Business Lawyers Bad HabitsFirst of all, business lawyers rock.  They’re among the sharpest thinking professionals in business, routinely pulling together complex deal structures, making sense out of rules and regulations, and giving great general business advice to clients. (Disclosure: Yes I’m biased, I started my career as a business lawyer.)

Since leaving law for the tech world I’ve been on the client side, a consumer of primarily corporate and transactional legal services. During those 10+ years, I’ve worked with several different business lawyers, running the gamut from savvy solos to Big Law partners, and they’ve almost all been outstanding. In the rare instances when my experience hasn’t been a great one, it’s usually been attributed to one of these 5 things.

1. Redonkulous billing practices

If you send a bill for the “XYZ contract negotiation” more than a month or so after the XYZ deal closed, you’re creating at least 2 problems for me.  I know you don’t mean to create trouble – in fact, you might even think you’re doing me a favor by holding off on the bill, but you’re not.

First, if it’s a significant size bill, it probably means I’m going to have to spend time re-analyzing things that are – by now – likely distant memories to me. (Yuck, more admin “make work.” ) Stale invoices have a good chance of going to the bottom of the to-do pile, along with the other things I’m putting off until I have more time to look into them. It’s not a great pile to be in if you’re looking for quick turnaround.

Second, if I’m in a spot where I can’t personally authorized the final sign-off on the bill, I’m going to have to explain to someone else why I’m turning in a late bill.  The people who actually pay bills – the accounting folks (I’m also one of those), really dig things that are “normal”, “routine”, “ordinary course” – you get the idea. Things that are easy to process, simple to record.  On the other hand, things that fall outside of the norm raise eyebrows and, at best, end up resulting in extra scrutiny.  Translation: delay.

So, to get paid faster, please send me the bill on time. Neither of us are better off if you stall.
That said, if you’re having trouble getting your bills out on time, consider investing in a simple practice management app. Bottom line: It’ll save you a ton of time. I promise you’ll quickly recover the $2/day.

2. Not really understanding my business

If I’m talking about our “key metrics”, and you’re on the other end of the line furiously Googling for inches-to-centimeter formulas, trouble probably isn’t far off. That’s a silly exaggeration, but you get the point.

So many business attorneys have such an incredibly valuable accumulation of knowledge to share. You have seen hundreds of deals and been part of negotiations that ranged from silky smooth and amicable to crazy contentious and difficult. I get giddy thinking about having access to all that experience. However, without some specific knowledge of what drives my particular industry (or better yet, my specific business), it’s just not nearly as valuable as it could be.

Ideally, it’d be great if you could invest a little time now and then to read up on what’s happening in my space, read our press releases once and awhile, ask me for a copy of our financials, or even just meet for coffee to chat about what we’re working on lately. If you have the level of knowledge of our business equal to that of, say – someone on our advisory board – your ability to help increases exponentially.
The client has responsibility here too. On my end, I should never ask you to help me with a project until I invest the time to thoroughly explain the entire big picture: why we’re doing something, what our goals are, any “politics” or sensitivities involved, any trapdoors or land mines I can think of, and so forth. It’s my responsibility to get you all the information, as opposed to just dumping something onto you and expecting miracles. (I was on the bad end of that a few times early in my career; I know it’s the worst.)

An experienced business lawyer who knows my business well enough to be able to accurately and proactively advise, to help me avert potential problems or seize opportunities before they actually emerge – that is an incredible valuable partner.

3. Wasting time on (likely) trivial issues or, worse yet, spending time on trivial issues while missing important ones.

It’s tough to hear how my lawyer has tried to mark up the indemnity clause three times already yet “the other side” (usually more accurately characterized as “my business partner to be”) is being unreasonable and won’t budge. This is a double bummer when I’m independently reviewing the same document and notice that the payment terms, or some other material business term, doesn’t remotely resemble the term sheet or what we had discussed in the meeting.

Yes, I know the “boilerplate” can be important, and I absolutely want you to point things out to me that you find grossly unreasonable or uncustomary. However, if it’s something that could be a teesny bit more favorable if we drafted it differently, or something that could protect us a little better in the 1 time out of 1,000,000 that the event may occur, that’s cool too – but let’s save that stuff until we’re happy with the key business terms. That works both ways; that is, if I’m the one (unintentionally) focusing on minutiae, please tell me in no uncertain terms. In buying legal services, I’m acutely aware that the customer is NOT always right.

Basically, if we’re doing this right, neither one of us should ever have to ask the other: “We’re holding up this deal over that?”

Also, if you and I are providing the first draft of documents, let’s agree to provide a first draft that’s fair and mutual instead of trying to make every little bit completely one-sided. That one little move can not only save oodles of time, but can also send a very valuable message.

4. Passing too much work to inexperienced attorneys

Delegating work to junior (read: less expensive) associates can be a good thing. Sometimes, junior associates can handle certain things more efficiently. However, frequently that lower billing rate doesn’t offset the additional time it takes for a well-intentioned, hard-working, smart – but inexperienced – associate to get something done. Basically, try not to send a bill out that includes time or costs that are more fairly charged to your own Firm’s training budget.

Actually, I think this is going to become an increasingly tricky issue for the entire profession as technology (e.g. document assembly) evolves. What used to be “junior associate” work can now frequently either be done by the client (with a senior lawyer “proofing” it later on), or directly by a senior lawyer in an extremely short amount of time. This puts a squeeze on the junior transactional lawyer, and that can mean less of an opportunity to learn the ropes.

I think all lawyers have an obligation to help train the next generation, and that clients (particularly in-house attorneys and law departments) need to become even more accepting, even encouraging, of junior corporate attorneys observing, attending meetings and deal negotiations, and so forth. However, the expense of the junior’s time – at least insofar as hourly billing goes – should usually be borne solely by the Firm. It’s an interesting and important issue – a topic for further discussion in a separate piece.

5. Inventing Non-Issues, A/K/A Putting a Turd in the Punchbowl.

A corollary of the “don’t get hung up on trivial issues” is the: “Wait, what if …”, followed by a crazy, convoluted fact pattern akin to the one offered up by your Criminal Law professor on your 1L final exam.  This is particularly gnarly when offered up about 15 minutes after we’ve finally reached agreement on what everyone believes to be the last key business issue. Yes, it’s useful to be able to carefully identify the single fact pattern that lies 214 legs down the decision tree that, if materialized, could result in a consequence that neither I nor my new business partner would anticipate.

At the same time, there are few worse feelings in a business context than everyone feeling as though they’ve finally successfully struck a deal, only for the lawyers to start raising brand new issues that: (a) for whatever reason they hadn’t thought of during the negotiation; and (b) are theoretically possible, but in practical terms extremely unlikely to occur.

In the rare event when there’s a good reason for that (e.g. the facts suddenly dramatically changed), we can “off-line” it; that is, have a private side conference to talk it through. The way NOT to raise it is in the very common situation where all parties are on a conference call, none of us are in the same physical locations, and we’re all about to give the final OKs to sign. The dreaded “what if ….” gets thrown out onto the Skype line like a deal grenade, and then there’s 5 seconds of dead silence until it explodes into a bunch of mumbling and “let’s reconvenes”. If there are big issues, let’s try to surface them early and – if they unavoidably come up late – make sure they’re really important enough to make all of us dump out that big tasty bowl of punch we’re just about to drink.

As I mentioned, business lawyers are among the smartest and hard-working in the profession. Avoiding a few of these things can make the relationship with a business even more valuable and mutually beneficial.