Off the VPN

If you want to escalate, we can escalate


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Jasmine bought a sauna and “Deb” lost her job. One of those stories is relaxing—the other, not so much. This week, Allison brings a tale straight from the tech trenches: a PM asks for a little backup on a big customer call, and somehow ends up ousted from the team. From calendar drama to missed deadlines and a total breakdown in trust, this one’s got everything except a single honest conversation.


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Highlights:

  • The Vibes Are Immaculate… Until They’re Not: When leadership excitement turns into a pressure cooker.
  • Fake Demos & Fast Deadlines: How a half-baked prototype turns into an urgent, must-ship-now nightmare.
  • Burnout & Moving On: What happens when work keeps piling up and the recognition is absent?

Jump into the conversation:
(00:00) Intro
(03:08) A classic PM vs EM power struggle
(04:26) Deb asks for help on a customer call
(07:24) Missed deadlines and broken expectations
(10:56) Performance issues derail the launch
(12:29) EM questions Deb’s 1:1s with data
(14:49) Control, ego, and influence at play
(18:02) Deb gets cut out without warning
(22:59) Bad PM-EM dynamics hurt everyone
(25:28) Crashing out together, one story point at a time

...more
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Off the VPNBy Jellyfish