The Skip Podcast

Hosted by Nikhyl Singhal

Business Careers Education

Website RSS feed YouTube

Episodes

Latest episode

Aug 2026

Language

About the show

The Skip podcast helps tech professionals get ahead in their career. It's hosted by Nikhyl Singhal, a three-time founder, CPO, and product executive at Meta and Google. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. He now runs Skip Coach, a career service powered by the world's top CPO community, and has coached hundreds of product leaders through career decisions, management challenges, and transitions. Subscribe for career insights distilled from real coaching conversations. theskip.substack.com

Listen to episodes

56 recent

August 20, 202659 min

To Invent Waymo, They Had to Reinvent PM

In this episode, Saswat Panigrahi, Waymo's CPO, joins me for the third conversation in the "Inside PM" series. Saswat joined Waymo in 2016, back when it was still Google's self-driving car project and the entire product team was fewer than five people, and has spent all ten years since on the same product. In this episode, we discuss how his product org had to invent its own way of measuring good when there was no dashboard to check, why he hires and promotes for competence, courage, and compassion, and what it takes to be an executive builder at Waymo. – Key topics: • Cutting severe injuries "sixteen-fold" • Why measuring good driving became its own product, staffed by dedicated eval PMs • Why specifying what good looks like is AI's hardest problem • Injecting rain and fog into simulated scenes instead of waiting a decade for the real thing • The living room pitch to Waymo's first driverless riders • Avoiding "Brownian motion": channeling vision into tracks a team can actually execute • Spotting curiosity and grit in candidates in the age of AI • Training to the point of failure – Timestamps: 00:00 Introduction 03:25 Joining Google's self-driving car project before it was Waymo 07:15 Why "feeling the pain" of failures builds real product leadership 08:56 Motivating a team a decade away from a real product 14:38 Was there ever a moment you thought this wouldn't work 16:15 Why measuring "good" driving became its own product, staffed by dedicated eval PMs 18:55 The living room pitch to Waymo's first driverless riders 21:11 Confronting the 40,000 deaths US roads accept every year 23:46 Cutting severe injuries "sixteen-fold" 27:59 Training to the point of failure 33:27 Spotting curiosity and grit in candidates in the age of AI 37:14 Integrity, and sleeping at night over what you approved 41:02 A tree of metrics, not a union list of 37 dashboards 47:14 Competence, courage, and compassion: what builds followership 53:53 What AI has democratized for product discovery and research 57:41 Why specifying "what good looks like" is AI's hardest problem – Brought to you by: • Firecrawl —the web data API for AI agents. Use code THESKIP for 10K free credits • Jira —Do the right work with Jira – Referenced: • AMD • Edwin Markham's poem on preparedness • Google X • Inside PM at Meta • Inside PM at Stripe • MMLU • NASA • Piccadilly Circus • Transformers • Waymo – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Saswat: • Twitter/X • LinkedIn – Join The Skip: • Skip Coach • Skip Community – Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts – Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

