The rest of the team will end up having to go out of their way to accommodate you, your accomplishments won't be as visible, and you'll be passed over for performance-based compensation and/or promotion.

Though I guess that's fine if it's a job you plan to take for a year or whatever and move on.

You end up being an "external" person. They'll make plans without you. The primary communication channel is always in person. As a colleague put it, you end up the drunk person in the group who's going, "huh??? what are we doing??" while the rest of the team feels like they have to drag you along. You may well be the most productive person on the team, but people tend to resent accomodating you.

I do believe the entire team remote is better than the whole team onsite, but it's also a lot more work. It's like adopting a framework; it may be better or worse in the long run but it's complex and requires some investment, and you can't have one person running on a different framework.

We've also had things like drama and internal politics - these are always much better handled in person. As in we've had corrupt assistant managers just completely screw up the senior devs, but because that assistant manager met with us in person, we'd favor them instead of the people actually doing the work.

Keep in mind that it's usually a culture thing. Programmers working from home makes sense, sometimes the janitors, security, chefs, CS want to work from home too, which makes less sense. Whenever I've done crunch time on weekends, the managers or more senior ones are always there too, even when they're doing nothing, sometimes all the way up to the CEO. A lot of office cultures seem to encourage this form of suffering together. This is also more likely where the staff is mostly offline e.g. Tesla or Amazon.

So I see absolutely no reason to give up compensation for this - this might actually hurt your argument. One option is taking on a part time contract instead so they're not under the same benefits as the ones who are working from office.

Your friend needs to demonstrate that they are an exceptional hire, only then does negotiations about compensation and working arrangements come into play.

The first of those really sold me on joining their company about how they were the greatest employer ever. This one didn't work out. They weren't as great as they thought they were because software was not their primary business and they had not worked out the economics of a software business in a way that makes any kind of sense. When the financials are in trouble your job is not stable.

The second of those didn't have to sell me, but they gave me to time to train up for a required certification and promoted me within one year of employment. They also respect my time even during office hours. This second one is a wildly different contrast to the former.

My best recommendation when interviewing is to focus on what they want from your daily activities. Really drill in and ask probing questions to test the water because that lets them know whether you will be compatible. Ignore all the work culture insanity they will attempt to sell you on and focus on how they want you to spend your time and what they expect you return to them. Be very specific.

When you are working remote you really need to operate with a superior level of communication. The more you are able to communicate at the level of senior management the better off you are. If that isn't you or your friend then working remote can be a risk. If it isn't them the risk applies equally, but only to you and/or your friend.

To be fair, most people would.

I negotiated to go remote after working at a company for a few years (this was pre-COVID and much less common.) I worked hard, went above and beyond and proved that I was a valuable employee and discussed the possibility with my boss. We did a phased approach: I'd be remote one day a week for a month, then two days the next month, etc until I was fully remove. After a few months of being fully remote and still being as productive (or I'd say even more productive) they let me do global remote.

IMHO Working remotely is a privilege, you have to earn it and work hard to keep it.

Perhaps theoretically, but I don't really see this being a winning strategy, you're just going to waste everyone's time. If a company doesn't want to do remote, they aren't going to change their mind for you. There are all sorts of tax and logistical reasons to not have remote, and a place that isn't setup for any remote employees isn't going to go through the cost of setting it up for one easily replaceable person just because they interviewed well.

Yes, no.

>Is there an approach that is better than just asking directly?

No.

Remote rules vary by company and job. Some jobs advertise remote ok. Some you can ask to do remotely. Some companies have hard rules for working on-site all of the time or a few days a week.

More senior people and those with in-demand skills have more leverage. Freelancers often work remotely.