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We will all encounter a myriad of personalities throughout our work lives, and some will inevitably challenge us more than others.


Every organization is composed of a range of different personalities. The workplace would be a very boring place if we were all the same! With such variety, there is bound to be some individuals whose working relationships require a little extra effort. When those people are reporting to you—under your management, looking to you for guidance, responsible for your project outcomes—those relationships become more important and the impact of your ability to effectively manage them increases exponentially. Here are six skills to build as a leader that will help guide your more challenging team members toward success.

1. Approach with an Encouraging Mindset.

Managing a challenging individual can become frustrating and easily dampen your morale and the morale of your team. It can be tempting to fall into despair and think the situation is hopeless. Approaching the situation with an encouraging spirit and cultivating the mindset that each of us can personally grow and develop will help remind everyone that problems are solvable, and the situation can be improved. Rewarding and applauding the wins, no matter how small, can inspire a forward momentum and uplift even the most difficult personalities.

2. Search and Stand up for the Truth.

Don’t shy away from the truth. Being the leader who is willing to bring up hard facts and work through issues with integrity and kindness will maintain a culture of transparency and honesty in your teams. It creates a sense of accountability, which may encourage more challenging individuals to own their mistakes and be a part of solutions rather than creating hurdles. It is also important to recognize the truth of how our own personalities as leaders might be contributing to the challenge!

3. Focus on the Common Goal.

Bringing attention to your shared goals encourages people to keep their heads in the game. Some people get sidetracked by personal agendas and ideas. When things are a bit chaotic, heated, or emotional, directing people back to the reason you’re all there can take pressure off the situation and bring clarity to move forward.

4. Demonstrate Calm Patience.

Staying levelheaded during difficult conversations or when things become too animated can help restore productive thinking. Being calm creates a safe space for people to think clearly and resolve conflicts, avoiding the unnecessary eruptions that occur in a more volatile environment. Individuals with a more turbulent personality will find stability in your example.

5. Find the Silver Lining.

Being willing to see the positive attributes of all different types of personalities can make you a binding force in your organization. Utilizing the best of what people have to offer makes for a more effective, productive team. People who feel valued are more willing to work together with others. While superfluous positivity can be toxic, recognizing your team members’ assets makes it possible to move past current obstacles to the opportunities on the other side.

6. Keep Your Mind Open.

When working with and leading challenging people, it helps to think outside the box and innovate new ways to interact. Not every person can be managed in the same way—different people need different communication styles and different solutions. Allowing for creative thinking and being open to try new methods can alleviate the difficulties that arise with more rigid or taxing personalities.

We will all encounter a myriad of personalities throughout our work lives, and some will inevitably challenge us more than others. There is no one-size-fits-all approach to working with and leading individuals who may try our patience but developing these skills can increase the probability we will find an effective way forward in our relationships with them. 


Want to learn more about how to work with, influence, establish relationships and learn from the different personality types you interact with daily? Register for an upcoming Achievers II program, our trainers will help you build these skills so you can successfully work with and manage challenging personalities.