<p>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.</p><p><strong>Key topics</strong></p><p>• What to do when leadership goes dark, and you can't tell if a reorg is coming</p><p>• The stay-vs-go framework: when brand matters, when comp overrides it, and why short tenures are more common than most people think</p><p>• The one question that puts your manager in an impossible position</p><p>• How to navigate an underperforming direct manager</p><p>• Why acting before a restructure is announced gives you a head start</p><p>• How to build the relationships you'll need on a rainy day before you actually need them</p><p>• What happens when VP sponsorship and calibration approval still aren't enough to get promoted</p><p>• How to start fresh on a new team when you're leaving a dysfunctional one behind</p><p>• The five-point playbook for navigating office politics without getting swept into them</p><p></p><p><strong>References:</strong></p><p>• Claude: <a target="_blank" href="https://www.claude.ai">https://www.claude.ai</a></p><p>• Floodgate: <a target="_blank" href="https://www.floodgate.com">https://www.floodgate.com</a></p><p>• LinkedIn: <a target="_blank" href="https://www.linkedin.com">https://www.linkedin.com</a></p><p>• Meta: <a target="_blank" href="https://www.meta.com">https://www.meta.com</a></p><p>• OpenAI: <a target="_blank" href="https://www.openai.com">https://www.openai.com</a></p><p></p><p><strong>Brought to you by</strong></p><p>• Framer—Build websites with enterprise needs at startup speeds: <a target="_blank" href="https://framer.link/dFacxBQ">https://framer.link/dFacxBQ</a></p><p>• <a target="_blank" href="http://Customer.io">Customer.io</a>—The customer engagement platform for human messaging: <a target="_blank" href="http://customer.io/skip">http://customer.io/skip</a></p><p></p><p><strong>Where to find Nikhyl</strong></p><p>• <a target="_blank" href="https://x.com/nikhyl">Twitter/X</a></p><p>• <a target="_blank" href="https://www.linkedin.com/in/nikhyl/">LinkedIn</a></p><p><strong>Where to find Carly:</strong></p><p>• <a target="_blank" href="https://www.linkedin.com/in/carlymalatskey">LinkedIn</a></p><p>• <a target="_blank" href="https://www.sheleadspod.com/">She Leads Podcast</a></p><p>• <a target="_blank" href="https://x.com/carlymalatskey">Twitter/X</a></p><p></p><p><strong>Join The Skip</strong></p><p>• <a target="_blank" href="https://skip.coach/">Skip Coach</a></p><p>• <a target="_blank" href="https://skip.community/">Skip Community</a></p><p></p><p><strong>Find The Skip</strong></p><p>• <a target="_blank" href="https://www.skip.community/">Website</a></p><p>• <a target="_blank" href="https://theskip.substack.com/">Substack</a></p><p>• <a target="_blank" href="https://www.youtube.com/@theskippodcast">YouTube</a></p><p>• <a target="_blank" href="https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ">Spotify</a></p><p>• <a target="_blank" href="https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202">Apple Podcasts</a></p><p></p><p><strong>Timestamps:</strong></p><p>00:00 Introduction</p><p>03:18 Why organizational politics are so top of mind</p><p>04:59 “Everything’s changing, and no one’s telling me anything”</p><p>06:35 The two common reasons behind radio silence</p><p>12:41 Tough conversations shouldn’t be your first conversations</p><p>15:05 Why confrontation isn’t always the answer</p><p>17:35 Avoid putting your manager in a defensive position</p><p>22:12 Why role tenure is more malleable than you think</p><p>26:18 When a company reorg shifts you into a new role</p><p>29:55 How modern is your skillset?</p><p>33:57 How to identify whether burnout is worth it</p><p>40:03 Is the cost of your ambition future regret?</p><p>45:12 How to deal with an underperforming manager</p><p>55:23 Leaving a dysfunctional team for a new one</p><p>59:14 Drive impact first, talk long-term goals second</p><p>1:02:06 Why managers respond positively to specific goals</p><p>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 <a target="_blank" href="http://skip.coach">skip.coach</a>. 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 <a target="_blank" href="mailto:[email protected]">[email protected]</a></p> <br/><br/>This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit <a href="https://theskip.substack.com?utm_medium=podcast&#38;utm_campaign=CTA_1">theskip.substack.com</a>