Dealing with Complicated Staff Isn't Complicated

September 11, 2025

by Dan Angelo

 

The message Ryan Leak delivered to attendees at his CAMEX25 Afternoon Main Stage session was a pretty simple one: People are complicated. But you can work with them.

 

Leak, author of Chasing Failure and his soon-to-be-released title, How to Work with Complicated People: Strategies for Effective Collaboration with (Nearly) Anyone, regaled attendees with stories of a life that has led him to be a successful motivational speaker and CEO of the Dallas leadership firm, the Ryan Leak Group. He also described six no-cost strategies for working with complicated people, starting with the reminder that we’re all complicated.

 

“We’re not talking about evil people, we’re talking about complicated people,” he said. “The reality is there are people who are working for you that bring complications to work with them every single day.”

 

Part of Leak’s story is the research he’s done for his books. He’s found that 48% of working Americans say they work with or for complicated people who make them so stressed they have skipped a day of work. On the other hand, the research found that the average person works with just three to five complicated people on a weekly basis.

 

“The way some people talk about complicated people, you’d think the number was hundreds,” Leak said, “You’re going to quit over three to five people? The reality is working with complicated people is an absolute super power. Anyone can thrive when they surrounded by supportive like-minded colleagues that match their energy and hue the same communication style and work ethic. But the ability to collaborate with people who challenge you, who frustrate your assumptions? Now you are a super colleague.”

 

To begin figuring out ways to deal with individuals who seem complicated, Leak reminds it’s a good idea to look in the mirror because you, as a leader, are bringing your own complications to the table.

 

After you’ve taken that look in the mirror, he suggested considering your options. It’s not like you can fire, change, or just ignore everyone who frustrates you. Besides, the impracticality of firing every annoying employee or ignoring an infuriating boss dismisses the fact that we want to be given a space when it comes to our own frailties.

 

“For a lot of us, it’s ‘If they hurt me, let’s cancel them,’ but that makes it harder to give them a break,” Leak said. “I’m challenging you to be the leader who moves towards others the way we would want others to move towards us.”

 

Leak’s third strategy for effective leadership is to grow connections. His studies found that building a connection with complicated individuals requires being decent and being a person with the level of care for others that is difficult to walk away from.

 

“I don’t want you to have common courtesy, I want you to show uncommon care,” he said. “I tell people to connect and create the kind of place people want to show up for.”

 

It’s also important to allow for that difficult person to grow on us. A leader has two choices, according to Leak: Either be proactive or reactive. The proactive approach means the leader is the person who sets the culture and is prepared for any sort of behavior.

 

A proactive leader also uses language to phrase questions in ways that invite engagement rather than to shut down opinions. A well-phrased question allows the leader to give the difficult person the chance to be part of the solution.

 

The fifth strategy is for the leader to use his or her attitudes to influence others. The greatest tool are a smile and a positive attitude. In addition, simply showing gratitude can shift the energy of most situations.

 

“There are people who are glass-half-empty people and people who are glass-half-full,” Leak said. “How about you be the leader who is grateful for the glass. Just being a grateful person puts a big smile on my face. I know things aren’t always going to be ideal, and that’s okay. But it also doesn’t mean we can’t have an ideal perspective.”

 

The final strategy is making adjustments to our own expectations because Leak has found that most frustrations come from the complicated individuals not living up to our expectations. The expectation is that everyone is simple and perfect, and yet they are really complicated and flawed.

 

Once a leader adjusts their expectations, they need to stop trying to change people who aren’t trying to change anyway.

 

“The difference between being the best boss they’ve ever had and just another is showing them you care,” Leak said. “I want to encourage you to begin to change your expectations. I want you to expect complicated and I want you to expect different. We are all a little different and yet we can all come into the room and try to figure out different strategies as leaders for our campuses, our students, and for their families.”