Book SummaryHow to Work with Complicated People, by Ryan Leak

1-Page Summary1-Page Book Summary of How to Work with Complicated People

When asked to think of a person at your job who’s difficult to work with, someone probably springs to mind instantly. Maybe it’s the boss who’s always micromanaging your tasks, the coworker who seems to thrive off of disagreeing with you, or the employee who comes in late every day. Whoever they are, executive coach Ryan Leak challenges you to view them differently. Instead of writing off these complex coworkers and doing your best to avoid them, he says you can learn to collaborate with them, improving your work experience and broadening your perspective.

Leak is a motivational speaker, executive coach, and author. He has worked with Fortune 100 companies, professional...

How to Work with Complicated People Summary Embracing the Inevitability of Complex People

Leak argues that learning how to work with people you find challenging is a vital professional skill. It’s almost inevitable that you’ll encounter complex (what Leak calls “complicated”) people in your job—people whose traits or behaviors make your work experience more difficult.

(Shortform note: Developing your ability to work with many different personality types is beneficial in part because it gives you an advantage with teamwork, the importance of which is only increasing. Research shows that teamwork helps prevent burnout because it distributes the workload, and team members can offer each other emotional support around shared work experiences. Likewise, working alongside team members can be motivating—one survey found that the number one reason participants put in extra effort at work was to gain the respect of their colleagues.)

So, why does learning to work with complex people matter? Most of us spend a lot of time at work—around half of our waking hours—so our professional relationships have a strong impact on our overall health and well-being. Leak’s team found that people report experiencing...

How to Work with Complicated People Summary Strategies for Working With Complex Characters

Now that we’ve examined the nuances of interpersonal complexity in the workplace and the importance of fostering understanding, let’s explore Leak’s advice for putting it into practice. He says the most effective method for working with complex people is to forge connections with them. This involves learning to see where they’re coming from, empathize with them, accept messiness, and recognize that you don’t have to completely agree with someone to work together. This isn’t always easy, but it’s a practice anyone can develop.

Why It’s Important to Balance Conflict and Connection

In Collaborating with the Enemy, Adam Kahane explains that effective collaboration requires both embracing conflicts and nurturing relationships. He contends that all human interactions are shaped by two fundamental drives: the drive for power and the drive for love. The drive for power motivates us to seek self-realization and opportunities to assert our individual interests. We express this when...

Shortform Exercise: Work With Complexity in Yourself and Others

Leak argues that every person is complex in their own way, but it’s also possible to improve your working relationship with just about anyone. Consider how you could better work with the complexity in yourself and others.

Think of a person from your past or current job who’s been challenging to work with. What qualities or behaviors do they have that introduce complexity to your interactions? (For example, maybe you have an employee who consistently misses deadlines, so you’re often frustrated with them.)