How Do You Work with a Complicated Person?

Ugh! That feeling of dread that washes over you as you’re about to meet with that colleague/client/boss who just drives you nuts. They’re just so, so difficult to deal with, so … complicated.

Ryan Leak, CEO of The Ryan Leak Group, based in the Dallas/Fort Worth area, has some suggestions for handling those people. The motivational speaker and author of Chasing Failure: How Falling Short Sets You Up for Success (Thomas Nelson, 2022) has a new book, How to Work with Complicated People, (Simon & Schuster, 2024) which will be out in October. 

Leak’s organization conducted a survey of 1,000 workers in the U.S.  on how to work with complicated people. His book delves into the findings. Among those findings: 80% of respondents think they work with a complicated person, but 74% believe they’re not themselves complicated.

“Mathematically, we have an issue,” Leak observed.

That’s because oftentimes, we may feel like we have a behind-the-scenes story that validates our own behavior, Leak said, but the person we are butting heads with has “no excuse for their behavior.”

He shared his thoughts ahead of his June 25 presentation at the SHRM Conference & Expo 2024 (SHRM24) in Chicago. Leak promised that his session will be a very fun talk but also a very deep one. It is available to registered in-person and remote attendees.

Responses have been edited for length and clarity.

SHRM Online: You will be speaking on “How to Work with Complicated People” as part of SHRM24’s Changemakers series. How do you define complicated people?

Leak: Complicated is in the eye of the beholder. You could be complicated to someone else but not complicated to me. Part of working with complicated people is coming to the realization that I am complicated to someone else.

Some of the commonalities of complicated people: their personality, work pace, and preferences. They make communication difficult.

One chapter in my book is on working with different generations.

SHRM Online: You’ve said there are options for dealing with complicated people—ignoring them, trying to change them, cutting them out of your life. Yet, you also say these don’t work. Why not?

Leak: Some people try to avoid complicated people to the degree that they shift their schedule; 50 percent of respondents in our survey have skipped a day of work to avoid a complicated person. Numerous people have actually quit their job instead of working with a complicated person. Guess what you’re going to find when you get [to your new job]—someone else who is complicated. Sometimes, you’ll wish for the complicated person you used to have [to deal with]. And [avoidance] doesn’t help you grow as a person or leader.

One approach is to try to change the other person. We subtly try to twist their arm and pull them toward our pace, our preferences, our personality. It’s a bad option, because we’ve all been on the other side of someone twisting our arm, and it didn’t feel good. It’s a treadmill—you’re running in place, and you’re exhausted [from the effort]. While changing somebody is an option, it’s not effective.

Some people cut complicated people out of their lives. This is beyond avoiding; I’m going to pretend you don’t even exist. One leader told me a person was “dead” to them.

SHRM Online: You have identified a fourth option—understanding them.

Leak: We give complicated people so much time in our heads. We expend a great deal of emotional energy toward this person whether we want to or not because negative energy requires time.

I’m finding out more and more that when you start to really hear people’s stories, what often happens is we get a little more empathy from that person. We have a behind-the-scenes story that makes our complicated behavior valid.

Understanding doesn’t mean you have to be their best friend or take them to lunch and hear their entire life story. You very respectfully ask questions: “How did you learn to do [X] your way? Could you explain that to me?” Now, I have an understanding of where they are coming from.

The reason I like this option the most: Isn’t it the one we want at the end of the day? We loathe being misunderstood.

SHRM Online: How do you apply this approach to your boss?

Leak: The boss piece is very complicated. It requires speaking leader/C-suite language. Part of understanding leadership language is paying attention to what they celebrate, champion, and complain about. Every leader celebrates something different. Some leaders celebrate sales. Some leaders celebrate the bottom line. Some celebrate their values. What do they give budget to? 

Tie what you’re bringing to them to what they celebrate, champion, complain about. Pay attention to company emails: The moment they start talking, they are telling you what’s important to them. Take notes.

In Case Leak Seems Familiar …

Attendees may recognize Leak from his film “The Surprise Wedding,” which documented him and his longtime girlfriend getting married the same day he proposed during a trip to Miami, where friends and family had gathered for the event he had prearranged.

This experience led to an appearance on “The Queen Latifah Show,” where Leak, a former All-American basketball player for a Division III school, met his hero, Kobe Bryant, and was invited to a game and to meet the entire Los Angeles Lakers team.

Leak told Bryant about his idea for a documentary on embracing failure and said he wanted to “stop being scared to lose.” Leak shared his dream of trying out for the NBA.

“ ‘Yeah, man. Do it,’ ” Leak recalled Bryant telling him. “When a Hall of Famer tells you to go for it, you have now passed the point of no return,” Leak wrote on his blog. “ ‘Chasing Failure’ went from a lofty notion to an irresistible destiny in just four words.”

He made the documentary and, in the pursuit of failure, tried out for the Phoenix Suns.