The Skip podcast (Nikhyl Singhal)
Explore every episode of The Skip podcast
| Pub. Date | Title | Duration | |
|---|---|---|---|
| 21 Jan 2024 | Is my next job at a startup or big tech? | 00:33:08 | |
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.
— Where to find Nikhyl:
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| 20 Jun 2024 | Battling job search anxiety | 00:51:34 | |
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:
– Referenced: – Where to find Nikhyl: – Find The Skip: 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) 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 | |||
| 24 Apr 2023 | Should I join (or leave) an ex-hypergrowth company? | 00:29:39 | |
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.
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| 30 Jan 2025 | The Insider's Guide to Tech Compensation, Negotiation, and Career Growth | 00:55:57 | |
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking to understand tech compensation better, this episode offers practical insights for making informed career decisions. – Key topics:
– Referenced: – Where to find Carly: – Where to find Nikhyl: – Find The Skip: – 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 nikhyl@skip.community – Timestamps (00:00) Tactic for negotiating comp (01:54) Unpacking the mailbag format (03:09) Three job offers: which one should I take? (06:02) Understanding bonus structures (09:32) Why equity still matters today (17:38) Breaking the equity exit trap (25:29) Equity versus your market rate (30:37) Don't chase comp early on (34:12) Aligning the role to your superpower (37:47) Negotiating comp: Start with what matters most (47:30) When to discuss salary (51:49) Problems with averaged comp | |||
| 01 Oct 2023 | Greatest hits on career advice with Peter Yang (Roblox, ex-Reddit) | 00:50:31 | |
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: Creator Economy by Peter Yang: Referenced in this episode: Timestamps: Where to find Peter: Where to find Nikhyl: Where to find The Skip Podcast: | |||
| 10 Jan 2025 | The Widening Tech Career Divide: Big vs Small Tech | 00:57:31 | |
In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company? With the rise of AI and new economic conditions, these choices have never been more different. We break down how industry dynamics have changed, the tradeoffs associated with each path, and some exercises for determining the best fit for you. - Key topics:
- Referenced:
- Where to find Carly: - Where to find Nikhyl: - Where to find The Skip: - 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) Teaser: Big tech vs small tech: Should you do both? (00:35) Intro (03:15) Why this discussion matters (05:06) The biggest change in tech during 2024 (08:20) Why everyone should consider being a founder (10:14) How to assess your potential as a founder (14:44) How PM & engineering changed in 2024 (23:06) The all-important differences between big and small tech (28:55) Assessing your fit for big vs small tech (36:18) The challenges and benefits of working at both scales (42:31) Do the best PMs work in big tech? (52:17) Who this advice doesn't apply to (54:56) Key takeaways (56:33) Get in touch with Nikhyl | |||
| 01 Nov 2024 | Live from Lenny's Summit | Career advice highlights | 00:22:15 | |
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:
– Referenced:
– Where to find Nikhyl: – Find The Skip: – 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 nikhyl@skip.community – 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 | |||
| 27 Feb 2023 | How to avoid getting stuck in your career with Shreyas Doshi | 01:01:15 | |
#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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook Shreyas Doshi: LinkedIn | Twitter | Website
Full Show Notes:
—----- 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. | |||
| 03 Apr 2023 | The Quest for Success: A Career Story in the Age of A.I. With Markie Wagner | 00:51:35 | |
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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook Markie 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. | |||
| 11 Dec 2023 | Are you short changing your career by not managing people? | 00:37:13 | |
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:
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:
Where to find The Skip Podcast:
Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. | |||
| 13 Mar 2023 | Balancing Work and Life: Insights from Nikhyl and the Skip CPO group | 00:54:48 | |
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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook Anneka Gupta: LinkedIn | Twitter
Full Show Notes:
—----- 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. | |||
| 11 Feb 2024 | Shedding perceptions: Moving from lone wolf to team player | 00:33:57 | |
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:
— 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: — Where to find The Skip Podcast: — 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. | |||
| 30 Jul 2023 | Shadows of Superpowers (Part 2) | 00:39:07 | |
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:
Timestamps: Where to find Nikhyl: Where to find The Skip Podcast: | |||
| 08 May 2023 | Revisiting career frameworks: How Big Tech, management and IC roles have changed | 00:36:32 | |
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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook
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| 20 Sep 2024 | Mastering your 30 second resume | 00:53:30 | |
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:
Referenced: Where to find Nikhyl: Find The Skip: 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 nikhyl@skip.community Timestamps (00:00) Episode teaser: Mastering your 30s resume (01:15) Common mistakes everybody makes (09:42) Why you need a 30s and 2m career story (12:21) Showing the trailer, not the movie (16:44) Example 1 (17:28) Thinking about story sequencing (19:04) Example 2 (19:44) Avoiding detail (21:21) Example 3 (before) (21:54) Avoid abstract stories (23:52) Example 3 (after) (24:41) The art of thematic narratives (28:29) Example 4 (before) (29:18) Crafting a theme (29:51) Example 4 (after) (31:24) Avoiding jargon (34:51) Tailoring communication tempo (36:19) Example 5 (before and after) (39:04) Example of a strong 30s resume (41:13) Preparing multiple versions (45:20) 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 | |||
| 19 Jun 2023 | Six Superpowers for Product Managers | 00:34:32 | |
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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl 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:
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| 16 Jan 2023 | Crafting a career framework with Nikhyl Singhal | 00:25:59 | |
You’re wondering if you should stay in your current role, or maybe you’re stressed about accepting a new one. Well, you’re not alone. In his decade of career coaching, Nikhyl Singhal has often listened to executives wrestle with these dilemmas. And in this first Skip Podcast, he poses five specific questions that he believes can help you create your best path forward and shape your career framework.
