Dealing with Difficult People: How to Convert Workplace Challenges into Cultural Strengths
Let's face reality: difficult people exist in every workplace. In fact, a recent Psychology Today study found that 75% of young adults and 67% of older adults report having difficult people in their networks. If you're nodding in agreement right now, you're in good company.
But here's a perspective that might surprise you: difficult people aren't necessarily bad for your team. In fact, when handled effectively, they might be exactly what your organization needs to develop resilience, adaptability, and growth.
The traditional approach to difficult people often centers on minimizing their impact or removing them from the equation. However, as discussed in The Culture Base Podcast, there's a more nuanced and ultimately more productive approach—one that converts workplace challenges into cultural strengths.
In this article, we'll explore the crucial difference between creating a cult (where no differences are tolerated) and building a culture (where differences are effectively managed). You'll discover practical filters for identifying the real issues behind difficult interactions, strategies for setting and respecting boundaries, and techniques for turning potential conflicts into opportunities for growth.
Whether you're dealing with a challenging team member, navigating personality clashes, or simply looking to improve your conflict management skills, these insights will help you create a workplace where differences strengthen rather than weaken your organization.
Cult vs. Culture: Why Difficult People Might Actually Benefit Your Team
Many leaders strive for workplace harmony, viewing conflict and difficult personalities as problems to eliminate. But this approach often leads to what might be called "cult thinking"—an environment where conformity takes precedence over genuine growth and innovation.
“When you’re trying to get rid of the problems or the issues, that’s a cult. Culture is dealing with the right people and having those issues, it’s stepping into the hard times and dealing with those things in a way that everyone gets better and everyone grows and everyone transforms.”
The Difference Between Creating Harmony and Creating Growth
There's an important distinction between artificial harmony and productive tension. Artificial harmony occurs when people avoid expressing differing opinions or challenging perspectives out of fear. This creates the appearance of cohesion while actually undermining the team's potential.
Productive tension, by contrast, emerges when different viewpoints are encouraged, respected, and effectively managed. This tension isn't always comfortable, but it leads to:
More robust decision-making as ideas are thoroughly vetted
Greater innovation as diverse perspectives generate unique solutions
Stronger team resilience as conflict resolution skills develop
Deeper trust as team members learn to navigate disagreements positively
Organizations that prioritize artificial harmony often stagnate, while those that effectively manage tension continue to evolve and improve.
The Michael Jordan Example: How the Bulls Managed Dennis Rodman
The Chicago Bulls dynasty of the 1990s provides a perfect case study in managing difficult personalities. Dennis Rodman was notoriously challenging—unpredictable, eccentric, and sometimes disruptive. Many teams would have considered him too difficult to manage.
However, Phil Jackson and the Bulls organization recognized that Rodman's unique strengths (elite rebounding, defensive versatility, relentless energy) outweighed the challenges he presented. They didn't try to make Rodman conform to conventional standards. Instead, they:
Set clear boundaries around what truly mattered (game preparation, on-court performance)
Adapted their management approach to accommodate his personality
Leveraged team leaders like Michael Jordan to help integrate Rodman
Focused on his contributions rather than his nonconformity
This approach helped create one of the greatest teams in NBA history. The Bulls didn't succeed despite Rodman's difficult personality—in many ways, they succeeded because they effectively channeled the strengths that came with that personality.
When Diversity of Personality Strengthens Your Organization
High-performing organizations recognize that homogeneous teams—where everyone thinks and behaves similarly—rarely achieve exceptional results. Diverse teams that include various personality types bring different strengths to the table:
Detail-oriented personalities who ensure nothing falls through the cracks
Visionary thinkers who challenge conventional approaches
Relationship-focused team members who strengthen connections
Direct communicators who prevent waste and inefficiency
Analytical minds who identify potential pitfalls
Creative spirits who generate innovative solutions
What might initially seem "difficult" about these personalities often contains the seeds of their greatest contributions. The key isn't eliminating differences but creating a culture where diverse approaches and perspectives can be effectively integrated.
Key Filters for Identifying the Real Issue
Before addressing a difficult person, it's essential to ensure you're addressing the right problem. These filters help you identify what's actually happening beneath the surface.
Is It a Difficult Person or a Difficult Situation?
Many "difficult person" problems are actually situational challenges in disguise. Before labeling someone as difficult, consider:
Is this a pattern of behavior or an isolated incident?
Has this person demonstrated difficult behavior across multiple contexts, or only in specific situations?
Are external pressures (deadlines, resource constraints, personal issues) contributing to the behavior?
Would most people react similarly under the same circumstances?
One financial services team was ready to let go of a "difficult" team member until they realized the real issue was an unrealistic workload that would have made anyone irritable and uncooperative. By addressing the situation rather than the person, they retained a valuable employee and improved overall team functioning.
Are You Approaching with Empathy or Anger?
If you are angry with this person, try some different emotional tactics to get yourself into a place where you're more empathetic than you are angry with them. Because here's what's going to happen, as Dustin notes: “If you try to deal with a difficult person that you're angry with and you have more anger than empathy towards them, the only resolution for you is for you."
