About the Author
Esquire | Mac is a blog by Adam Greivell, a 20+ year Mac veteran and Maryland litigation attorney. Adam practices law primarily in Hagerstown, Maryland. Macs are his weapons of choice.
Email Adam
Follow Adam on Twitter
Click here for more about Adam...
Subscribe to this Blog
The Twitters

(1) It should go without saying, but, I'm a lawyer and I can't keep from saying it: This site is for informational purposes, and is not to be construed as legal advice. I can't imagine how anyone could possibly think anything here equates to legal advice, but in case you did: it doesn't. 
(2) Although I work for the above referenced law firm, this site is not affiliated in any way with that firm. This site is solely a personal endeavor. 
(3) This site has nothing to do with the magazine "Esquire" or esquire.com. Esquire is used in the title here in a purely descriptive sense invoking the traditional definition of the word as a label for an attorney.


There Will Never Be A Great Law Practice Management App for the Mac

It's been almost three years since I last posted anything here.  In that span, the world has changed. The cloud has taken over.  There remains exciting development afoot in the Apple sphere, but it's concentrated in iOS (and rightfully so, with hundreds of millions of users).  That's not to say that there's no energy in the Mac realm, but, generally, the Mac comes last after iOS and the web.  I have concluded (or, accepted, really) that the reality is that there will never be a great law practice management solution written for the Mac.

For nine years, I have agonized to find one.  It doesn't exist.  To be fair, it doesn't exist on for Windows, either.  Actually, most Windows based law practice management software I have seen is total shit, from a usability standpoint.  I have my pet theories as to why, and you may or may not agree with them.  But, although there are apparently more law office management "solutions" for the Mac than you can shake a stick at (just ask Randy Singer - he'll tell you), I think most of us would agree that none of them are awesome.  Many (most) of them downright suck. When I say "awesome," I mean the kind of app that gives you a visceral reaction when you think about it.  YES - I LOVE THIS APP!  I'm talking about the kind of app that is a genuine joy to use.  The kind of app you don't have to browbeat your staff (or diplomatically persuade your partners) to actually use on a day to day basis.

A good law practice management app has to be better than ... nothing.  Because that's what most lawyers seem to be using.  Or, more accurately, they are using a hodge-podge of separate and distinct solutions cobbled together to get the job done.

I think it's safe to say that most lawyers are not using a single, centralized, law practice management app to run their practices.  Certainly, most Mac using lawyers are not using a single, centralized, law practice management app built for the Mac.

There's nothing necessarily wrong with the hodge-podge approach.  That approach grows out of the frustration we realize when we fail to find a great all in one solution, and most of us "get by" using it.  After all, it's more important to be a great lawyer than it is to be a user (or discoverer) of great software.

Every lawyer needs to manage contacts, calendars, matters, tasks, documents, notes, emails, time and billing, trust accounting, and the like.

Sure, every Mac using lawyer can use Contacts (formerly Address Book) or the upcoming BusyContacts to manage their contacts, Calendar (formerly iCal) to manage their calendars, Reminders or OmniFocus to manage their tasks, Evernote or Plain Text files to manage their notes, Spreadsheets or Billings Pro to handle their time and billing and Quickbooks to handle their trust accounting.

But, if you keep your notes in text (or Word, or Pages) files, when a client calls, you type your notes and save them to a file.  Wouldn't it be nice to associate those notes with the client's contact record in Contacts?  Or, associate that note and that contact with a calendar event for next Tuesday?  Or, link it to a particular Matter or Case, so that when you view the case file, you can see all notes related to that matter?  And, while you're there, check out the upcoming tasks and events related to only that Matter?  And see all the contacts related to that matter?  Maybe just the witnesses?  Sounds cool, right? Yeah, you can't do that with the hodge-podge approach.  Or, if you've magically found a way to do it, I would eat my hat if you've managed to do it in a way that isn't a user-experience abomination.  And I would eat your hat if you've managed to get your staff to follow your system reliably and without gnashing of teeth.

