PDF Summary:How to Work with Complicated People, by Ryan Leak

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.

In this guide, we’ll define a complex coworker and explore Leak’s argument that it’s best to embrace their complexity and find common ground. We’ll discuss his strategies for cultivating a collaborative mindset, communicating effectively, and recognizing when collaboration isn’t possible. We’ll also look at other experts’ advice on improving workplace harmony, honing communication skills, and navigating difficult interactions.

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Strategy: Identify Your Personal Perspective and Its Limitations

Leak explains that we all view other people through our own perspectives, which include our personal biases, assumptions, and emotions about others. If we don’t consciously work to deconstruct these biases, we end up unable to recognize other people’s points of view, and we treat them as others rather than as fellow humans with valuable insights and ideas. This happens especially with the people we find challenging, as the emotions we feel about them are often deep-seated and intense.

To move past this pattern, Leak says you must recognize that the narratives you tell yourself about others are inherently incomplete. Consider which of your emotions and biases might be obscuring the full truth of the situation. Instead of framing a complex coworker as the antagonist, consider what the narrative looks like from their point of view. This can allow you to see their strengths alongside their flaws.

For example, say you have a coworker who frustrates you by making every meeting run long because they ask so many questions at the end. Maybe you have a lot of project work on your plate, so you want to keep meetings as short as possible and you prefer when people email with questions. Thus, this coworker feels like a barrier to you getting your work done. However, just because their communication style is different doesn’t mean it’s bad—instead of viewing them as someone with no regard for others’ time, you could view their inquisitiveness as thorough and detail-oriented. By asking questions, they could be trying to prevent mistakes and clarify points of confusion for people who aren’t as comfortable speaking up.

How to Increase Your Self-Awareness at Work

To recognize and move past your personal biases, you must practice self-awareness. Experts suggest the following strategies:

Strategy #1: Ask people in your professional sphere—such as bosses, coworkers, and employees—for honest feedback. It can be difficult to hear criticism, but getting both positive and critical feedback on what it’s like to work with you is a necessary part of identifying your personal blind spots.

Strategy #2: Identify your go-to defensive reactions. When you’re triggered or uncomfortable, how do you usually respond? Maybe you immediately get angry, you default to agreeing with the other person, or you try to shift the blame onto someone else. Recognizing this can help you see the automatic narratives your brain relies on in challenging situations.

Strategy #3: Consider how your past affects how you respond to things today. Are there any values and beliefs from your family that affect how you view people at work? Do you have stereotypes and biases you’re holding onto from how you were raised? This can be an uncomfortable process, but you must know where your beliefs come from to be self-aware.

Element #2: Communicating Effectively

Another fundamental element of working with complex people is refining your communication skills. Leak describes two main pieces of this: learning to tailor your communication style based on who you’re communicating with, and learning to manage conflict effectively.

Strategy #1: Tailor Your Communication Style

Leak argues that when you’re communicating with complex people at work, you must pay attention to the other person’s position in the organizational hierarchy relative to yours. The way you communicate should change depending on whether you’re talking to someone at your same level, above you, or below you.

When communicating with people at your same level—especially the complex ones—respect their autonomy. You’re not in charge of them, so don’t try to control them. When you disagree, instead of telling them why they’re wrong, ask questions that help them think about the problem differently.

(Shortform note: What Leak is describing is leading with curiosity instead of judgment when you disagree. According to some experts, the difference is that curiosity is about exploring something (such as an idea), while judgment is about evaluating something. They’re not opposites, but rather tools to be used together—leading with curiosity instead of jumping to conclusions allows you to make a more accurate and fair judgment.)

Additionally, when communicating with complex people at your same level, educate yourself about their day-to-day work, including what people in other departments are working on and the challenges they may encounter. Knowing what their work world is like helps you find points of connection, identify common goals, and show that you value their perspectives and contributions.

(Shortform note: Knowing what’s going on with other departments may also help you improve your own team’s processes. Being able to see how other departments function and get their work done can help you identify points of weakness in your workflows and figure out better ways to do things.)

When communicating with complex supervisors and executives, Leak says to frame your messaging around their goals and priorities. They’re approaching problems from a high-level, strategic perspective, so you should keep that in mind. Finally, keep your communication succinct and clear to avoid wasting management’s limited time.

For example, say you're a nurse who wants to implement a new patient check-in process. To a colleague, you might complain that the intake forms are redundant and take forever to fill out. But when bringing this issue to the hospital administrator, you’d be better off explaining how streamlining the intake process could reduce average patient wait times and improve patient satisfaction scores.

(Shortform note: If you have to have a difficult conversation with a supervisor (whether they’re complex or not), it can help to role-play with someone you trust to practice what you want to say. Start by explaining the facts of the situation as neutrally as possible to the person helping you, giving them an overview of both sides. Then, have them pretend to be you while you role-play as your supervisor. Respond how you think your supervisor would respond, thinking through how they’d act and what they’d say. After that, have the other person act as your supervisor, and go through the conversation again. Practicing on both sides will prepare you for the most likely scenarios during the real conversation and help you tailor your message.)