August 5, 20261 hr 1 min

Lessons From Three Product Leaders Living in the Future

This is the next episode in a series on what product management becomes when the AI hype meets real constraints. I sat down with three CPOs living about a year ahead of the rest of us: Sharmeen Chapp, Midjourney's first-ever product hire; Jiaona Zhang (JZ), CPO at Laurel; and Henrik Berggren, who runs product and design at Mutiny. Their teams are tiny on purpose, yet these are companies with years of history, paying customers, and enterprise contracts—not the frictionless blank slates that "AI-native" suggests. We get into who should actually be building, how customer signal should move through a company, and how each of them installed an AI-first operating system without tipping into theater. – Key topics: • What never changes in PM • Laurel's "captain" model: everyone is a builder • Zoning the codebase like a garden so everyone can build safely • Making the whole company understand the customer • The AI Operations team: pairing hackers with leaders • Treating the AI transformation as a product, with employees as the users • Moving at "Cheetah speed": sprint when the tools jump, then rest • Current PMs are managing a fleet, not an empire • Why the strongest leaders are going hands-on now – Timestamps: (00:00) Introduction (03:30) Meet the three CPOs: Midjourney, Laurel, Mutiny (08:45) Laurel's "captain" model: everyone is a builder (13:03) Zoning the codebase like a garden (17:19) Governing change when anyone can ship to production (18:23) Sharmeen at Midjourney: installing product judgment (21:53) Henrik on finding the line by stepping over it (24:57) A Slack channel that pings on every meaningful action (26:59) Running AI in public so skeptics convert (29:29) The AI Operations team: pairing hackers with leaders (32:15) Incentives, public systems, and evergreen context (36:46) Managing context overload with distributed PM (39:45) A user interview to shareable clips in 45 minutes (45:16) First-party vs. third-party: what to build, what to buy (47:34) The token-maximization "blip" and raising the floor (49:31) Managing a fleet, not an empire (53:40) "Cheetah speed": sprint when the tools jump, then rest (56:37) Why the strongest leaders are going hands-on now (57:29) Does the pendulum swing back to old-school PM? (59:48) What never changes: business, customer, orchestration – Brought to you by: • Firecrawl —Power AI agents with clean web data • Use code THESKIP for 10K free credits – Referenced: • Anthropic • Cursor • Devin • Dropbox • Dust • GitHub • Google Drive • Grain • Granola • Laurel • Meta • Midjourney • Mutiny • Notion • Procter & Gamble • Slack • Stripe • Twitch – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Sharmeen: • Twitter/X • LinkedIn – Where to find JZ: • Twitter/X • LinkedIn – Where to find Henrik: • Twitter/X • LinkedIn – Join The Skip: • Skip Coach • Skip Community – Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts – Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

July 22, 20261 hr 1 min

Inside PM at Stripe: What Comes After "Become a Builder"?

Kevin Yien is the Head of Product for Merchant Experiences at Stripe. Before that he led Product at Mutiny and Square. In this episode, Kevin and I discuss how to keep AI from becoming theater, why a PM shipping to production can be a red flag, and why AI is pulling product management back to its fundamentals of strategy, opinion, and judgment. – Key topics: • Why "PM is dead" is the wrong frame, and every function is "shifting left" • The three PM archetypes, and how zero-to-one changed most "Killing your darlings" and keeping the blast radius small • From a personal knowledge corpus to a shared "team brain" • The "floors and ceilings" of a shared knowledge base • Why building 10 prototypes no one sees is just theater • Writing as "clarity at scale," and why LLMs still can't do it • Why vibe coding is a wasted learning opportunity unless you interrogate it • The "eight and 80 test" for joy, pace, and hard family seasons – Timestamps: 00:00 Introduction 03:40 What Kevin owns across Stripe's merchant experiences 05:24 Stop asking which role dies, focus on the outcomes 08:05 The three PM archetypes, and why zero-to-one changed most 10:50 Kill your darlings: keeping the blast radius small 14:30 The PM as the "arbiter of context" 17:55 Floors and ceilings of a shared "team brain" 20:43 "Does this obsolete me?" The PM layoff fear 22:50 Are wikis and knowledge artifacts back? 28:42 How Stripe incentivizes sharing: carrots over sticks 31:35 The pet peeve: 10 prototypes, zero users 35:20 Onboarding as a product: the first 100 days 38:16 Writing as "clarity at scale," and why LLMs still can't do it 45:35 The "piano scales" for a PM: forming an opinion 48:37 Do engineering-background PMs still win? 52:30 Are product, design, and engineering roles merging? 55:30 Joy, pace, and the "eight and 80 test" – Brought to you by: • Asana —The operating system for human agent teams – Referenced: • Andrej Karpathy • Block • Claude Code • Contentful • Dovetail • GitHub • Kevin on Lenny's Podcast • Lindy effect • Lovable • Obsidian • Patrick Collison • Stripe • v0 • Writer – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Kevin: • Twitter/X • LinkedIn • Website – Join The Skip: • Skip Coach • Skip Community – Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts – Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

