How Lawyers Work: Damien Riehl, Tech Lawyer and Technologist

In this week’s edition of How Lawyers Work, we talked to Damien Riehl. Damien is a technology lawyer who has advised clients on technology, litigated technology issues, and developed software. He has also implemented cutting-edge technologies such as artificial intelligence, machine learning, and natural language processing to improve the practice of law. 

You can follow Damien on LinkedIn and Twitter

What apps or tools are essential to your daily workflow?

Word. What lawyer worth their salt doesn’t love/hate this program? When one’s trade is ideas expressed through words, quickly pushing one’s brain into pixels (paper optional) is sacrosanct. Word is the best tool I’ve found for that. Whenever I get a new machine, the first thing I do is install Word and connect my highly personalized Normal.dotx, complete with customized styles (Microsoft installations should include a style set for legal writers, incorporating the excellent advice in Typography for Lawyers), keyboard-shortcut-enabled macros (e.g., homemade wordiness macro [similar to WordRake], replace two spaces with one, sentence case, title case), and keyboard shortcut mapping (e.g., section symbol; paragraph symbol; highlighting in yellow, green, and red). I’m drafting this using Google Drive—to see if it’s a worthy substitute — and it’s killing me. Em dash with five keystrokes: [Alt]+0151? No ability to create a new Style, like Body Text? C’mon!

Google Calendar. Being able to quickly coordinate work and life schedules — from any device — makes life easier. Real-time sync of my family’s calendar is a godsend.

LastPass. Password managers are huge performance boosts, masquerading as security improvements. A single, secure password (I use a pass sentence) unlocks hundreds of website credentials. LastPass generates randomized and long passwords that I don’t have to remember; I just unlock LastPass on my mobile device or browser plugin, and it auto-fills passwords. Bonus: LastPass includes a dead-man switch, so when I die (or if I’m incapacitated), my spouse can get access to all of my online accounts, helping avoid digital death problems (especially where state statutes follow UFADAA).

Google Music. I probably spend more time with this app/service than any other. It’s on during my workouts, work time, and family time. Same price and music selection as Spotify, plus it eliminates YouTube ads.

Trello. Kanban is king. Moving tasks from Backlog to Doing to Done is among life’s great joys. Everyone reading this should pay attention to John Grant and his Agile Attorney advice, including his Lawyerist posts and podcast episode.

BeyondPod (Android). During windshield and airport time, podcasts provide great food for thought and ideation. One downside: my listening backlog often increases to the point where I’m listening to last month’s hot topics.

Google Keep. It’s like Evernote: simple, fast, multi-platform. I use it for storing fleeting ideas, shareable to-do lists (e.g., groceries), photos of parking-ramp spots, receipts.

Dropbox and Google Drive storage. I have 1 TB on each system, and I distribute my files according to context: Dropbox is my primary location, and Google Drive is for personal projects (e.g., music recording and production, home movie storage). For information I need to remain doubly secure, I encrypt through VeraCrypt.

Feedly. Like my datasets, I prefer my news structured. While some use Twitter as their catch-all news source, I curate my reading through RSS feeds, sorted by priority and category.

What does your workspace look like?

Standing desk. I’ve been using one since 2011. After first trying traditional-desk modifications (e.g., Ergotron Work-Fit S), I found myself standing 100% of the time—and missing the larger desktop real estate. So I use a standing desk in the always-up position. The discontinued but much-beloved Ikea Jerker are my two primary desks (in an “L” configuration), though Ikea’s current Bekant models look like they would work just as well. Essential component of standing desks: an anti-fatigue mat (enables longer standing sessions). Bonus component: bathroom rug atop the anti-fatigue mat (it’s like standing on a cloud).

Permanent desk screens: Three 24” monitors. Two are in portrait orientation; one is landscape. Portrait is perfect for documents and websites. (Documents are almost invariably in portrait orientation, so your monitors should be, too. Also consider how frequently you scroll vertically vs. horizontally.) Landscape is better for many-columned spreadsheets and tables. Multi-monitors allow me to read from one document/website, simultaneously drafting on another. For a paperless office, the size of one’s desk is the size of one’s screen(s).

Mobile screens: Laptop + second monitor on tablet. I’ve loved my Surface Book, providing the best of both tablet/laptop worlds — plus the no-compromises Windows OS. A make-do solution for mobile multi-monitor is adding a 10-inch tablet, extending the desktop through Splashtop Wired XDisplay (Android) and a tiny tablet stand. I have small-screen claustrophobia, though. When I return to my desktop setup, it’s like leaving smog: again breathing clean mountain air.

Good speakers/headphones. As an undergrad, I wrote a paper on the Mozart effect. Although those results haven’t been replicated, I am still more productive when listening to music. And more recent studies appear to correlate music listening with increased productivity. If the task is complex (e.g., brief-writing, coding), then I listen to ambient music without lyrics (e.g., EDM, classical, jazz). If the task is less intellectually taxing, then I shift to more-popular music with lyrics (e.g., indie rock, indie folk, modern singer-songwriters).

Ambience. Dim natural light with a little backlight from behind the monitors. The dim environment minimizes distractions, permitting better focus on that important information in the glowing box.

How do you keep track of your calendars/deadlines?

Google Calendar is king. For important near-term deadlines, I use OK Google for alarms (“Okay Google, set an alarm for 2:30 to prep for __.”) and reminders (“Okay Google, remind me to __.”).

What’s your coffee service setup? (Other beverages are fine, of course, but you should really be serving coffee!)

I’ve been loving the Aeropress. It makes delicious (and strong) coffee, and it’s a great example of design simplicity.It brews fast and cleans up quickly. Bonus: it’s essentially a syringe, providing a tangible reminder of caffeine addiction. But since it brews only a single cup, I do wish that there was a larger, multi-cup version.

What is one thing that you listen to/read/watch that everyone should?

Like an overbroad interrogatory, answering this multi-faceted question requires a response for each component part. (If you have a problem with that, go ahead and file a motion to compel.)

Listening apps. Google Music and BeyondPod. Listening content. See my answers above.

Reading apps. Kindle and Feedly. Reading content. Typography for Lawyers, Tomorrow’s Lawyers, The Future of the Professions, Checklist Manifesto, Power of Habit, Brain Rules, The Design of Everyday Things, Don’t Make Me Think, The Zero Marginal Cost Society, the blogs above.

Watch. Black Mirror (“the way we might be living in 10 minutes’ time if we’re clumsy”), TED talks, Westworld.

What’s your favorite local place to network or work solo?

I have a rotating list of coffee shops, varying by context:

Networking: Smaller local shops (e.g., Dunn Brothers, Workhorse, Dogwood) or Caribou.

Working: Somewhere with fast Internet, which is usually Starbucks (>10 Mbps).

What are three things you do without fail every day?

Run or bike (Jerry Seinfeld’s “don’t break the chain” method works). Two cups of coffee. Family time (e.g., music, chess, dancing, piggyback rides, tickling).

Who else would you like to see answer these questions?

I’ve already learned a lot from the luminaries in the Lifehacker series, so excluding those, it would be interesting to see a profile of Richard Susskind.


  1. Avatar Damien Riehl says:

    For those who were asking for a photo my workspaces, here’s one:

  2. Avatar Carolyn Elefant says:

    I did a similar feature – albeit not as detailed – at MyShingle back in 2010. Lawyer Tech Bios – See It is amazing that not all that much has changed – except perhaps the way lawyers accept payments (which wasn’t specifically addressed). That, and of course, I think we are all more health conscious, cognizant of benefits of stand-up desks, meditation and mindfulness.

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