When To Outsource

Once upon a time, I would have taken the Sidley Austin Word Processing Department back behind the bleachers and gotten it pregnant. To be able to drop off marked-up docs at 1 a.m. and have edits turned by 10 a.m. — assuming the slackers who deigned to leave at midnight hadn’t given WP too much work on their way out — was a godsend, and quickly became part of my normal working life. (Just like leaving at 1 a.m. every night.)

Unfortunately, the support we quickly get used to in Biglaw doesn’t always survive the move to SmallLaw. Now that I have my own practice, I’ve been having trouble finding people to turn my comments. My NY office is next door to an acupuncturist, and while she’s great about accepting deliveries when I’m working out of the DC office, she’s rather uninterested in turning my comments to draft registration statements. (So much so I should probably stop asking her.) The labor union office down the hall doesn’t seem too promising either. I guess I could give in to some of the random solicitations I get and contract with a company in Bengaluru and spend two hours every morning proofing their work, but I’d rather have my mornings free to Google myself think deep thoughts.

In the early stages of a SmallLaw practice, you pretty much have to pick your battles in terms of what you can pay someone to handle. The diverse personnel once relied upon — the marketing staff, the IT department, the librarians, not to mention your administrative assistant — has now been whittled down to one person, who also has to bill hours. As a practice grows it can become unmanageable.

I’ve found that if I’m spending a large chunk of my time each week or month handling a particular administrative task, then I need to find a way to contract it out. Case in point: I used to spend the first weekend of every month totaling my hours and typing up invoices for the prior month. Back when I first started, I could do this during a single halftime, then it started taking up entire games (fortunately, none of my teams were good last year), and then finally it was a weekend boondoggle. Once getting through everything and making the invoices look halfway decent turned into a multi-day affair, I decided to take the plunge and buy Clio, a law practice management software popular with the SmallLaw set.

Compared to my old invoices, these Clio invoices are a work of art. I even re-sent my clients all the outstanding bills for the prior month, just because they looked so much more attractive than the old bills. Crazy as it sounds, I actually get excited about billing hours now, knowing at the end of the month I’ll be sending out a professional-looking invoice. (Please feel free to email me if you’d like for me to send you one of these nice clean Clio bills. I’ll only bill you an hour.) It’s definitely been worth the investment.

Even with the Clio success story, evidently I haven’t out-sourced everything just yet. The other night I was drafting an LLC agreement and Word for Mac kept insisting it knew better than I how to space the paragraphs. I got so frustrated I finally had to call my firm’s IT department. My cell phone rang.

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