Is my next job at a startup or big tech?

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.