Sampling of Challenging Personalities and Tips for Dealing with Them
As in other parts of this book, we try to not only teach you theory, but pragmatic and actionable advice. Figure 14.1 shows 10 archetypes of challenging personalities you may come across, each embodying many (or in some cases, all!) of the traits described above.
Some archetypes may be clients, some may be third parties, some may be colleagues, but in effect all are bosses and all are somebody you may have to serve or at least have a collegial and functional working relationship with.In this section we attempt to (i) accurately describe certain challenging personalities with a moniker; (ii) describe how to identify such individual; (iii) provide a few specific tips on how best to manage each of them; and (iv) score each on a numbered scale of 1 to 10 based on level of difficulty: 1 being yourself, because we all know that we are easy to deal with, and 10 being a wicked combination of Carrot Top, Logan Roy, Bobby Axelrod, Sideshow Bob, and the advisor wherever you take your car in for service.
| Lack of Empathy | Manipulative | Bends the Truth | Lack of Self-Control | Refusal or Inability to Focus | Refusal or Inability to Accept Reality | Shifts Responsibility or Blame | Incompetence | Treats Some People Worse than Others | Inconsistent Behavior | Always Angry | Acts Like a Jerk | |
| Self-Proclaimed Smartest in the Room | • | • | • | • | • | • | ||||||
| The “It's Not a Good Idea Unless It's My Idea” Guy | • | • | • | • | • | • | • | |||||
| The Biggest Small Business Owner | • | • | • | • | • | • | • | |||||
| Mr. Something to Prove | • | • | • | • | ||||||||
| The All-Powerful Government Lawyer | • | • | • | • | ||||||||
| Mr. I've Never Been Told “No” | • | • | • | • | • | • | • | • | • | • | • | • |
| High-Performing Senior Associate/Junior Partner | • | • | • | • | • | |||||||
| Unresponsive But Super Important Third Party | • | • | • | • | • | |||||||
| The Abrasive Adversary | • | • | • | • | • | • | • | • | • | • | ||
| The Turf-Protecting Academic or Nonprofit Director | • | • | • | • | • | • | • | • | • |
FIGURE 14.1 Challenging Personality Traits Belonging to Each Challenging Personality Archetype
Note that these archetypes are presented in no particular order:
1. Self-Proclaimed Smartest Person in the Room
How to Identify:
o Proclaims him or herself to be the smartest person in the room.
o Classic “know it all” personality who responds to everything with “I know” and then adds something showing he knows it better than you.
o Most likely talks over you.
o Has impeccable credentials but struggles to name personal references that aren't a classmate or former professor.
Tips to Manage:
o Be super smart on those topics you will engage with this person on.
Be proactive on performing recon, diligence on the latest developments in the area, and do deep dives on the details.o Show that you are just as smart, quietly and discreetly.
o Know that the people who are actually the smartest in the room never act this way.
o Make them look even smarter by supporting where necessary and correcting where appropriate but always with, “Yes, I hear you but also you were probably going to say…”
o When you are wrong and this individual corrects you in front of others, respond with humor. Our preferred line when this occurs is to simply say, “Thank you. You passed my test.” Humor disarms most of the population.
o Employing apathy is key here; do not let their behavior get under your skin.
o Consider whether you can connect with this person on a topic outside of your current engagement so that they feel like you are on their team.
Level of Difficulty:
o 6. Many hard charging clients and mid-level lawyers act this way. Get used to it, as they can be valuable clients and helpful colleagues once you understand how they operate.
2. The “It's Not a Good Idea Unless It's My Idea” Guy
How to Identify:
o Makes you sing the opening stanza of “Emotional Rescue” by The Rolling Stones in your head, “Is there nothing I can say, nothing I can do, to change your mind?”
o Speaks first, always. Interrupts others, often.
o Demands attention and immediate responsiveness to their own thoughts or suggestions but seldom provides feedback on other colleague's ideas.
o Is a “no person” to everyone else's ideas.
Tips to Manage:
o You'll need to not only lead this horse to water, but you'll also need to get that horse to drink. Get in their head and start speaking in their language. Use phrases like, “That idea you had was incredible! Imagine if you slightly modified it so that it was legal!?”
o Managing this type of personality can be useful not only as a junior lawyer but also as a business partner, parent, spouse, friend, or just when trying to pick a place for lunch among colleagues.
Whenever you are trying to get someone else to embrace your idea as their own.o Give it a little less gas on the empathy pedal and a little more on being an active listener to understand exactly how this person operates and speaks. Start to speak this way and try to predict the way this person thinks.
