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Friday Five
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Five Ways to Supercharge Gmail

By The Editors

Email! We may love it for its convenience or hate it for its omnipresence, but it’s tough to imagine a life, especially a productive work life, without it. But what you might really like to imagine are some new ways to enhance its daily use. Well, for the Gmail-using lawyers out there — and based on our contacts lists, there are an amazing number of them — today we have five Gmail “superchargers” from the experts on all things Google for lawyers.

We asked Internet For Lawyers’ Carole Levitt and Mark Rosch, authors of “Google Gmail and Calendar in One Hour for Lawyers,” for some tips on the nifty Gmail tools and add-ons. Here are their five picks du jour.

1. Get around Gmail’s 10MB attachment limit. Many email systems limit the size of attachments that can be included with email messages. Gmail users have a fairly large 10MB limit when adding attachments, but that size might be too large for some email systems to receive. Google, though, recently added the ability to “attach” documents to emails via your Google Drive. To use this feature, look for the “Insert files using Drive” button at the bottom of your Gmail message composition window. Use that button to upload the desired file to Google Drive, then just click on “Insert” and Gmail will add a link in your message that recipients can click to view the file in your Google Drive. This way, you can send files of up to 25 MB (the file size limit of Google Drive), regardless of any size limitation imposed on the recipient’s end.

2. Easily attach pictures you take on mobile devices. Another neat feature Google has added to the bottom of the Gmail composition window is the “Insert photo” button (next to the “Insert files using Drive” button). Clicking the “Insert photo” button accesses the photos you have stored in your Google+ account and lets you attach them to email messages from your laptop or desktop computer. To take full advantage of this feature, however, you must have the Google+ app installed on your mobile device and enable the app’s Auto Backup feature, so the photos you take on your device are automatically uploaded to your Google+ account.

3. Schedule it to go at a future time. You can also supercharge your Gmail with Boomerang, which allows you to write an email now, while the subject is fresh in your mind, and schedule the message to be sent at a later time — like tomorrow, or next week, or in a month. Scheduled messages can be one more good way to remind clients of upcoming deadlines or to prompt them for information (again). Scheduled messages can also allow you to draft messages to clients after-hours, without them knowing you’re working late at night or on the weekend. Plus, Boomerang lets you create a reminder if you don’t hear back from an email recipient within a predetermined amount of time. It’s available as a browser plug-in to Chrome, Firefox and Safari, as well as an add-on to your Gmail or Google Apps domain. Pricing ranges from free (to send 10 scheduled messages per month from your Gmail account) to $14.99 per user per month (to send unlimited scheduled emails from accounts in your Google Apps domain).

4. Send encrypted messages with SecureGmail. Available from the developer, Streak, or through the Chrome Web Store, SecureGmail is a free, third-party extension for the Chrome browser that lets you send encrypted emails so the messages cannot be read without a password to unlock the text. It’s compatible with free Gmail accounts, as well as paid Google Apps accounts. Once installed in your Chrome browser, the extension can be used with any of your Gmail-based accounts that you access from that browser. One drawback to SecureGmail is that it requires the recipient to use the Chrome browser and also install the extension before they can enter the password to decrypt the message. Luckily, recipients are prompted to do so (if they haven’t already) when they open your message. (Earlier this week, Google announced its own new encryption extension for the Chrome browser called End-to-End that would encrypt “data leaving your browser … until the message’s intended recipient decrypts it, and that similarly encrypted messages sent to you will remain that way until you decrypt them in your browser.” However, as of this writing, the extension is not yet available in the Chrome Web Store.)

5. Know more about the people who email you. This last one continues to amaze. Rapportive can help you learn more about the people who email you by displaying publicly available information about them in the margins of your Gmail inbox. Rapportive aggregates information from their profiles on Facebook, LinkedIn, Google+ and Twitter to display their profile picture, job title, etc., as well as links to the respective profiles so you can see more information. This is all accomplished by matching the sender’s email address to publicly available social networking profiles. Rapportive may also display a list of other recent emails from the person, which can be pretty convenient. It’s a free plug-in for the Chrome, Safari and Firefox browsers and for Mailplane (a standalone Gmail app for Mac OS) and works with Google Apps domains, too. Google Apps domain administrators can also add Rapportive for all of their users.

Carole Levitt and Mark Rosch are the principals of Internet For Lawyers. Carole is a lawyer, law librarian and legal educator with more than 30 years in the legal field. Mark is a frequent speaker on the topics of Internet research and using technology more effectively in the practice of law. Together, they have conducted hundreds of in-person MCLE programs for bar associations, law firms, corporations and other professional organizations. In addition to the ABA’s “Google Gmail and Calendar in One Hour for Lawyers,” they are the authors of “The Cybersleuth’s Guide to the Internet,” “Google for Lawyers” and “Find Info Like a Pro, Volumes I and II.”


Categories: Daily Dispatch, Friday Five, Lawyer Productivity, Legal Technology
Originally published June 6, 2014
Last updated October 16, 2018
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