General Approaches to Managing Challenging Personalities
One caveat to this section on general approaches: if a challenging personality asks or tries to steer you to do or agree to something that is (i) illegal, (ii) wildly unethical, or (iii) completely against your core values as a human, do not do that thing and immediately put down the pencil and walk away from that person, task, or matter.
Find someone more senior at your employer or whomever manages that relationship and talk to them.1 By doing so you will rid yourself of guilt, keep your integrity, and, perhaps most importantly, exculpate yourself from such nefarious activity and the inevitable consequences thereof. In our future chapter on happiness, we reiterate this guidance as a core point of remaining a happy lawyer.Here's the good news. The best approaches to managing challenging personalities also happen to primarily be the core concepts of lawyering as described in Chapter 2 of this book. Sure, there are novel concepts around the edges and strategies to deploy that we will explore below, but the bottom line is that lawyers aren't typically called in to deal with easy-going, pleasant-to-deal-with, and predictable personalities. While the core concepts apply to all aspects of executing your job as a lawyer, they are particularly applicable to dealing with difficult and challenging personalities, not just in the practice of law but in all aspects of life.
1. Be an Incredible and Attentive Listener. A misconception, particularly prevalent among junior lawyers, is that they must contribute or “add value” in a highly visible or noticeable way. Nonsense. Some of the best and priciest lawyers employed by the top law firms on this planet contribute and add a ton of value but are quiet, nuanced, and most of the time fly so low under the radar that the client and even their colleagues forget that they are even there. How does this work? For starters, they listen much more than they speak.
Second, when they do speak, it is typically to either draw out more information or steer people into a certain direction in seeking truth or to influence them to think a certain way. When dealing with challenging personalities, getting them to talk in more detail is a great strategy to disarm and understand their motivations and needs. Many times, this strategy entices a person to say things they were not prepared to tell you or even things they've not consciously thought themselves.2. Live and Breathe Empathy. Current times (and quite likely throughout all human history, really) society does not necessarily encourage us to look beyond ourselves. As such, those who can do so are important because innovation and success on a broad scale typically come from collaboration or work amongst and with a community, not just one individual toiling away in isolation. There are outliers to be sure, but that is not the focus here.
Pope Francis coined the phrase “globalization of indifference,” but you don't have to be Catholic to agree that there is a dearth of empathy among the general population these days. Pope Francis was generally referring to the indifference of groups of people, those standing by silently, not paying attention to the suffering of others, the results of which disproportionately affect marginalized or vulnerable populations. This indifference, however, on a smaller scale affects just how individuals face, manage, and interact with people on a one-on-one basis. That's intense and perhaps a bit heavier than what a junior M&A lawyer typically deals with on a day-to-day basis, but it's no less relevant or accurate.
There is a misconception that to be empathetic is to be soft, gentle, or caring. If you can be empathetic and transplant yourself to another person's worldview or emotions, then you have just attached a turbocharged jet pack to your ability to serve that client, boss, or person. Or maybe more importantly it gives you great insight into an opponent.
Harnessing empathy will likely bring out kindness, at least as third-party observers can tell. The secret is that empathy doesn't just make you more effective but also more powerful. Put another way, if you are truly empathetic, you'll know which buttons to push should you need to.Keep in mind that the person across the table, on the phone, or in the Zoom meeting most likely will not be Peter Frampton and close each conversation with “Do You Feel Like I Do?” [Editor's note: Dave is a music superfan. He is also old and therefore makes references to folks like Peter Frampton. We are sorry that almost none of you will understand this reference and ask for your forgiveness.] No, this will require work on your part to consider the person's past experiences, their future desires, and present intentions. This will require you to think, be curious, and remain open minded.
3. Employ Apathy. Yes. Apathy. You may be thinking to yourself, “Self, didn't they just say that empathy is the most important approach to managing or dealing with a challenging personality? And doesn't apathy fly in the face of that suggestion? Is this a typo or just a sneaky lawyer trick?”
These are all great points, and we certainly do not fault you for scratching your head here. Apathy is a tool that may come in handy when managing your own feelings and emotions. You will most certainly be attacked, belittled, taken for granted or worse by certain challenging personalities and it is important to remember that your personal emotions and feelings are not that important to people paying your bill. They want their problem solved. As much as they may like you, that is really their only goal.
Whatever comes your way, your reactions and ability to execute are in your control. Take an apathetic approach when it comes to yourself and do your best to be indifferent and remove emotion from how you handle your words and course of action. There are healthy ways to process the aggravation, frustration, and stress of dealing with these unsavory or difficult personalities.
Your feelings should be tucked away in the backseat and have zero impact on your work. This does not mean to ignore your feelings. That comes after the work is done, and we will explore that later in the book. Just don't let your feelings affect your work. It's not only bad for your clients but also for your reputation.4. Espouse Understanding. This is being empathetic, but on steroids. It's one thing to put yourself into someone else's shoes, but this strategy involves talking and asking questions that show you have thought deeply about an issue and what someone has told you. If you can supply evidence of deep understanding, not just empathy, you will likely be able to get to the heart of the matter easier and, even better, morph that challenging personality to a manageable client or trusted colleague.
5. Commit to a Plan and Act. Our two favorite lines in the True Detective TV series both come from season 1 and are both uttered by Detective Rust Cohle, the haunted detective portrayed by Texas's favorite son, Matthew McConaughey:
1. To his partner in episode 5, “Good to see you commit to something.”
2. To an adversary in episode 8, “I strike you as more of a talker or a doer, Steve?” Like many things in life, when dealing with challenging personalities, it's best to commit to an approach and then act accordingly. To do otherwise would cause you to spin your wheels and waste time, resources, and energy on thinking rather than simply acting and moving on. So, make Detective Cohle proud. Formulate a decision, commit to it, and act. Simply making a decision is one of the best-known productivity “hacks.”
6. Be the Calmest Person in the Room. Combine items 1 through 5 above: listen, practice empathy, put aside your personal feelings, do your best to understand the nuances of the situation, the people, and their intentions, commit to a plan, and take action. Do all while neither raising nor lowering your heart rate. Be the calmest person in the room. If you take away only one thing from this chapter, let it be the immediately preceding sentence.