If you’re communicating with people below you in the hierarchy, Leak advises repeating yourself a lot to ensure your message gets across. Figure out how to say things differently to different people in terms that they’ll understand, and get their buy-in by showing them why your message matters to them. Additionally, to encourage motivation and trust, be simple and direct, and keep your messaging hopeful. This helps when training people, outlining processes, or establishing expectations, but be especially clear and encouraging when discussing difficult topics, such as staff cuts or company changes. These conversations evoke complex feelings in employees, which can lead them to behave in complex or difficult ways, so good communication is essential.

More Advice on How to Communicate Effectively With Employees

Other business experts warn that too much repetition in a leader’s messaging can be a bad thing—after a while, your employees may start to ignore the repetitive communication because they’ve heard it too many times already. Thus, they argue that repetition should be used as a tool in certain cases, not a default.

To help keep your communication with employees clear, tailored, and concise, these experts also say to identify your goals for the communication before you begin. Deciding what you want to say beforehand can help to ensure you’re able to answer questions that come up, get the right message across, and avoid going on tangents.

Finally, pay attention to your employees’ nonverbal cues, especially when discussing difficult topics. Employees might be uncomfortable verbally disagreeing with something you’ve said, so it’s important to recognize body language that suggests discomfort, disagreement, disengagement, and so on. For example, if someone has their body angled away from you and their lips are pursed, this could indicate they disagree with you. These kinds of cues can show you when you need to adjust your messaging.

Strategy #2: Practice Good Conflict Management

According to Leak, conflict is an inevitable and necessary part of workplace interactions. This is especially true when working with complex people. Therefore, it’s important to learn techniques for managing it well—when you do, it can be a source of momentum and innovation. (Shortform note: Conflict can also be a useful indicator that something could be improved. For example, conflict between team members about project responsibilities could indicate that you or your manager needs to clarify roles and expectations.)

In this section, we’ll share five of Leak’s principles for healthy conflict.

Principle #1: Get the conflict out in the open as quickly as possible. When you let points of disagreement sit and develop for too long, you risk nurturing resentment that builds up over time. Additionally, once they’re introduced, try to resolve conflicts swiftly.

(Shortform note: In Powerful Phrases for Dealing with Difficult People, Renee Evenson says that once a conflict has surfaced, you should pause before addressing it. Conflicts of any kind are often emotionally charged, so it's natural to feel hurt, angry, or defensive if you believe someone has wronged you. However, if you confront the other person while your feelings are strong, you’re likely to escalate the situation, triggering intense emotional reactions. Thus, the two of you will be less likely to cooperate and look for a mutually satisfying resolution. Instead, when you first realize that conflict resolution is necessary, take time to calm down, analyze the situation rationally, and make a plan before talking to the other person.)

Principle #2: Don't manipulate, pressure, bully, or coerce to get your way—Leak explains that these intimidation tactics stifle collaboration. Instead of focusing on which person is correct, focus on finding the best solution.

(Shortform note: Manipulation and bullying also undermine psychological safety at work, making a team less effective overall. Research shows that psychological safety is correlated with team functioning because a perception of greater safety means people are more willing to share their opinions, share information, and take ownership over group decisions.)

Principle #3: To maintain as much objectivity as possible, base your arguments on factual information. This should include all of the relevant information, not just facts that support your position. Additionally, if someone brings up a relevant point you didn’t think of, acknowledge its merit. When you focus on facts and recognize when others have good ideas, over time, your coworkers will come to trust your integrity. Your opinion will have more value, since you’ve made it clear that doing the best job and being honest is more important to you than being “right.”

(Shortform note: Consciously focusing on all of the facts (not just those that benefit you) helps to avoid confirmation bias, which is the tendency to interpret, gather, and remember information that supports what you already believe. When we fall prey to this cognitive bias, we ignore anything that doesn’t support our existing beliefs, leading us to lose sight of the full picture and draw potentially false conclusions. The commitment to the truth that Leak discusses is called intellectual honesty. When you’re intellectually honest, you evaluate the reasoning and evidence for every viewpoint fairly, are willing to acknowledge your limitations and mistakes, and are willing to hear out all sides of the argument.)

Principle #4: Keep conflicts focused on work-related issues. Conflicts that involve differing approaches for processes, projects, and shared goals can help teams make progress together. Conflicts that involve personal frustration or tension between individuals, or that stem from differing values—such as those involving politics or religion—should be limited in the workplace, since they usually draw focus away from the work and can escalate.

How to Deal With Personal and Values-Based Conflicts

Though it may be best to avoid them, personality clashes are common in workplaces, stemming from communication issues, competitiveness, and misaligned assumptions about roles and decisions. If you have to deal with personal conflicts at work, experts advise speaking directly to the other person and not talking about it with people who aren’t involved. Try to use neutral language that leaves room for the other person to express their perspective. If you can’t reach a resolution yourselves, an objective, third-party mediator could be necessary.

