I worked at a very small company where HR was directly reporting to the CFO (who was gunning for CEO and trying to also spawn his own grandiose IT projects). Our DBA made his negative opinions known in the midst of a data warehouse project sponsored by the CFO. This triggered Mr. Pointy Hair CFO and put the DBA on his shit list.

One day the DBA casually submits a query to HR asking "what is my package if I quit?" The HR director immediately runs to the CFO and tells him about the question posed by the DBA. The CFO flips his shit and is quoted as screaming something about wanting him fired immediately. We just had a change in management and the new CIO wasn't having it. He just ignored the CFO. It didn't end there. Over the next six months the CFO plodded on and eventually got the DBA fired...though the DBA was not trying to smooth anything over. He went to HR a second time to ask about his package. LOL.

Yep, this is how reality works. Have to be careful about what you ask.

That's why I never bothered asking my company if I could permanently WFH, just went along with everything until I found a new job.

Asking for a raise doesn't get you "flagged as a troublemaker" unless you're really an ass about it.

You are assuming that the management is rational at your company. That's quite a big 'if'.

If they flag you and management is not rational that's one big red flag to leave that place ASAP

This is the thing that many people in this discussion are missing. There are many many many bad managers out there. Maybe this thread has all the good tech managers in the industry who would never do anything against their employees interest - but that isn't the reality facing most tech workers.

In my experience - good managers tend to get promoted quickly, while average/below average line managers tend to stagnate. In this environment, it's likely most line managers aren't the greatest managers and the ones interacting directly with ICs have a lot of skills to develop in the manager role.

The reality of most people is that they go to the job for a paycheck and put up with the (bad) management as a cost of that. In this environment, the most effective path towards higher pay is switching jobs, instead of risking navigating the inclinations of typically bad management.

Job market isn't equally friendly for all of IT around the world.

Why do you want to stay at a company in this situation, then?

You may not have other option. IT workers aren't drowning in jobs in many places around the globe.

Asking for 30% or else, is kind of assholish. But quite reasonable for new job.

Not if you're making 40% below market (and can prove it).

Have you ever seen that happen, or heard of it? I can't think of a time I've heard of an employee being fired for asking for a raise

If it gets discussed among management it's because the person already has a reputation as a troublemaker. The salary demand (in that case) is just icing on the proverbial cake.

Right on. If they think you're about to leave, they'll also be less likely to promote you.

Focusing on switching jobs when you already have a stable job puts you in a win-win situation.