Level of Difficulty:
o 3. Once you get the hang of being a chameleon, you'll be able to crack this nut regularly.
3. The Biggest Small Business Owner
How to Identify:
o Walks into a professional meeting with various counterparties, throws their keys on the table and says, “That's right. New Jaguar. Just picked up next year's model. Got the convertible.” Seriously, we've seen this happen.
o Built a business from the ground up, likely struggled initially and then absolutely killed it. Executed perfectly and now has vendors, banks, competitors, and job seekers clamoring to team up or get their business.
o Considers lawyers to be a waste of money.
o Risk taker and incredible businessperson.
Tips to Manage:
o Find out how they built their business. Be genuinely interested. There's a very good chance that they view lawyers as risk averse and, therefore, inferior. You need to show how you can be a helpful resource and a trusted compatriot (if a client) and a respectful admirer (if a counterparty or other third party).
o Show them respect that they've built something from the ground up. Empathize that it is hard to do and rare to achieve.
o Dive deep on long-term goals and always ask how you can be helpful, be it in terms of legal work, introductions, or other. Junior lawyers should consider themselves incredibly fortunate should they find themselves dealing directly with clients like this or even their lieutenants.
Level of Difficulty:
o 4. These are incredibly enjoyable and fulfilling clients to have. However, they can be a complete pain in the keister as counterparties on a transaction.
4. Mr. Something to Prove
How to Identify:
o Quietly doubts their own decision-making.
Asks for reassurance on big-ticket items, even those that may not be primarily legal issues.o Hesitant to talk about credentials or themselves.
o Takes pleasure in outperforming or otherwise destroying competitors or other adversaries (real or imagined).
o Dominating feels good to them.
Tips to Manage:
o Figure out the source of insecurity. Is it due to how they grew up? Did they go to school somewhere that isn't a brand name college or university? Are they short? If you can relate to any of these sources of insecurity, identify them and bring it up. Everyone wants to be heard.
o Build trust and figure out the best method of communication. Try to get into a rotation of communication with this client so they anticipate speaking with you often and begin to look forward to it.
Level of Difficulty:
o 6. This is above a 5 simply due to the amount of trust one needs to build to manage this personality.
5. The All-Powerful Government Lawyer
How to Identify:
o Works for the government.
o Has unlimited discovery power and resources.
o Denies he or she has unlimited discovery power and resources.
o May have a chip on their shoulder if you have a more prestigious or wealthy pedigree.
Tips to Manage:
o Good luck.
o Try to win with flattery. Subordinate yourself as you have no chance of out muscling them.
Level of Difficulty:
o 9 to 10.
6. Mr. I've Never Been Told “No”
How to Identify:
o Filthy rich, typically due to an inheritance or a one-time highly unusual windfall.
o Or parents were this way and they've never had to work for anything.
o Has literally not been told “no” in the preceding 10 to 20 years.
o Admires Kim Jong-un's negotiation style (i.e., what's mine is mine, what's yours is negotiable).
Tips to Manage:
o When negotiating, be prepared to bring the cake and the hammer but be mindful that unfortunately the hammer won't do much good if your client is on the receiving end of this person's wrath (and if Mr.
INBTN has a bigger hammer (which is likely)).o If this is your client, your job is to keep them rich, out of the papers, and above the fray. If this is your client's counterparty, then it is your job to suggest to your client they find another counterparty. If that's not an option, you must, under all circumstances, stay on this challenging personality's good side until they no longer have the resources to live a life of never being told no.
Level of Difficulty:
o 8.5. Second only to the All-Powerful Government Lawyer, solely since the APGL can unilaterally shut down a business, impose large fines, or put someone in jail.
7. High-Performing Senior Associate/Junior Partner
How to Identify:
o Stressed, hurried, and receives 10 calls a week from headhunters.
o Weighs 15 to 20 pounds heavier than a few years earlier.
o Responds to requests for time off due to a family emergency or other significant life event such as a wedding with “Ok. You have to live your life, I guess,” or “That's fine but make sure you are available for anything that comes up,” or “Did you know I closed a deal in the delivery room as my wife was giving birth? There's a picture of me with the kid in one arm and my phone up against my ear with the other!” Fun fact: we have heard one lawyer give two of these responses.
Tips to Manage:
o Make a great, no, incredible first impression.
o Listen, listen, listen. And follow up the listening with thoughtful clarifying questions.
o As you would with anyone, do great work, be a great communicator, and do exactly what you say you will do.
o Anticipate their needs and deadlines, and tackle anything you can that will make their life easier.
o Do not hesitate to push back when you know something they do not or spot something they have missed. Your job is to make them look great in front of everyone else.
o You may have to outwork them on a project to prove your value. Hopefully it's just one project.
