How To Master Difficult Conversations At Work

Mastering Difficult Conversations for Leaders

By Lyssa deHart

The world, as well as business or non-profit organizations, is filled with difficult decisions and the difficult conversations that go with them. Difficult conversations show up with friends, family, employees, peers and bosses. How do you discuss situations that have the potential to create conflict? And what connections or opportunities open up when you feel confident to speak?

Difficult conversations arise in every organization, with people all across the organizational hierarchy. Challenging work or interpersonal situations arise and need to be discussed. This difficulty is aggravated by stress because most folks are juggling multiple priorities as fast as they can. “What, you want to add another ball here? Sure…” This additional stress often leads to anger, frustration or people opting to say nothing about struggling with an unbalanced workload.


HALF DAY ONLINE SEMINAR: Mastering Difficult Conversations for Leaders


Between Stimulus And Response

When humans get overwhelmed, it’s easy to have negative reactions. Our brain is designed to manage survival. It is also predictive. Our early ancestors didn’t have time to decide if the shadow in the tall grass was a tiger or just a shadow. They survived by erring on the side of predicting “Tiger!”

If you have ever been overworked or had unrealistic expectations placed on you, your experience might be that these conversations about workload don’t often go well. So, you’ll err by assuming that any new conversations won’t go well either. 

Based on your past experiences, each time a similar situation shows up, your brain will predict an outcome and create a plan for survival. That might look like arguing or it might look like shutting down, and both are aspects of the fight, flight and freeze response. Understand that responses depend on the person, the context of the situation and the desired outcome. Our brains are often predicting outcomes by making assumptions based on previous experiences. 

Between stimulus and response is an opportunity to pause. Let’s take that pause to explore how to better control our reactions during difficult conversations:

What’s Your Goal?

The first step in any difficult conversation is to have clarity about your end goal.

I recently had a conversation with a mid-level manager. He was being tasked to onboard a new team member, accomplish his deliverables and step into more leadership roles all at the same time.

As we worked together, we discovered he had five main goals:

• To be a good team member and onboard the new teammate effectively.

• To continue to meet his own aspirational goals and produce his deliverables.

• To avoid taking on the new team members’ goals and carrying their workload as they on-boarded.

• To get the promotion that went with the leadership role. 

• To maintain some sort of healthy integration of work and life.

Nowhere in these goals was the desire to whine, argue or to appear as if he wasn’t a good team member. 

Exploring The Important Conversation

There are myriad conversations one might have with their supervisor about their work concerns. Difficult conversations run the gamut from whining to argumentative. My client was clear, he didn’t want a conversation anywhere along that spectrum. He wanted to have a productive and effective conversation. 

He had some concerns that the expectations for the new team member were unrealistic, given that they were still getting their feet wet. And there was a valid concern that his qualities of conscientiousness and desire to be helpful might have him overreaching his capacity and his performance might suffer.

Yet, going to the boss and saying, “This isn’t going to work. Your expectations are unrealistic and I don’t have time to carry the new teammates’ load” didn’t seem like the best course of action.

As we discussed his concerns, he started to recognize that he might be making some of the following assumptions:

• He didn’t yet know what his new teammate thought about their 30-, 60- and 90-day goals.

• He was making a plan of attack without knowing what was needed of him. 

• He needed clarity if his own goals were actual or aspirational.

• He was guessing that there was an expectation for him to sideline his own work to support the new teammate.

By exploring his assumptions, my client began to get some clarity around the actions that might be most useful in his situation.

Next Steps

The conversations he was choosing to have no longer felt so fraught with tension. Through the process of exploring his own assumptions, he developed awareness around what fueled those assumptions and then crafted an action plan for tackling the sticky conversations.

The first conversation he needed to have was with his new teammate about how they viewed their 30-, 60- and 90-day expectations and where, if at all, they needed his support. If the new teammate wasn’t concerned, he could stop there and focus on his own work. If they were overwhelmed, he could discuss what they saw as concerning and see where he could offer support. 

They could then go to their boss to ask him about solving any concerns and how to prioritize the work. My client could do this, secure in having communicated that he wanted to be part of the solution and knowing that his boss could assess what was and wasn’t imperative in terms of deadlines.

Mastering The Difficult Conversation

Difficult conversations rarely have us feeling warm and fuzzy. Yet, they offer us a unique opportunity to grow ourselves into better people, contributors, team members and ultimately better leaders. If we can name our goal for the conversation and explore our assumptions, then we can move from feeling overwhelmed toward our desired outcomes. 

It is only when our mind is in this open mindset that we can be curious and creative. Assumptions about what is and isn’t known, and what is and isn’t possible, often come from a brain that was focused on surviving and not on solving.

Learning to hit that pause button and develop curiosity about your hidden biases and responses is the work of mastery. Realizing that not every shadow in the tall grass is a tiger takes practice and often requires some external support. Accessing your capacity to breathe into and through frustration and to get curious about yourself and others will help you formulate a plan that will have a more useful outcome. You will be several steps closer to mastering yet another difficult conversation.

Lyssa deHart, LICSW, MCC, is the author of StoryJacking and works with bluSPARC as an executive and leadership confidence coach.

*This article first appeared on forbes.com website.

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