Ten Things: The Art of Delivering Bad News

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.

3.  Who needs to know?  A critical part of delivering bad news is knowing who to deliver it to.  Sometimes it’s pretty easy.  It may just be one person or a handful of people at a relatively low level of management at the company.  Easy peasy!  Sometimes it’s the CEO or President.  Not so easy peasy.  And depending on the news, you may also need to talk with corporate communications, investor relations, insurance, finance, internal audit, other members of the legal department, and so on.  I kept a checklist of the different people in the company who might need to know about something.  Not everyone on the checklist needed to know about any particular issue, but it helped me focus when time was short about who to notify.  When things blow up, it’s easy to forget to contact someone important.  A checklist of “who may need to know” can save you a lot of headaches.  Checklist or not, it starts with your ability to understand who has a stake in whatever issue you are dealing with and then making sure you are communicating with them when there are things they need to know.  If the news is bad enough, be sure you spend time with the corporate communications team (both in terms of external and internal messaging).  While surprising to some, most in-house lawyers are generally very deft at crafting communications that work both from the business and the legal angle.  Use that skill!

4.  Figure out what you want to say.  So, the bad news has come in.  You have identified who you need to speak with.  You are hell-bent on being first in line.  Before you go charging out the door or dialing the phone, you must take a moment (or longer) to figure out what you are going to say.  This is where all your lawyer superpowers come into play.  Depending on the situation, you may have a small amount of information to deal with or a boatload.  Regardless, you need to quickly synthesize it and figure out four things:

  • What happened?
  • Why did it happen?
  • What does it mean?
  • What do we do next?

Do not try to deliver bad news until you have answers to all four of these questions.  You may not have perfect answers, but walking into a room to deliver bad news and not being able to discuss all four of these bullets in some manner is asking for trouble.  Which, on top of the fact that you are there to deliver bad news, is the equivalent of throwing a bucket of kerosene onto a dumpster fire.  Yep.  It’s just going to get worse.                     

5.  Deliver it in person.  If you have bad news, try very hard to deliver it in person.  Bad news is not generally something you want to try to deal with via email (or worse via text or Teams/Slack chat).  At a minimum, do it on the phone.  I realize all of this has become harder in the post-Covid world, but delivering bad news via email increases the chances of miscommunication and invites a lengthy dialogue (via email) that is rarely productive when it comes to complex issues.  If you cannot meet in person or speak on the phone (your client is traveling overseas for example and the time zones are a mess), then it is okay to use email to foreshadow the discussion and let whoever know that you need to meet or speak with them right away.  Here is an example of what I mean:

Sarah – I tried to call but realize now you are on the road.  We had a pretty significant setback in the Jones case today.  There is a lot to unpack and that is best done either in person or on the phone.  Let me know when you might have some time and do my best to move things around to discuss it.  Thanks – Sterling             

The important part of the message is that you have succinctly spelled out that there is a problem that requires their attention.  That way, even if they hear more detail from someone else, you were still the first one to tell them.  And, by foreshadowing the problem, they will be braced for bad news when they can talk on the phone, which can greatly reduce the need to deal with Number 8 below.

6.  Stick to the facts.  When things go wrong, it’s way too easy to get caught up in a “sky is falling” mentality.  So, leave Chicken Little and Ducky Lucky in the hallway.  Instead, focus on sticking with the facts – or at least as many of the facts as you know.  As counsel to the business, they are depending on you to be calm and collected when things go wrong.  When you come into the room or get on the bridge line and are measured and sticking to facts, it helps the executives calm themselves as well.  It’s okay that it may be an act on your part.  Your stomach may hurt and you can be sweating bullets on the inside, but outwardly you need to be everything you (and they) would expect a highly-trained, experienced, and skillful lawyer would be in such a situation.  A rock they can hold onto.  It all starts with sticking to the facts and avoiding hyperbole.  If there is information you need to know but do not have yet, note that along with the promise to follow up as quickly as possible.  Your role is “truth-giver” and it is important that you do not get too high or too low and that you play things down the middle, i.e., that you are (and are perceived as) an honest broker who is there to lay out the situation and help coordinate (or lead) the response.

7.  Understand the playing field.  Not all clients are created equal.  I know that sounds a little harsh, but it’s true.  It is a vastly different experience giving bad news to the CEO than it is to give it to a frontline manager.  The news is still bad, but the ability of the person to whom you are relaying the news to impact what happens next is light years apart.  As part of your planning, you must consider who you will be delivering the news to and what that means, both in terms of the next steps and for you personally.  Botching the delivery of bad news to a peer (or lower in the pecking order) is not great, but botching the delivery to someone at the top of the pyramid can be fatal to your career.  If there is one thing executives look for when meeting any employee it is whether this person is worth having around and whether are they someone that can be entrusted with bigger or better things.  You are always being measured.  And the higher up you want to climb, the tougher gauntlet you will need to run when it comes to this, sometimes, withering scrutiny.  As to the next steps, you can come up with a less-than-ideal plan when dealing with someone lower on the food chain as there will be plenty of opportunities to pull back or change direction.  If you go into the C-Suite with a less than thought-through plan on what to do next and they sign up for it, it could – if things go wrong – be your ticket on the Titanic and a place alongside Leonardo DiCaprio as you both sink helplessly into the cold, deep north Atlantic ocean.

