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Re:Ask HN: What are the biggest challenges preventing startu... by allday on Tuesday May 08, 2018 @12:33PM (#17022243)
The biggest challenge to making remote workers successful is the existing company culture. If the organization has not been built with a conscious "remote-first" mindset, new remote collaborators will inevitably be excluded from necessary communications and decisions. Making a remote worker a true part of the team requires a massive culture shift if your company does not already (successfully) do distributed work.
Re:Ask HN: What are the biggest challenges preventing startu... by redundo_twa on Tuesday May 08, 2018 @01:18PM (#17022661)
You also need to maintain the culture. A phenomenon I just went through is a company that started remote-first, then someone had the brilliant idea to get an office for this or that geographical cluster of people, and slowly but inexorably remote workers were marginalized.

Some people feel really insecure without an office, deep inside they think it isn't a "serious business" unless you own real estate in a "serious" postcode. I don't know if it's just an European thing but it's definitely an attitude I've encountered.

Re:Ask HN: What are the biggest challenges preventing startu... by jamie_ca on Tuesday May 08, 2018 @01:39PM (#17022845)
It also depends on the business somewhat, but actually having an office you can invite outsiders to (investors, prospective clients) can be an indicator of success. Truthful or not, it's the perception that counts.
Re:Ask HN: What are the biggest challenges preventing startu... by redundo_twa on Tuesday May 08, 2018 @01:50PM (#17022955)
I understand, but that's such an "old world" style. It's like building a datacentre, in the age of cloud computing, simply because owning big iron is an indicator of success (all the big boys have datacentres, right?).

In IT, tbh, I think we should just own it. There are more productive and creative ways to send out that sort of signal.

Re:Ask HN: What are the biggest challenges preventing startu... by hluska on Tuesday May 08, 2018 @02:28PM (#17023387)
I'm jumping in to say that I agree with you. Our industry quite literally invented tools to make physical offices obsolete. Speaking as a tech person, it strikes me as hypocritical at best and self sabotaging at worse to maintain this interest in physical space as a marker of success.

But, then the marketing/sales part of my experience chimes in and I think of all the various times in my career that having physical space added to my credibility. I think of the sectors (government tech and financial tech instantly come to mind) where decisions makers are heavily moved by AAA office space. And, I think of how many times I've seen spending an obscene amount on rent actually convert into paying customers.

My inner developer is saying "right on" but my inner marketer/sales type is thinking of all these times when physical space has a positive ROI from a sales/marketing point of view.

Re:Ask HN: What are the biggest challenges preventing startu... by hashkb on Tuesday May 08, 2018 @12:49PM (#17022408)
This takes extraordinary discipline on the part of the in-office team. Fortunately, everything that's good for a remote-first culture is also just good for communication in general. A culture of documenting everything, living in public, and over-communicating is good for any company; and burning those habits into teammates levels them up for life.
Re:Ask HN: What are the biggest challenges preventing startu... by chris11 on Tuesday May 08, 2018 @01:23PM (#17022699)
>This takes extraordinary discipline on the part of the in-office team. Fortunately, everything that's good for a remote-first culture is also just good for communication in general.

I think it's even harder for companies that have open open offices or are doing Agile. Those two things usually mean the companies are explicitly stressing in-person collaboration. In-person communication isn't a bad thing by itself, but I think that explicitly valuing in-person communication ends up making remote work harder.

Re:Ask HN: What are the biggest challenges preventing startu... by ruffrey on Tuesday May 08, 2018 @01:02PM (#17022522)
I've worked remote for 6 years. This comment echoes my experience.
Re:Ask HN: What are the biggest challenges preventing startu... by deedubaya on Tuesday May 08, 2018 @12:50PM (#17022414)
This is the best answer.

It is really hard for established companies, full of many different humans with their habits, to shift from shouting across the room to some sort of distributed, async, communication.

Re:Ask HN: What are the biggest challenges preventing startu... by jamestimmins on Tuesday May 08, 2018 @08:36PM (#17026576)
I don't understand why companies don't build specific teams that are 100% remote, with perhaps an onsite project manager (or something like that). Then the team could develop its own norms and culture, and while it would be isolated from the rest of the company, it collectively gives the remote workers much more of a voice than if they were each on different teams.
Re:Ask HN: What are the biggest challenges preventing startu... by dredmorbius on Tuesday May 08, 2018 @01:07PM (#17022557)
Red Hat v. Debian.

Arguably, one of Ubuntu / Canonical's failings.

Re:Ask HN: What are the biggest challenges preventing startu... by tych0 on Tuesday May 08, 2018 @01:08PM (#17022566)
Huh? Canonical is excellent for remote work, and I know many people who work at Red Hat who say the same about it.
Re:Ask HN: What are the biggest challenges preventing startu... by dredmorbius on Tuesday May 08, 2018 @05:42PM (#17025458)
I meant far more the former.

The Debian - Canonical distinction is milder, though the latter has at least some centralisation. Nowhere near as much RH's.