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All Mac Practice, Part 2

Lawyers Who Use Macs: Why They Do It and How

By Brett Burney

In Part One of this “all-Mac” series, “Still Want an All-Mac Law Office?,” we talked about what you need — hardware, software, cloud services and more — and how you can get your Mac law office going. For Part Two, I reached out to four of the most prolific and proficient Mac-using lawyers to ask how they run their practices on a Mac, so you can benefit from their insights.

Benjamin StevensBenjamin Stevens

The Stevens Firm, PA Family Law Center

First up is THE Mac Lawyer himself, Ben Stevens, who runs The Mac Lawyer blog as well as his three-lawyer family law practice in South Carolina. The firm has been all-Mac for a long time.

What was the primary reason for using a Mac in your practice? Because Macs just work and they allow me to work from anywhere. I can be just as efficient and effective working on my 11-inch MacBook Air from a park bench as I can working at my desk with my 27-inch iMac Retina. There is rarely a learning curve with any Apple hardware or software, so I can spend more time practicing law.

What is the most frustrating thing about using a Mac in your practice? The most frustrating thing that I still encounter is having one rare mission-critical program that is Windows-only and not web-based. For instance, our Child Support Guidelines program in South Carolina falls into this category, and it’s something that we have to use all the time. Thanks to solutions like Parallels, we can still use it, but using PC programs, even briefly, is a great reminder of how much better off we are using Macs.

What piece of software is crucial for managing your practice? The two programs I use most often (and can’t imagine practicing without) are Rocket Matter and Gmail (Google Apps for Business). Because Rocket Matter integrates with so many other programs (Gmail, Evernote, Dropbox, etc.), it’s truly the hub and heart of our practice, and it enables everyone on our team to stay on the same page all the time.

What is your favorite software utility on the Mac? There are three utilities that make my practice better and my life easier:

  1. Streak enables me to control my email instead of it controlling me. I can snooze emails and have them reappear in my inbox when I need them, which is extremely powerful.
  2. TextExpander enables me to work so much faster and more efficiently. I can create letters, pleadings, emails, etc., with only a few short keystrokes. TextExpander is easy to learn, and it allows you to create powerful snippets that can be used in many different parts of your practice.
  3. If you’ve ever used 1Password, you will never want to use the Internet without it. It has so many great features, including generating and managing complex and secure passwords, syncing them across multiple computers or devices, and allowing you to have your credit card information always (safely) at your fingertips.

What is your favorite Mac-related gadget? My BookBook from TwelveSouth. It looks great and provides outstanding protection for my MacBook Air that goes beyond mere cushioning. At a conference, I had a lady look at my BookBook and say, “It’s so refreshing to see someone actually using a pen and paper instead of a computer.” As I opened the BookBook, I said, “I hate to disappoint you, but this is really my laptop.” She was shocked beyond words.

Victor MedinaVictor Medina

Medina Law Group

Next is Victor Medina, who runs the Medina Law Group in New Jersey. Victor is the organizer of the MILOfest Conference — an annual “Mac-Lovin’ Lawyers Event” held in the fall. If you’re interested in learning from other Mac-using lawyers, MILOfest is a can’t-miss event.

What was the primary reason for using a Mac in your practice? I had two primary reasons. First, I wanted rock-solid reliability with my hardware and software. Mac offers that in a way that no other system does. Second, I wanted to hang around with relatively cool attorneys. Not until I organized the MILOfest Conference did I realize just how true that was. I’ve been to every kind of attorney event there is, and MILOfest is the only one where I’d have a beer with any one of the attendees. They are just the best, most collegial group of lawyers.

What is the most frustrating thing about using a Mac in your practice? Honestly, the most frustrating thing is having to explain to non-Mac users that, yes, in fact, I can do everything they do with their Windows PC. Some people are still stuck believing that Macs are more expensive, or just for play — and it can be a little sad knowing they’ll never experience the joy and tactical advantage of driving a Mac in their practice. I still get challenged on why a lawyer should switch to the Mac, and although I’ve long given up trying to teach that particular pig how to sing, time has only made the argument for an all-Mac office stronger.

