The Skip podcast

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 caller’s 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.—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 doesn’t exist in big techHow to use the founder mindset in a large org—Timestamps:(00:00) Introduction(01:56) Caller context(05:02) Caller’s reputation as a “rebel leader”(07:11) How can I change people’s perception of me?(08:37) Nikhyl’s 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] Nikhyl’s advice on risk and reward(17:38) Should I leave big tech and become a founder?(19:25) Nikhyl’s notes on compromise(20:57) Should I play organizational Game of Thrones?(21:45) Nikhyl’s recommendation(25:39) Key takeaways from today’s episode(33:03) Key links for this podcast—Where to find Nikhyl:TwitterLinkedIn—Where to find The Skip Podcast:WebsiteYouTubeTikTokSpotifyApple Podcasts—Don't forget to subscribe to The Skip to hear Nikhyl teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.

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.—In today's episode, we discuss: Aligning the stage of company to your specific situationCompensation expectations Risk tolerance in making career movesThe risks and benefits of joining big tech Why top product executives do tour duties at big companies How to break a big tech tenure into two roles Why some big tech projects are more data-driven than othersWhy experienced managers should consider IC roles —Where to find Nikhyl:TwitterLinkedInWhere to find The Skip Podcast:WebsiteYouTubeTikTokSpotifyApple Podcasts—Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. —Timestamps: [00:00:00] Introduction and caller context [00:02:17] Caller’s question[00:07:40] Nikhyl’s follow-up questions [00:10:15] Matching the stage of company to the caller’s situation[00:11:03] Nikhyl’s recommendation[00:16:56] Should I join a big tech company?[00:18:03] Nikhyl’s response [00:22:08] How do big tech product teams operate?[00:22:55] Nikhyl’s response[00:25:58] Why managers should consider IC roles at late-stage companies[00:29:44] Key takeaways from today’s 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 I’m 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 caller’s 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] Caller’s question [00:06:35] Nikhyl’s 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 company’s 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.

Welcome back to The Skip; this episode is a little bit special as I’m 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 we’ve 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 executive Timestamps:(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:TwitterLinkedIn Where to find The Skip Podcast:WebsiteYouTubeTikTokSpotifyApple Podcasts Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons.

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.Today’s 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 someone’s 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) Nikhyl’s 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 I’ve learned as a mentor and mentee.In today’s episode, we discuss:Why you shouldn’t conflate success at your company with success in your careerHow and why you should form a “Personal Board of Directors”Resources for people who can’t 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 coursesLenny’s PodcastReforgeTimestamps:[00:00:00] Intro[00:01:54] I feel like I’m not doing enough to advance my career, what should I do?[00:04:34] What if I can’t access mentorship?[00:06:11] The 4 buckets of people in your network[00:09:55] The “Personal Board of Directors” framework[00:12:02] How to connect - not “network” - 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 you’re 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.community/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

Today’s 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 you’re 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. Today’s discussion covers 5 rules:1. Product manage your career like a product2. Ensure each transition is career additive3. Who you know will matter as much as what you know4. Find a strength area and build a superpower around it5. 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 don’t guarantee you’re 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/nikhylLinkedIn: https://www.linkedin.com/in/nikhyl/ Where to find The Skip Podcast:Website: https://www.skip.community/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

Today’s episode is the second part, and deeper analysis, on “the shadows of your superpowers”. These are a type of development areas that are associated with your greatest strengths. I use example personas to detail 5 common shadows I’ve 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.Today’s discussion covers:A recap of the “shadows” 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 “shadows” 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/nikhylLinkedIn: https://www.linkedin.com/in/nikhyl/Where to find The Skip Podcast:Website: https://www.skip.community/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

Today’s 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. Today’s 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 action Where to find Nikhyl:Twitter: https://twitter.com/nikhylLinkedIn: https://www.linkedin.com/in/nikhyl/Threads: https://www.threads.net/@nikhylsinghal Timestamps:[00:00:24] What’s 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 they’re 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

