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

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• 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

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Where to find Carly:

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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

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