I have a lot of fun with this blog – and I hope that comes through.  But every once in a while, I like to delve into something more challenging, more serious.  Today is one of those days.   Last year, I wrote about how to deliver “bad news” to the business.  A year or so before that, I discussed how to fire someone.  Neither is a particularly pleasant topic, but if you are going to succeed in the in-house world, these are conversations you will have and you need to know how to handle.   Now it’s time to discuss the last of the trifecta of pain, how to have hard conversations at the office.  It’s a close cousin for the first two but, as you will see below, requires a slightly different skill set and mentality.  Hard discussions for in-house lawyers usually fall within a handful of categories, i.e., you are acting as a manager (or the subordinate), as a co-worker in the legal department, dealing with a co-worker outside the department, or you are dealing with someone outside the company (like outside counsel).  Regardless of who you are dealing with, most of us (including myself, even today) avoid these types of discussions because they are not fun and because no one wants to be the bad guy.  For in-house lawyers, it’s an even more arduous chore because – while lawyers are usually great when arguing for a client or for a client’s position – we are the worst at having discussions involving ourselves.  No worries though, grab some coffee and stick with me; we’ll get through this because this edition of “Ten Things” discusses how to have hard conversations at the office:

1.  Don’t avoid it. Wow.  Damn, Sterling. Starting off with the hardest one!  But, yes, the first rule about hard conversations is pretty basic: do not avoid or delay having them. The only caveat is do not have a tough conversation when you are mad or upset.  That will go sideways on you very quickly – like drunk-posting on Twitter[1] about political issues.  Instead, find a time in the relatively near future to have the conversation when you are calm and thoughtful about what you need to communicate (using the tools below to help you plan).  For example, if you have regular one-on-one meetings with someone, you can use that time.  Or, more likely, you’ll need to set up a separate meeting.  The key is not to let a lot of time pass.  Clearing the air needs to happen sooner rather than later because there is a cost to inaction, usually in the form of your unhappiness at work, low morale among the team, or a toxic work environment that may lead to regrettable attrition – good people heading out the door, leaving you with the “problem” that you should have dealt with much sooner.  So, once you know there is an issue that needs to be cleared up, start making plans for addressing it as soon as possible.

2.  Reframe it.  One trick I learned early as I was failing and flailing in my early efforts at having hard conversations was to flip the problem on its head.  That is, instead of dreading the conversation as something negative, get excited about resolving the problem.  Instead of building it up in your mind as some awful experience you must endure (or dread), think of it like any other conversation you would have as a lawyer, i.e., just another day at the office and something that needs to get done.   In other words, remember, the goal regarding difficult conversations is not to avoid the issue but to approach the problem in a way that looks for solutions to problems and best promotes understanding, collaboration, and positive outcomes.[2]  It may not always end that way, but going into the conversation with the expectation that it will ultimately lead to something positive will help you prepare in the right way.

3.  Have a plan.  Trying to wing a difficult conversation is a pretty bad idea.  I don’t care how smart you are, how articulate, or how quick on your feet you may be, going into a hard conversation without a plan is a recipe for a very unpleasant experience.  And since it’s already hard enough, why add to the pain quota by not taking time to plan out the conversation you want to have?  At a high level consider these building blocks:

• Define your goal.  What is it that you want to get out of the discussion?  Without a clear goal, your discussion is doomed as doomed can be.[3]
• Have your facts together.  Whatever the point, you must have examples to share.
• Do not script it out.  Write out the bullet points of what you need to convey.
• Right time and place.  Determine the best time and place for both of you to have the conversation.  In-person is always better but that is not always possible in the world of remote work.   But consider all the circumstances of the discussion you want to have and let those guide you in finding a place that is convenient, comfortable, and private.
• Be flexible.  The odds of the conversation going exactly how you have planned it are low.  Adjust to the circumstances.  Otherwise, it will be a very awkward discussion – the antithesis of what you want to have happen.
• Think about the possible reactions of the other person and consider how you will respond.  Again, not a script, but you cannot go into a hard discussion and not expect the other person to debate with you.
• Have an escape hatch.  If everything goes to shit (and it can), have your plan ready for taking a break or having a second conversation on the topic.

4.  Facts only.  A big part of your planning is gathering examples of whatever it is you feel needs to change.  When doing so – and when relaying your concerns and issues to the other person – give concrete examples and stick to the facts.  For example, do not say “you always” or “you never” because it is highly unlikely that anyone always does something or never does something.  If you are addressing a specific incident, be sure you have gathered all the facts about what happened.  And always expect that the other person will have a different version of what happened, i.e., there are always two sides to every story.  Also, if the issue involves you and the other person, be ready to accept responsibility for the things you did that led to or exasperated the issue.  When you gather and stick to facts, it is also easier to control your emotions.

