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Home Columns

6 Tips for Having Difficult Conversations

Heather Hartmann by Heather Hartmann
May 20, 2025
in Columns, Education
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Do you enjoy conflict?

If you’re like most people, probably not. However, conflict is necessary in both personal and professional relationships, and often, it starts with a conversation.

But, how to have that conversation in the most productive manner has eluded me personally. Whether I say the wrong thing, lose track of my point or let my emotions lead my response, difficult conversations have been just that — difficult.

Knowing this is an area I need to grow in, I recently read “How to Have That Difficult Conversation: Gaining the Skills for Honest and Meaningful Communication” by Henry Cloud and John Townsend.  They talk about conversations in both personal and professional environments, even stating “employees in good companies confront each other every day.”

With that in mind, I wanted to share some of the biggest lessons I learned in hopes leaders in this industry and beyond can move forward in having those needed difficult conversations:

1. Before Any Conflict, Find Out the Reality.

Ask how the other person, whether it be a boss or coworker, would best like to resolve conflict whenever it arises. The key of course is to do this before you need to have a difficult conversation.

2. Grace and Truth.

As the authors state, “a successful confrontation will always involve balancing grace and truth.”  Grace is you being for the other person and helping the relationship move forward. Truth is the reality of what you need to bring up about the problem. You need both when having difficult conversations.

3. Stay on Track.

Oftentimes, we can get derailed by the other person’s response to a problem we bring up. Maybe they respond with issues they are having concerning you or they get defensive. What’s key to remember is to keep going back to the problem you’re trying to address. You can say, “I hear you and want to discuss about those things your brought up, but right now I’d like to get back to what I was saying about…”

4. Be Specific.

Avoid those tricky words like “never” and “always.” Known as global statements, they can do little to resolve something. State specifics about the problem, what you want to be different and how to get to a place of resolution.

5. Be Humble.

The authors write, “when confronting, don’t do it from a deficit balance. In other words, don’t confront someone if you owe them an apology first.” This can be hard to do, but it’s important to analyze ourselves and the role we may be having in a problem that needs to be addressed. Humility can pave the way for a better conversation about something that’s difficult.

6. Be Clear About a Problem’s Effect on You.

In the book, the authors share that “often, if you can be clear about a problem’s effect on you and if you can help the other person see that this is the reason you are talking about it, you can resolve it. When you express how you are being hurt by something, as opposed to how someone else is ‘wrong,’ many co-worker issues go away. Teamwork begins with understanding how we can help make one another’s load lighter.”

These are just a handful of the nuggets I gleaned from this book. All in all, it’s essential that we have those difficult conversations both personally and professionally. But, practice makes perfect. So, let’s commit to starting today.

 

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Heather Hartmann

Heather Hartmann

Heather Hartmann is the editor for Campus Rec Magazine. She can be reached at heather@peakemedia.com.

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