In this episode of The Skip podcast, Nikhyl Singhal presents an enlightening discourse aimed at aiding tech industry professionals in their career growth. Through a new 30-minute coaching format, Nikhyl explores the transitions between managerial and individual contributor roles, emphasizing the significance of tackling six ambiguities in product management: product, growth, domain, market, organization, and team. He introduces these distinct skills and types of product managers, each uniquely contributing to the tech landscape. Nikhyl also addresses the often-overlooked organizational complexities and the vital role of team management. Most importantly, he stresses the significance of expertise and specialization over general managerial roles, busting common misconceptions about career growth. Tune in to this invaluable episode for profound insights into career development in the tech industry.Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | Facebook  Time-codes:00:00 - Introduction to the Skip podcast and new format focusing on 30-minute coaching sessions.01:46 - Discussion on the positive transition from manager to individual contributor (IC) and its impact on the tech industry.02:30 - Introduction of six distinct skills to tackle ambiguities in product management.04:30 - Leadership and its role in solving bigger, more ambiguous problems.06:00 - Explanation of the six ambiguities: product, growth, domain, market, organization, and team.07:57 - Analysis of product crafters, focusing on features and improvements needed for a product to succeed.09:10 - Detailed description of the role of growth product managers, focusing on data and consistent product growth.11:57 - Introduction to domain experts who bring specialized knowledge to specific areas.15:00 - Examination of product managers skilled in navigating market ambiguity.17:23 - Discussion on the role of internal consultants, strategic thinking, and execution.18:20 - Emphasis on organizational ambiguity and its significance in delivering complex projects.20:37 - Analysis of the increasing complexity of the organization with every new feature, product, and product line.22:56 - Discourse on the importance of team management and executive leadership.26:18 - Recap of the six skills crucial for product managers.30:30 - Guidance on using the new language of skills when interviewing for better understanding of candidates.5 Impactful Concepts:Transitioning from a managerial role to an individual contributor can have a positive impact on a tech career.Six key skills can help navigate ambiguities in product management, leading to successful project execution.There are different types of product managers, each with their unique roles and contributions to the product's success.Navigating organizational ambiguity is crucial in delivering complex projects, highlighting the importance of understanding organizational dynamics.Specialization in one or two areas, rather than general management, is vital for career growth in tech. 

In this episode of The Skip Podcast, host Nikhyl Singhal explains how he helps product managers negotiate compensation. An industry veteran in the tech sector, Nikhyl has worked with 50+ leading executives and dozens of companies to ensure they establish optimal pay packages.  He unpacks the concept of equity in both public and private companies and offers a method for comparing job offers based on annual expected value and potential liquidity events. He then transitions into salary negotiation tactics, cautioning against pushing for the maximum offer and instead recommending a self-valuation approach. Nikhyl explores how companies establish compensation ranges using market data and explains how to compare early-stage, growth-stage and late-stage tech offers. . He later discusses the impact of a candidate's "eliteness" on negotiation power and offers a detailed guide on salary benchmarks in the tech industry. Finally, he concludes with tips on calibrating compensation expectations, hinting at the topic for the next compensation episode: negotiation strategies.Summary of PM Compensation chartPrevious Skip episodes on compensation:Tech compensation: Beyond the offer letterHow equity in tech companies worksExplaining Equity and Executive Compensation with Goodwin ProcterTime-codes:00:54: Nikhyl introduces compensation challenges and equity's role in public and private companies.02:20: Nikhyl recommends comparing job offers based on the annual expected value and potential for liquidity events.06:54: He warns about the pitfalls of over-negotiation in job offers.08:20: Suggests a "price to retain your services" approach to salary discussions.10:40: Discusses how companies use market data to determine compensation ranges.11:20: Advises asking about a company's compensation philosophy before discussing specific numbers.12:20: Highlights how a company's compensation philosophy impacts the quality of people they hire.13:37: Talks about the significance of a candidate's "eliteness" in negotiations and compensation command.16:07: Discusses salary buckets for product managers in the Bay Area tech industry as a strategy for ensuring fair compensation.21:16: Details average salaries for various roles in product management, from entry-level to executive positions.29:32: Shares his method of calibrating compensation expectations based on a candidate's background.30:34: Explains how he uses market ranges to ensure people are getting the right offer.33:33: Wraps up the discussion, teasing the next episode on negotiation strategies. 