5.  Control your emotions.  See what I did there?  Pretty slick.  But keeping emotions in check is an important point regardless.  Head into the discussion with the goal of keeping everything professional, from the talk points to the tone.  This is especially critical for having hard conversations in the legal department because the odds are very high that you work closely with the other person and, no matter what, you need that relationship to continue going forward.  Being aware of how emotion can change the tenor of the discussion is important, and sticking to facts helps keep you in control.  Likewise, just remind yourself that keeping emotions in check enables you to communicate more clearly and concisely.  All good things.  Can things get emotional?  Absolutely.  But staying calm, pausing and collecting yourself where necessary, remembering to breathe, using an even tone, and keeping everything as professional as you can minimize the chance that things go completely off the rails during your conversation.

6.  Start with “I.”  Perhaps one of the oldest and most effective tricks to having difficult conversations is to start your points with “I.”  For example, instead of saying “You always do [behavior],” say “I feel [emotion] when [specific event happens].” Starting with “You” almost always puts the other person on the defensive and sounds accusatory.  Starting with “I” generally prevents the other person from feeling put down or attacked and makes the conversation less about placing blame – and hopefully more about finding a solution.  One way to look at “I” statements is the following template: I feel _________ when ________________ because _______________ I need ____________.[4]  It doesn’t fit every situation, but it is helpful as you are planning out what you want to say and how best to say it.  Here is a real-life example: “I feel very frustrated when you do not take time to edit and proofread your work because then I have to do it and it prevents me from getting my other work done.  I need you to take more time with your work product before you send it to me.”

7.  Listen to their side.  In my “Ten Things” post on “Maxims” to live by, my first one was “There is always another side to the story.”  This is never more true than when you are preparing for a difficult conversation.  No matter how right you are (or think you are), you need to prepare yourself to listen to their viewpoint.  First, it’s a discussion, so unless you were thinking it was a lecture, then a discussion requires at least one other person to participate.  Let them.  And welcome it.  Second, in many cases, the other person will be a lawyer, so they will do exactly what you would do when someone is discussing your behavior – they will lawyer the shit out of it.  Lawyers, in general, do not take criticism well, so not only must you prepare yourself to listen (more on that below), but be prepared for them to want to “win” the discussion.  This is not exactly helpful, but it is likely.  Here are a few things you can do to help keep the conversation on track and not become a frustrating point-by-point rebuttal:

• Avoid blame: Try to keep the focus on a solution.
• Stay calm: If the conversation starts to heat up, take a deep breath and remain calm. No matter what happens, avoid raising your voice or using confrontational language. If you do, the discussion will fail.  While you may be “right,” it’s not about being right, it’s about trying to resolve the problem and clear the air.
• Agree to disagree: Sometimes, you might not reach a consensus. If this happens, it’s okay to acknowledge your differences and simply move on.  In other words, no matter how much you try and no matter how many of the “techniques” you use to avoid failure, there are times when you simply cannot bridge the gap.  Recognize when that happens and move on.  If you are the manager, it may mean some hard decisions.  If you are peers in the realm, it may mean living with the problem or trying to minimize situations where the behavior or problem you have been trying to resolve can manifest.  If you are the subordinate, you may have some hard decisions to make.  In other words, not all problems can be resolved and sometimes you or they will need to move on to someplace else.  Don’t be shocked or dismayed.  It happens all the time.

8.  Use active listening.  Active listening, compassion, and empathy are incredibly valuable tools when dealing with other people, especially when there is friction or problems.   I wrote about this skill earlier this year when I talked about how to manage people and last year when “Ten Things” took up business skills all in-house lawyers should master.  While not meaning to be a broken record, I cannot underscore the importance of being a good listener when it comes to having any discussion, e.g., litigation settlement, contract negotiation, or hard conversations at the office.  In short, active listening involves the following, among other things: (a) giving the speaker your undivided attention. This means putting away distractions, such as phones or other devices, and focusing solely on the speaker; (b) using body language to show you’re engaged. This includes maintaining eye contact, nodding occasionally, and having an open posture; (c) allowing the speaker to finish their point before you respond. Don’t jump in with your own thoughts or solutions immediately; (d) paraphrasing or summarizing what the speaker has said to ensure you’ve understood correctly. For example, “So what you’re saying is…”; and (e) asking open-ended questions to clarify certain points. For instance, “Can you explain more about that?” Active listening is an incredibly helpful technique that can defuse tension and get hard conversations over the hump.  For more on active listening, look at this article, It Is the Privilege of Wisdom to Listen: Remembering an Underappreciated Legal Skill by James Flynn.  Lastly, by using this technique you may find that there is something deeper at the root of the problem that you were simply unaware of (e.g., an illness, stress at home, etc.) and you may be able to help the other person overcome that problem which will, in turn, solve your problem.  In other words, don’t go into the conversation thinking you know everything.  You don’t.