What piece of software is crucial for managing your practice? There are three crucial pieces I use in my practice:

  • First is Daylite, which serves as my practice management, contact management, calendaring and communications management hub (i.e., it tracks projects and tasks, all of my clients and referral sources, the calendar for everyone on my team, and mail and phone messages).
  • Second is OmniFocus, which is my personal task management and productivity solution. It’s the best for a number of reasons, but the top one has to be that it’s available to me on my computer, iPhone and iPad (and now AppleWatch) all the time. That’s an essential ingredient for superior productivity.
  • Third is DocMoto which is the only Mac-native document management solution. As my team grows, so does the need to manage documents at a professional level.

Thinking back, I was introduced to all three through MILOfest. At the first MILOfest, OmniGroup sent someone to show off their “new” program OmniFocus. After that, MarketCircle sent a representative who helped me migrate to Daylite and use it effectively. The conference is so good at giving access without subjecting everyone to boring sales pitches. Finally, the nice people from England who run DocMoto reached out to me to sponsor and attend MILOfest one year (and they’ve been back every year since), and I was convinced to begin implementing a document management system.

What is your favorite software utility on the Mac? It turns out that I own lots and lots of utilities. I end up using most of them poorly until someone shows me how much more effective I can be using them. The two that stay open all the time are TextExpander and 1Password. One of the best features of those programs is that they sync seamlessly with my iOS devices.

What is your favorite Mac-related gadget? My newest favorite gadget, by far, is my AppleWatch. With it I can see my next appointment just by lifting my wrist, or I’ll know when I’ve received a text message and I can leave my iPhone in my pocket (or even in another room if I’m on the Wi-Fi at home). When I’m in a new city (as I was in Santa Monica a few weeks ago), I can set walking directions and let the AppleWatch buzz me when it’s time to take a left or right. It’s lowered the “will he get mugged looking like a lost tourist” risk tenfold.

Jeremy WorleyJeremy M. Worley

Sanders Law Firm

Jeremy Worley is a shareholder at the Sanders Law Firm in New Mexico. The firm has three offices, 13 attorneys and more than 30 computer stations. Jeremy was instrumental in transitioning his entire firm from Windows to Mac about six years ago.

What was the primary reason for using a Mac in your practice? We made the decision to switch to Macs in 2009 as part of a long-term vision we had for the firm. There were many reasons for taking on this challenge: First, we recognized that to become the premier law firm in New Mexico in our practice areas, we needed to commit to being one of the most technologically advanced firms out there. This was not simply a one-time infusion of some money into new computers. We set forth a vision of how we could incorporate new technologies to create unique competitive advantages in a crowded legal field. Once that commitment was made, we started on the journey to identify what hardware and software combinations could provide the most reliable, technologically advanced foundation to build on. Most importantly, we wanted the most reliable machines out there so that our downtime was limited.

Prior to 2009, we suffered through many years of PC blue-screens-of-death, with mounting costs and increasing headaches. We made it a priority to invest in machines that could more than pay for themselves in saved IT costs, time and energy. Macs proved to be the solution. We took baby steps, initially ordering two test Mac units and spent an enormous amount of time testing and re-testing, so when it came time to order 30 machines we were satisfied it was the right move for us. We achieved greater stability and reliability in all aspects once we made the switch.

This further allowed us to more confidently shift to a paperless office (another long-term objective), since we now had a more reliable and efficient system in place. Had we not switched to Macs, we never could have gained the trust of our attorneys to let go of their precious, paper-stuffed files.

Using Macs in our law office has been as much a culture, attitude and identity change as it has been a technology one. This switch has allowed our small firm to grow from being a local law office servicing our local community to a competitive, innovative firm operating statewide through three separate offices.

What is the most frustrating thing about using a Mac in your practice? The limited software available for the legal industry is probably my greatest frustration. There are more options now than when we first switched, but it would be nice to see even more legal-specific software. We have at times run virtual Windows machines (I hate this!) for some specific needs like bankruptcy and accounting software.

