How to Build Confidence, Resilience, and Preparedness for Tough Conversations

Many leaders today are doing their best to ensure they are communicating with their teams with honesty and transparency. One area that’s particularly challenging is initiating and engaging in tough conversations with team members. The new work-from-home model can be a powder keg of issues that result in difficult conversations; overwhelming workloads, insufficient work-life balance, understaffing, variances in technological ability, generational differences, and differences stemming from cultural or identity backgrounds. Resolving these issues often requires engaging in conversations that may are at best, uncomfortable.

One of the most difficult places to establish trust, respect and safety is in conversation, and a challenging conversation can be a minefield where everything can go awry.

The main reason why most people avoid having tough conversations comes from a fear of conflict, and not without reason. Conflict indeed can have negative repercussions. Robyn Short, a conflict specialist and mediator, reports that $359 billion in paid hours, which is the equivalent of 385 million working days, is wasted each year in the US due to conflict. This is based on studies that suggest the average American employee spends about two hours a week dealing with conflict.

A tough conversation may also lead you to take responsibility for your role in a problematic situation. You may discover that you were in fact the cause, or one of the causes, of the situation in hand. You may uncover that while you did not create the problem, your actions or decisions – such as letting someone’s poor behavior go unchecked – exacerbated the problem. It’s challenging to take ownership of our role in problems like these and sometimes easier to avoid  tough conversations entirely.

One of the biggest reasons why conversations with potential conflict are so tough is because we get caught in what I call “The Trap.” We each enter a conversation or situation with all the information and experiences of our past. We rarely come into a conversation without first drawing upon similar encounters we’ve had in the past. When we rely on our past experiences like this, we [unconsciously] also bring any biases, judgments, or personal narratives we carry as well.

This is normal and natural. We are human beings having a human experience and we all have each created stories about people that originate from our past experiences. For example, I may unconsciously be short with or have an attitude with my new co-worker Kendrick because he reminds me of a terrible ex also named Kendrick. I may be more inclined to favor Sarah at work because her personality and mannerisms are EXACTLY like my best friends and found myself treating and talking to her as if she really were my best friend.  The things people say and do around us can trigger our own emotional baggage, good or bad, to come out in conversation.

If we create a system that allows us to prepare for the conversation, then the conversation has a greater chance for success. Preparation provides an opportunity to reflect and fully engage in what you want to say. With practice, proper preparation will allow you to view all sides of a situation, filter out your own emotions or biases, confront any remaining personal responsibility, and empower yourself to confidently and securely engage in the actual conversation.

When engaging in a conversation that’s more challenging or that requires a deeper level of thought and inquiry, prepare for the conversation by asking yourself the “5-A” questions:

  • Aware – What are you feeling?
  • Accurate – What is the truth here? Drill it down. Is it accurate or just your own personal interpretation?
  • Acquire – What learning are you meant to acquire from this situation?
  • Accountability – What is your part in the situation? How can you take responsibility?
  • Action – What proactive action can you take?

After you thoroughly write down the answers to the 5-As above consider these additional prompts: Given what you wrote, how do you plan to engage in the conversation with curiosity? What judgments and biases will you let go of in order to be fully present?

If you are triggered during the conversation, what questions can you ask that will bring you back to the present moment and the actual conversation you are in? What questions will you ask to gain further insight?

The degree to which you set a clear intention and prepare to engage in a tough conversation will set the stage for how the conversation will go. While there is no guarantee to the level of success or outcome of any given conversation, you can ensure your own role and ability to be fully present and engaging through proper preparation.

Esther Weinberg is the Chief Leadership Development Officer and Founder of The Ready Zone. To dive deeper into the ideas and strategies offered in this article, complete our Needs Assessment and we’ll schedule time to connect. In the meantime, download our FREE eBook – “Better Leaders. Better People. Better Results. Six Eye-Opening Strategies to Thrive Through Change You Did Not Ask For