July 10, 2025
“On the other side of complicated is the wonderful, wide-open world of effective collaboration and a workplace you love”.

Ryan Leak

In every organization, some people are simply complicated—those whose behaviors, communication styles, or attitudes challenge even the most seasoned leaders. Whether they’re prickly, unpredictable, or just difficult to read, these individuals can create friction that ripples through teams and cultures. But what exactly makes someone “complicated,” and how can leaders not only survive but also thrive in their presence? Complicated people have been a double-edged sword to organizations for time immemorial. The British Intelligence group MI5 had a large number of authors who wrote fictionalized stories about spies. One member was Ian Fleming, who memorialized a very complicated yet productive spy, James Bond. The Naval Combat Intelligence Department at Pearl Harbor during World War II “broke” the Japanese code. Their leader, Commander Joseph Rochefort, remains celebrated as the brilliant and somewhat quirky mastermind behind the code-breaking success that made the Battle of Midway a decisive victory. His breaking the code and sending out false information set the stage for the sinking of four Japanese aircraft carriers in one day. Rochefort was known for his unconventional habits and somewhat eccentric personality. He reportedly rarely showered and was often seen in the office wearing slippers and a robe. He was also known for smoking a pipe while working in the office. These quirks did not diminish his brilliance and dedication; instead, they added to the legend of the man who played a crucial role in one of World War II’s most important intelligence victories.

Both of these individuals thrived and made significant contributions to changing the course of World War II. Many other complicated people thrived in less dramatic ways within their organization. For example, the quirky scientist who invented the adhesive that made Post-it Notes possible was Dr. Spencer Silver, a chemist at 3 M. In 1968, while trying to develop a super-strong adhesive, Silver accidentally created a unique, low-tack adhesive that could stick lightly to surfaces but was easily removable and left no residue. He often described his invention as “a solution waiting for a problem to solve.”George Bush brought in spy and espionage fiction authors, such as Tom Clancy, in the aftermath of 9/11, as well as foreign affairs and military experts to consider possible options.

These people all added value because leadership saw beyond their quirks to their potential contribution, As John Maxwell says “Everything rises and falls on leadership” High Road Leadership, as articulated by John C. Maxwell, offers a transformative framework for leaders who seek to bring people together, value every individual, and navigate the complexities of working with all types of personalities—including those considered “complicated.” High Road Leadership is about valuing, respecting, and adding value to all people, especially those who are complex. Leaders who adopt these principles foster unity, collaboration, and a culture where everyone’s humanity is recognized and celebrated. By consistently choosing the high road, leaders not only bring out the best in others but also elevate the entire organization.

Ryan Leak’s “How to Work with Complicated People” offers a practical, research-based approach and companion to help you succeed with complicated individuals.

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This Thursday’s Leadership Insight explores how leaders win with complex individuals. First, using the data from Ryan Leaks’ book, we consider what is complicated. Second, what is the cost of complicated people in workplaces? Finally, what are the traditionally employed strategies for dealing with complicated people? Four methods to build bridges of connection and collaboration are shared.

Ryan Leak’s 2024 study, “The State of Complicated People in the Workforce,” is essential work for three reasons. By using the term “complicated” instead of the often-used term “difficult,” people’s judgment is set aside. Second, the report’s findings are based on current data, encompassing both personal leadership and group leadership. Ultimately, although understanding is crucial, there is no suggestion that leaders condone or tolerate toxic or dangerous behaviors.

What Makes Someone Complicated at Work?

Complicated people aren’t just those who disagree or have strong personalities; they are also those who have a complex inner life. According to Ryan Leak’s 2024 study, The State of Complicated People in the Workforce, these individuals are defined by the persistent challenges they present to collaboration, trust, and productivity. They may be unpredictable, resistant to feedback, or prone to conflict, which can make teamwork and progress challenging. The study found that 78% of working Americans encounter complicated individuals at work on a weekly or more frequent basis, and 77% believe these individuals pose a serious problem in most work cultures.

Interestingly, the perception of who is complicated varies by generation. Gen Z and Millennials are often perceived as complicated, even by their peers. In fact, 41% of Gen Z respondents believe their co-workers would describe them as complicated, highlighting both a self-awareness and a generational divide in workplace dynamics.

