Live from Lenny's Summit | Career advice highlights

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 Community–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 brand–Where to find Nikhyl:TwitterLinkedIn–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTok–Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re 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) How to help the Skip community(01:37) Lenny’s Summit(04:10) Breaking your career into levels(07:33) Crafting a compelling career story(10:26) All elite PMs find “peak roles”(12:15) “The reputation you build today is the brand you’ll have tomorrow”(13:17) Avoiding burnout(16:13) Knowing the shadow of your superpower(18:13) Don’t build a career alone(18:53) Summary of advice(20:19) Special announcement

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 – 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 you’re 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](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) Nikhyl’s strong but generic resume(47:50) Nikhyl’s deeper version(50:57) How to submit your career story(52:50) Get in touch with Nikhyl

In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s 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 Graham’s "Founder Mode": https://paulgraham.com/foundermode.htmlShreyas’ Tweet on founder mode’: https://x.com/shreyas/status/1830767630917214318Six superpowers of product managers: https://www.youtube.com/watch?v=OnsSwHP3d-cShreyas’ 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 you’re 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](00:00) Teaser: Unpacking founder mode(02:47) What Shreyas has been up to(04:04) Shreyas’ 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) Shreyas’ observation about John and Patrick Collison(38:17) Nikhyl’s 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) Shreyas’ 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

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.–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 culture–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=2053s–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 you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]–Timestamps(00:00) Episode Teaser: How to 10x your career(01:10) Introducing the framework(03:41) The caller’s 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

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.–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 anxiety–Referenced:Avoiding burnout for high achievers–Where to find Nikhyl:LinkedInTwitter/XThreads–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: [email protected]–Timestamps(00:07) Applying my career framework to the caller’s case(02:13) Caller context(02:52) Why one option is a “no-brainer”(03:58) The value of wartime leadership experience(07:43) Why you won’t regret choosing family > career(09:53) The wisdom in “playing it safe”(11:11) Key takeaways(11:44) How to get in touch

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 you’re 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) What’s unique about early-stage PMs(15:24) How PM evolves when there’s 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 it’s 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

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 don’t need to become an influencerThe power of ‘peak roles’ 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 you’re 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 ≠ 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

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 today’s episode, we tackle job hunting in today’s 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.–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 game–Referenced:Avoiding burnout for high achieversSteve Jobs 2005 Commencement speech–Where to find Nikhyl:LinkedInTwitter/XThreads–Find The Skip:WebsiteSubstackYouTubeSpotifyApple PodcastsTikTokDon't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.–Timestamps(00:00) Episode teaser(01:45) Navigating a job transition(04:34) The caller’s crisis of confidence(10:22) Nikhyl’s 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: Don’t 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: Don’t try to find the ‘perfect role’(47:55) Pro Tip 8: Bet on yourself(48:59) Key takeaways from this episode(51:02) How to get in touch

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.–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 work–Referenced:Balancing Work and Life: Insights from Nikhyl and the Skip CPO group–Where to find Nikhyl:Twitter/XLinkedIn–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 you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter/X.–Timestamps(00:00) Why you resent your company(01:35) People experience burnout differently(04:52) Today’s 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

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 today’s 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.—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 didn’tConclude—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 PodcastsTikTok—Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.—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) Nikhyl’s commentary(18:09) Step 2: Role context(18:43) Nikhyl’s commentary(21:12) Step 3: Frame the challenge(22:15) Nikhyl’s commentary(25:14) Step 4: What you built and why(25:19) Implementing step 4(32:05) Step 5: What worked and what didn’t(31:58) Nikhyl’s commentary(37:08) Step 6: Conclusion(37:30) Nikhyl’s commentary(38:39) Key takeaways from today’s episode(39:42) How to work on your career story with Nikhyl