Oil and Water: Leading Difficult Personalities

Leadership often involves orchestrating a complex landscape of individuals (who themselves are complex) to achieve bigger things together. Coming fresh off a senior leadership offsite where the goal was alignment across 20 or so leaders, I cannot help but think of how deceptively simple that previous statement is and how the difficulty level jumps up when dealing with certain individuals.

Inspired by Amy Gallo’s insightful categorizations in “Getting Along: How to Work with Anyone (Even Difficult People),” let’s talk about strategies we can use to enhance collaboration among….ahem… diverse personalities.

Understanding Challenging Personalities

In any organization, you’re bound to encounter a variety of challenging personalities that can disrupt team dynamics and productivity. Understanding these personality types and recognizing their behaviors is the first step in managing them effectively.

I’ve combined Amy Gallo’s categories with other archetypes my team and I have encountered most frequently —those that we’ve found to have the most significant impact on culture and performance:

The Danger of Labels

It’s important to recognize that many of these challenging behaviors often stem from a place of insecurity, whether that insecurity is rooted in the realities of your organization or not. These behaviors are typically learned as survival mechanisms—strategies that have historically protected this person and/or yielded results in difficult situations. While it might be easy to label these people as “difficult,” understanding their ‘why’ helps you develop more effective strategies for working with these teammates.

Strategies & Tips for Fostering Collaboration

Navigating challenging personalities in the workplace is tough, but it’s also an essential part of effective leadership. While you can’t change everyone, you can certainly change the dynamics of your team by adopting strategies that promote healthy collaboration, clear communication, and mutual respect. Here are some ideas to consider:

  1. Align Messaging with Rewards
  2. Your reward system should reinforce the behaviors you want to see. If you value teamwork but only reward individual achievements, you might unintentionally encourage “The Political Operative” or “The Hoarder.” Make sure your incentives align with the behaviors that foster a positive culture.

  3. Consult Your Mirror
  4. Before addressing others, reflect on your own behaviors. If you expect accountability, make sure you’re not falling into the trap of “rules for thee, but not for me.” This is particularly relevant when dealing with behaviors like “The Tormentor Saboteur” or “The Passive-Aggressive Teammate.”

  5. Understand the Underlying Drivers
  6. Many challenging behaviors, such as those exhibited by “The Perpetual Victim” or “The Pessimist,” stem from insecurities or perceived threats. Understanding what’s driving these behaviors can help you address the root cause with empathy, leading to more constructive interactions.

  7. Leverage Strengths… Strategically
  8. Focus on the potential strengths within challenging behaviors. For example, The Pessimist may be valuable in pressure testing big changes (especially if they have a critical role) and can serve as a bell weather for potential reception (especially if they have been with the organization for a long time and are well connected). To minimize negative impact on morale, contain their comments and channel their input into constructive discussions with a smaller subset of the team. This allows them to feel heard and for you to capture ideas on how to make the initiative better and to create plans to pre-empt resistance.

  9. Set Clear Expectations
  10. Ambiguity breeds dysfunction, especially with behaviors like “The Hoarder” or “The Political Operative.” Ensure everyone knows what’s expected of them to maintain a cohesive work environment and minimize the impact of these behaviors.

  11. Shrink the Change
  12. Behavioral change is tough, particularly with ingrained behaviors like “The Know-It-All Bulldozer.” Break down the desired change into smaller steps, like asking team members to set aside unhelpful behaviors for the duration of a meeting, to gradually foster more constructive interactions.

  13. Prioritize Real Talk
  14. Develop rituals that encourage direct, honest conversations to address behaviors like “The Passive-Aggressive Teammate” or “The Political Operative.” A real talk ritual might be putting a symbolic elephant on the table at certain parts of a meeting and asking the team to name what is not being said but is being thought. Over time, this practice can become part of your team’s culture, making it easier to resolve conflicts and improve collaboration.

  15. If You Can’t Change Them, Change Them
  16. When behaviors like those of “The Tormentor Saboteur” persist despite your best efforts, it may be time to consider whether that individual is the right fit for the team. Weigh the impact of their behavior on the team against the potential disruption of their departure.

Managing difficult behaviors is part of the leadership journey, but with the right approach, even the most challenging dynamics can be transformed into strengths. By setting clear expectations, practicing empathy, and fostering open communication, you can create a more harmonious and productive team. So, the next time you encounter a tricky personality, how will you approach the situation? Have you faced these challenges before, and what strategies have worked for you?

Are you ready to tackle tough personalities?

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