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The Real Cost of Complicated People

The impact of complicated people extends beyond mere emotionality. Leak’s research reveals that the presence of complicated individuals leads to avoidance behaviors, reduced morale, and increased turnover. 61% avoid complicated people, and 48% will leave a job with a complicated co-worker or leader,

Gallup data underscores this, estimating that disengaged employees cost U.S. companies up to $550 billion annually in lost productivity. McKinsey estimates the average cost to replace a single employee at $52,000, but the ripple effect, including missed deadlines, damaged relationships, and eroded trust, can escalate costs into the hundreds of thousands or even millions for larger organizations.

The McKinsey contributors wrote, “A bad hire isn’t just someone who doesn’t align with company culture or lacks specific technical skills; it’s a significant mismatch that disrupts the delicate balance within an organization… Trust, the cornerstone of any successful organization, crumbles as colleagues question each other’s judgment and abilities. Productivity plummets as employees, demoralized by dysfunction, disengage and seek exit routes.”

Four strategies are commonly employed with complicated people in the workplace.

1. Avoidance: 61% of respondents in the study practice avoidance. Often, it is noted that it doesn’t work.
2. Change them. Forcing people to change is often complicated and counterproductive.
3. Cancel them. Remove them from the committee and task force. Project or outright release them. Any skill or talent advantage goes with them, plus the cost of replacement
4. Understand them. Much more difficult for leaders. Seeking to understand first will guide better decisions, even if that decision means the person transferring or leaving the organization.

Four Strategies for Winning with Complicated People

Practicing High Road leadership and utilizing Ryan Leak’s practical, empathetic roadmap for leaders provides a High Road path to working with and winning with complex people for leaders who want to move beyond frustration and toward effective collaboration. His four core perceptual shifts and four practices and questions to enhance collaboration:

Four perpetual shifts

1. See challenging individuals as human beings to understand, not problems to solve.
2. Shift your mindset. David Yaeger suggests this mindset shift in 10 to 25. Moving from an Enforcer “fixing or else” mindset to a Protector mindset, allowing low-quality work, to a Mentor mindset with high standards and providing high support and understanding. Ask questions, listen actively, and look for the story behind their behavior.
3. Detach from unrealistic expectations and become comfortable with the complicated.
4. Understand and accept that complexity is part of every team. Lower your expectations that everyone will be easy or the same to work with, and focus on progress, not perfection.

Below are four practical strategies to enhance collaboration.

“You might be someone else’s complicated person.”

Ryan Leak

Four practices and questions for enhanced collaboration with complicated people

1. Self-Awareness Asks

What is it like to be on the other side of me?

2. Ownership Asks What is my part to play?
3. Curiosity Asks

What is it like to be you?

4. Connection Asks

What brings us together?

Some additional considerations

“When the leader gets better, everyone else does too.”

Craig Groeschel

1. Learn to communicate effectively in complex environments.

Be clear, direct, and compassionate. Use structured frameworks, such as Jon Gordon’s STAR3 model—Small Ego, Tell the Truth, Assume Positive Intent, Rules of Engagement, and Respect—to keep conversations productive and focused on shared goals.

Embrace healthy disagreement as a tool to discover better solutions. Don’t shy away from conflict. When managed well, disagreement can spark creativity and lead to stronger, more resilient teams.

Use the following steps to navigate conflict

1. Fight fair, no manipulation
2. Fight Fast: get in front of conflict on your terms
3. Fight to stay objective
4. Fight focused on the incident and relevant themes only
5. Fight Forward, what is the plan going forward

Leak also emphasizes the importance of setting boundaries—letting people into your world without letting them run your world. This means protecting your energy and focus while still being open to collaboration.

Mastering the art of working with complicated colleagues isn’t just about survival; it’s a catalyst for growth. Consider these five key benefits:

Greater creativity: Diverse perspectives (even challenging ones) lead to more innovative solutions.

Stronger teams: Teams that navigate complexity together build deeper trust and resilience.

Increased productivity: Less time is wasted on avoidance, conflict, and miscommunication.

Better decision-making: Healthy disagreement surfaces risks and opportunities that might otherwise be missed.

A workplace you love: When leaders model empathy and effective conflict resolution, the entire culture shifts toward openness, collaboration, and mutual understanding.

As Ryan Leak puts it, “On the other side of complicated is the wonderful, wide-open world of effective collaboration and a workplace you love”.

Leaders who embrace the challenge of working with complex individuals using High Road Leadership, along with the data and practices on how to work with them, will succeed at work. They will be equipped with empathy, strategy, and a willingness to grow and collaborate. These leaders will practice High Road Leadership to unlock the potential for transformation, both in themselves and in their teams.

The Leadership Questions for you then are:

Are you the complicated person you need to work on first?

What practices can you use to work with the complicated people in your organization