Get ready for an engaging episode of the Skip podcast, where host Nikhyl Singhal dives into the evolving world of startups, head of product roles, and the fascinating field of product management. Discover how the head of product role has transformed in response to growth and hypergrowth dynamics, gain insights into the current market shifts and challenges, and explore the diverse career paths available, including joining healthy growth companies, considering number two roles, or even founding your own startup. Whether you're a product management professional, an executive, or simply curious about the dynamic landscape of the tech industry, this episode offers valuable perspectives and guidance that will inspire and empower you on your career journey.Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | Facebook Full Show-notes:0:00 Introduction and setting the focus on the changing role of the Head of Product.3:10 Discussing the critical nature of the Head of Product role in hyper-growth companies.6:15 Explaining the shift from hyper growth to sustainability and its impact on the Head of Product role.8:17 Candid observations on the current Head of Product market.9:37 Offering guidance to those seeking top roles.11:43 Discussing the current state of companies and CEOs.13:08 Emphasizing the opportunities in healthy growth companies.16:00 Discussing the benefits of a number two role in a company.19:00 Sharing wisdom about shifting between startup companies and big tech roles.21:00 Discussing the challenges of big tech roles.22:00 Addressing the dilemma faced by Heads of Product. 23:36 Discussing the appeal of post-product market roles.25:32 Suggesting considerations for choosing roles at different quality companies.28:16 Addressing objections to starting a company.30:58 Sharing insights on finding a partner for a startup.31:57 Challenging the notion that startup work is harder than big company work.32:56 Providing advice for executives considering founding a startup.39:46 Discussing the changing job market and considering alternative career paths.

Join host Nikhyl Singhal in this fascinating episode of ‘The Skip’ Podcast, as he explores the unique characteristics and opportunities of big tech companies in the current economic climate. Nikhyl discusses the challenges and advantages of working in big tech, defined by companies like Microsoft, Apple, Google, Meta, and Amazon. Learn about the changing landscape of the industry and how professionals can make the most of their big tech experience, such as leveraging transferable skills, networking opportunities, and the chance to work on diverse projects. Additionally, Nikhyl shares insights into the increased number of individual contributor (IC) roles in the industry and why delaying managing teams can be highly career additive. Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | Facebook Full Show-notes:00:00 - Nikhyl explains why growth companies aren't as attractive and how big tech is different.02:07 - Defining big tech and examples of companies that fit this category.04:09 - The culture and hiring practices in big tech companies before 2022.10:30 - Challenges big tech companies face in creating new innovations… and their track record.11:27 - The changing environment and opportunities for working in big tech pre- and post-2022.13:03 - Transferable skills gained from working in big tech make employees attractive in the job market.15:46 - Networking opportunities available at big tech companies due to their large employee base.20:12 - The ease of distribution in big tech and the challenge of creating connected products.22:20 - Larger organizations require employees to stay longer to make a significant impact.23:50 - Challenges of building things in big tech companies, such as finding the right role.24:41 - Big tech companies are hiring fewer managers and pushing them closer to individual contributors (ICs).28:37 - Industry push for management roles led to weaker managers and less depth of craft.30:53 - Importance of building a strong skill set before becoming a manager.31:48 - Four major types of ambiguities in careers: growth, crafting and market, organizational complexities, and domain expertise.

