How to Work with Complicated People

1. Recognize Your Own Complications First

We are all somebody’s idiot.

Universal complexity. The initial step to effectively working with complicated people is a humbling self-realization: you are complicated too. It's easy to fixate on others' quirks, believing our workplaces would improve if only they changed. However, a national research study revealed that 74% of people believe they are less complicated than the average person, a statistical impossibility that highlights our collective blind spot.

Self-awareness is key. This inherent self-deception means we often overlook our own idiosyncrasies, mood swings, or communication styles that might be baffling to others. Embracing your own "complicatedness" – whether it's a phobia of dogs, an obsession with cleanliness, or a tendency to be hard to read – fosters humility and honesty. This self-reflection is crucial because it allows you to approach others with greater empathy and less judgment.

Shift perspective. Instead of an inner narrative that blames "them," consider: "Maybe I am the problem. Maybe I need to change. Maybe I am hard to work with." This shift doesn't mean taking blame for others' issues, but rather acknowledging your role in interpersonal dynamics. It's about recognizing that understanding others begins with understanding yourself, paving the way for genuine collaboration rather than insisting others conform to your preferences.

2. Adopt Realistic Expectations and Cultivate Curiosity

Don’t let them surprise you.

Manage expectations. Often, people are labeled "complicated" because they fail to meet our unspoken expectations. To avoid constant frustration, it's essential to go on an "expectations detox." This involves honestly evaluating what you think others should do and why your assumptions might be misaligned with reality. Stop expecting people to change if they aren't actively trying to, and instead, adjust your own outlook.

Embrace imperfection. Like Baron, the pharma executive who learned to embrace the "beautiful chaos of human imperfection," you can choose to expect messiness and surprises. This doesn't mean lowering standards, but rather building room into your plans for human delays and mistakes. When you anticipate that interactions might be awkward or challenging, you prepare yourself emotionally and mentally, reducing the likelihood of being caught off guard or offended.

Override triggers. Your brain's primary goal is safety, often leading it to catastrophize or label anything different as dangerous. Recognize triggers like discomfort, uncertainty, and a lack of control. Instead of letting these instincts drive a fight-flight-freeze response, consciously push back with curiosity. This allows you to see differences as potential gifts rather than threats, opening the door to new perspectives and connections.

3. Embrace a Holistic Collaboration Mindset

What could we create together?

Beyond individual effort. True collaboration transcends individual struggles, viewing work as a "collab" where unique strengths merge to create something greater. This mindset shifts focus from individual shortcomings to collective potential. Research shows that effective collaboration leads to significant improvements in job satisfaction, productivity, morale, communication, and innovation.

Four pillars of collaboration: A healthy collaboration mindset is built on four key elements:

• Self-awareness: "What is it like to be on the other side of me?" Understanding your impact on others.
• Ownership: "What is my part to play?" Taking responsibility for your reactions and contributions.
• Curiosity: "What is it like to be you?" Seeking to understand others' perspectives and motivations.
• Connection: "What brings us together?" Identifying shared goals and common ground.

Synergy over superheroes. A team's collective intelligence isn't solely dependent on individual smarts, but on its ability to connect. Factors like social sensitivity, equal conversational turn-taking, and diversity (e.g., more women) significantly boost team "smartness." By focusing on these elements, you foster an environment where people function like an interconnected brain, turning a roomful of individuals into an unstoppable force.

4. Master the Five People Qs for Deeper Connection

Can you use your smarts to connect to other people?

Student of people. To work effectively with infinitely complex individuals, you must become a "student of people." This involves developing five "People Qs" – quotients or skills – that build bridges of understanding and connection, moving relationships from difficult to dynamic. These are not just competencies but active efforts to engage with others.

The five People Qs:

• IQ Connection (Intelligence & Knowledge): Use your intellect to understand others' worlds and "speak their language." This means actively learning about their industry, role, or even personal interests to bridge knowledge gaps and build credibility.
• EQ Connection (Emotions & Feelings): Develop emotional intelligence to identify and manage your own and others' emotions. Emotions are powerful connection points; listening without judgment can defuse tension and build trust.
• AQ Connection (Adaptability & Change): Cultivate an adaptability quotient, the ability to adjust to change in real-time. This means being flexible, pivoting quickly, and embracing experimentation, rather than resisting new approaches or people.
• TQ Connection (Technology & Innovation): Leverage technology to communicate better and connect more effectively. Understand different tech proficiencies (from tech-challenged to tech-savvy) and use digital tools to foster human connection, not just efficiency.
• DQ Connection (Decency & Kindness): Embody a decency quotient, showing genuine care, empathy, and integrity. This means treating others with respect and kindness, even when they are difficult, ensuring your IQ and EQ are used for good, not harm.

