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Ten Things: The Art of Delivering Bad News

Editor’s Note: As we often do, here’s another article ostensibly aimed at attorneys, but 100% relevant to anyone who might have to deliver bad news.

By Sterling Miller

Most days being an in-house lawyer is a pretty good gig. It has certainly gotten more demanding over the last ten years or so, but there have been corresponding gains in both compensation and prestige. Those do not always offset the increase in expectations, but they are pretty nice! When things are good and the relationship with the business is productive, your days are busy but manageable. And when you get to deliver good news to the business, things can really take a positive turn. Everyone likes to give and get good news. Unfortunately, unless you work in a very magical, wonderful place, not all the news in-house counsel must deliver is good. While hopefully infrequent, there comes a time when all in-house counsel must deliver bad news. And, depending on the content and context, this can be both a painful and scary proposition. Believe it or not, there is an art to delivering bad news. For some, it’s instinctive. For others (yours truly included) it must be learned. This edition of “Ten Things” will walk you through the art of delivering bad news:

1. Plan ahead. I know that the last thing people want to think about is all the things that can go wrong with something. Yet, the very first step in learning how to deliver bad news is planning for it ahead of time. This means several things. First, no matter how good you feel about a lawsuit, a contract, a merger, or whatever, you must take time to peer around the corners and consider what can go wrong. Can you lose the case, not get the contract, or have your merger blocked? The answer is almost always “yes.” Bad things can happen with any piece of legal work, so put away the rose-colored glasses and keep the “bad” front of mind even as you work toward the good. Second, lay the groundwork with the stakeholders about what could go wrong. If all you are telling the business is happy news 100% of the time, they will love you. But, they will want your head on a pike if that big happy burger you’ve been serving them suddenly turns into a shit sandwich. In other words, spend time with the business up front talking about how things can go wrong. Don’t over-promise. And keep expectations reasonably managed and properly caveated from day one.

2. Be first. I can think of many lines I would rather be heading up (like the line to see a REM reunion), but you must be at the head of the line when it comes to delivering bad news about something you are responsible for. There is little worse for an in-house lawyer than getting a call from the general counsel or the client, especially from a member of the C-Suite or the Board, where they tell you of the bad news they just heard about the project you are working on and, among other things, wondering why they didn’t hear it from you first. This violates one of my core rules of being a successful in-house lawyer, i.e., don’t let the boss be surprised. While there are times when there is nothing you can do about it (as sometimes bad news reaches someone before you learn of it), most of the time you will be the first person to learn if something has gone wrong or is on the verge of going wrong. You must be vigilant for bad news about your projects and spend the time necessary to be tied into the right sources, especially ensuring that outside counsel knows to call you (not email) immediately if they learn of something going off the tracks. Your job then becomes preparing as quickly as you can to go deliver the bad news before anyone else beats you to it.

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Photo by Sora Shimazaki:

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