There are really only a couple contenders (with reasonably modern interfaces and that are reasonably actively developed) in the Mac market that can handle all or most of those functions. Daylite (at least when coupled with Billings Pro) and Studiometry come to mind.  But, these apps are not built for lawyers.  They're general purpose apps.  That means in order to get them to work well, one must spend an awful lot of time fiddling (instead of working).  Even then, I'm sorry to say, while those programs may have the "feature set" to "get the job done," they are a far cry from being awesome - or a delight to use (ask any Daylite user if they've ever spent half a day figuring out why the database won't load, or ask them how long it took to update Daylite, Daylite Server and Daylite Mail Assistant on the five macs, three iPhones and 2 iPads in the office, and I'm sure the word "delightful" will not once be uttered).

Great software is not a five page bullet-point list of features.  All software should do what it needs to do.

Software that simply does what it needs to do is minimally competent.  Not exactly high praise.

Great software is software that does what you need it to do in a delightful way, or, at least in a way that does not suck.  Or, if it must suck, it should at least suck to the smallest possible extent while still performing the basic functions.  

Perhaps I'm being too harsh.  Maybe beauty is simply in the eye of the beholder.

Consider this.  When asked, "what's the best task management app on the Mac?" people break into fist-fights over whether it's OmniFocus, or Things, or Wunderlist.  When asked, "what's the best email app on the Mac?" people claw each others' eyes out over whether it's Apple Mail, or Mailbox, or Mail Pilot, or MailPlane, or AirMail.  People are passionate about these great apps.

When someone asks "what's the best law practice management app on the Mac?" people overwhelmingly react, "ehhhhhhh....., hmmmmm..... I don't know.... it depends on your taste..."  Save for a (not altogether insignificant) handful of die-hard Daylite users, very few Mac using lawyers are passionate about their law practice management apps.  Most have settled for some cobbled solution that "gets the job done."  Because you can't spend a decade looking for software that doesn't exist.  You eventually have to be a lawyer.

There is some hope, however.  Since about 2008, there has been exciting movement in the cloud.  There are finally some talented and passionate designers building applications that approach a modicum of joy in their use.  This is progress.  And, the future is bright.  But, these are not Mac apps.  Sure, you can use them on a Mac, but they will never be native apps.

Which brings me to the point of my post.  Virtually all of the positive energy in this space is centered in the cloud.  And, rightfully so.  The internet is effectively ubiquitous.  And that's where the money is.  Why build for the Mac only when you can build for the cloud and dramatically expand your market?

No great law practice management app was never built for the Mac, and I submit one never will be.

The reason most Mac using lawyers are using Macs is because they care deeply about the user experience.  I have witnessed many a Windows refugee make the exodus to the Mac and become delighted.  Beyond that, they are amazed that they can even be delighted by a computer after so many years exiled in Windows XP purgatory.

Steve Jobs said, "You've gotta start with the customer experience and work backwards to the technology.  You can't start with the technology and try to figure out where you're going to sell it."

I will be happy when the day comes that I can have a great user experience managing my law practice on my Mac - from the cloud or otherwise.  I'm not loyal to the death to using software written for the Mac.  I am desperate, however (and I don't suspect I am alone in this), for software that does what I need in a delightful way.  In the meantime, I will gleefully settle for a solution that does not suck.



Why We Love Apple Products

Why do we love Apple products? Because Apple makes products they want to use.

This quote from Steve Jobs in 1997 says it all (it's from 30 minutes into the video, below - though, it's worth watching the whole thing):

I think every good product that I’ve ever seen in this industry and pretty much anywhere, is because a group of people care deeply about making something wonderful that they and their friends wanted. You know? They want to use it themselves. And that’s how the Apple I came about, that’s how the Apple II came about, that’s how the Macintosh came about. That’s how almost everything I know that’s good has come about. It didn’t come about because people were trembling in a corner worried about some big company stomping on them. Because if the big company made the product that was right, then most of these things wouldn’t have happened. If Woz and I could have went out and plunked down 2000 bucks and bought an Apple II, why would we have built one? We weren’t trying to start a company; we were trying to get a computer.

Right after that, Jobs also made the excellent point that:

It’s incredibly stupid for Apple to get into a position where for Apple to win, Microsoft has to lose. That’s really dumb. ... Apple can win without having Microsoft lose.

And, that has, in fact happened.


Billings Pro Is Out (and Multi-User)

Back in April, I posted about Marketcircle's popular Mac billing application, Billings, announcing that it was "going pro," a.k.a., multi-user, and headed to beta testing. Tonight, The Unofficial Apple Weblog reports that Billings Pro has gone live.