Holistic development. These People Qs are interconnected and crucial for navigating the nuances of human interaction. By consciously developing these skills, you become more valuable, effective, and secure in any workplace, transforming complicated interactions into opportunities for growth and stronger relationships.

5. Bridge Generational Gaps with Empathy and Innovation

The differences within a generation can be far larger than the differences between them.

Beyond stereotypes. Generational differences are often oversimplified and based on stereotypes, leading to unnecessary conflict. It's crucial to remember that "generations" are constructs, and individual differences within a generation can be greater than those between them. Many perceived "generational" traits are actually tied to different "seasons of life" (e.g., parenting young children vs. nearing retirement), which affect how people show up at work.

Cultivate respect. To work effectively across age groups, challenge your own age-related prejudices. Whether someone is younger or older, avoid dismissive labels like "entitled" or "out of touch." Instead, actively seek to understand their unique experiences and perspectives. CEOs who seek advice from younger employees exemplify this humility, demonstrating that wisdom and valuable insights can come from any age.

Intentional collaboration and innovation. Don't settle for mere tolerance; actively build cross-generational teams. Everyone brings something valuable: veterans offer hard-earned knowledge, while younger generations bring fresh perspectives and technological fluency. When in doubt, err on the side of innovation, making room for new ideas and approaches. This ensures your company remains sustainable and relevant, serving evolving customer needs and fostering a dynamic, diverse workplace where core human needs are met across all ages.

6. Communicate Strategically Across All Organizational Levels and Mediums

The great enemy of communication, we find, is the illusion of it.

Mind the gap. Communication is inherently imperfect, especially with complicated individuals. A significant gap often exists between what we intend to say and what others hear. This is evident in workplace surveys, where only 7% strongly agree that communication is accurate, timely, and open. To bridge this gap, consider two critical factors: the direction of communication and the medium used.

Directional communication:

• Speaking Up (to leaders): Learn to "speak C-suite" by framing information in terms of their strategic goals (ROI, KPIs). Stay ready by understanding what they celebrate, champion, and complain about (the "3 Cs"). Value their time with succinct, prepared messages.
• Speaking Across (to peers): Start with respect for their autonomy and expertise. Ask really good, open-ended questions to foster connection and problem-solving, as research shows high question-askers are better liked. Identify intersecting interests to build rapport.
• Speaking Down (as a leader): Embrace your role as "Chief Repeating Officer" (CRO), reiterating messages in diverse ways. Keep it real, simple, interesting (with stories), and hopeful, especially when delivering challenging news.

Medium mastery:

• Video Calls: Master virtual etiquette (appropriate attire, active listening, platform knowledge, engaging presentation) to maintain presence and connection. Overcommunicate to ensure clarity.
• Written Communication (Emails): Prioritize brevity, a positive tone (avoid passive aggression), a touch of personality, and absolute clarity (using bullet points). Aim to be "unmistakable," not just "understood."
• In-Person Interactions: Rebuild "soft skills" like small talk to build trust equity. Learn to read and utilize body language (60-70% of communication) and practice good conversational manners (eye contact, no interrupting, using names).

Intentionality is key. Effective communication with complicated people requires intentionality, adapting your style to the audience and context. By mastering these strategies, you can transform potential misunderstandings into opportunities for clearer, more productive interactions.

7. Transform Customer Service with Kindness and Creativity

The customer is not always right—but you can still treat them right.

Rethink the mantra. While the adage "the customer is always right" has historical roots in building loyalty, today's customers can be demanding and complicated. However, your business depends on them, making effective outward-facing communication crucial. Instead of blindly accommodating every whim, rethink customer service as an opportunity to connect on both practical and emotional levels, even with the most challenging individuals.

Proactive kindness. When confronted with a bad-tempered or ill-mannered customer, go on the offensive with kindness. The bar for customer service is often low, so genuine human decency can de-escalate situations and build long-term loyalty. The food truck cashier's unwavering smile, for instance, transformed a frustrating wait into a positive experience, demonstrating the power of choosing your response regardless of external negativity.

Creative solutions. Don't get mad; get creative. Often, complicated customers are seeking solutions to genuine needs, frustrations, or concerns, even if their demands are unrealistic. Listen deeply to understand the underlying emotional component, as the fitness club manager did with the irate member. While you may not always be able to provide the exact solution they demand, you can often offer alternative solutions or, at minimum, provide empathy and a listening ear. This approach transforms conflict into an opportunity for innovation and strengthens customer relationships.

8. Embrace Healthy Disagreement for Growth and Progress

When two men always agree, one of them is unnecessary.

Conflict as a catalyst. Disagreements are an inevitable part of working with people and, when handled correctly, are not inherently bad. They are a tool for progress, not a problem to avoid. The downfall of companies like BlackBerry, plagued by "groupthink," illustrates the danger of stifling dissenting voices. Healthy conflict, like that encouraged by William Wrigley Jr., forces deeper thinking and leads to more robust solutions.