July 15, 202639 min

Builder-Executives Are Getting Paid Like Pro Athletes

Product pay is detaching from the old bands the way it did for AI researchers. In the past few weeks I've seen three offers go out to product executives at $10 million a year, and while almost nobody gets that number, it pulls the whole field up. The builder-executive who can build with modern tools and operate at scale now commands two to three times what the same profile did a year ago. In this episode, my co-host Carly Malatskey and I walk three real career decisions end to end: a leader worried the AI bubble will pop and playing it too safe, a consultant trying to become a product builder, and an elite executive trying to match joy, purpose, and income in one role. The throughline is the "Skip" question: not how to maximize today's job, but which next move opens the path to elite a few years out. – Key topics: • Why builder-executive pay detached from the bands • The three questions every career-maximizer should ask themselves • Thinking of constraints as a risk budget • Why staying current beats the biggest job at the best company • How to test whether a company is actually "current" from the outside • Why top-of-market pay comes with strings, and how to sequence what you optimize for • The mercenary vs. missionary approach Timestamps: (00:00) Introduction (00:39) The 100-day shift: builder execs and $10M offers (04:04) Case 1, Angie: two safe offers and an AI-bubble fear(05:04) Optimizing to be elite, or just to be prudent? (06:58) Why a failed hot startup can leave you better off (10:58) Thinking about what your next role sets up, not just the salary (15:40) Case 2, Gary: Series A vs. Fortune 20 (16:36) Working backward from the PE operating-partner dream (18:58) The biggest job at the most current company, not the best (22:40) How to tell if a company is actually "current" (25:26) Case 3, Monica: elite, comfortable, and chasing joy (26:57) One more operating role, then founding (29:33) Choosing mercenary over missionary (35:26) Would the right company help her find a co-founder (37:18) The three questions that shape modern career advice – Brought to you by: Asana —The operating system for human agent teams – Referenced: • Anthropic • Meta • Microsoft • OpenAI • Stripe – Where to find Nikhyl: • Twitter/X • LinkedIn – Where to find Carly: • LinkedIn – Join The Skip: • Skip Coach • Skip Community – Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts – Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

June 24, 20261 hr 2 min

How Meta Is Reinventing Product Management

Meta is one of the biggest dinosaurs in the park, yet in a matter of months it rebuilt PM top to bottom, and almost none of it was bought. My guest is Jagjit Chawla, a VP of Product at Meta who’s running a growing share of the Facebook app: Feed, Reels, and more recently Search. I worked alongside Jagjit for nearly ten years across Google, Credit Karma, and Meta, and almost nothing is as I remember it. These systems were built by the teams themselves, sometimes in a single evening, on tools you already have. Jagjit walks me through how a product org of a few thousand people learned to move like a startup again. Key topics: • Inside Meta’s “no-meeting week” that set the org loose on the tools • The one job AI can't take: influencing other humans • Why the PMs winning on Jagjit’s team aren't engineers • What to do when you’re the bottleneck • How to become an "AI captain" • Triaging tens of thousands of bug reports with agents that validate and pre-write the fix • Why letting AI write code made site incidents spike, and how Meta clamped down • Building a morning brief that flags the decisions only you can make • Why the management "compression algorithm" is dead and what replaced it Timestamps: 00:00 Introduction 05:47 Why the biggest change is pace 07:29 From detailed PRDs to a paragraph, a prototype, and an eval set 09:32 Why the management "compression algorithm" is dead 10:37 Visibility is high, but synthesis is scarce 14:45 "Finding a scissor" when you don't have fancy tools 16:10 A morning brief that flags the decisions only you can make 22:37 When the agent quietly drops your source links 25:53 The one job AI can't take: influencing other humans 30:18 Getting an analyst's answer in five minutes, not 24 hours 33:33 Three ways AI changed the products, not just the process 37:25 Why letting AI write code made site incidents spike 40:39 The no-meeting week and the birth of "AI captains" 44:55 The world's largest Jenga game: why institutional knowledge wins 48:41 Why economics and physics PhDs are "out-PMing" engineers 52:14 Ideas and agency before tools 56:19 "AI lowers the floor and raises the ceiling" 58:40 Closing advice: once you taste it, you can't go back Brought to you by: • Glean —Work AI that works • Framer —Design and build your website effortlessly with Framer Agents Referenced: • Claude Code • Credit Karma • Facebook • Ferrari • Gmail • Google • Google Chat • Google Drive • Indian Premier League (IPL) • Instagram • Meta • Porsche • Prince of Persia • TikTok • Workplace from Meta • Zoom Where to find Nikhyl: • Twitter/X • LinkedIn Where to find Jagjit: • LinkedIn Join The Skip: • Skip Coach • Skip Community Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