In this episode of 'The Skip' podcast, host Nikhyl Singhal discusses the challenges and implications of ex-growth companies in the current market landscape. He delves into the consequences of overvaluation, the impact on employees and company culture, and the emergence of a new crop of prudent, conservative growth companies. Nikhyl provides valuable insights for those considering joining or staying in ex-growth companies and emphasizes the importance of exploring other stages of companies for more lucrative opportunities.Time-codes:00:00:00 Introduction to the episode focused on growth companies and ex-growth companies.00:02:00 Explanation of the three main stages of companies: startups, growth companies, and big tech or late-stage technology companies.00:05:00 Market shift towards sustainability, impacting growth companies and their focus on innovation.00:07:00 The challenges faced by executive teams in ex-growth companies as they transition from growth to sustainability.00:10:00 - Executives are getting fired or layered in growth management teams due to skills mismatch or other factors, leading to organizational changes.00:12:00 - The cultures in hypergrowth companies are becoming more aggressive and toxic as CEOs exert pressure and anxieties increase.00:13:00 - Compensation was great in these companies, but with the drop in valuations, executives are making significantly less than they expected.00:17:00 - Advice for individuals in or considering joining an ex-growth company: the culture will likely worsen, equity may not generate expected returns, and exits may not happen easily.00:23:00 - Nikhyl discusses the consequences of overvaluation and adjusting expectations in terms of growth and valuation.00:25:00 - He highlights the potential resentment and frustration among employees who feel undervalued while contributing to the company's survival and eventual success.00:26:00 - Nikhyl points out the existence of a new crop of growth companies that are more prudent and conservative, offering a more attractive option for job seekers.00:28:00 - He emphasizes the need to be wary of ex-growth companies and consider other stages of companies that could be more lucrative. 

On this episode, The Skip Podcast host Nikhyl Singhal interviews Markie Wagner, an AI expert and founder of Delphi Labs. Markie and Nikhyl discuss the transformative impact of artificial intelligence and its potential to reshape workflows. Markie shares her early experiences with computers and how her passion for building things and writing code led to her impact on the world through STEM education. The conversation explores the implications of AI for individuals at different stages of their careers and the boundless opportunities it presents.Markie Wagner is the founder of Delphi Labs (@delphi_labs), a research and advisory firm focused on applied AI and frontier technology. Her goal is to partner with companies to build ambitious applications of new technology and play a mission-critical role in the creation of institutions that matter in the human story.Prior to founding Delphi Labs, Markie worked as a researcher at Stanford and Waymo. Her interests include automating everything, new nations, psychographics, zk-proof applications, and artificial intelligence, particularly reinforcement learning and graph neural nets. Connecting with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookMarkie Wagner: Twitter | Website Show Notes:00:18 - Introducing AI expert Markie Wagner and her unique story.03:12 - Markie's early days with computers and engagement with Yahoo Answers and online games.07:17 - The anonymity of the internet allowed Markie to interact with others without revealing her young age.11:34 - Markie's early experiences with website creation and learning through experimentation.16:10 - Markie's school project focused on her love for the iPhone.18:39 - Markie's middle school experience creating a charades game for the App Store.21:28 - Learning from tech greats and building an institution to change the world.25:56 - The difference between good and bad quests and why people tend to fall into bad quests by default.34:21 - Markie's transition to making a meaningful impact on the world through STEM education.36:56 - Markie's efforts to set up STEM programs in her high school and neighboring schools.41:53 - Markie's fascination with machine learning and artificial intelligence begins in high school.45:34 - Markie's love for startups and working with founders during her time at Stanford.47:30 - Setting up AI teams and orgs for public companies and those about to go public.48:00 - Markie's decision to leave Stanford and focus on Delphi Labs.49:12 - Markie's perspective on the hype around AI and its genuinely transformative nature.53:19 - Career guidance for those worried about the impact of AI on their careers.55:21 - The importance of individual contributor work and transitioning to management.56:53 - Markie discusses the secret to her success: judgment, interesting work, and grit.58:52 - Markie shares her experience with perseverance and grit in achieving her goals.01:02:01 - Reflecting on the impact of one's work and considering a change if it doesn't make a meaningful difference.