Five principles for healthy disagreement:

• Fight Fair: Focus on finding the best solution, not on being "right." Avoid dirty tactics like bullying, manipulation, or character assassination.
• Fight Fast: Address conflicts quickly to prevent resentment from festering. Don't let disagreements brew for months; speak up and work it out efficiently.
• Fight Factually: Stick to objective data and diverse perspectives. Listen to veterans (experience), nerds (technical knowledge), and newbies (fresh eyes) to gain the broadest understanding.
• Fight Focused: Concentrate on task conflict (projects, processes, goals) rather than relational or value conflicts, which are often less productive.
• Fight Forward: Use disagreements to propel you toward new solutions. Don't fall for false dichotomies; seek third options that incorporate everyone's needs and spark creativity.

Value the "Richard." Just because someone asks hard questions or holds unpopular opinions doesn't make them complicated; it makes them valuable. Leaders like Mark, who intentionally invited a "Richard" (an empathetic, feelings-oriented person) to meetings, found that this balance led to better outcomes. Embrace those who challenge your assumptions, as their unique perspective is often the gift hidden within the discomfort of disagreement.

9. Set Effective Boundaries for Personal Well-being and Productivity

Boundaries are lines you draw that define what you will and will not allow in the workplace.

The "nearly" person. Not everyone is capable of effective collaboration. For these "nearly" impossible individuals—the incessantly negative, the manipulative, the unchangeable—boundaries become crucial. Boundaries are not about controlling others or magically fixing their issues; they are about controlling what you can control: your responses, what you allow, and how you feel.

Boundaries' true purpose:

• Keep you safe: They minimize threats to your job performance, emotional, mental, or physical health. This might mean refusing inappropriate physical touch or reporting harassment.
• Make you more productive: Healthy boundaries foster a better work-life balance, reduce emotional drain, allow focus on your core tasks, and shift you from defense to creative mode.
• Keep you connected: Boundaries are delineative, like a picket fence, not defensive like a castle wall. They define the conditions for ongoing interaction, allowing you to collaborate with minimal damage and maximum effectiveness, even if it's a formal truce rather than a deep alliance.

Practical boundary setting:

• Start small: Implement quick wins like using headphones, turning off notifications, or setting out-of-office replies.
• Practice saying no: Decline requests graciously but firmly, focusing on what you can do rather than what they should do.
• Communicate clearly: A boundary isn't real until it's communicated. Be explicit about your limits and avoid "boundary creep" where exceptions erode your rules.
• Keep it classy: Maintain professionalism and courtesy, even when others are toxic. Use documentation to support your boundaries objectively, especially for HR discussions.

Your autonomy. Setting boundaries is an art that requires practice and patience. It's a continuous process of adapting to a changing world and new complicated people. Ultimately, boundaries restore your autonomy and hope, ensuring you don't sell your soul to a toxic work environment but instead work safely and effectively.

10. Choose Forgiveness to Liberate Your Future

Forgiveness is letting go of the anchor.

Release the burden. The workplace inevitably brings offenses, betrayals, and frustrations, leading to anger and bitterness in a significant portion of the workforce. Holding onto these grudges is like "scuba diving with an anchor," draining energy and limiting your ability to move forward. Forgiveness is not about condoning the wrong done to you, but about liberating yourself from the emotional weight, allowing you to find peace and healing.

Intentional choices for freedom:

• Choose your identity: Decide what kind of colleague you want to be. Opting for forgiveness, rather than bitterness, leads to higher job satisfaction, engagement, and lower burnout rates. This is a conscious decision that shapes your future self.
• Let go of small stuff: Many grievances are petty. Acknowledge them, but choose to release them quickly. This frees up mental and emotional energy for more important things and makes you more resilient to daily office drama.
• Give bitterness an expiration date: Acknowledge your hurt, but don't let it become a permanent state. Set a timeline for processing pain, then actively work towards moving on. This prevents past offenses from haunting your present and future.
• Practice pre-forgiveness: Make a life decision to forgive people before they hurt you. This proactive choice prepares you to respond with grace and understanding when inevitable offenses occur, preventing immediate reactions from escalating into long-term resentment.
• Move forward: Forgiveness is not forgetting, but choosing to shift your focus and energy away from what others did to you, towards what you can do now. This builds resilience, enabling you to adapt and bounce back from harm, even if the pain lingers.

Your power. While you can't control others' actions, you always control your reaction. Choosing forgiveness is choosing yourself, reclaiming your joy and peace from the grip of past hurts. It's a powerful act of self-preservation that allows you to live fully and freely, regardless of the complicated people around you.

Last updated: December 2, 2025