June 10, 20261 hr 8 min

5 Career Questions Your Old Playbook Can’t Answer

In today's episode, we work through five questions from leaders in the Skip community who are doing well by any measure: a director whose career keeps ending in short stints despite strong performance, a manager whose top performer turned adversarial, an exec fielding multiple outsized offers, a PM who does her best work with a great manager, and a first-time manager whose first report is more experienced than they are. In each case, the old playbook can't answer the real question. Key topics: • The "layoff merry-go-round": why short stints compound and what it actually takes to break the cycle • Why the decision to found should only stay on the table if you're obsessed with a specific problem — not just bullish on AI • How a sponsor-to-manager dynamic turns adversarial • "Every superpower comes with a shadow", and what that means for the manager who created the monster • Why some management relationships reach a graduation, and how to recognize when you're there • The mercenary vs. missionary question: and why the person asking usually already knows their answer • Why senior product leaders should remove "great manager" from their job search criteria entirely • The pretzel framework: how to identify the culture where you have to “bend yourself” the least • Why being "safe" as a manager matters more than matching your direct report's experience level Referenced: • Anthropic • ChatGPT • Claude • Copilot • Facebook • Google • Meta Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 Brought to you by: • Glean —Work AI that works • Guru —Trusted knowledge for every AI tool and team Where to find Nikhyl: • Twitter/X • LinkedIn Where to find Carly: • LinkedIn Join The Skip: • Skip Coach • Skip Community Find The Skip: • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps: 00:00 Introduction 03:32 Finding the question behind the question 06:00 The director with three short stints weighing their next option 07:17 Breaking out of the "layoff merry-go-round" 14:37 Why founding should only stay on the table if you're truly obsessed 17:18 The manager whose top performer turned adversarial 18:41 How the sponsor-to-manager collision actually happens 24:48 "Every superpower comes with a shadow" 25:30 Why some management relationships reach a graduation 35:02 The exec fielding multiple offers and the question underneath 41:27 How to know you've earned the right to seek balance 46:50 Remove "great manager" from your job search checklist 51:17 The pretzel framework: find the culture where you bend least 57:20 The new manager whose first direct report is more experienced than them 58:25 Why being "safe" matters more than matching your report's credentials 1:02:40 "I don't need a bigger version of myself" This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