“If you try to deal with a difficult person that you’re angry with and you have more anger than empathy towards them, the only resolution for you is for you.”
Your emotional state dramatically affects your ability to resolve conflicts. When approaching a difficult situation with anger:
You'll likely focus on winning rather than resolving
Your perception becomes distorted by negativity
The other person will likely respond defensively
Solutions become about relief rather than growth
Conversely, approaching with empathy allows you to:
Understand the other person's perspective
Identify underlying needs or concerns
Create solutions that address root causes
Build relationship strength through the conflict
One effective technique mentioned in the podcast is "four square breathing" (inhale for four counts, hold for four, exhale for four, hold for four) before difficult conversations. This simple practice helps regulate emotions and creates space for empathy.
Do You Have a Role in the Conflict?
Self-awareness is crucial when dealing with difficult people. Ask yourself:
Have your actions contributed to the situation?
Are you responding to the current situation or bringing baggage from past interactions?
Do you have blind spots about your communication style or expectations?
Are you making assumptions about the other person's intentions?
One manufacturing leader was consistently frustrated by a "difficult" team member until he realized his own communication style—direct and sometimes abrupt—was triggering defensive responses. By adjusting his approach, the difficult interactions virtually disappeared.
Setting and Respecting Boundaries
Both setting and respecting boundaries is important. So when dealing with hard people and dealing with something that you're just not used to, realize what puts the other person in a place that they respond in a hard way. And realize what puts you in a place that you respond in a hard way.
Boundaries provide the framework within which diverse personalities and approaches can coexist productively. Without clear boundaries, minor differences can escalate into major conflicts.
Establishing Cultural Boundaries Before Conflicts Arise
Proactive boundary-setting prevents many difficult situations from occurring at all. This includes:
Clearly defining acceptable behavior in your team culture
Establishing communication norms that respect diverse styles
Creating explicit expectations around collaboration and feedback
Developing processes for addressing disagreements
These boundaries don't constrain; they create freedom by providing clear parameters within which people can operate confidently. One technology company reduced interpersonal conflicts by implementing a "team charter" that clearly outlined behavioral expectations and conflict resolution processes.
Respecting Others' Boundaries While Enforcing Your Own
Effective boundary management works in both directions—respecting others' boundaries while clearly communicating and enforcing your own. This dual approach requires:
Being attentive to verbal and non-verbal cues about others' boundaries
Communicating your own boundaries clearly and consistently
Acknowledging when boundaries have been crossed (in either direction)
Addressing boundary violations promptly and respectfully
For example, many people respond better to constructive feedback when it’s delivered privately and directly, rather than in group settings.
How Clear Boundaries Prevent Most Difficult Situations
Many difficult workplace situations arise from unclear or inconsistent boundaries. When boundaries are clear, people know where they stand and how to interact appropriately. This clarity:
Reduces anxiety about appropriate behavior
Prevents unintentional boundary violations
Creates a framework for addressing issues when they arise
Builds trust through consistency and predictability
Understanding Personality Differences
Part of dealing with difficult people is understanding different personality types and accepting and having those different personality types on your team.
What appears as "difficult" behavior often reflects fundamental differences in personality and work style rather than intentional negativity or opposition.
Recognizing Different Personality Types
Various personality frameworks can help you understand the different ways people process information, make decisions, and interact with others. While no framework is perfect, tools like the Enneagram, DISC, or Working Genius provide valuable lenses for understanding differences.
For example, someone who appears "difficult" because they ask challenging questions might be operating from a personality type that values thoroughness and risk mitigation. Their questioning isn't obstruction—it's their way of ensuring quality and preventing problems.
Understanding these differences doesn't excuse genuinely problematic behavior, but it provides context that can transform how you interpret and respond to behavior that initially seems difficult.
The Strategic Value of Various Personalities
Different personality types bring distinct advantages to teams:
Direct communicators cut through ambiguity and prevent wasted time
Detail-oriented team members ensure quality and catch potential issues
Relationship-focused individuals build team cohesion and customer loyalty
Creative personalities generate innovative solutions and fresh approaches
Analytical types provide data-driven insights and logical frameworks
Action-oriented members drive completion and maintain momentum
The Culture Base worked with an organization that initially struggled with an "abrasive" team member. But later that team came to value his direct communication style when they realized how many hours it saved in meetings and how many potential problems his straightforward questions prevented.
Using Personality Assessments to Better Understand Your Team
Personality assessments can provide a common language for discussing differences and a framework for leveraging diverse strengths. When implemented effectively, these tools:
Create self-awareness about personal preferences and tendencies
Build understanding of different approaches and their value
Provide language for discussing differences constructively
Help team members adapt their communication to different styles
It can be a really valuable practice to have your team do personality assessments and host team workshops on leveraging different styles. What had previously been seen as "difficult" behavior might be reframed as valuable if you take the right approach.
