Alas, this isn't sufficient. For the same reason that unlimited vacation results in people actually taking less vacation, if you say this to someone without a ton of security in their position they will work approximately as much as their boss.

If the boss keeps sending emails on Friday there is no way that other people will really feel secure disconnecting.

Bingo. People are social animals and we take our cues from other people. "Unlimited vacation" sounds good but is not great in practice.

Unlimited Vacation is great if there is a base guarantee of vacation given to the employees. That is, give them their usual 2 weeks (or more) of PTO in their contract. Then anything on top of that is unlimited.

But companies know full well what they're doing. They know that if they replace guaranteed PTO with unlimited, not only does the employee take less vacation (more bang for the company's buck), but they also get to skirt around state laws on paying for unused PTO when the employee quits.

Plus, without any guaranteed PTO, companies can just decline your request for vacation any time. They can say they're in busy season, or they need office coverage, whatever. Whereas with guaranteed vacation, the manager would have a harder time declining those hours you earned due to bad optics.

Unlimited vacation without a guaranteed PTO base is a scam.

Unlimited vacation is, like you said, dependent on social cues.

Plenty of places with unlimited vacation cue or even pressure employees to take a minimum amount of vacation.

How much vacation you have is how much the company is required to pay out as earned income when you separate from the org. Anything else is generosity that can be rescinded without notice or recourse.

Edit: u/babycake's comment says it better: https://news.ycombinator.com/item?id=29879742

Yes, this is extremely easily solved. We have unlimited holiday, but you must take off at least 28 days (the statutory minimum in the UK).

I work for a small org, joined when it was like.. 7, now we're ~50, and fully remote. The where doesn't matter, but the when does for us. We still exploit synchronous communication quite heavily.

Yes i know some orgs can async everything. Some people prefer it. You could argue many cases on why async makes for a more mature interaction process, more efficient, etc. However we have not managed it. I'd say largely 50->80% of our communication is sync, and i don't see anyone advocating for changing that with us, despite having basically fully flexible hours and a global team.

Even if most communication is async there is a part of "somewhat async" and a part of "mostly sync" communication. And then there is the social aspect of not being alone, but "seeing" that others are working as well.

On the semi-async stuff: If I am stuck with a task I probably can grab a coffee and eat a snack or check mails, but I would like to get some feedback soon, while I'm in the state of mind of that task. Else I switch completely to a different task, which has effort to come back on speed on the initial task on e the feedback is there. And if there is some clarification needed, it is good if all parties focus on that topic for a while, till key questions are cleared and everybody is unblocked.

Of course it is a balance.

I agree. Async communication is hard. Humans are not equipped for this. We are limited in our focus and prioritization ability. It is the same reason calling someone on the phone gets you results and information 10x faster.

Fully async is hard; I prefer it however a lot of people do not. So I adapt to the timezone of who I work with as I am usually the most flexible (no children and enough space to not disturb my wife or dogs). I overlap significantly with Asia now and in other years with the US. Works well enough to not risk too much change.

I think the issue is coordination costs. In fact, Coase's entire theory of the firm is predicated that they exist to minimize coordination costs. I think it is interesting to think about this shift (and the remote from work phenomena as a whole), as adaptations that are essentially following a drastic reduction in coordination costs. More of our work can be asynchronous, done from disparate places, communication tools are infinitely better, etc. If you take the theory seriously, all else equal, you'd expect smaller company sizes, remote work weeks, and more generous time off. But that you'd still have a sense of needing to know "when it happens" equally makes sense given that coordination costs for a lot of these scenarios haven't reached zero (i.e. I can decide to work Tuesday but if I need Bob and he's decided to not work Tuesday that's a problem. Yes, maybe we could work something out individually, but if this happens enough times, and with enough people, its more efficient for the company as a whole to dictate a schedule when we can reasonably expect folks to be available)

How much are you "supposed to achieve"?

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Edit

Since some of the replies seem to have missed what I was alluding to, I want to put here what I replied below:

Sprint goals are based on capacity, which is loosely defined by how much your team works. Defining how much you need to work by basing it on how much you should achieve, which is based on a number defined by how much you roughly work, is circular reasoning.

> How much

Some jobs are process oriented in which the value contributed is in volume and efficiency.

>> achieve what I'm supposed to achieve

Other jobs are development oriented in which value contributed in defining the process or the end result of the process.

It seems like the former is more amenable to "regular hours" and the latter to great swings in hours spent in effort directly related to a specific purpose.

Incredibly difficult to quantify, but there are heuristics.

Look at what your peers with a similar level of experience are doing.

Look at what you're committing to do during sprint planning or 1:1s with your manager. (Assuming you're in a reasonable organization with a healthy workload.)

Anything above that is deserving of a raise or promotion.

Hence the need for good managers to set expectations and manage timelines.

Sprint Goals.

Sprint goals are based on capacity, which is loosely defined by how much your team works. Defining how much you need to work by basing it on how much you should achieve, which is based on a number defined by how much you (and your team) work, is circular reasoning.

World Without Email by Cal Newport talks a bit about the challenges here.

Specifically, Peter Drucker advocated for autonomy in knowledge work. However, this often leads to a lot of creep around meetings, Slack pings, and other context-switching activities. Cal, in the book, talks about the need to have good, organization level policies AND org-level processes to actively align to the work traits that the org needs.