May 20, 202659 min

10 Job-Search Rules That Just Broke

In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten different ways. All three reported feeling something I’ve started calling smiling exhaustion: working hard, going long, and surprised by how good it feels. If you're a senior leader, sitting in a stable role debating a move, weighing how you can ride the AI shift, or quietly wondering if founding finally belongs on your career path, this conversation is for you. Key topics: • How AI agents have flipped the first year at a new role from headwind to tailwind, and are even bringing joy to the first year of a new role • The new founding math: fast, fun, and skill-additive, with a much lower downside than it used to be • How to navigate the job search when you don’t live in San Francisco—and remote jobs are dwindling • Why structured AI learning is the wrong move, and what to build instead, so your fluency is hard to fake • How to signal hard boundaries to a new boss, and differentiate between real respect and performative virtue-signalling • Why holding your professional identity loosely matters when the role of senior leader is getting reformatted in real time Referenced: • Airbnb: https://www.airbnb.com/ • Atlassian: https://www.atlassian.com • Claude Code: https://claude.com/product/claude-code • Harvey: https://www.harvey.ai • Loom: https://www.loom.com • Modern Animal: https://themodernanimal.com Brought to you by: • Guru—Trusted knowledge for every AI tool and team: https://www.getguru.com/?utm_source=the-skip&utm_medium=podcast&utm_campaign=skip-promo • Customer.io —The customer engagement platform for human messaging: http://customer.io/skip Where to find Nikhyl • Twitter/X • LinkedIn Where to find Dana • LinkedIn Where to find Briana • LinkedIn Where to find Pei-Chin • LinkedIn Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps: 00:00 Introduction 04:08 Welcome, and why this is the second job-search postmortem 05:50 Meet Dana, Briana, and Pei-Chin 06:15 What the "smiling exhaustion" state is 09:58 Three career transitions, three different triggers 15:26 Has founding become a must-have on the modern career path? 17:09 Why "AI company" doesn't need to be a hard filter 21:43 The new founding math: Three-month traction windows and "everyone codes" 26:16 How AI agents flipped onboarding from headwind to tailwind 31:33 How to navigate the decline of remote-friendly roles 36:27 Setting hard family boundaries in the 996-company era 40:47 How proactive do senior leaders need to be to build their role pipeline? 43:10 Standing out to recruiters when your CV lacks traditional experience 47:43 Discovering Claude Code: "I felt like a sorcerer" 53:21 Why structured AI learning isn't necessary 57:21 When your resume doesn't fit the pattern, teach the interviewer 58:48 Closing wisdom: hold your identity loosely This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

April 29, 202643 min

The product skill you must now master: Reinvention

If you're in a career transition right now and wondering whether you did something wrong, you didn't. Every question coming into Nikhyl.AI keeps circling the same idea: do I really have to reinvent? In today’s episode, Carly and I dive into four questions, from people in very different scenarios: A senior PM who feels her career’s gone backwards, an IC5 at a FAANG anchored by immigration constraints, a 50-year-old veteran a year into a job search, and a mid-career operator convinced he's hit a dead end. Each of them feels behind. None of them are. The whole industry is in a state of reinvention — if they'd reinvented five years ago, they'd be reinventing again today. Key topics: • Why the first stage of any transition is mourning, and why most people get stuck there • The builder vs. manager divide: why "capital-P Product Managers" are thriving and "capital-M product Managers" are not • Why proving to yourself and others that you’re a builder is the currency that keeps you alive in the next round of layoffs • The uncanny valley of mid-to-late-career PMs and how you can climb out of it • Why coaching, consulting, and advisory roles are shrinking careers in a world of rapidly-improving LLMs • The “double-jump” job search strategy and why you should stop optimizing for the 10-year role • How you can turn a non-PM background into a superpower with AI and product skills Where to find Nikhyl Twitter/X LinkedIn Where to find Carly LinkedIn Join The Skip Skip Coach Skip Community Find The Skip Website Substack YouTube Spotify Apple Podcasts Timestamps: 00:00 Introduction 00:40 You're not behind, you're right on time 03:23 The senior PM who stepped backwards and lost her identity 04:36 Why "you're in mourning" is the first thing to say out loud 08:38 Builder vs. capital-M Manager: who the industry is actually hiring 12:28 The IC5 at a FAANG, the immigration clock, and infrastructure work 13:31 Why last year's "suck it up" advice stopped working 18:30 If you have builder instincts, you need to make sure people know about it 20:02 Navigating layoff season: Who should be worried and who should relax 23:02 The ageism reframe: Why a beginner's mentality beats pedigree 25:47 The 50-year-old veteran caught between coaching and "a real job" 27:29 Why coaching isn't a durable career in the LLM era 28:51 The "double jump" job-search strategy: get back in motion first 33:12 The mid-career operator who's convinced he's hit a dead end 35:30 Why being "non-technical" is no longer a blocker in 2026 36:09 How to reframe breadth of experience to form a power combination 39:03 "You didn't defer reinvention. You waited until now." 42:27 Embracing reinvention: First, mourn — then get back into motion This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

