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 tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re considering a career move now or just want a structured way to assess future opportunities, this ep...
Feb 27, 2025•50 min•Ep. 35
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 ...
Jan 30, 2025•56 min•Ep. 34
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 to...
Jan 10, 2025•58 min•Ep. 33
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders. Key topics: Which PMs are secretly great founder material Red flags: when founding isn't for you The right time to start your company Key skills that set you up for success Thriving in ambiguity Debunking the "venture scale or...
Nov 18, 2024•1 hr 6 min•Ep. 32
Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss: Rethinking retirement The career-defining question every leader should ask Power years versus foundational years Leveraging career stories Finding peak roles Un...
Nov 01, 2024•22 min•Ep. 31
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 capt...
Sep 20, 2024•54 min•Ep. 30
In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders. We also discuss: Why founder mode is a mindset, not a title Whether founder mode is good or bad Balancing detail and delegation The importance of product sense and good judgment Mastering founder mode as a product...
Sep 10, 2024•1 hr 16 min•Ep. 29
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 ...
Aug 29, 2024•21 min•Ep. 28
In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior role post-maternity leave, or seek opportunities elsewhere. – We also discuss: Maximizing career potent...
Aug 21, 2024•12 min•Ep. 27
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 makin...
Jul 30, 2024•44 min•Ep. 26
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 leg...
Jul 10, 2024•38 min•Ep. 25
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 too...
Jun 20, 2024•52 min•Ep. 24
Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies. In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set healthy boundaries, and cultivate a resilient mindset. – In today's episode, we discuss: Why burnout is a...
May 28, 2024•33 min•Ep. 23
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 articu...
May 14, 2024•41 min•Ep. 22
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 ...
Feb 11, 2024•34 min•Ep. 21
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 t...
Jan 21, 2024•33 min•Ep. 20
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...
Jan 07, 2024•34 min•Ep. 19
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 p...
Dec 11, 2023•37 min•Ep. 18
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 bui...
Oct 01, 2023•51 min•Ep. 17
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 an...
Sep 10, 2023•51 min•Ep. 16
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. U...
Aug 13, 2023•28 min•Ep. 15
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 ...
Jul 30, 2023•39 min•Ep. 14
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 t...
Jul 16, 2023•31 min•Ep. 13
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 c...
Jun 19, 2023•35 min•Ep. 12
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 t...
Jun 05, 2023•35 min•Ep. 11
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 yo...
May 22, 2023•41 min•Ep. 10
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, network...
May 08, 2023•37 min•Ep. 9
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 mo...
Apr 24, 2023•30 min•Ep. 8
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 ca...
Apr 03, 2023•52 min•Ep. 7
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 ma...
Mar 13, 2023•55 min•Ep. 6
