Anybody thinking of angling for a severance package?
I've done this several times. It isn't that different from what happens when you resign - you have a compelling event (employee who is exiting). Doing something with this event is the trick.
The real problem you will run into is that people like to think in periods of years.
Depending on your level and criticality, you could probably go, right now, and get a 1Y retention package by making it really clear you are going to leave. Strategically, "I have another option I'm thinking of pursuing" is better than "I'm retiring" even if "I don't need the money" might seem like a better argument (it's not). That's easy. Given that, for some amount of effort, your management chain can arrange package if they're going to do anything.
However, it's a lot harder to do something like a "severance" package or a < 1Y package. The reason for this is that for anything special or out of the norm, the verbiage matters a lot, your boss is either themselves able to green light the package himself (e.g., an EVP) or may need to actually get sign-off by an SVP, EVP or some chain. There is annoyance friction at each layer. The right nomenclature matters (retention vs severance) but either way, none of those people are really going to want to put in work for "only {3|6} months."
As an aside, asking for a cash equivalent to what would _otherwise be_ stock vesting acceleration is actually a superior framing device.It's a pain in the neck to modify vesting schedules, etc., on an individual basis. The only reason this is possible for layoffs is that it's a mass action and the effort is delegated and amortized. But using it as a framing device is probably OK, just make sure you are clear about that because otherwise you risk being classified as some crazy.
I'm actually going through this right now.
Btw, I agree with you that the Financial Samurai "Engineering Your Layoff" book is probably trash. I have a lot of experience and have spent a ton of time dealing with layoffs, EVPs, CEOs, SVPs, and so on. I think most of what he writes about how business culture works is bafflingly naive if not straight up fan fiction.