Values-based conflicts are also sometimes inevitable, and they’re challenging because they involve the beliefs that are most central to our identities. Typically, they’re centered on foundational differences in ideologies about what’s right, wrong, and important. This makes it difficult to compromise—however, it’s possible to navigate these conflicts. Experts suggest first determining how rigid the values involved in the conflict are. Are these beliefs that are truly inflexible, or is there a compromise that captures the essence of what both sides care about? Likewise, consider whether the other side of the values spectrum has any positive traits. This can set the stage for better collaboration.

Element #3: Knowing When to Give Up

Though the ideal is to cultivate a collaborative relationship with complex and challenging coworkers, Leak notes that you might encounter some people who are truly impossible to work with. These people may frequently engage in harmful and inappropriate workplace behaviors, neglect their job responsibilities, or be unwilling to listen to the feedback and opinions of others. They won’t respond to your attempts to find solutions and common ground, and they refuse to change. In such cases, your focus should shift from collaborating to protecting yourself.

Workplace Bullying on the Rise

Workplace bullying has risen 68% since 2017, harming millions of American workers’ health and careers. It occurs when someone repeatedly mistreats a coworker (as Leak discusses), causing them emotional or physical harm. This harassment can come from supervisors, subordinates, or coworkers, and often operates within established workplace rules and policies, making it difficult to address.

Over 32% of employees said they were bullied at their job in 2024, while close to half of American workers—75 million people—experienced or witnessed workplace harassment. Employers can address workplace bullying by creating an environment where employees can share concerns and report problems without fear of embarrassment or punishment, developing clear anti-bullying policies, and implementing training and awareness programs.

Strategy: Set Boundaries

According to Leak, when complex coworkers refuse to compromise or improve their harmful behavior, you must set boundaries. Boundaries are rules you set for yourself that let others know what you are and aren’t comfortable with. In the workplace, these may center on your availability and time, workload, communication, interpersonal interactions, and so on. They can help you establish transparent expectations and protect your mental and physical health.

One important thing to understand is that boundaries are meant to help you change your behavior, not someone else’s. They won’t make the other person improve or smooth out all of your interactions. In the short term, setting boundaries may even make challenging people angry as they lose the hold they had over you and the benefits they gained from it.

For example, if you set a boundary that you won’t meet with anyone during your lunch break, the difficult coworker who pesters you for help and information during lunch every day won’t automatically stop. It’s your responsibility to maintain the boundary by taking actions such as not answering emails and meeting invites during your break, eating outside, or verbally reinforcing the rule.

Leak also emphasizes that boundaries can’t be followed until they’re explicitly communicated. For instance, if you never told your coworker that you want to keep your lunch break free from work tasks, it’s not fair to get annoyed with them when they ask you questions during that time.

Once a boundary is stated, you must also be consistent in upholding it. People respond more to actions than words, so if you say you’re not OK with something but continue to act as if you are, they’ll follow your behavior. Finally, it’s common for people to test boundaries over time, so they require reinforcement. Be careful about making exceptions, as each time you do, the boundary becomes less clear.

Different Types of Boundaries and Why People React Negatively to Them

In Set Boundaries, Find Peace, therapist and author Nedra Glover Tawwab writes that when you set boundaries, you ensure that the people in your life know how you’d like to be treated, which can make things more comfortable both for them and for you. On the other hand, if you don’t set boundaries, you’ll likely experience resentment, anxiety, and exhaustion in your relationships. Without boundaries, your friends, coworkers, and loved ones will fail to live up to your standards, as they won’t know what those standards are in the first place (as Leak suggests).

Tawwab outlines the difference between healthy and unhealthy boundaries. She argues that healthy boundaries allow you to feel safe and comfortable in your relationships. Unhealthy boundaries could be those that are too weak or too strict. Weak boundaries are too flexible to protect your needs. They make it hard to say no, even when you’re already feeling overwhelmed. Signs you may have weak boundaries include a desire to make everyone happy, fear of rejection, and needing approval from others. And as Leak describes, it’s also unhealthy to make too many exceptions to boundaries you’ve set—this weakens those boundaries.

Strict boundaries lead you to push people away to try to keep yourself safe. If you have strict boundaries, you might refuse to forgive people for minor offenses and instead opt to cut them out completely. While this might keep those people from hurting you, setting such strict boundaries may lead you to lose connections and experience loneliness.

Other experts point out that setting boundaries is a way to differentiate yourself from someone, which can feel unfamiliar and threatening to them. Therefore, people may get angry with you for setting boundaries because they have poor boundaries themselves and feel that you should be the same. For example, a colleague who changes their schedule all the time to accommodate other people’s requests may get frustrated with you when you won’t move your agreed-upon meeting time. They may think you should make the same sacrifices they do.