What's my best option for my company's email and to-do lists?

May 18, 2012 6:10 AM

How difficult is it to switch to Microsoft Exchange? And is it worth it for my needs?

Basically, my business partner will be taking a much smaller role and I need to be able to keep track of what he's getting done in his new limited position. Right now, we use imap for our inboxes, sent folders, and drafts, while almost all other folders are localized in order to avoid a crazy sync time on our mobiles. From the end of this month on, I will need access to his email account and it needs to be clear who answered what email (me or him) in real time. I'd like to be able to have access to all his folders on my phone. Thing is, he has like 1gb of mail from over the years. We also need a collaborative to-do list that's able to be edited (with notes added) by either person. This list should be able to both have set dates/times and allow for items with no specific date. The to-do list will pretty much consist of calls that need to be made by him, as well as follow-up emails he needs to remember to send.

I mentioned how we're currently dealing with email, but I'm also not really liking our current collaborative to-do list set-up, which is Evernote.

I'm wondering if Microsoft Exchange is my best option? And how difficult it is to set up and convert folders over, including localized ones in Thunderbird, given my limited needs listed above. I've also briefly looked at Google Apps for Business. How do either of those two options deal with syncing on Android? ie do all email folders sync at specific intervals? I'd imagine this would take forever.

Thanks very much.

posted by gman to computers & internet (12 answers total)

Exchange is not your best option. You'll still be trying to get it all organized under Exchange in a month. If you set up IMAP to only download message headers on check it shouldn't be that big of a deal. Your phone will only download the message if you click on it. I would think that is the default set up on a phone mail client.

However, given what you are trying to accomplish I wonder if what you really need is a lightweight CRM such as Highrise. That will be much better at tracking who did what than trying to trck it all via email accounts.
posted by COD at 7:46 AM on May 18, 2012 [3 favorites]

Agreed. You think about using something like Salesforce or Highrise for this sort of work?
posted by chunking express at 7:52 AM on May 18, 2012 [1 favorite]

Android is Google's baby, and I would expect Google's mail back-end to work more smoothly with it than Microsoft's.

I also can't think of anything an Exchange client can do with an Exchange server that an IMAP client can't do with an IMAP server using roughly equivalent bandwidth.
posted by flabdablet at 8:08 AM on May 18, 2012

I'm not sure if this is the best option, but one way to handle this is to get all of your email into a Gmail or Google Apps email account and connect to it through IMAP. Gmail / Google Apps allows you to set a maximum # of emails to sync in each IMAP folder (the smallest # is 1,000). So if you start using Google, you can connect your phone to both email accounts, but you won't be syncing 2 GB of emails, you'll just sync the most recent messages. Maybe that would solve the problem?

Migrating old email from one IMAP account to Gmail over IMAP is very simple with any email client (e.g., Thurderbird) - here's one article on how to do it. The more difficult part is how to keep sending email to that Gmail / Google Apps account, but with forwarding or Google Apps that's not a huge challenge.

This brings me to your second question: for a dead-simple to-do list, you could put the to-do list in Google Docs. Both of you can access the same doc at the same time and see each other's edits instantly, so there's no more sync conflicts. The best part is your Google Docs would be tied to your Gmail account, so it's all one login, and to share a doc with each other one person just shares it to the other's Gmail account.

But these are quick-and-dirty options and you could get running in a week or two. As COD and chunking express say, if you're looking for a robust long-term solution, you probably want some kind of CRM. That requires you two to set up the CRM and learn how to use it, which is a longer project but may pay out in the end with much more efficient processes.
posted by Tehhund at 8:09 AM on May 18, 2012

Oh, these are great suggestions. I'm going to check out those CRM's, but I have a question about the Gmail solution and how that would work vis-a-vis my Gmail account. Okay, so basically, I have a Gmail account right now that is used to sign in on my phone for buying apps, etc., as well as my RSS feed, and a few other Google things. I do not currently use my Gmail account for mail, whatsoever. Would Tehhund's idea work with my current Gmail account that has all this other shit tied to it? Or would I want to set up another Gmail account for business? Can one even have two Gmail logins on an Android? Oh yeah, not sure if this matters, but my email domain is currently handled by SmarterMail and I'm on my own server. Thanks!
posted by gman at 8:31 AM on May 18, 2012