9.  What to do when it’s your turn.  Oh yeah, forgot to tell you this earlier.  You may be the person someone needs to have a hard conversation with, i.e., you may be the problem.  I can tell you from experience, it feels very weird.  Everyone likes to think of themselves as the “good employee” or the “good guy,” but that is simply not always the case.  We all have things that we do that can irritate others or come across in ways we do not intend – and we are often blind to how we are perceived.  When this happens, a lot of the same rules set out above apply:

• Stay engaged and don’t tune out.  If someone has the guts to ask for a discussion with you to clear the air, the very least you can do is be present and pay attention.
• Keep your emotions in check.  Even if the other person sucks at engaging in hard conversations (perhaps deciding to skip this week’s edition of “Ten Things”?), try not to lose your cool.  You can use the same tools above in terms of active listening and controlling your emotions to get the conversation to the right place.  Don’t be defensive and don’t try to over-lawyer the conversation (even though every bone in your body is pulling you in that direction).  Be open to the thoughts and concerns of the other person.
• Consider the conversation an opportunity for you to get better, i.e., be a better co-worker, a better leader, a better follower, or whatever the situation may call for.  Criticism is the foundation of improvement.  You should ask for it and certainly do not minimize the other person’s concerns or issues.
• Respond with tact.  You may not have liked what you heard, and you may even vehemently disagree, but the better path is to thank the person for coming to you with their concerns. A small amount of appreciation for their viewpoint will go a long way in resolving any problems. If you do not see an immediate way to reach an agreement on the issues (fully or partially), just say you would like some time to think it over and come back with some ideas.  And then do that.  Even if the other person was inartful, if there is validity in what they are saying, take it to heart and see if there is something you can do to address their concerns.  It is hard to think of a situation where there is absolutely nothing you can do to help bridge the gap.  Bridging gaps is what lawyers do best.  Turn that superpower inward when the occasion calls for it.

10.  Resources.  Many people a lot smarter than I am have thought about the issue of having hard conversations at work.  You can a find a lot written on the topic but here are a few resources that I have found useful in educating myself on how to be better at it:

• How to Handle Difficult Conversations at Work (Harvard Business Review)
• How to Have Difficult Conversations at Work (THNK Blog)
• 3 Steps to Having Difficult – But Necessary – Conversations (Ideas.Ted.com)
• We Need to Talk: Difficult Conversations in the Workplace (YouTube)
• Difficult Conversations: How to Discuss What Matters Most (book)
• Getting to Yes (book)

*****

Well, that wasn’t so bad now, was it?  Like most hard conversations, it’s never as bad as you think it’s going to be.  Especially if you prepare properly and do the basics to get yourself ready to have the conversation you need to have.  It is difficult to pick any one thing from the list above as more important than the other, but if I had to pick I would go with the first two points: don’t delay and reframe the discussion as something positive, and not something to dread.  Doing those two things will put you far ahead of most in-house lawyers when it comes to having difficult conversations in the legal department and at the office.

Sterling Miller

September 29, 2023

I am working hard on book number six on productivity (yes, there is a lot of irony involved).   My fifth book, Showing the Value of the Legal Department: More Than Just a Cost Center is available right now, including as an eBook!  As the ABA says, “Sterling, we need to have a hard conversation about your new book.”  Yikes! Buy more books and help keep the ABA off my back for another month!.  You can buy it HERE.

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 also on sale on 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 (not X) @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 twisted 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 at smiller@hilgersgraben.com.

[1] Sorry but I refuse to call it “X” because that is pretty stupid and dumb, much like Twitter has become generally.  Thank goodness for Truth Social… (yes, that was a joke).

[2] Did I just write that?  Now every guidance counselor in America is laughing their ass off at me.

[3] I have to give Ed Grimley $.25 every time I use that phrase.

[4] I stole this from my daughter’s MadLibs book…

[5] I made this mistake a lot in my early days of being a manager, i.e., that I could just tell someone to “knock it off” and that would solve everything.  It didn’t.