From Awkward to Authentic: How to Navigate Difficult Workplace Conversations
Think about how you feel before you have a difficult conversation. Worried? Anxious? Maybe you have a pit in your stomach? Now think about how you feel after you've had a conversation that went really well. Are you relieved? Proud? Perhaps even energized?
The gap between the dread before and the relief after is exactly why this topic matters so much. Most of us avoid difficult conversations, and I certainly have been guilty of doing the same. But avoidance often only makes things much worse.
Over the years, I have facilitated countless workshops and coaching sessions on this topic, and I always come back to the same truth: the goal isn't to make difficult conversations easy. The goal is to make them authentic. And the good news is that authenticity is something we can all practice and improve.
Keep reading for my tips and best practices for making your next conversation less awkward and more authentic.
Before the Conversation
One of the biggest mistakes people make is not preparing for a tough conversation. The conversation itself might last 20 minutes, but the preparation you do beforehand can make all the difference.
I like to think about preparation through six simple questions: Who, What, When, Where, How, and Why.
Who do I need to talk with? Consider how this person prefers to communicate. Are they an introvert who needs processing time, or an extrovert who thinks out loud? Are there other factors that might shape how I approach this conversation? For example, is this person from a different generation? Are they neurodivergent?
What kind of conversation is this? Am I giving feedback, addressing a miscommunication, or trying to work through a disagreement? The "what" shapes everything else in the conversation.
When should this conversation happen? Aim for a time when everyone is present and distractions can be kept to a minimum. Having a difficult conversation when someone is stressed, rushed, or distracted is rarely a good idea. I make a habit of never having a difficult conversation on a Friday afternoon or first thing on a Monday morning.
Where will the conversation take place? In person, on the phone, or virtually? Will it be in a group setting or one-on-one? One thing I feel strongly about: do NOT have a difficult conversation via text or email. In person or virtual is best but sometimes the phone works, especially if you know the person really well and body language isn’t as critical. Most difficult conversations are best in a one-on-one setting, but sometimes you may want to share key items after with a larger group (e.g., your team).
How can you ensure the conversation is both authentic and productive? Think about exactly what you want to say. Consider writing down a "script" beforehand, not so that you read from it verbatim, but so that you've thought through your words carefully and aren't scrambling for them in the moment.
Why are you having this conversation? This is perhaps the most critical of the questions. You should think about this carefully: When you walk away from the conversation, what is it that you want to achieve? Sometimes, by starting with this question, you may realize that the conversation isn’t even necessary.
Beyond the who/what/when/where/how/why, a few more things are worth reflecting on before the conversation begins:
Be aware of your own bias. We all carry assumptions and biases, often without realizing it. Check in with yourself before the conversation and ask: Am I approaching this situation with an open mind? Are there past situations that are coloring my judgement?
Focus on the facts, but lead with empathy. My dad always says: “Focus on the facts”, which is critical and helps from your emotions getting the best of you, especially in a business conversation. But, while facts matter, but so do the feelings of the person you are talking with. Leading with empathy doesn't mean avoiding the hard truth; it means delivering it in a way that acknowledges the humanity of the person you're talking with. It means leading with curiosity and questions. There may be something bigger going on in that person’s life that you do not yet know about that is contributing to the very issue you need to discuss. Some questions that can be helpful here: “I’m curious…is there something else going on that I may not be aware of?” and “Can you help me understand?”
Check your listening battery. Are you truly ready to listen, or are you so focused on what you want to say that you're just waiting for your turn to talk? Listening researcher Oscar Trimboli draws a distinction between active listening (listening to what people say) and deep listening (listening to what people don't say). Deep listening requires focus, presence, and intention—and it starts before you even walk into the room.
During the Conversation
With your preparation done, it's time for the conversation itself. A few practices have consistently made a difference for me and my clients.
Truly listen. As Oscar Trimboli has said, we learn to listen before we learn to breathe or speak (research has shown that we learn to listen in the womb at 26 weeks)…and yet most of us are not very good at it. Deep listening means paying attention not just to the words, but to tone, body language, and what's not being said. Trimboli says that it's about giving attention, not just paying attention. These two things sound similar, but they are meaningfully different. (Check out a great podcast about deep listening, Mastering Deep Listening with Oscar Trimboli: Unveiling the Art of Understanding Unspoken Communication.)
Share your own vulnerability. Authentic conversations are two-way streets. When you share your own uncertainty, feelings, or limitations, it creates space for the other person to do the same. This doesn't mean oversharing, but it does mean being real. I have found in my own leadership journey that I have had the best conversations with my team after I have shared my own emotions and vulnerability.
Use the "Fast Food Rule." This is one of my favorite communication strategies, borrowed from pediatrician Dr. Harvey Karp. I learned from his book, The Happiest Toddler on the Block, when I was looking for ways to communicate with my 1-year old toddler. But I was amazed at how well it not only works with my daughter but also in the business world. The idea is simple: before you respond to what someone has said, summarize back to them what you heard, just like a fast food cashier who repeats your order back. It sounds simple, but it accomplishes a lot. It demonstrates that you were listening, gives the other person a chance to clarify if you misheard, and helps prevent misunderstandings.
Use "I" statements and "from my perspective." Framing your thoughts from your own perspective rather than making declarations about the other person's behavior or intentions tends to keep a conversation from escalating. "From my perspective, this project is behind schedule" lands very differently than "You're not moving fast enough."
Wrapping Up the Conversation
How you close a conversation matters just as much as how you open it. Before wrapping up, create space for final thoughts. "What else is on your mind?" or "Do you have anything else to share?" can surface important things that didn't come up during the conversation.
Always say “thank you”. Acknowledging that someone showed up for a hard conversation and gave you their attention is meaningful. Provide an opportunity for future dialogue so the conversation doesn't feel like a one-and-done event. And wherever possible, document outcomes and next steps so that the conversation leads to real change (this is especially critical if you are having a conversation about a team member’s performance or documenting an incident with a client).
A Final Thought
Mr. Fred Rogers, one of my favorite role models, once said: "Anything that's human is mentionable, and anything that is mentionable can be more manageable. When we can talk about our feelings, they become less overwhelming, less upsetting, and less scary."
Difficult conversations are human. They're messy and uncomfortable and sometimes they don't go perfectly. But they are also how we build trust, repair relationships, and grow…as individuals, as teams, and as organizations.
The next time you have one coming up, take a breath, do your prep work, and remember: the goal isn't perfection. The goal is authenticity.
Do you have a difficult conversation on the horizon? I'd love to hear how you're thinking about it. Feel free to reach out or connect with me on LinkedIn.