In this podcast episode, Nikhyl is joined once again by Anneka Gupta, Annie Pearl, Briana Ings, and Shirley Lin. The group explores the topics of how to recognize and recover from burnout, as well as to achieve a healthy work-life balance. They discuss the personal nature of burnout and how it's not simply a matter of comparing the two columns of “work” and “life.” The group suggests that if you're feeling burnt out or unsure if you're on the right path, it's time to reflect on your work and make changes to achieve a more balanced state. Nikhyl advises aiming for the "yellow" as a North Star and taking corrective action to prioritize tasks and achieve a healthier state.Overall, the episode provides practical advice for anyone experiencing burnout, emphasizing the importance of self-reflection and taking action to achieve a healthier work-life balance. Nikhyl's advice to aim for a more balanced state and prioritize tasks is a helpful reminder that perfect balance may be unattainable, but making incremental changes can lead to significant improvements in mental and emotional well-being.Thanks to this group of incredible women for joining and sharing their endless wisdom. We hope to have further discussions on other big career topics. Please share the podcast with your friends :) Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookAnneka Gupta: LinkedIn | TwitterAnnie Pearl: LinkedIn | InstagramBrianna Ings: LinkedIn | InstagramShirley Lin: LinkedIn Full Show Notes:[0:00] Welcome to The Skip![0:10] Introducing our guests Anneka, Annie, Briana, and Shirley![0:30] Starting with Anneka Gupta, CPO of Rubik, Inc. - how does she handle “work/life balance?”[0:45] “I would phrase it not as ‘what do I have to fit into the box of my life’, but what do I want to fit into the box of my life?”[2:30] Brianna Ings - VP of Product at ClickUp - how does she handle work/life balance?[2:30] “I have a four month old daughter. And so the big thing for me is figuring out my new normal. So I really wanna prioritize spending time with my daughter, my husband, we used to have dinner together every night, and I wanna maintain that.”[4:00] How does Shirley Lin find joy in her life?[4:30] “my husband and I try to make sure we're connecting, but we confess, there are some nights where we kind of stand at the kitchen counter and we're eating a dinner of Salami, cheese and a glass of wine, and we're saying like, that's pretty good; good enough.“[5:30] Does being an experienced Project Manager help Annie Pearl, CPO of Calendly, decide how to effectively optimize her time?[9:00] As part of the new norm for Executives in the Zoom era, Briana vividly narrates her experience of multitasking; juggling between an important meeting, and keeping an eye on her baby daughter as she pumps breast milk.[11:30] Has anyone ever had to hold back professionally because of the need to balance time and commitments, even if it meant passing up a great opportunity at a top company?[15:45] In a graduation speech, Shonda Rhimes talked about the challenges of being a working parent. She said that whenever she appears to be succeeding in one area of her life, it often means she's struggling in another.[17:00] The additional pressures of being a working parents and the worry of the expectations of others[22:30] Many people are struggling with burnout and a sense of failure. To overcome this, it's essential to examine our relationship with work and make changes that will lead to a more fulfilling and sustainable path forward.[24:30] Nikhyl advises those feeling burnt out to aim for a more balanced state, using the "yellow" as a North Star. He emphasizes the importance of taking corrective action to prioritize tasks and achieve a healthier state, even if perfect balance is unattainable.[26:30] “There's always things that are going wrong, but can I find joy in growing and trying to get through the hardship?”[31:00] How do you make sure you prioritize yourself?[34:00] Briana struggled with saying "no" in her career, including a time when she was asked to travel for work despite not wanting to leave her daughter. She learned to prioritize her own desires and set boundaries by saying "no" when necessary, allowing her to feel more in control of her time.[36:00] Nikhyl shares his thoughts on the challenges of outsourcing and asks for personal tips from the group who are all working moms with busy schedules. Are there any "executive hacks"?[38:00] How does this group plan and schedule vacations?[46:00] Nikhyl advises leaders who are considering bigger, more demanding roles to check in and test their capacity before taking the plunge to avoid burnout.—-----The Skip podcast is designed to help tech professionals take control of their careers and achieve their professional goals. Hosted by Nikhyl Singhal, a successful founder, head of product, and executive, the podcast offers guidance on navigating important career decisions, management challenges, and personal crossroads.Nikhyl has helped hundreds of leaders in the tech industry maximize their happiness and professional life. He understands that career is one of the most critical parts of a person's identity and that many people struggle to navigate the complex landscape of job transitions, skills development, and long-term career planning.

