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How to Have Difficult Conversations at Work

Nobody likes having uncomfortable conversations, but without them we cannot grow as people, or as businesses. As businesses navigate the challenges of the pandemic and calls to reexamine themselves for racial bias, there are plenty of tough conversations to be had. It’s important that our dialogue skills are up to the task.

Start With You

Though we’ve all had bad experiences with a difficult conversation in the past, the simple fact that we label them “difficult” can affect your mindset. If you are prepping your mind for a negative experience, you are more likely to be anxious and upset. “A difficult conversation tends to go best when you think about it as a just a normal conversation,” says Holly Weeks, the author of Failure to Communicate. So remember to breathe and refocus yourself away from negative emotional armoring.

Experts agree that jotting down notes and goals for the conversation is a good idea, but writing a script is not. When you write a script, you have already decided how the conversation is going to go. This will keep you focused, but will completely stifle any growth the conversation could have led to. Instead, ask yourself these questions from Crucial Conversations to keep yourself on topic:

  • What do I really want for myself?
  • What do I really want for others?
  • What do I really want for the relationship?
  • How would I behave if I really wanted these results?
  • Lastly, before entering the conversation, make sure you have the facts. Emotions often cause us to exaggerate, or conversely, second guess ourselves. By sticking to the facts, you can keep the conversation on solid ground.

Entering The Dialogue

According to a 2009 study conducted by the authors of Crucial Conversations (Kerry Patterson, Joseph Grenny, Al Switzler, and Ron McMillan), more than 70% of employees avoid confrontational dialogue with their peers and managers. Incredibly, this statistic still stands today. Employees still fear repercussions from these conversations so they avoid them, ignoring them and letting them fester . To keep this from happening, leaders must create a safe environment where employees can speak freely.

Creating a safe environment isn’t going to be achieved in one team-building retreat. It needs to be a true commitment to active listening and an openness to improvement. A great way to keep communication open with employees is to establish a recognition program. When employees feel seen and valued, they are more likely to feel comfortable addressing a tough topic. Empower them to affect positive change in the workplace, and they’ll feel like they can speak up. By having many positive conversations under your belt, it will make the “difficult” conversations come much easier.

When entering the dialogue, the most important thing you can do is “start with heart.” By demonstrating that you are coming from a good place, the person you’re speaking with is more likely to reflect compassion back to you. The two of you (or however many in the conversation) are working towards a respectful understanding and course of action, not an arm wrestling match. When the mindset is about teaming up against a problem, the conversation is bound to be much more productive.

Other important things you can do are to listen and learn. Crucial Conversations offers some “power listening tools” to actively engage and direct the conversation in a productive way:

  • Ask to get things rolling – Start by simply expressing interest in the other person’s views.
  • Mirror to confirm feelings – Increase safety by respectfully acknowledging the emotions people appear to be feeling.
  • Paraphrase to acknowledge the story – As others begin to share part of their story, restate what you’ve heard to show not just that you understand, but also that it’s safe for them to share what they’re thinking.
  • Prime when you’re getting nowhere – If others continue to hold back, prime. Take your best guess at what they might be thinking or feeling.
  • Finally, make sure that whatever decision comes out of the conversation, and how it was decided, is absolutely clear. Everyone should be on the same page to effectively move forward.


I learned a lot from writing this month’s blog, and there is some great information out there if you want to learn more about improving your conversation skills. The desire to improve and reevaluate means you’re already well on your way! Below are some resources I found helpful:

Shorter Reads

Haven Life put together a more bullet-pointed list of tips on their blog with some very helpful templates that cover a variety of sticky work scenarios.

The Harvard Business Review also has a good quick-bite article that includes two real-life case studies.

Longer Reads

"Crucial Conversations: Tools for Talking When The Stakes Are High," by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler.
A bestseller and go-to book for thought leadership

"Failure to Communicate: How Conversations Go Wrong and What You Can Do to Right Them," by Holly Weeks
A fun read full of real-world examples