Effective Strategies for Handling Difficult Workplace Conversations

difficult conversations in the workplace

We are often trapped in difficult conversations in the workplace, and most of us will do anything to avoid conflict, especially face-to-face. I don’t even mean the uncomfortable conversations that are bound to occur with family members, romantic partners or close friends. 

The difficult conversations most people avoid at all costs are those that arise in the workplace. Most of us do not relish engaging in difficult conversations at work and I’m one of those people.

I’m grateful for my extensive experience as a matchmaking professional, female keynote speaker and business owner. I’ve never grown to love, or even gotten used to, delivering difficult truths. Feedback is an essential part of creating lasting relationships for my clients and helping them grow, so it’s imperative that I don’t hold back. They rely on me to tell them the truth, even when it can be painful to hear. Yes, I relay the occasional bad news, but I do it with a great deal of thought. Which sounds weird, because I’m pretty good at it. When your business is so people-oriented, you must learn how to be relatable and deploy empathetic communication. 

Developing these skills, following specific techniques, and seeking the guidance of a motivational speaker well-versed in the art of improving communication in the workplace are essential for anyone, especially a leader, who works with people. And unless robots took over and nobody told me, I’m pretty sure that is all of us. 

Common Mistakes When Approaching Difficult Conversations at Work or in Life

People bring their unique experiences, perspectives and emotions to any conversation, especially those involving conflict. With that in mind, let’s unpack some of the most common mistakes people make when engaging in difficult conversations at work, or in life. 

1. Not Speaking the Truth 

The truth is hard. Most of us don’t like making other people feel bad. When holding onto an uncomfortable truth, we may fear causing harm or bringing negativity to someone. It’s not that we prefer to lie; we just worry about the potential fallout of speaking our truth. Unfortunately, the concern overrides the truth and in this case, no one wins. We don’t get what we want and need and people don’t grow. Not because they aren’t capable, but rather because they simply didn’t know there was another path.

As a leader, it is vital to foster a psychologically safe environment where difficult conversations in the workplace can occur constructively. Encourage employees to deploy empathetic communication when approaching difficult conversations at work. This approach will help them deliver the truth in a considerate and thoughtful manner rather than cause unnecessary friction and upset.

You’ve likely experienced various reactions and responses as you converse with employees or address communication issues in the workplace. This is important because understanding how an individual will receive and interpret the truth will help you tailor your message to resonate with them on a deeper level. 

And always remember, sharing the truth is an act of kindness. It’s the delivery that is sometimes harsh, but when you approach the conversation with empathy, it doesn’t have to be a difficult one. And to complement the empathy, be transparent. This offers the other person a chance to shift, make positive changes, refine their habits or even gain a deeper self-awareness. Think about the people you trust. I imagine your circle of friends and colleagues tell you the truth no matter what. Be that same person in every area of your life and encourage others to do the same with you. No one should cringe when they have truth to share. It’s an opportunity and one to look forward to if you have the right mindset. 

2. Not Taking a Beat

Have you ever been on the receiving end of bad or harsh feedback? Depending on the delivery, your natural reaction might have been to momentarily shut down while processing the information. Other people may immediately respond with anger, feeling like they need to fight fire with fire or defend themselves. Some dissolve into tears, unconsciously displaying how let down or hurt they feel or simply go quiet. I’ve seen my share of all of this running a business that brings people together. We’re human. We’re all going to process differently depending on our circumstances, upbringing, values and even what happened the moment before we received the feedback. 

Regardless of the reaction, it is crucial to take a beat after delivering or receiving an unpleasant truth. It allows both parties a moment to simply feel all the feelings. Those instant feelings and reactions will be impulsive, which is not the most constructive approach. The key to breaking this cycle is to tap into what I like to call “emotional curiosity.”  

Deploying emotional curiosity means instead of leaping into a reactionary and defensive stance, take a beat to explore the “why” behind the behavior. Delve into the truth to gain a deeper understanding before responding. It opens the door for effective problem-solving and the opportunity to unearth the root cause of the issue, which can improve communication in the workplace. An example of this would be to ask yourself why someone might have been upset in the first place. Perhaps you could answer to this first before reacting. Or, asking the other person what they would like to gain from relaying the information. When we see the humanity under the behavior, we can get right to the heart of the matter. It’s been my experience, that this is always the more productive pathway to solving problems. 

3. Not Seeing Growth Potential

I want to share one of the most important cornerstones of my journey as a professional matchmaker and the bedrock of my matchmaking company’s incredible evolution — feedback.  Feedback has catalyzed growth for me, my clients and my company. It is so much more than random advice, it has empowered me to be innovative and creative. 

Feedback is truly transformative. But it doesn’t work unless you are open to receiving it. In fact, it’s one of the first questions I ask each new client before I begin. “Are you available to receive and share feedback as we work together and how much do you value feedback?”

If they embrace it, I’ll work with them. If not, it’s best we don’t work together. It’s not a matter of judgment but rather my knowledge that feedback is crucial and without it, we can’t grow and achieve the success we all crave.

Feedback is about embracing the honesty, positivity and directness being offered. When someone invests in sharing the truth simply to help you, that is a gift to be cherished. I get it; it may be easier to fight something you don’t want to hear, but it’s essential to keep the bigger picture in mind as it offers potential for profound growth in yourself and your relationships.