#5: Welcome back to the Skip podcast! In this episode, Nikhyl invites Shreyas Doshi to discuss the ever-evolving role that Product managers have in today's business world, finding yourself “stuck” in the ‘middle-stage’ of your career and how making high-quality career decisions is more important than ever. Using more than a decade of experience, Shreyas also describes vastly different experiences in similar roles at similar (or sometimes very different) companies, following your own internal excitement to help guide you in the proper direction, and how to optimally manage the critical transition from an operator role into an advisory role.Shreyas Doshi has led & scaled products at Stripe, Twitter, Google, and Yahoo in over 15 years as a product manager & PM leader. In this next chapter of his career, he is an advisor for fast-growing startups across the globe and is building out content & courses based on his experience of building successful products & teams across various domains. Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookShreyas Doshi: LinkedIn | Twitter | Website Full Show Notes:[1:00] Welcome to The Skip![2:00] Introducing our guest Shreyas Doshi[3:00] “Careers are made by not one playbook, but having many playbooks. Every new challenge is not a page out of a previous playbook, but it's a blend of all these different lessons that one's learned.“ - Nikhyl Singhal[4:00] Sheryas’ experience as PM at Stripe, and redefining the idea of Product Management[9:00] “Trying to put product management as a role in a spreadsheet with cells and specific rules doesn't quite work in my opinion.” - Shreyas Doshi[10:00] How different companies and different company cultures impact the role of Product Managers[14:30] In the 'Act Two’ of your career, how do you best shift to an advisory role?[20:00] It can be useful to follow the emotional excitement about particular opportunities, and using that to gain momentum that eventually leads you to the right opportunity down the road[22:30] Quality Questions as a Superpower… The efficacy of your role as an advisor likely depends largely on the quality of the questions you ask.[24:00] Nudge, nudge: Follow Shreyas on Twitter[25:00] Sheryas’ sought his own advisors to figure out what’s next, and the answer was building effective courses[28:00] “My hypothesis was that if I structure this in a unique way and if I treat this course, like I would treat a product and kind of basically just like product manage it, since that I can have the right kind of effect on my users, in this case, my students, then that would be a wonderful kind of experience and hopefully useful for students. And that hypothesis, I would say, has been proven at this point because a lot of people have told me that it substantially changed the way they were thinking about their career.” - Shreyas Doshi[32:00] Discussing Shreyas’ tweet on success in academics vs. professional life[36:00] One's career may reach a point where they feel like they are no longer advancing or growing, which is commonly known as career plateauing, and this stage often causes a great deal of frustration[42:30] The difficulties of going from a large company with many layers of structure to a startup with essentially no multi-domain structure[44:00] Eric Wienstein’s “High Agency”[48:00] “Especially as leaders, most of our problems are actually in many ways messaging problems - because we know what the right thing is, and how we got to that conclusion, but there are so many challenges along the way to kind of message it in a way that resonates with everybody.” -Shreyas Doshi[51:00] It is important to keep in mind that both internal and organizational changes require a significant amount of time[52:00] For individuals who feel like they are at a standstill in their career, Shreyas offers advice on how to move forward.[53:00] Be rigorous about your career decisions. Take pride in your career. [1:00:00] Find Shreyas on Twitter and Linkedin!—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.Join entrepreneur, coach, and Facebook VP Nikhyl Singhal as he offers guidance on navigating important career decisions, management challenges, and personal crossroads. For many, career is one of the most critical parts of identity. Yet most people don’t have a clear sense of how to maximize their current position, evaluate job transitions, or invest in the right long-term skills to optimize their professional life. Unfortunately, if you work at a company, your manager is rarely capable or incentivized to help you develop the necessary skills or to think through transitions. And most self-help books and articles focus on your current role, not on the next one or on any sort of long-term career roadmap.Nikhyl advises nearly a hundred leaders on their tech careers. Nikhyl is certain, however, there are many others also looking to become more intentional about their career choices – which has led him to produce this podcast. Each edition, Nikhyl will dive into some of the common questions he encounters and give his distinctive insight with the hope of reaching as many people as possible. Though Nikhyl mostly works with tech leaders, he believes the themes apply to anyone looking to shape a fulfilling career.

