Difficult Conversations: Leaders need to Understand Employees' Points of View

In the complex landscape of modern leadership, few skills are as critical yet challenging as navigating difficult workplace conversations. For managers, especially those newly promoted from within, these interactions can feel like walking a tightrope.

Human Dynamics

Let’s start with a revealing exercise I use with new managers: the best boss/worst boss reflection. Think about the worst boss you’ve ever had, the one who left you feeling frustrated, undervalued, or constantly on edge. What specific behaviors made you feel that way? In hundreds of conversations, the top issues consistently revolve around communication:

• Not knowing where you stand
• Unclear expectations
• Feeling like you’re not getting the whole truth
• Sensing unexpressed anger or disappointment

Now, flip the perspective. Recall your best boss, the mentor who helped you grow and made you feel supported and understood. What sets them apart? The answers are remarkably consistent:

• Clear, transparent communication
• Consistent feedback
• A genuine commitment to your professional development
• Providing constructive guidance
• Creating a sense of psychological safety

Understanding exactly what makes team members feel comfortable with and confident in their leaders provides important context for leadership skills and reinforces the importance of effective communication. 

Acknowledge the fear

At our core, no matter our age, profession, or other traits, we are human. We’re designed to protect ourselves from perceived danger, and when our brains don’t have clarity, they prepare for potential danger.

When workplace communication breaks down, our brains immediately interpret the uncertainty as a potential threat. This triggers a mechanism that prompts us to start creating elaborate scenarios to better understand the “what ifs.” If we can understand the potential scenarios, we can begin to think through how we might protect ourselves from them.

Imagine an employee sitting across from you with their mind racing with questions: “Am I going to lose my job? How will I pay my bills? What about my family?” These underlying fears can transform a simple performance or problem-solving conversation into a high-stakes emotional encounter.

A strategic approach

Effective leaders understand that communication is not a one-time event but an ongoing process. From the moment they step into a leadership role or bring on a new hire, it’s important to establish clear expectations while being as granular as possible. Even the smallest things (e.g., “I prefer to be texted about urgent issues rather than emails”) should be discussed.

This allows team members to hold the keys to their own success. They know what’s expected of them, and they do not leave work wondering if they have fallen short of any unspoken expectations.

Still, mistakes will happen. Eventually, a difficult topic will have to be discussed, and in these cases, the approach is everything. 

Timing is crucial. It’s important to have difficult conversations as soon as possible, but this urgency should be balanced with self-regulation. If you know you are going to need 24 hours to cool down before leading an effective conversation, take that time and initiate the conversation as soon as you are ready.

Start the conversation by explicitly stating your intent: “I know our shared objective is to serve our clients and follow our guidelines. I want to discuss how we can improve our approach together. I’m not here to criticize but to help us both succeed.”

In many cases, you can physically see someone relax once this is communicated. They understand that you’re on their side, and they’re able to de-escalate from an emotionally charged fight-or-flight state.

It’s also important to remember that almost no one comes to work intending to disappoint their leader or fail. Employees generally want to do well, succeed for their own professional benefit, and make positive contributions. Approaching difficult conversations from a place of blame, frustration, or superiority and overlooking the team member’s intentions can damage trust and create resistance.

The benefits

Why should leaders invest time and emotional energy in mastering these conversations? The reasons are plentiful:

• Retention costs. The financial and time investment required to hire and train a new employee far exceeds the effort required for a constructive conversation.
• Operational stability. Losing an employee creates ripple effects, overburdening existing staff, creating gaps in scheduling, and potentially losing the trust of remaining team members.
• Personal growth. As a leader, you have a unique opportunity to impact someone’s professional and personal trajectory regardless of their current role or compensation level. Playing this positive role can be incredibly rewarding.

Taking the time to invest in people ultimately benefits the business. Research consistently demonstrates that workplaces with high employee satisfaction and engagement financially outperform their counterparts. The businesses can be in the same industry or a part of the same brand, but there are dramatically different outcomes based on leadership approach.

Litmus test

Before your next difficult conversation, pause and ask yourself: What is my true intention? Am I looking to prove I’m right and demonstrate my superiority? Or am I genuinely interested in helping this person grow and improve in their role to better serve our common objectives?

If your intentions are to support, guide, and elevate, you are already on the path to becoming a leader people will trust, appreciate, and remember.

Nichole Holles, PHR/SHRM, is the senior vice president of people strategy and governance at Right at Home. She has a deep passion for transforming HR departments into strategic business partners and enhancing employee experiences.