What piece of software is crucial for managing your practice? Clio (in conjunction with Dropbox) has been huge for us. We use it for document and time management, calendaring, and in a number of other ways. Virtually everything we do is run through Clio in some form or another. The cloud-based functions have been a great fit for us. Apple Mail is likewise critical for us.

What is your favorite software utility on the Mac? I use TextExpander and am a big fan because it allows for greater efficiency. For the most part, though, between Clio (with Dropbox), Apple Mail, Microsoft Word and Adobe Acrobat, I can handle just about everything I need. I tend to think less is more — no reason to overcomplicate it. I have started using CudaSign for my Mac, iPhone and iPad and I am loving the flexibility it gives me to sign documents and get signatures away from the office.

What is your favorite Mac-related gadget? The most important one is my Fujitsu ScanSnap because I have a very document-intensive practice. My assistant and I both have one and use it every day.

My iPhone and iPad are likewise integral to my practice. For instance, when I meet with clients, I type notes on my iPad, while recording the conversation in the Notability app. I take their picture and add it in those same notes. From that app I can save my notes directly to my Dropbox-linked Clio file, which is where I ultimately want it to land. I can also then have them sign my fee agreement letter on my iPad, which allows me to immediately save the signed agreement to Dropbox and email a copy to the client in a matter of seconds. This all saves me time and energy by not having to print, scan and save paper documents.

In other words, everything I need for an initial client interview and intake is accomplished on my iPad, whether in my office or anywhere. The fact that my Mac, iPad and iPhone sync seamlessly is an added benefit.

David SparksDavid Sparks

Sparks Law

David Sparks is affectionately known throughout the Mac-using community as “MacSparky,” since that’s where you’ll find his blog. David recently left a large firm in Orange County, California, where he used his Mac, to start his own firm — where, of course, he still uses a Mac.

What was the primary reason for using a Mac in your practice? It’s all about the software. As a solo practitioner, one of my biggest advantages is the fact that I don’t need enterprise software. There are some really smart Mac developers and I use their software every day to run circles around opposing counsel. (Ed. Note: David is also the co-host of the Mac Power Users podcast, and the most recent episode focuses on the tools and software that he uses in his practice.)

What is the most frustrating thing about using a Mac in your practice? Proprietary software that is PC only. I know I could run virtual Windows but putting Windows on your Mac is like putting your dad in a dress. I used to like CaseMap, which remains PC only, but I’ve worked around that since.

What piece of software is crucial for managing your practice? I don’t have one key app so much as a collection of applications. OmniFocus is great for managing tasks — and without it, I’d be in trouble. I also rely on Apple Pages and Microsoft Word on a daily basis.

What is your favorite software utility on the Mac? I’ve automated the heck out of my practice. I use TextExpander, Hazel and Keyboard Maestro to manage filing documents (I’m paperless!) and generate documents. I run my calendar through Fantastical and have many other little applications and utilities to get my work done.

What is your favorite Mac-related gadget? I’m always on the hunt for the next gadget. I know this is not an accessory, but I am still in the honeymoon phase with my 12-inch Retina MacBook. I know a lot of people don’t like the keyboard but I’m used to it and the ability to have a Mac with me anywhere is awesome. I’m writing these very words on this super-light new Mac in a Japanese garden down the street from the courthouse. I’m living right.

Be sure to read “Still Want an All-Mac Law Office? What You Need and How You Can Do It” for more tips from Ben, Victor, Jeremy and David.

Illustration ©

Categories: Daily Dispatch, Lawyer Apps, Legal Technology, Managing a Law Firm
Originally published August 20, 2015
Last updated May 11, 2020
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Brett Burney Brett Burney

Brett Burney is Principal of Burney Consultants LLC, an independent legal technology consulting practice. Brett provides litigation support for law firms and assists corporations with e-discovery questions. Brett is also a highly sought-after trainer and presenter for lawyers who seek to integrate Macs and iPads into their practice. Brett is a past ABA TECHSHOW Planning Board Chair and a popular speaker on legal technology. You can follow him on Twitter @BBurney.

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