I think you want Google Apps for Business, not Gmail. There are migration tools to import your mail (it says Exchange but that tool is also for generic IMAP). Additionally, with Apps you get an SLA and do not fall under Google's consumer privacy policy (you own your data, not them). Mail delegation ("send on behalf of") is supported by both Apps and regular Gmail. You can have multiple Google accounts on one phone, it's fairly seamless. Syncing works well, and with the Gmail client you can do server search (that is, find mail which is not on your phone) so that's handy too. You will need to be able to change the MX records on your domain to cut over to any other mail server, but that's pretty easy to do.

I have a similar set up for my own stuff, if you want to see it in action or have other questions I'll be around Queen/Spadina later this afternoon and could give you a quick demo. Send me a memail.

I also can't think of anything an Exchange client can do with an Exchange server that an IMAP client can't do with an IMAP server using roughly equivalent bandwidth.

Actually in an enterprise environment I can think of quite a few things you can only do with Outlook/Exchange, but it's generally big company make you want to shoot yourself in the face type nonsense.
posted by tracert at 10:22 AM on May 18, 2012

Oops, I completely skipped your last paragraph.

And how difficult it is to set up and convert folders over, including localized ones in Thunderbird, given my limited needs listed above.

I can't speak for how difficult it is to migrate email to Exchange. It appears that Microsoft has an Microsoft Transport tool to help with this. But if I had to guess, I would guess that Exchange, which is designed for very large enterprises, has more configuration and more ways that can go wrong. That's just an educated guess - your operation sounds a little small for the complexity of Exchange.

As for migrating IMAP folders to Gmail, it's very simple - especially with Thunderbird. The link in my first answer explains it (and googling Gmail Thunderbird IMAP Migration turns up lots of hits), but here's the short version: In Gmail, create a label for every IMAP folder you want to transfer. Then connect Thunderbird to the old email account and the Google Apps/Gmail account - all of those labels will appear as IMAP folders in Thunderbird. In each IMAP folder, select all of the messages and choose "Copy To" the IMAP folder in Gmail. This operation will take a long time, but when it's done all of your old messages will live in Gmail. I've done this twice in the past month and it was a breeze.

The real question is how you'll migrate your old email ([e-mail]) to Google Apps. But that's something that people do every day, so it's definitely a solvable problem (Google it :).

I've also briefly looked at Google Apps for Business. How do either of those two options deal with syncing on Android? ie do all email folders sync at specific intervals? I'd imagine this would take forever.

Good news: it won't take forever. I wish every app worked as well as Gmail syncing on Android. Let's break it down:

Android devices can connect to any number of Google accounts. I currently have 5 Google accounts on my Android - 3 personal Gmail accounts, 1 Apps for business account, and 1 Apps for Education account. They all play nicely: I can access the email for each account separately. So don't worry if you need a few accounts. And you can control how many days of email to sync on each account. So you might do 5 days on your personal account and 6- days on your business account.

As for sync intervals, Gmail and Google Apps both support push email to Android phones, and the push integration is silky-smooth - I never notice any big syncs or slowdowns. So just use the default Gmail app on your phone - the app makes connecting to Google very easy, and push is automatically enabled without you having to do anything special. Now this is where it gets cool: Google's email / Android integration is extremely good. New emails or changes you make on your phone appear in the other location very, very quickly, meaning the web app and the Android app both connect to Google's severs and deliver their changes very efficiently, and the changes are pushed to the phone rapidly. I've never had my phone slow down while sending or receiving email; I don't know Google's architecture, but I believe actions on your phone (e.g., mark as Read) go to Google individually and new emails go to your phone individually, instead of requiring a gigantic sync of every single folder. Anyway, in my experience there's no "giant email sync" problem on Android if you're using Gmail. I'd strongly recommend it.
posted by Tehhund at 10:35 AM on May 18, 2012

I'm wondering if Microsoft Exchange is my best option?

