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

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.