#4: Equity, stock options, and other compensation; a complex topic that has essentially limitless negotiable options. We are going to be walking through the basics to lay a foundation and then we will break down the most common mistakes that people make in this area. If you need to know more about offer letters, vesting stocks, and managing exits this episode is for you!Connect with The SkipThe Skip: Newsletter | Website | LinkedIn CPO GroupNikhyl Singhal: LinkedIn | Twitter | FacebookLynda Galligan: Goodwin ProfileAnthony McCusker: Goodwin Profile Full Show Notes:[0:00] Welcome to The Skip![2:30] Introducing our guests Anthony McCusker and Lynda Galligan - Attorneys at Goodwin Procter[4:00] Our first example: Startup X offers you an equity package[10:00] What questions do you typically want to make sure that the employee just sort of understands when they're looking at compensation?[12:30] Is the number of shares in the offer important? Balance against the percentage of shares available[16:30] Tax liability when a company has more value on paper than reality[21:30] An 83B election[14:30] Vested options vs unvested options[27:30] Post-termination exercise periods[29:30] Incentive Stock Options or ISOs[37:00] Exploring rainy day scenarios[41:00] You have stock options but the market or company value is going down. What do you do?[43:00] Risks that are specific to private company scenarios[45:00] 409A evaluations[48:00] Important tax stipulations that disallow repricing the same option[49:30] A reminder that none of the conversation today should be regarded as legal advice[50:00] Thank you Anthony McCusker and Lynda Galligan![51:30] Episode summary and wrap up with Nikhyl—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.Join entrepreneur, coach, and Facebook VP Nikhyl Singhal as he offers guidance on navigating important career decisions, management challenges, and personal crossroads. For many, career is one of the most critical parts of identity. Yet most people don’t have a clear sense of how to maximize their current position, evaluate job transitions, or invest in the right long-term skills to optimize their professional life. Unfortunately, if you work at a company, your manager is rarely capable or incentivized to help you develop the necessary skills or to think through transitions. And most self-help books and articles focus on your current role, not on the next one or on any sort of long-term career roadmap.Nikhyl advises nearly a hundred leaders on their tech careers. Nikhyl is certain, however, there are many others also looking to become more intentional about their career choices – which has led him to produce this podcast. Each edition, Nikhyl will dive into some of the common questions he encounters and give his distinctive insight with the hope of reaching as many people as possible. Though Nikhyl mostly works with tech leaders, he believes the themes apply to anyone looking to shape a fulfilling career.  

