Office (logo)There are two different ways to get email hosting from Microsoft: outlook.com which is primarily targeted to consumers and free (ad-supported), and Office365 targeted to professionals and at a monthly fee. I’ve been using both for a long time and would definitely recommend either one, but there are some differences between them.

Sync Speed

My Office365 emails arrive within seconds to my BlackBerry as well as to my desktop Outlook. My outlook.com emails arrive within seconds on my BlackBerry, but sometimes can take as long as an hour to reach desktop Outlook. That hour could be a substantial difference in productivity. You definitely cannot have a quick back-and-forth conversation, the kind of things that are common in my daily work.

For me, I’m happy to see a personal outlook.com email quickly on my BlackBerry, but then I’ll often ignore replying to it thinking I’ll get around to it once it’s available in desktop Outlook. If it is urgent, I do have a few options:

  • I can reply directly on my BlackBerry. I have a Passport with a physical keyboard, but it still isn’t as fast as a full-size computer keyboard.
  • Reply from my phone via BlackBerry Blend on my computer. This has one feature oddly missing – email signatures – but I do typically have it open for BBM anyway, so it isn’t really slowing me down much. It’s my most common feature regardless.
  • Go to outlook.com using my browser. It’s a few extra steps – sometimes several extra steps if I have to sign out of one of my other accounts to sign into the one I want. It can be worth it if it’s an ongoing conversation that makes it worth briefly leaving the tab open, but I rarely bother.

I really hope this improves. It seems strange to me that outlook.com can be so slow getting to a desktop app with the same name, but if you really prioritize speed on desktop Outlook, it’s probably worth paying up for Office365.

Domain Name

In terms of branding, if you want to use your own domain name, you have to use Office365. There used to be a service called Windows Live Domains which would allow you to have the equivalent of outlook.com for free with your domain, but that was discontinued (not long after Google had discontinued a similar offering). If you’re a professional, your email probably should look like it with an email address at your own domain. That marketing element alone might be worth a few dollars a month to you.

Bundling

Office365 hosted email by itself is only a little bit less per month than the Business Essentials package. This package provides a lot of other potentially useful items, including 1 TB of OneDrive for Business storage, a Yammer network, Planner, Office Groups, and more. If you want hosted email anyway, this is a pretty good bargain to pad on top of it.

Draft Sync

Office365 email accounts can synchronize drafts, which outlook.com cannot do. This can be helpful if you’re in a situation of having to switch devices partway through sending an email. I can start something on my BlackBerry on a bus, then finish on the desktop when I arrive later. If I’m writing a monthly newsletter that I might not finish one sitting, I don’t have to worry about finishing it on the same machine I started it.

Calendar and Task Differentiation

In outlook.com, Calendar and Tasks are the same app. Suppose I wanted a different task list for each client. To do that, I would also need a different calendar for each client. In many cases the calendar may be empty, but I want the differentiated task list, or vice versa. It’s not a big deal, but it is a nuisance and takes up screen real estate with links to empty calendars or task lists.

Moving Between Accounts

When using desktop Outlook, you can move files into an Office365 email with a simple drag and drop. For example, I often get emails from people I know asking a question about website design, to my personal outlook.com email address. I can quickly drop that from there into my business email account. The same goes for contacts and tasks. I cannot do the same in reverse.

Conclusion

The main three are probably your major selling points, but the last three are definitely nice to have once you get used to them as well. The bottom line to me is that outlook.com is sufficient for personal use, but if the email is being used for business, you probably want to pay up for Office365.