Level of Difficulty:
o Somewhere between a 1 and a 10. If you are at a law firm, a high-performing senior associate or junior partner can make or break you in the early stages of your career. If you earn the trust of this person, then you will be given opportunities, responsibilities, and obligations that most junior lawyers only dream of. If you meet expectations, then the level of difficulty is closer to a 1. But if you cannot commit and execute, you will find yourself miserable working with a high performer.
8. Unresponsive But Super Important Third Party (think vendor, expert witness, opposing counsel's assistant, graphic designer, etc.)
How to Identify:
o Misses deadlines, cancels calls at the last minute, and requires constant attention up until a task is complete.
o Work product or participation is vital to whatever project, case, or deal you are working on.
Tips to Manage:
o You typically realize that your super important third party is unresponsive when it is too late, i.e., after you engage them, and they begin the work. All is not lost, however, and you can still work to salvage the efforts, but you must be quick and attentive to this personality in the beginning to make sure there will be no surprises later.
o Provide fake deadlines. Seriously. Like how you would set a sixth-grade child's alarm clock 15 minutes earlier than the true time to ensure they don't run late in the morning. You can provide deadlines to a third-party vendor that gives you a cushion in the event they blow it.
o Heavy on the communication and employ more than one method (emails, follow up texts, biweekly check-in calls).
o Here is where you need to really focus on empathy. In many instances, these third-party service providers or vendors are very likely treated poorly by other lawyers who haven't read this book. Treat each vendor how you would like to be treated and there is a great chance that your project will go to the top of their pile.
o If you don't want to or can't provide empathy, buy them something like a nice bottle of wine. Sometimes you can buy loyalty.
Level of Difficulty:
o 7. A lot depends on just how super important the work product is that the third party is involved in producing. If its importance is extremely high, then you may do yourself a favor and have a backup vendor or plan in place as well.
9. The Abrasive Adversary
How to Identify:
o Fallback position is intimidation tactics, whether it's cursing, yelling, or calling others mean names. Asks questions without waiting for an answer (e.g., “You think you're pretty smart, huh? Well, you're not!”)
o Spits a lot when speaking. Listens to Five Finger Death Punch to calm down for bed.
o Believes that Johnny Lawrence (The Karate Kid version, not Cobra Kai) was misunderstood.
o Acts hostile even when responding to a yes-or-no question (e.g., Q: “Sir, do you want chicken on your salad?” A: “What the hell do you think!?”).
Tips to Manage:
o Let them talk. A lot and often. Eventually they will wear themselves out, and if it's in front of a judge or jury, don't worry; those folks will see right through it. If it's in front of clients, even better. The only clients who like their lawyers to be loud, angry, and abrasive are those on TV or those who have a bad set of facts on their side.
o They may test your mettle in terms of trying to stay out of the muck. Remember to employ apathy when it comes to your own feelings. Don't let them ruffle you and simply stay the course.
o Keep them in check. If their behavior crosses the line and goes from unprofessional to harassing, consider filing a complaint with the state bar or their own law firm or company, but do so coming from a place of calm, measured contemplation and not anger or retaliatory thinking.
o Employ apathy and be the calmest person in the room.
Level of Difficulty:
o 2.5. Surprised by this? Don't be—typically the angry bluster is thrown your way as a cover for lack of good facts, lack of good lawyering, or lack of adequate resources. A point or two subtracted here, too, because this challenging personality's behavior will likely give you great tales to tell at your next dinner party.
10. The Turf-Protecting Academic or Nonprofit Director
How to Identify:
o Self-righteous and self-important.
o Resources are typically scarce so there is a heightened sensitivity to others who may encroach on such resources.
o So entrenched in their space that they no longer focus on the population they set out to serve and instead focus on themselves and their public relevancy.
o This is their work, their space, their kingdom, and their turf. They have no other identity outside of their job.
o Unwillingness to allow new participants into the space without first “kissing the ring” and asking the “right” people for blessing simply to help others.
How to Manage:
o Deploy your network and figure out whether there is common ground between you, your organization, and the challenging personality with which you will have to work or otherwise interact.
o Build trust slowly via sincere and substantial communications and ask what favors you may be able to do for this person.
o Determine early on whether there is a workaround, i.e., another person at the organization you can deal with who may not be as challenging.
Level of Difficulty:
o 8. Different from a typical client that values money or prestige. Like a politician in that power and turf are most important. Incentives may be difficult to identify initially; therefore, choosing which levers to pull may be a challenge.