Jason Webb, Milwaukee-based Pastor and Public Speaker Reveals How to Overcome Fear of Confrontation

Employees across the board are desperate for brave leaders, leaders who give honest feedback in real-time. Fear of confrontation often makes such leaders a rarity. To be a productive leader, you must learn to address difficult conversations boldly and thoughtfully. It takes practice to attain the characteristic of bravery, just as it does to improve technical skills. Here, Jason Webb, Milwaukee-based pastor, public speaker, and leader, details three steps that can transform difficult discussions into empowering conversations.

Studies indicate that employees in the US spend approximately three hours each week dealing with conflict. Stress caused by workplace conflict costs companies millions of dollars each year.

As a business leader, it is incumbent on you to have the potentially difficult conversations that will resolve workplace conflict before it spirals out of control and costs your company more than it already has. Follow these three steps each time you are about to face a difficult conversation.


When we think of having a conversation, we often envision what needs to be said, not what needs to be heard. Next time you’re headed for what could be a problematic discussion with an employee, avoid writing a mental script of what you think you will say. Instead, approach the situation determined to let the other person say whatever they want to say.

Don’t let the silence make you anxious. A pause in a conversation is often a good thing. It means the person you are speaking with is formulating their next idea. Let them think. Don’t be in a hurry to break the silence. Even if it feels uncomfortable, wait until the employee speaks again. It is often after these seemingly awkward silences that the real issues start to surface.

Ask questions to get beyond the surface

When feeling threatened or misunderstood, employees rarely let their honest feelings surface. Fear, anger, and frustration can cloud their thoughts.

You can get below the surface by letting them speak then asking open-ended questions designed to lead them to examine their true feelings. Asking an employee about other aspects of their life, such as their home life, family, and relationships can sometimes help them realize that conflict unrelated to work may be manifesting itself in the workplace.

Always ensure you understand your company’s policies and relevant laws regarding probing an employee’s personal life.

End on a good note

Even the most difficult employees have some redeeming qualities. Always end a difficult conversation with a focus on some positive aspects of this employee and their work.

Ending on a positive note will prevent the employee from stewing in resentment and possibly acting out in a manner that will lead to a more complicated conversation.

Be honest and genuine in expressing appreciation for the positive attributes of the employee.

About Jason Webb

Jason Webb is a movement leader, public speaker, advocate for racial reconciliation, and an entrepreneur from Milwaukee, WI. His skillset includes networking, fundraising, strategic planning, leadership, merger and acquisition, recruiting, and business expansion. Mr. Webb has mobilized these skills to establish and manage churches and non-profits and their budgets. He recently obtained a new leadership role for Great Lakes Church in Kenosha, Wisconsin.