Biglaw, General Counsel, In-House Counsel, Partner Issues

The 5 Deadly Sins Of Outside Counsel

I worked at law firms for 25 years. I observed many things and heard many others.

Now I work in-house, and I have to select counsel to represent me.

If I saw you in action (or heard about your reputation) back then, will I hire you now?

It’s obvious how you could have impressed me: You could have put the client’s interests first, and you could have been breathtakingly good when analyzing issues, negotiating settlements, preparing briefs, or appearing in court.

But what could I have seen or heard that forever removed you from my subconscious “approved” list? What are the deadly sins?


Nah. I’d probably hire you anyway.


Nah. It’d disqualify the lot of you.

Incomprehensibility? The early Christians may have overlooked it, but I’m classifying that sin as “mortal.”

If you produced incomprehensible written work, then I really don’t care how smooth-talking you were in court or how often you blew away potential clients in beauty contests. If, when I received written work directly from you, I was forced to act as translator — converting your English into English — you’re off the approved list. If you can’t write, you probably can’t think, and you surely can’t persuade. I don’t need you.


Now we’re onto something.

Missing deadlines is a deadly sin. I’m not talking about the person who prepared stuff on time and right fifteen times in a row, and later missed a deadline because of a death in the family. (That’s not “irresponsible.” That’s “absolutely trustworthy, but human.”) I’m thinking of the folks from whom extracting work was like jamming toothpicks in your eyes. If, when we were working together in private practice, I couldn’t trust you to get things done on time, I don’t need you now, when I’m in the hiring seat.

I’m not thinking here only of missed deadlines that affected me personally. Occasionally my law-firm running buddies would regale me with stories as we hit the one-and-a-half-mile marker and turned back toward home: “Brutus called me into his office yesterday. He handed me a slip of paper and asked me to return a phone call for him. Brutus had missed the deadline to answer the complaint, and he couldn’t bear to call opposing counsel and beg for relief himself, so he pawned the task off on me.”

Another jogger piped up: “You, too?!! He did the same damn thing to me a couple of months ago.”

Third jogger: “Oh, yeah. Didn’t you know? He does that all the time.”

As I assemble the subconscious “unapproved” list, I add a mental post-it at the bottom: “Et tu, Brute.”

How else could you have come off the approved list and gone on the other list? You could have argued long and forcefully in favor of stupid ideas. Again, I’m not thinking of the guy who makes a mistake, as we all do. But when a smart person makes a mistake, he acknowledges it promptly and moves on. “Oh, of course. Two plus two doesn’t equal five. That was silly of me. What else are we considering?”

And I’m not thinking of people who debate hard issues at length: “In our case, the former CEO — who was already paid $50 million in salary and bonuses — is suing the company to recover another $150 million. We have a strong, but quite technical, legal defense. Should we demand a jury? On the one hand, a jury will hate the guy. On the other hand, the jury is pretty unlikely to understand our technical legal defense. What shall we do?”

Debating that choice is called “intelligent discussion.” I’m not thinking about that. I’m thinking about the guy who defends some utterly preposterous idea long after it’s obvious that he’s wrong: “We’ve been sued in 20 putative class actions in different state courts and once in federal court. In our motion to dismiss the federal case, we can argue either (1) the complaint doesn’t state a claim or (2) the complaint doesn’t state a federal claim and so should be dismissed for lack of federal jurisdiction.” Both arguments are equally strong; indeed, phrased delicately, the two arguments could be made in almost the same words.

You’re allowed to say, once: “Let’s move to dismiss for lack of jurisdiction.” But when someone mentions that the client may someday want to try to remove the state court cases and create a federal MDL, you have to concede: “Oh! Of course! There’s no reason to undercut a jurisdictional argument that we may later need. There’s only a thin line between jurisdiction and the merits, but we may be able to walk it. Let’s move to dismiss for failure to state a claim.” If you don’t promptly concede, and instead go on arguing for days about the need to launch a jurisdictional attack, you’ve dropped off the approved list.

How else could you drop off the approved list? Blabbing confidences. If I heard you revealing client confidences because you just couldn’t resist — you had to prove at the cocktail party that you were in the know; you had to regale the boys at the club with an insider’s story — you’re off the approved list. If you couldn’t be trusted with the other client’s confidences, why should I trust you with ours?

Let’s end with greed, another sin that can land you in perdition: You could have blatantly put the law firm’s interest ahead of the clients’. That sin comes in many different forms — padding bills (you know who you are, and many of your colleagues know who you are, too); overstaffing; failing to push work down to the least expensive person capable of doing it; intentionally blowing up a perfectly reasonable settlement to keep the case alive and billing — but those of us who witnessed this at law firms are quite unlikely to forget it when we move in-house.

Remember that you’re building your professional reputation, for better or worse, with everything that you do every day at your firm. Don’t expect folks who see you in action as a colleague to forget what they saw after they move on.

Mark Herrmann is the Chief Counsel – Litigation and Global Chief Compliance Officer at Aon, the world’s leading provider of risk management services, insurance and reinsurance brokerage, and human capital and management consulting. He is the author of The Curmudgeon’s Guide to Practicing Law and Inside Straight: Advice About Lawyering, In-House And Out, That Only The Internet Could Provide (affiliate links). You can reach him by email at

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