For couples, it can be the tipping point of a budding relationship. If one or both parties don’t feel free to honestly reflect what they are experiencing, the relationship can end abruptly due to hurt feelings and a sense of being criticized. I can’t overstate the importance of tone, timing and delivery.

As a leader, sharing that truth often falls to you. Revealing your thoughts, feelings and vulnerabilities as a leader may feel daunting, but it’s where the real magic happens. By offering someone honesty, delivered with empathy, you can spark growth for them, both personally and professionally. You’re already aware that our life at work affects every aspect of our lives. The more seamless we can be, the happier we will be. Integrating all of yourself as you thoughtfully engage in these conversations and inspire your team to follow your lead, you also mitigate communication issues in the workplace.

5 Strategies for Handling Difficult Conversations and Improving Communication in the Workplace

The difficult conversations have to be had. There is no way around that. When ignored, issues will simmer under the surface until they bubble over, creating significant problems. Most often, people won’t share their disappointment and that is the biggest danger. When people don’t feel free to share, they disappear without warning. This can be a costly mistake both personally and professionally. But when addressed with empathy, the truth can be life-altering in the best way.  

Let’s explore five strategies for handling these difficult conversations so they aren’t, well…..so difficult. As a bonus, by constructively sharing the truth, you will help your team manage their emotions in the workplace, combat employee relations issues and enhance the culture of transparency.

1. Prepare Thoughtfully

When considering a challenging conversation, channel the Boy Scouts and be prepared. Remember, you’ve had time to sit with the truth, but the other person hasn’t. And what you are sharing with them may come as a complete and unwelcome surprise. By clearly outlining the key points and ensuring you fully understand the issue, you can anticipate and be prepared to address any potential reactions. You aren’t building a case. You’re creating an opening for a conversation and quite possibly a transformation. I like to use the sandwich method. Start with a compliment, add in the layer of truth and constructive criticism and top it with another compliment. 

Set up a private space and time to approach the conversation. This will create an atmosphere of trust and aid in managing any emotions that arise without others in the workplace becoming aware and potentially interrupting. An intimate and welcoming space also encourages openness on both sides. 

2. Active Listening with Empathy

The challenging conversation isn’t over when the truth lands. In fact, that is where it begins.  And the moment where your understanding of how to be relatable, deploy active listening and display empathy is most needed. Armed with these abilities, you can transform a difficult conversation into a growth opportunity. 

Deliver the truth, listen to their words, and observe their actions.  

Absorb everything the other person is saying, both verbally and non-verbally. Pay attention to the nuances and emotions just under the surface. When you authentically try to feel what they are experiencing, you offer empathy and understanding. Your support is instrumental in their ability to accept the information and leverage it for change. It will help peel away the layers of fear and uncover the nourishing truth at the heart of the exchange. It’s going to feel like a journey of mixed emotions. Just take it step by step, moment to moment. Remember, you’re not having a conversation about one topic. It’s going to shift as the conversation moves. Be flexible, nimble and stay in the moment.

3. Stay Emotionally Aware

When approaching difficult conversations in the workplace, especially those related to employee relations issues or personal topics, it is essential to keep your own emotions in check. Be mindful that your tone, facial expressions and body language may say more than your words. Being calm and even-keeled is critical to getting through the conversation without emotions reigning supreme. 

As you initiate the conversation, be present in the moment. Rather than focusing on your final destination, approach the exchange as a journey of discovery. As you deliver the truth, you will likely witness the person’s vulnerability, which opens up opportunities to delve deeper into their world to understand their motivations and the experiences that have shaped them. Lead with kindness. Ask feelings-based questions, such as, “How are you feeling?” or “Is there anything you’d like to share?”. Regardless of their response or how upset they become, keep your tone rooted in curiosity, compassion and connection.  

This will create the best outcome for this particular employee and inspire them to approach future conversations with compassion, creating a ripple effect that improves communication issues in the workplace overall.

4. Focus on Behavior, Not Personality

Let’s face it: in life and work, you won’t click with everybody. That’s okay. As a leader, you must treat everyone fairly, regardless of how you feel about them personally. Especially when addressing issues, sticking to the specific behavior or situation is essential.  

Keep any personal feelings you may have about an employee inside. Instead, anchor the conversation to the core issue, rather than veering into subjective issues or a personal attack on someone’s character. This approach not only helps maintain a respectful and positive environment but also encourages a more effective and solution-oriented exchange.

5. Offer Solutions Together

Although you are the one approaching the topic, remember that it arises from a behavior or situation the employee is either involved in or has created. Many leaders address situations with a solution already in mind, but that is not the most constructive way to arrive at a desired outcome. If the employee is part of the problem, shouldn’t they also be part of the solution? 

Invite them to join you in brainstorming an innovative solution. This not only fosters mutual respect and nurtures a sense of ownership, but it also ensures they feel invested in the resolution. So, go ahead….let their voice join yours in a harmonious symphony of collaborative problem-solving.

How to Unlock Heart-Centered Communication with Expert Advice

So, do you love difficult conversations? Probably not. Will you ever get used to them? Doubtful. Are you going to approach them anyway? Yes! And you will do so by deploying all the tools I shared, ideally with the support and guidance of an expert female keynote speaker.  

And you will emerge on the other side feeling proud — proud of the other person for the journey of self-growth they will embark on and proud of yourself for delivering a difficult truth in the most empathetic, thoughtful and meaningful way possible.

After all, isn’t that how you would want someone to approach you?

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