowers"
(41:55) Nikhylâs advice for dealing with a common shadow
(47:43) ConclusionWhere to find Peter:
⢠Twitter
⢠LinkedIn
⢠NewsletterWhere to find Nikhyl:
⢠Twitter
⢠LinkedInWhere to find The Skip Podcast:
⢠Website
⢠YouTube
⢠TikTok
⢠Spotify
⢠Apple Podcasts -
This episode is about mentorship. Mentorship is a powerful personal development tool that naturally attracts ambitious people. However, it can be a complicated tool to maximize. Mentorship comes in many forms, with varying degrees of accessibility, quality, and suitability for a given individual. In this episode, I answer questions on 3 topics surrounding the complications of mentorship: how to navigate the resources available, how to be coachable, and tips and tricks Iâve learned as a mentor and mentee.
In todayâs episode, we discuss:
Why you shouldnât conflate success at your company with success in your careerHow and why you should form a âPersonal Board of DirectorsâResources for people who canât access certain types of mentorshipHow to identify and avoid bad adviceActionable tips for becoming more coachableWhy coaching others improves your ability to be coachedReferenced in this episode:
Meander: Match your career ambitions with the perfect mentor (Nikhyl is an advisor)Shreyas Doshi: links to his content and his coursesLennyâs PodcastReforgeTimestamps:
[00:00:00] Intro
[00:01:54] I feel like Iâm not doing enough to advance my career, what should I do?
[00:04:34] What if I canât access mentorship?
[00:06:11] The 4 buckets of people in your network
[00:09:55] The âPersonal Board of Directorsâ framework
[00:12:02] How to connect - not ânetworkâ - in 30 mins per week
[00:13:31] How to find people to connect with
[00:15:16] The value of free online content
[00:16:31] The value of communities
[00:18:41] Paid resources
[00:21:24] 2 things to consider when it comes to executive coaches and therapists
[00:24:48] 3 unique strengths of therapy
[00:25:51] The skill of being coachable
[00:26:43] Use specific requests when engaging with potential mentors or coaches
[00:30:33] The courage required to listen to feedback
[00:31:38] How to run an efficient process when being coached
[00:34:55] Why coaching others helps you to be coached
[00:36:42] How do you know if youâre getting good advice?
[00:38:45] Beware of extremists and contrarians
[00:40:04] Beware of copycat coaches
[00:41:12] Coaches must know you and your situation
[00:42:19] My own personal board of directors
[00:46:03] How I think about new requests to be coached by me
[00:47:07] My new idea for a live coaching format
[00:48:21] ConclusionWhere to find Nikhyl:
Twitter: https://twitter.com/nikhylLinkedIn: https://www.linkedin.com/in/nikhyl/Where to find The Skip Podcast:
Website: https://www.skip.show/ YouTube: https://www.youtube.com/@theskippodcastTikTok: https://www.tiktok.com/@theskippodSpotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJApple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202 -
Todayâs episode breaks down my 5 rules for optimizing the most important product in your professional life: your career. These rules synthesize some of the key takeaways from all of my other content about product management and career growth. I break down why each rule matters, and outline some associated mistakes and misconceptions that you should avoid. Whether youâre at a career juncture or are firmly positioned in a role, these rules come with actionable tactics you can implement tomorrow. Ultimately, I believe that following these rules will lead you to a healthier career where you think long-term and control your own outcomes.
Todayâs discussion covers 5 rules:
1. Product manage your career like a product
2. Ensure each transition is career additive
3. Who you know will matter as much as what you know
4. Find a strength area and build a superpower around it
5. Bet on yourself
Timestamps:
[00:00:00] Intro
[00:01:33] Overview of the 5 rules
[00:02:00] Rule #1 Product manage your career like a product
[00:05:43] The importance of seeking out feedback
[00:07:13] Rule #2: Ensure each transition is career additive
[00:10:40] The external vs internal realities of a company
[00:13:08] Rule #3 Who you know will matter as much as what you know
[00:15:03] How to build your network authentically
[00:18:38] Rule #4 Find a strength area and build a superpower around it
[00:21:16] The shadows of your superpowers
[00:22:08] Rule #5 Bet on yourself
[00:24:08] Why promotions donât guarantee youâre advancing
[00:26:11] Conclusion
References
- My Product School talk on the 4 essential product skills: https://productschool.com/product-podcast/pm-to-csuite-by-facebook-vp-of-product/
- My podcast on the shadows of superpowers, part 1: https://www.skip.community/shadows-of-your-superpowers-part-1/
- My podcast on the shadows of superpowers, part 2: https://www.skip.community/shadows-of-superpowers-part-2/
Where to find Nikhyl:
Twitter: https://twitter.com/nikhyl
LinkedIn: https://www.linkedin.com/in/nikhyl/
Where to find The Skip Podcast:
Website: https://www.skip.show/
YouTube: https://www.youtube.com/@theskippodcast
TikTok: https://www.tiktok.com/@theskippod
Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202
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Todayâs episode is the second part, and deeper analysis, on âthe shadows of your superpowersâ. These are a type of development areas that are associated with your greatest strengths. I use example personas to detail 5 common shadows Iâve noticed across my career and coaching. For each, I breakdown why the shadow is elusive, common reactions to receiving feedback around it, and actionable advice for addressing the development area. Whether these shadows remind you of yourself or of others - in a personal or professional context - this reflection will help you cast the shadows into the light.