8.  Brace yourself.  Unfortunately, no matter how well you plan, no matter how balanced and thoughtful you are with the delivery, and no matter how well you have anticipated questions and next steps, it is highly likely that you may get your ass chewed out.  You need to go into any “bad news” meeting with that in the back of your mind and a plan for what you will do if things go sideways and the messenger is in danger of being shot!  I know this first hand because early in my tenure as general counsel at one company I had to deliver bad news that arose on my predecessor’s watch but just happened to hit the first week I was in the role.  I figured I would just run on up to the president’s office and tell him what happened.  I really hadn’t planned it out much more than that.  Huge mistake.  Even though I knew little about the case and had zero do to with any of the decisions, presentations, or promises that were made before I took over, every bit of frustration and anger landed on me.  And it wasn’t pretty.  And, on reflection, that was in large part on me for not bothering to properly prepare myself for the meeting.  From that moment on, I always had a “bad news” plan that focused on the following:

  • How fast might this news leak out?  Do I have time to spend on properly preparing to deliver it or will this be a rush job?
  • Be honest and factual – “Just the facts, ma’am.”
  • Explain what happened and why you think it happened.  This requires that you understand the background facts of the problem too.
  • Don’t look to cast blame, disparage anyone, or try to dodge responsibility.
  • Have a plan for next steps (even if that plan is “we are working on next steps and will get back to you as soon as possible on that” which is better than nothing).  Focusing on the future is always a good way to create confidence and trust.
  • Brace for a negative reaction and understand that it is not personal and, as Henry Hill said in Goodfellas, “Everybody takes a beating sometime.”  It’s just your turn.
  • Don’t be defensive – let them vent.
  • Listen with empathy.  You live in the world of legal, business people don’t.  Accept that they can get frustrated and angry at the outcomes or the process.
  • Try to find a positive in the bad news (but don’t overreach), e.g., “We can appeal.”  Or, “There is only one issue separating us from a deal.  We are working on options to bridge the gap.”

9.  Fall on the grenade.  If you are the boss, understand that sometimes you will have to fall on the grenade to protect someone on your team.  You don’t serve up one of your own to face the firing squad while you sit back and try to hide or escape any blame.  That is not leadership and everyone on your team will know what you did or let happen.  Leaders take responsibility for everything under their purview (and great leaders rarely take credit for anything under their purview).  It’s tough to do.  But I cannot see any other way to step up and lead when the moment calls for it.  If you think there is an acceptable teaching moment opportunity, you can accompany your report to the meeting to deliver the news, teach them how to deliver it, or at least let them watch you do it if appropriate.  As general counsel, I always felt it my responsibility to know when bad things happened and to be the one to bring the news to the senior executives if that is what the situation called for.  You may not agree and that’s fine, but I can tell you I always had the loyalty of my team because they knew I had their backs no matter what.

10.  It will be okay.  As someone who has had to deliver plenty of bad news as an in-house lawyer, let’s end with the good news:  it will be okay.  No matter how bad the news, the sun will come up tomorrow, your family will still love you, and life will go on.  I have survived some pretty awful bad-news-delivering-days and so will you.  When the time comes, take a deep breath, get yourself right, and just get on with it.  Use what you have (hopefully) learned from the above to make it go as smoothly as possible.  Don’t dwell on what has happened, fixate instead on what to do next.  That’s all that matters now.  Only once you have a plan as to what to do next should you worry about the post-mortem on “what went wrong.”  Though, doing a post-mortem is a valuable and powerful learning tool.


It’s only a matter of time before it’s your turn to deliver bad news.  If you want to sit at the big kid’s table, you will need to master this skill.  No one wants to do it, but real leaders embrace the challenge when it arises.  Smart leaders have a well-thought-out plan on how they will deliver the bad news, to whom they will deliver it, and what next steps the company must take to overcome or minimize the impact of the bad news.  It all starts with managing expectations on the front end of any legal project.  Nothing is ever 100% awesome or 100% terrible.  Be sure you do the one thing that lawyers do best: analyze the situation, think through the different outcomes (good or bad), and discuss those possible outcomes with your client in advance.  And when the day comes when it’s your turn, know that you will get through it and the sun will come up tomorrow.  If it doesn’t, that’s really bad news.

Sterling Miller

September 29, 2022

I have started working on book number six which will deal with productivity and will come out in 2023.  But, my fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available now, including as an eBook!  As the ABA says, “Do you want us to give Sterling bad news?  Think about what will happen if you don’t buy this book!”  So, let’s all skip the bad news and just buy a copy of the book (and spare the ABA having to give me bad news).  You can buy it HERE.

Cover of Value Book

Two of my books, Ten Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies and Ten (More) Things You Need to Know as In-House Counsel – Practical Advice and Successful Strategies Volume 2, are on sale now at the ABA website (including as e-books).

I have published two other books: The Evolution of Professional Football, and The Slow-Cooker Savant.  I am also available for speaking engagements, webinars/CLEs, coaching, training, and consulting.

Connect with me on Twitter @10ThingsLegal and on LinkedIn where I post articles and stories of interest to in-house counsel frequently.  

“Ten Things” is not legal advice nor legal opinion and represents my views only.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers.  If you have questions or comments, or ideas for a post, please contact me at sterling.miller@sbcglobal.net, or if you would like a CLE for your in-house legal team on this or any topic in the blog, contact me at smiller@hilgersgraben.com



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