Connect with The Skip: Newsletter | Podcast | CPO Group Follow Nikhyl Singhal on LinkedIn | Twitter
Full Show Notes:
—----- 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. | |||
| 10 Sep 2023 | How to find a great Mentor | 00:50:30 | |
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:
Referenced in this episode:
Timestamps: Where to find Nikhyl:
Where to find The Skip Podcast: | |||
| 18 Nov 2024 | Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google) | 01:06:01 | |
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders. Key topics:
Referenced:
Where to find Shreyas: Where to find Nikhyl: Find The Skip: 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 nikhyl@skip.community Timestamps (00:00) Teaser: Why average PMs can make great founders (01:17) Introduction (02:34) The essential first step before founding (06:21) Successful founder traits (10:48) Managing at scale vs managing uncertainty (18:25) Thriving in ambiguity (21:29) Red flags: when founding isn't for you (23:34) The surprising link between average PMs and founding success (25:51) Building better product sense (29:35) The right time to start your company (37:03) Beyond venture scale: rethinking startup success (44:26) A guide to avoiding burnout (49:23) The real truth about big tech working hours (52:27) Why taking a "demotion" might be a good move (58:45) Learn more: Shreyas' Product Sense course (63:15) Key takeaways (65:22) Get in touch with Nikhyl | |||
| 13 Feb 2023 | Explaining Equity and Executive Compensation with Goodwin Procter | 00:58:07 | |
#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 Skip The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook Lynda Galligan: Goodwin Profile
Full Show Notes:
—----- 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. | |||
| 29 Aug 2024 | 4 secrets of career-boosting companies | 00:20:58 | |
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:
– Referenced:
– Where to find Nikhyl: Find The Skip: 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, Twitter or email me at: nikhyl@skip.community – 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 | |||
| 21 Aug 2024 | Navigating careers while expecting | 00:12:19 | |
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:
– Referenced: – Where to find Nikhyl: – Find The Skip: 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, Twitter or email me at: nikhyl@skip.community – 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 | |||
| 16 Jan 2023 | Discussing career transitions with Heads of Products from Calendly, ClickUp, Divvy Homes, and Rubrik | 01:26:26 | |
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 Group Follow Nikhyl Singhal on LinkedIn | Twitter Follow Anneka Gupta on LinkedIn
Full Show Notes:
—----- 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. | |||
| 09 Jan 2023 | The Skip podcast trailer | 00:04:43 | |
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 has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, management challenges, and personal crossroads to maximize their happiness and professional life. So subscribe to this podcast to hear from him and other executives as they teach unique career lessons. | |||
| 10 Jul 2024 | The art of building your personal brand | 00:37:31 | |
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:
Referenced:
Where to find Nikhyl: Find The Skip: 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) 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 | |||
| 07 Jan 2024 | Coaching grit, patience & tenure | 00:34:27 | |
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:
Timestamps Where to find Nikhyl: Where to find The Skip Podcast: Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. | |||
| 28 May 2024 | Avoiding burnout for high achievers | 00:33:13 | |
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:
– Referenced: – Where to find Nikhyl: – Find The Skip: 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/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 | |||
| 16 Jan 2023 | Career FAQ with Nikhyl Singhal | 00:28:37 | |
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 Group Follow Nikhyl Singhal on LinkedIn | Twitter
Full Show Notes:
—----- 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. | |||
| 14 May 2024 | Crafting a compelling career story | 00:41:19 | |
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:
— Referenced:
Where to find Nikhyl: Find The Skip: — 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 | |||
| 22 May 2023 | Exploring Head of Product career choices: From founding a startup to growth phases | 00:40:39 | |
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.
The Skip: Newsletter | Website | LinkedIn CPO Group Nikhyl Singhal: LinkedIn | Twitter | Facebook
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. | |||
| 10 Sep 2024 | Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo) | 01:15:42 | |
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:
Referenced:
Where to find Shreyas: Where to find Nikhyl: Find The Skip: 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 nikhyl@skip.community Timestamps (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 | |||
| 30 Jul 2024 | Stage of company: a career unlock | 00:44:08 | |
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:
Referenced:
Where to find Nikhyl: Find The Skip: 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) 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 | |||
| 05 Jun 2023 | How much money do product managers make? | 00:34:43 | |
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 chart Tech compensation: Beyond the offer letter How equity in tech companies works Explaining Equity and Executive Compensation with Goodwin Procter
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.
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| 13 Aug 2023 | 5 rules that will unlock your Product Management career | 00:27:55 | |
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 product 2. Ensure each transition is career additive 3. Who you know will matter as much as what you know 4. Find a strength area and build a superpower around it 5. Bet on yourself
Timestamps: [00:00:00] Intro [00:01:33] Overview of the 5 rules [00:02:00] Rule #1 Product manage your career like a product [00:05:43] The importance of seeking out feedback [00:07:13] Rule #2: Ensure each transition is career additive [00:10:40] The external vs internal realities of a company [00:13:08] Rule #3 Who you know will matter as much as what you know [00:15:03] How to build your network authentically [00:18:38] Rule #4 Find a strength area and build a superpower around it [00:21:16] The shadows of your superpowers [00:22:08] Rule #5 Bet on yourself [00:24:08] Why promotions 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/nikhyl LinkedIn: https://www.linkedin.com/in/nikhyl/
Where to find The Skip Podcast: Website: https://www.skip.show/ YouTube: https://www.youtube.com/@theskippodcast TikTok: https://www.tiktok.com/@theskippod Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202 | |||
| 16 Jul 2023 | Shadows of your Superpowers (Part 1) | 00:31:06 | |
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:
Where to find Nikhyl:
Timestamps: | |||