Todayâs discussion covers:
A recap of the âshadowsâ conceptExecuter who struggles to be a team player (Martin)Strong opinions, tightly held (Jackie)Team builder who becomes too political (Max)Organizational expert who is too hands-off (Jenny)Company veteran who struggles to innovate (Evan)How you can apply these reflectionsTimestamps:
[00:00:00] Recapping the âshadowsâ concept
[00:02:00] Where to apply these insights in your life
[00:04:38] Example #1: Executer who struggles to be a team player (Martin)
[00:09:31] Advice for Martin
[00:13:07] Example #2: Strong opinions, tightly held (Jackie)
[00:14:18] Advice for Jackie
[00:17:17] Example #3: Team builder who becomes too political (Max)
[00:19:12] Advice for political Max
[00:23:24] Example #4: Organizational expert who is too hands-off (Jenny)
[00:25:06] Advice for Jenny
[00:29:16] Example #5: Company veteran who struggles to innovate (Evan)
[00:33:09] Advice for Evan
[00:36:57] ConclusionWhere to find Nikhyl:
Twitter: https://twitter.com/nikhyl
LinkedIn: https://www.linkedin.com/in/nikhyl/Where to find The Skip Podcast:
Website: https://www.skip.show/
YouTube: https://www.youtube.com/@theskippodcast
TikTok: https://www.tiktok.com/@theskippod
Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ
Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202 -
Todayâs episode breaks down the shadows of your superpowers. These are a type of development area that is associated with your greatest strengths, and these apply to people inside and outside of tech. Shadows are one of the most elusive areas of self-development and, therefore, one of the most limiting to your potential. You may very well be unaware of yours. While shadows are surrounded by complicated personal and workplace dynamics, understanding them is likely one of your best opportunities to unlock the next step in your career.
Todayâs discussion covers:
What shadows areThe complex dynamics which make them easy to dismissHow to identify yours4 reactions people have when their shadows catch up with them10 common examples of shadowsHow to address your shadows and move from acknowledgment to actionWhere to find Nikhyl:
Twitter: https://twitter.com/nikhyl
LinkedIn: https://www.linkedin.com/in/nikhyl/
Threads: https://www.threads.net/@nikhylsinghalTimestamps:
[00:00:24] Whatâs covered in this episode
[00:02:16] Introducing the shadows of your superpowers
[00:04:00] How this episode is structured
[00:04:40] The unique nature of shadows and why theyâre so elusive
[00:07:24] When your shadows catch up with you
[00:08:02] Four reactions people have when their shadows catch up with them
[00:08:07] Reaction #1: Fight
[00:08:22] Reaction #2: Withdraw
[00:08:53] Reaction #3: Ignore the shadow
[00:09:31] Reaction #4: Confront the shadow
[00:10:29] What separates shadows from regular development areas
[00:14:07] 10 common examples of shadows
[00:14:14] Example #1 - The great storyteller
[00:14:51] Example #2 - The collaborator
[00:15:38] Example #3 - The straight shooter
[00:16:36] Example #4 - The process expert
[00:17:32] Example #5 - The idea person
[00:18:18] Example #6 - The wartime individual
[00:19:30] Example #7 - The industry expert
[00:20:44] Example #8 - The hard worker
[00:21:27] Example #9 - The sacrifice
[00:22:39] Example #10 - The future thinkers
[00:23:38] Advice on what to make of all this
[00:26:08] What it takes to address your shadows
[00:29:32] Episode conclusion - Mostrar más