All these people telling you about Google Apps For Business are entirely in the right. You don't want to use Exchange unless you have the resources to spend on a team of people whose full time job will be deploying, maintaining and just understanding Exchange. It's a monster; seriously, check this shit out. And that's just the Architectural Diagram, not the nuts-and-bolts of getting it running.

Organizations that have less than about 400 people in would need to be insane to even consider Exchange as a mail and calendaring tool.
posted by mhoye at 11:58 AM on May 18, 2012 [3 favorites]

In fairness, I should add a caveat: In response to this question I started playing around with my sync settings on my Android, and those changes caused my phone to re-download 6 days worth of email. During this big download, the Gmail app was a little slow to bring up my messages, and the syncing integration for all of my accounts was not silky-smooth as promised. But it didn't slow down the device at all, it just meant that the currently-syncing account took a minute to download the messages to display since it didn't have them stored locally.

Now that it's all re-downloaded, the syncing is back to silky-smooth. If I mark something as read on my phone, it's marked as read on the web about 30 seconds later without me doing anything else (such as manually initiating a sync). The integration is that tight.
posted by Tehhund at 12:50 PM on May 18, 2012

Organizations that have less than about 400 people in would need to be insane to even consider Exchange as a mail and calendaring tool.

Hah, do you work in IT? That is a bit of a stretch there friend. Exchange is a very competent and easy to manage mailbox server once you get to know it, I actually like it quite a bit. It's not a great MTA compared to Postfix et all, but for mailboxes I happen to think it is the bees knees. Not all deployments have to be super complicated, I have built highly available clusters with as few as 5 or 6 VM's (that's including HA load balancers and other infrastructure). If you are (very) easy with uptime requirements a single server and a passive standby can do the job for a hundred users, easy. You also don't need an army of people to manage Exchange, a single administrator who doesn't suck can handle infrastructure for hundreds of users. On top of doing other things (usually, a lot of other things).

Realistically I think for an organization of a few dozen people or more on site or hybrid Exchange is a viable option, depending on needs. Cloud services come with their own challenges in production, it's not all sunshine and rainbows.

Anyway, before we veer even more wildly off topic, I definitely agree with your sentiment if not your numbers. Exchange is not a good fit for a company of two people.
posted by tracert at 12:52 PM on May 18, 2012 [1 favorite]

As long as we're just throwing out ideas, I believe Office 365 includes Exchange hosted email. So if you decide you want to go with Microsoft you could look into a hosted exchange server instead of running one yourself. Touchdown by NitroDesk is an excellent Exchange client for Android that has more features than the built-in Exchange functionality (it costs $20, but buying it 3 years ago has been worth it).

I'd obviously still vote for Google Apps, but the hosted Exchange idea is an option.
posted by Tehhund at 2:57 PM on May 18, 2012

Hah, do you work in IT? That is a bit of a stretch there friend.

Listen to what you're saying. Six virtual servers just for Exchange plus the virtualization layer they run on (and the SAN storage layer backing it - and the offsite backups for that, you do have offsite backups, right?), a DC (and its concomitant GC somewhere set up for failover - you do fail over to somewhere, right?) and a separate log server (you do have centralized logging, right? And those logs are backed up through a separate channel?).

Exchange is quite powerful for sure, but it's a huge, complex investment of time and effort that requires a shocking variety of skills and resources to implement and manage properly. There might be two dozen people in the world who fully understand all of Powershell, SAN storage management and Microsoft's licensing terms, and as you might imagine, they're busy this week.

Exchange is the mainframe of mail servers. It only makes sense if you're a huge organization that's already heavily invested in Microsoft's technologies, and the competitive advantage they offer over hugely cheaper, much more easily scalable SAAS solutions like GAfB is not at all clear right now.
posted by mhoye at 8:50 AM on May 19, 2012