April 15, 202656 min

What PM Hiring Managers Actually Screen For

Most interview advice tends to come from the candidate’s perspective - how to prep, share your experiences, and follow up. This conversation pulls back the curtain on the other side of the table. I spoke with hiring leaders from Netflix, Rippling, and EvenUp to learn how three great, yet operationally-different companies evaluate candidates. Surprisingly, all three leaders agreed on one core truth: most candidates are operating from a playbook that’s two years out of date. AI has upended the job-search landscape: old signals are table stakes, and the goal posts have changed. Key topics: • The new PM: Why companies are looking for candidates who “push the limits of what’s possible” • The shift from behavioral to scenario-based questions • Does pedigree still matter? Why trajectory is the new alternative signal for recruiters • The three things that now separate a great take-home case study submission from a generic one • Why case study presentations are still valuable - and help demonstrate core PM skills • Whether website applications actually get looked at and why referrals are more binary than most people think • How to signal drive and a frontier-pushing mindset when everyone claims to be a high performer Where to find Nikhyl • Twitter/X • LinkedIn Where to find McKenzie • LinkedIn Where to find Sam • LinkedIn Where to find Sarah • LinkedIn Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps 00:48 Introduction 04:12 Meet our guests from EvenUp, Rippling, and Netflix 09:06 How has the hiring process changed since COVID? 11:17 Is AI fluency explicitly tested in interviews? 12:42 Why quality and speed are favored over prioritization ability 16:16 Past experience vs. scenario questions—where the balance is shifting 19:52 Does pedigree still matter to hiring managers? 23:10 Why trajectory is an underrated signal to index on 26:43 Why the LinkedIn DM isn't dead 29:31 Does the take-home case study still hold value in the AI era? 33:21 Using case studies to screen for brevity, agency, and strategic thinking 39:09 Rippling's product discussion and panel case study process 43:52 Unpacking red flags in case study presentations 45:43 The collaboration test: curiosity vs. defensiveness under pressure 47:56 How to get noticed — are website applications even worth it? 50:56 Where EvenUp proactively sources candidates 53:00 Closing advice for mid-career PMs navigating today's job market Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

April 1, 20261 hr 6 min

How to Navigate Org Drama

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 short tenures are more common than most people think • The one question that puts your manager in an impossible position • How to navigate an underperforming direct manager • Why acting before a restructure is announced gives you a head start • How to build the relationships you'll need on a rainy day before you actually need them • What happens when VP sponsorship and calibration approval still aren't enough to get promoted • How to start fresh on a new team when you're leaving a dysfunctional one behind • The five-point playbook for navigating office politics without getting swept into them References: • Claude: https://www.claude.ai • Floodgate: https://www.floodgate.com • LinkedIn: https://www.linkedin.com • Meta: https://www.meta.com • OpenAI: https://www.openai.com Brought to you by • Framer—Build websites with enterprise needs at startup speeds: https://framer.link/dFacxBQ • Customer.io —The customer engagement platform for human messaging: http://customer.io/skip Where to find Nikhyl • Twitter/X • LinkedIn Where to find Carly: • LinkedIn • She Leads Podcast • Twitter/X Join The Skip • Skip Coach • Skip Community Find The Skip • Website • Substack • YouTube • Spotify • Apple Podcasts Timestamps: 00:00 Introduction 03:18 Why organizational politics are so top of mind 04:59 “Everything’s changing, and no one’s telling me anything” 06:35 The two common reasons behind radio silence 12:41 Tough conversations shouldn’t be your first conversations 15:05 Why confrontation isn’t always the answer 17:35 Avoid putting your manager in a defensive position 22:12 Why role tenure is more malleable than you think 26:18 When a company reorg shifts you into a new role 29:55 How modern is your skillset? 33:57 How to identify whether burnout is worth it 40:03 Is the cost of your ambition future regret? 45:12 How to deal with an underperforming manager 55:23 Leaving a dysfunctional team for a new one 59:14 Drive impact first, talk long-term goals second 1:02:06 Why managers respond positively to specific goals Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at skip.coach . 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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com