Career transitions are filled with dozens of questions and pitfalls. Join Nikhyl Singhal and four product leaders from the Skip CPO group to discuss the challenges associated with big career decisions. Briana Ings (ClickUp), Anneka Gupta (Rubrik), Shirley Lin (Divvy Homes), and Annie Pearl (Calendly) bring dozens of years of leadership experience to the conversation, as they discuss when to leave (and not) leave your company, how to research the next opportunity, manage the interview process, and successfully interview and land that great next job. Don’t miss their inside tips on what they look for in interviews, common mistakes to avoid, and how they evaluate opportunities.Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | TwitterFollow Anneka Gupta on LinkedInFollow Annie Pearl on LinkedInFollow Brianna Ings on LinkedInFollow Shirley Lin on LinkedIn Full Show Notes:[0:00] Welcome to The Skip![1:30] Introducing our guests Anneka, Annie, Briana, and Shirley![3:30] Shirley Lin describes the company culture differences between Divvy Homes and Airbnb[6:00] The Skip Community for CPOs[8:30] “The head of product or a CPO role, it can be very lonely. You have a lot of pressure on you.”[12:00] Career errors, specifically in times of transitions into and out of roles[13:30] What to do when a company changes dramatically in size and/or in culture[14:30] “It was actually the point where I was frustrated, where I worked through those frustrations and helped solve those problems where I had the greatest growth. Both in terms of my title and getting responsibility, but also just from a personal level and having to figure out a way through those difficult times.”[17:30] Do good companies pass on good people?[21:30] Should you ask for feedback after an interview? Or after getting turned down for a position?[25:30] Pregnancy, life changes, and other times of absence[30:00] There really is no “one size fits all” for every career situation. Every person has a unique and personal journey to creating the career of their dreams[34:00] When looking for a new job, what is the process and where should you look first?[39:00] What does crafting a career framework look like?[45:00] A name with a well-known brand VS. a company that is a great unique fit for you[48:00] “It’s always easier to find a job when you have a job.”[54:00] Factoring in your seniority when thinking about finding a job (and leaving your current job)[1:01:00] Biggest pet peeves NOT to do in an interview![1:06:30] Interviewing and the “take-home” interview[1:13:00] How to decide which of your references to use for your interview and resume[1:15:00] Finding references for the company you are interviewing with or in other words interviewing in reverse.[1:16:30] Wisdom in determining if a company is worth joining or not[1:22:00] “Your boss doesn’t need to be your best friend.”  (And respect over friendliness)—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.

Tech moves fast and is ever evolving. But career worries remain constant and can weigh heavily. In this second Skip podcast, Nikhyl Singhal highlights what he calls “career frequently asked questions”: common concerns people share with him, and how you might approach these concerns to reach the best results for your own professional life. Building a career framework is important, but assessing the complexities branching off of it is vital as well. And he’s hoping you will keep the questions coming! Connect with The Skip: Newsletter | Podcast | CPO GroupFollow Nikhyl Singhal on LinkedIn | Twitter Full Show Notes:[0:00] Welcome to The Skip![1:00] The concept of “the double jump”[1:30] “If you look through most people's LinkedIn, you'll see there are multiple paragraphs because it'll be “I started in this role and then I went to the second role” and sometimes it's because things weren't working out, but most of the time it's because the company was growing and there was a new need. Companies aren't static, and in fact, if they are, that's probably not the best company to join.”[5:30] “Boring” jobs and the perception of long-tenure VS. short-tenure for a hiring manager[9:00] “Boring roles can be very career additive.”[10:00] “I'm more agnostic to the type of company I'm going to work for in terms of the product, and I'm more trying to make sure that the work I do is career additive, the culture, the people, the values, the speed in which I've seen… that matters a lot.”[15:30] How much time should you dedicate to personal professional development?[16:30] Sometimes, the best value an opportunity will bring you is the people that it connects you with[21:30] Nikhyl’s first startup experience[24:30] The size of the company can often dictate your ability to grow and develop professionally[25:30] Review and conclusion:Consider the double-jump, because the best roles aren’t often available to outsiders.Long tenures at your current company can be good to ensure that you are showing grit and learning.Boring is not a bug, it might be the most career additive.Your professional life should be more than your day job (lower pace might be smart).Meet the people you work with and stay in touch with them.Consider the talent band and ensure you are intentional about where you fit.—-----The Skip podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He coaches more than 100 executives, managers, and rising stars navigate important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life.