Gmail vs. Outlook for Lawyers

We recently moved to Outlook from Gmail.

Going in, I had really mixed feelings.

Outlook, being a Microsoft product, gets a reputation (at least among a young tech-savvy crowd) as being a dinosaur.

Enterprises use Outlook.

Startus use Google Apps.

But I am humble enough to be able to admit when I’m wrong.

Outlook isn’t bad.

Dare I say it, some things it actually does better than Google Apps.

So today, a dive into Google Apps / Gmail vs. Outlook.

We’re putting them head-to-head and seeing who excels where.

Main Features and Usability

They both send email. So that’s good.

Each has a different natural approach though to the inbox and to reading emails.

Gmail nests all conversations, whether you like it or not. Outlook as a default does not nest conversations, which can make your inbox seem a bit more cluttered. Though, you do have the option in Outlook to nest your email threads neatly.

Only thing I dislike about Outlook is that if I want to send an email, Outlook pops open a new window. Gmail has one window for everything. Though it’s quick to learn both Gmail and Outlook, there is a slight learning curve to Outlook, mainly because there’s so much you can do with it. Too many options can be overwhelming, but too few can be child’s play.

Spam Filters

When it comes to the spam filter, Gmail is pretty on-point.

Outlook, on the other hand, relies on your email host’s spam filter. If your filter is good, it’ll keep your inbox neat. If not, you’ll get spammy or phishy emails in your inbox and some important emails in your spam box, giving you the chore of having to regularly check up on your spam folder.

Winner: Gmail or Tie depending on how good your spam filter is


Google owns search. This is what Google does best. Not only are the search results extremely relevant, but they’re served back quickly.

Winner: Gmail


Google has defined parameters for keyboard shortcuts you can use. Outlooks’ quick shortcuts are extremely customizable. As an example, Outlook can let you create one keyboard shortcut that can mark an item as read while also forwarding it to a specific email address, and then mark the email as spam. You probably wouldn’t want to do this, but it’s an option.

If you want to get nit-picky about customization, Google does offer some unique wallpaper themes, but that’s not really a huge boost for me.

Winner: Outlook


Anecdotally, I have seen more unorganized inboxes among Gmail users compared to Outlook users. And after having used both Outlook and Gmail, I see why it’s so much easier to organize items in Outlook.

Gmail’s main method of organization is by categorizing items with labels. Though Gmail offers multiple tabs for emails that fit into specific categories like Social and Promotional, it can be a bit of a mess.

And if you choose to have one main inbox with items that go into different folders, there is the lag of loading time when moving between folders.

I recently hit Inbox Zero.

Yes, this was a big day for me.

As someone who has been so close for years – last year I briefly had 23 emails in my inbox – this was a personal challenge. Being able to easily move around emails to folders so that I could easily access them later was a challenge with Gmail. Gmail does have labels, but it’s not the most user-friendly system. Outlook’s organization by folders just makes more sense.

Want to flag an email to show up in your sidebar as being important to do today or tomorrow? The flags in Outlook can be easily grouped.

That being said, Gmail does allow you to Star items, but the stars are pretty purposeless in my estimation.

Winner: Outlook

Third-Party Integrations

Since Google Apps is completely cloud-based, it was pretty easy to integrate with other apps.

At Uptime JurisPage, we used a bunch of different third-party apps with Gmail to help with productivity. One example is Yesware, a sales productivity tool.

For lawyers, many of the web-based practice management apps mostly have Gmail integrations. But, the server-based / hosted practice management apps mostly have Outlook add-ins but not a Gmail integration.

For lawyers, Gmail vs. Outlook for third-party integrations is probably entirely dependent on what type of practice management software you use.

Winner: Tie


With email a big concern for lawyers is privacy.

What happens if Gmail is served with a subpoena or security letter demanding your emails’ contents?

Will Gmail definitely notify you when the government or another party has demanded the contents of your emails?

That’s not clear.

However, with Outlook, that entirely depends on your host. Whereas Gmail is both the provider of the client software and the email host, Outlook is just the client. For whoever is hosting your email service (whether that is a legal-centric email hosting provider or an on-premise server), it’s important to know how they deal with subpoena and security letter requests.

Beyond that. no one is serving advertisements to me or building profiles of me based on the contents of my emails in Outlook.

Winner: Outlook


A platform is only as secure as its weakest link.

Gmail has great security (as far as we know) with the ability to provide two-factor authentication (TFA). So, if someone wants to access your email account, not only will they need your password, they will also need to be able to access your secondary device that provides the OK to access Gmail.

Though TFA is no enabled by default in Gmail, it is an option and easy to enable at that.

As mentioned above, Gmail is both the client and the host. Outlook is a client; you are responsible for finding an email host.

Outlook can include TFA if your Exchange Provider supports it.

Winner: Tie

One more thing

An indispensable feature for me with Gmail was the “Undo Send” feature. An optional add-on, if I sent an email prematurely, Gmail can wait 10 seconds before actually sending out the email, giving you an opportunity to stop the email from sending with an easily-accessible “Undo Send” button. Outlook does not have this natively, though there is a work-around. You can delay sending all emails from Outlook for a minute or more, and when you have to undo an email from sending, you stop it by going to the outbox.


When choosing an email setup for your law firm, go with what makes the most sense to you. Condensing this entire article into one thesis: Gmail is lightweight and easy to use. Outlook is a powerhouse.

Good luck.

We’re all counting on you.

Andrew Cabasso
About the Author: Andrew Cabasso
Andrew Cabasso is a practicing attorney and VP of Web Services at Uptime Legal where he runs JurisPage, an Internet Marketing firm specializing in online presence solutions for law firms including website design, SEO, and search marketing. He has given many lectures and CLEs on website design and Internet marketing to legal professionals. He is the author of Search Engine Optimization for Lawyers and The Complete Guide to Attorney PPC. Follow Andrew on LinkedIn, Google+, or Twitter.

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