The Skip Podcast

Work getting political isn't new, but surviving it without derailing your career has never been more challenging. As organizations flatten and restructures accelerate, the instincts that used to work — push back, demand clarity, make noise — often backfire. In this episode, we answer five questions from people caught in reorgs, managing-up dynamics, and situations where the "obvious" move turns out to be the wrong one.

Key topics

• What to do when leadership goes dark, and you can't tell if a reorg is coming

• The stay-vs-go framework: when brand matters, when comp overrides it, and why shor...

Most of the conversation about rebuilding product management comes from two ends of the spectrum: AI-first startups with 30 people and no real installed base, or big tech with thousands of PMs and decades of process. This episode is about the third category: companies that went public in the last few years, have real customers and revenue to protect, and are now trying to move like startups again. The CPOs of Hims & Hers, Rubrik, and Figma joined me to discuss what that actually looks like. Several of their findings directly contradict the advice you'd get from either end of the...

Most job search advice comes from people still in the thick of it—anxious, second-guessing, pattern-matching off too little data. This episode is different. We sat down with three product leaders who recently landed roles at Netflix, OpenAI, and Abridge, and did a full postmortem. What they shared upends a lot of conventional wisdom: the spray-and-pray pipeline doesn't work, your AI credentials matter less than you think, and the relationships that land jobs are often years in the making.

Key topics

• Why you need curiosity, not experience

• The "AI hungry" mindset: search...

It's promo season, and I've gotten roughly 1000 questions through nikhyl.ai—the pattern is unmistakable: people aren't just asking how to get promoted, they're asking whether the system is broken and whether they should quit over it. In this episode, we dissect five real questions from PMs who've been passed over. What becomes clear is the mistakes aren't in execution—they're in how people think about promotions in the first place. The tough reality is promotions are harder to get in this market. The question isn't whether you'll get promoted. It's how you respond when you don't.

The "join a hot company" narrative gets even more complicated once you enter the AI-native part of the market. In Part 3 of our PM Career Framework for AI series, we close out with the doors everyone's obsessing over: AI labs, hot AI startups, ex-growth companies, and founding.

We unpack what these companies actually look for (spoiler: it's not "AI experience"), why hands-on builders win over managers, how location and pace become make-or-break constraints, and how to think about risk and chaos when the upside is real.

If you're trying to figure out whether you should...

The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a prestigious logo is quietly costing you career momentum. We break down nearly 600 listener questions, then map the first set of doors, from Big Tech and public enterprise to the “quality middle” of elite private companies and recent IPOs.

Key topics

• The “doors” framework: building a personal stack rank

• Golden handcuffs: when staying in Big Tech is ration...

The old PM career playbook doesn’t work in the AI era. In this episode of The Skip, we lay out a new career framework for product managers, and it’s a lot more “choose your door” than “climb the ladder.” If you’re wondering whether to stay in big tech, jump to an AI startup, double down as a builder, or rethink your whole path, this one’s for you. We talk about why your hard-won product intuition is quietly becoming obsolete, why some ex-VPs are happily taking senior IC roles, and how to prepare for what’s coming next.

Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six months. We explain why directors are taking IC roles (and thriving), why your Big Tech salary might be a golden trap, when to finally leave that stalled growth company, and why founding is suddenly on everyone's radar. If you're making any career move in 2025, your old playbook will hurt more than help.

The New Career Math:

• Why senior IC roles now trump management posi...

In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.

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Key topics

• Why your first job should feel like a sprint, not a stroll

• How to tell if your job is setting you up — or holding you back

• The truth about internships (they matter more than your degree)

• How to stand out when applying — and why “spray and pra...

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking your career.

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Key topics

6 common patterns holding leaders back

How mentors can spot them, and what advice to give

Breaking through organizational barriers

In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—and the shadow that comes with it.

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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 episode offers a practical guide to making confident job decisions.

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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.

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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.

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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.

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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:

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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 un...

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:

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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.

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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.

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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...

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.

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.

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.

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In today's episode, we discuss:

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 fo...

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 re...

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 ha...

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...

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...

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 di...

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:

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 c...

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.

Tod...

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:

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...

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 m...

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...

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...

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...

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...