As I am currently a solo practitioner, I have not put the multi-user version through its paces. I do religiously use Billings 3 for my billing needs, though, and highly recommend it. Time capture could be a little easier, but it is a solid program that has my full confidence otherwise.

The Pro, multi-user, version requires you to set up a "server" version of the application on any "stationary" mac. Billings Pro uses a web-based "Switchboard" to solve the problems related to "opening ports, worrying about static IP's, or crawling on the floor in search of your router's model name. Switchboard is the middle-man for your database connection."

The system establishes a web-based Timecard interface that Marketcircle describes as "a simple and intuitive web interface for Billings Pro with a laser focus on active projects with quick time, expense and mileage entry. We built it for non-management staff and have kept out the stuff they don't need such as financial data, reports, estimates and more."

Whereas Billings 3 will set you back $39.95, Billings Pro will set you back $199.95 per user. An upgrade for one user to go from Billings 3 to Billings Pro is $174.95. This means, if you're a solo using Billings 3 and you want to upgrade to Billings Pro to use with a partner or associate, you're going to have to fork out $375, minimum. That's quite a jump.

Of course, in light of the alternatives, the price-point probably makes sense. You can avoid the up-front cost by opting to go "Pay As You Go" and pay $24.95 per user per month. Of course, at $50/mo, after 8 months, you'll be paying more than if you just bought two licenses.

That said, Freshbooks is $39.95/mo for two users, and Harvest is $40/mo for up to 5 users. Freshbooks and Harvest have their own benefits, but with Billings Pro, the data is always yours and always stored only on your own "server."

Naturally, Billings Pro will sync with your iOS device via their app. Though, at the moment, it's not clear whether there will be a new "Billings Pro Touch" as is referenced on their website, or whether it will sync with the existing "Billings Touch." Presently, there is no "Billings Pro Touch" in the App Store.

Anyway, go check it out!


My Favorite Typinator (or TextExpander) Snippets

I know everybody raves about TextExpander from Smile On My Mac, but I got Typinator from Ergonis as a part of a software bundle about a year ago and I've loved it ever since. If you're into using one of these text-expanding utilities, here's a couple of snippets I find invaluable on - quite literally - a daily basis.

  • "dt" = {YYYY}.{MM}.{DD} (e.g., 2010.04.25) - This is my go-to for naming files. Just about every file I name in my practice is prefaced with the date in this format. This way, when sorting alphabetically, my files automatically fall into date order.
  • "dx" = {M}/{D}/{YYYY} (e.g., 4/25/2010) - This is how I record the date in my billing timesheet. As opposed to the reverse format above, this format is Numbers and Excel friendly, and will be recognized as a date.
  • "ttm" = {h12}:{m} {a} (e.g., 12:36 AM) - This inserts the current time. This is very helpful when I'm entering my start and end times into my billing timesheet. Using this, I don't even have to know what time it is - I just hit "ttm" when I start or finish something and it tells the time for me.
When I make or take a phone call and want to take notes on it, the first thing I do is type "dt" and "ttm" and automatically the date and time of the phone call are recorded and I don't have to think about it or break my attention from the conversation. Ok now, go and have fun.


Quick Tip: Put Your Templates Folder In Your Dock For Easy Access

This tip works for both Pages and Word, and it's very simple. I've been doing it for probably over a year, and I'll never go back. I make my own template documents for things like generic pleadings, fax cover sheets, letterhead, fee agreements, etc.

Instead of opening Pages or Word and then going into the templates chooser, by putting the templates folder in the right-side of your dock (or the bottom, if your dock is on the left or right side of your screen), you have two-click access to your templates.

  • For Pages, your templates folder is in Macintosh HD > users > [YOUR USER NAME] > Library > Application Support > iWork > Pages > Templates > My Templates.
  • For Microsoft Word [at least, for Word 2008], your templates folder is in Macintosh HD > users > [YOUR USER NAME] > Library > Application Support > Microsoft > Office > User Templates > My Templates.

Once you've located the folder, just drag it to the right/bottom side of your dock. Clicking on the folder spreads out the stack. Click again on the template you want to open. This opens up a new document based on the template you picked.

You just saved yourself a lot of clicks over the rest of your life. You can thank me later!