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Comment by nostromo | Hacker News Reader

I once convinced a CEO of a company with a few hundred employees to move from Outlook to Gmail.

For a while after I was a social pariah. My expense reports would go missing (want to find a Microsoft fan? look in accounting). My calls to IT (staffed with MCWhatever certified individuals) unanswered. The controller pulled me aside and said in a menacing Brooklyn accent I didn't know he had in him, "I would appreciate it if you would make this go away."

I learned a valuable about switching costs that day.

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I once recommended a 12 person company move from a self-hosted, internal exchange server to Google for email. They ignored me until a truck hit a telephone pole and we lost email for 2 days.

I worked for a similarly sized firm a few years ago and we also moved from Exchange to Gmail, partly because we had had a few severe outages with Exchange for various reasons. From a technical perspective, the migration went pretty smoothly. But there were at least a couple non-technical people on the business side who always hated the new system, partly because Gmail didn't have the hierarchical folder system they were used to. (And I don't think Gmail had sublabels at the time.)

I feel you, nested labels is the easy answer to this. However, the better answer is teaching people about archiving and search.

People used to folder their emails because searching was terrible. Gmail's search is pretty good, so the best workflow in my opinion is to archive email once you're done with it, and search if you need something specific. I do use labels too, especially auto-labels, but I've found search to be more useful.

Still, some people are reluctant to change, and just want to do things the way they've always done it. So that's why nested labels exist.

My issue with gmail search is that it's incomplete, and I don't know how incomplete.

I've downloaded my mail to mac's mail app. With identical search strings, the Mail app finds more messages.

This includes searching by sender email, which yields incomplete results in gmail.

There have been many occasions where I've only sent someone one email, or vice versa. Gmail often misses these.

So for anything I must find (e.g. tax documents) I label them.

Are you sure that isn't due to duplicates in Apple Mail? If I'm remembering right, things with labels (including "Inbox") will have copies in All Mail as well as each of their label "folders."

IMAP and POP use hierarchical folders and don't understand that a tax email might be marked as both "Government" and "Finances", or whatever your filing system happens to be.

I'm sure that could be an issue as well, but it's not causing the problem in my case.

I've found 1-2 emails in mail from a particular sender, where gmail was unable to find any results, even with their exact address.

I've likewise found perhaps 7/10 of a set of emails in gmail, and found the remaining 3 in mail (while confirming they had unique information not listed in gmail).

No, the better answer is a simple hierarchical folder system.

People only use search exclusively in Gmail because they don't have folders.

Actually, it has. You can nest labels. With the extra benefit a message can be in more than one folder if it pertains to two different subjects. Very powerful.

"...a message can be in more than one folder if it pertains to two different subjects"

That's not a benefit. It complicates things. Folders are simpler - one location, one parent, one place to go and find it. Average users can understand folders. Heck, expert users can use folders immediately without having to figure anything else out.

If nested tags are better than straight hierarchies for storing and finding things...where are all of the nested tag file systems? In a nested tag file system - would I have to go all the way to a settings dialog to create a new label like in Gmail?

Also, look at this guy's post about how "Gmail sucks when you have lots of mail" - and his response to someone recommending nested tags (Apparently, you can't just drag an email to nested tag.) - https://plus.google.com/105059362788808645801/posts/3amd9ZMi... All the web-app loving hipsters jump on his case for not "knowing the tool". I love it. How about just give us a tool that works like we expect? Who wants to invest time figuring out a new email client that has very questionable benefits?

I don't know how long ago that happened but if it happened today, I'd resolve that by going to Verizon and picking up a hotspot device. Connect the mail server to the hotspot and you have it working again.

Do you easily get a fixed IP on mobile?

I believe my mobile IP tends to remain the same for long periods of time but I was assuming they had a mail server off site which was relaying the mail to their exchange server which is how I do it. I wouldn't trust changing DNS settings to the mobile IP.

I use a remote data center email server because office/residential network connections tend to be unreliable. Even without the telephone getting knocked down, I get intermittent outages. I'd prefer to have mission critical services (like email receipt) working at a data center. This way the message is received and doesn't bounce back. Then, my local exchange server can pull the data when it's online.

So, I guess the mobile option wouldn't really work in this case unless you were sure the IP address won't change.

I believe Verizon's LTE network assigns a publicly routable, persistent IPv6 address.

I think you can also request an individual IPv4 address as well but I don't know if it's persistent.

Just get a backup MX. http://dyn.com/email/dyn-email-backup-mx/

wow please tell more. "for a while" means people's anger passed? or you guys switched back?

I wasn't at the company for much longer after that. No, I wasn't fired. ;)

The company was very East Coast, very sales-driven, not very tech-driven at the time. I don't like using age as a proxy for tech-savviness since there are plenty of tech-savvy older folks, but this was a bit of an older organization as well.

But yeah, people adapt. They will kick and scream and claim that their world is ending and then a month later they'll forget about the old way of doing things. (Or, as was often the case, IT just set up their Outlook to pull their emails from Gmail's servers.) And then the anger subsided.

>IT just set up their Outlook to pull their emails from Gmail's servers

I've noticed that using IMAP on multiple devices can cause Gmail to say that you're using too much resources. Tripped me when I first saw the limitations. I had not thought there were limits on Gmail. How did they handle issues where people might want to access Gmail from various devices? Google has some numbers and recommendations here[1] but I'm interested in how you handled situations like this in the real world.

[1] https://support.google.com/a/bin/answer.py?hl=en&answer=...

>want to find a Microsoft fan? look in accounting

I seriously doubt Accounting has Microsoft fans as such. They're very wedded to their tools and workflow in order to do their job because they spend their entire day on email and spreadsheets. Take away those and replace them with crippled alternatives like only Excel on the web, and they'll still hate it even if made by Microsoft.

How would a developer react if one day their vim editor was removed and replaced by EMACS or vice versa because of a mandate from the CEO?

No, it's worse than that. At least Emacs is roughly on par, in terms of capability. Replacing Excel with Google Docs Spreadsheets is like replacing vim with Notepad.

Maybe in accounting (who should have better tools, anyway) Excel is irreplaceable, but most other Excel users make all kinds of idiotic tables with it, all of them without even a single mathematical operation.

And that's to say nothing on the idiocy when those users decide they are empowered by their tools and decide they'll do math with them. I've seen more than one case where the AVG function was replaced with SUM and COUNT.

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