Fixing Communication Breakdowns
"Communication is only true when you know how they understood what you said,” Blake asserts in the podcast.
At the root of most "difficult person" situations lies a fundamental breakdown in communication. Addressing these breakdowns often resolves what initially appeared to be personality conflicts.
The Root of Most "Difficult Person" Problems
Communication problems typically manifest in several ways:
Different interpretations of the same information
Misaligned expectations about outcomes or processes
Unstated assumptions that create confusion
Variations in communication style that create friction
Failure to confirm understanding before proceeding
How do you interpret priority language? Is "urgent" the same as "today?" Or is “urgent” the same as "this week?"
How important is that “important report” you’re supposed to prepare? Does it mean your shift leader will read the report? Or the manager of your store? Or the CEO of your company? Or will it be published for the customer or even the general public?
Confirming Understanding vs. Assuming It
Most people in the world will not speak up and tell you, “I'm sorry, I don't understand what you're saying.”
True communication only happens when the recipient understands your message as you intended it. Yet as Dustin points out, most people won't volunteer that they're confused or misunderstanding.
Effective communicators:
Check for understanding rather than assuming it
Ask specific questions rather than general ones ("What are your next steps?" vs. "Does that make sense?")
Encourage clarifying questions without judgment
Summarize key points and agreements to confirm alignment
Practical Communication Strategies to Prevent Conflicts
Several practical approaches can prevent communication-based conflicts:
Match the medium to the message: Complex or sensitive topics require richer communication channels (in-person or video) rather than email or text
Establish communication norms: Create shared expectations about response times, appropriate channels, and communication styles
Use the "three perspectives" technique: When explaining important concepts, present them in three different ways to accommodate different learning and processing styles
Create feedback loops: Build in opportunities to check understanding and adjust approach if needed
Document key decisions and next steps: Provide a written record of important agreements to prevent misunderstandings
Practical Steps for Leaders
Managing difficult situations requires both mindset and practical techniques. Here are specific approaches leaders can implement immediately.
Self-Regulation Techniques (Four Square Breathing)
Before addressing difficult situations, manage your own emotional state:
Four square breathing: Inhale for 4 counts, hold for 4, exhale for 4, hold for 4
Perspective shift: Ask "What might I be missing?" or "What might they be experiencing?"
Reframing: Consider whether the behavior that seems "difficult" might serve a positive purpose
Preparation pause: Take 10 minutes to prepare mentally before difficult conversations
These techniques create the emotional space needed for productive resolution rather than reactive response.
Creating the Right Environment for Resolution
The setting and approach for addressing difficult situations needs to be considered:
Choose neutral territory: Select a meeting location that doesn't create a power imbalance
Ensure privacy: Difficult conversations should never happen in public spaces
Minimize distractions: Turn off notifications and create uninterrupted time
Set a constructive tone: Begin with positive intent and shared goals
Establish time boundaries: Neither open-ended nor overly constrained discussions work well
When to Involve Others and When to Handle It Directly
Some situations are best addressed one-on-one, while others benefit from additional perspectives:
Handle directly when:
The issue is primarily between you and one other person
Confidentiality is important to preserve dignity
You have a strong relationship with the person
The situation is relatively straightforward
Involve others when:
You've tried direct resolution without success
The issue impacts multiple team members
Additional perspective would be valuable
A neutral third party could help facilitate resolution
The situation involves complex team dynamics
Perhaps you could create a simple decision tree. Help leaders know when to handle situations directly versus when to involve HR, peer mediators, or other resources.
Transforming Challenges into Strengths
Difficult situations, when handled effectively, can become catalysts for individual and organizational growth. Rather than simply resolving conflicts, forward-thinking leaders use these opportunities to strengthen culture and develop capabilities.
Every successfully navigated challenge:
Builds conflict resolution skills across the team
Creates precedents for handling future difficulties
Deepens understanding between diverse team members
Demonstrates the organization's commitment to working through issues
Reinforces cultural boundaries and expectations
One of Blake’s teams that initially struggled with conflict began celebrating "breakthrough moments" where difficult situations led to positive outcomes. This practice changed how the entire organization viewed and approached differences.
Conclusion: From Difficult to Different
The journey from viewing someone as "difficult" to seeing them as "different" represents a fundamental shift in perspective that benefits the entire organization. When leaders create cultures that effectively manage differences rather than suppress them, they unlock new levels of innovation, resilience, and performance.
Remember the key filters and strategies we've explored:
Distinguish between difficult people and difficult situations
Approach challenges with empathy rather than anger
Set and respect clear boundaries
Understand and leverage personality differences
Fix communication breakdowns through confirmation of understanding
Implement practical techniques for self-regulation and resolution
As you implement these approaches, you'll likely discover that many "difficult" people are actually valuable contributors. Those differences just need to be properly channeled to strengthen rather than weaken your team.
Schedule a free 30-minute strategy session at TheCultureBase.com to discuss how you can build a culture that effectively manages differences and fosters growth.
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