How to Have a Difficult Conversation Easier

How to Have a Difficult Conversation Easier

You know that feeling you get in your stomach when you realize you’re going to have to have a difficult conversation?  The nervous flutter, followed by a quick flip, and then a heavy feeling in the pit of your stomach.  Yeah…that feeling.  For me, that feeling is usually a sign that I’m about to have a difficult conversation.  No one really enjoys difficult conversations, but there are people who seem to do them better.  And thankfully, over the years, I’ve become one of those people.  This is partly due to my training and skill set as a psychologist, but it is mostly a function of practice. Emotionally healthy people have difficult conversations on a weekly basis.  So whether you’re thinking about approaching your spouse, your boss, your mother-in-law, or the parent of another child in your kid’s class, here are some hints for making that difficult conversation a little bit easier.




Ask for time.  Blindsiding someone is a quick way to get a defensive and not so helpful reaction.  So let someone know that you’d like some time to talk.  Give them a time frame and give them a vague idea about what you’d like to address.  Try something like, “Susan, I hope this email finds you doing well.  At some point this week, I would like to take some time to sit down with you to discuss some concerns I have about the marketing team and their effectiveness.”  You’re giving an idea of the time, mindset, and theme needed to have the conversation.  This also gives the other person a sense of say in when the conversation happens, priming them to feel like a valued partner in the discussion, rather than a target.


Use “I statements.”  If you’re even done couples counseling, you’re probably familiar with this tool.  Using “I statements” prompts less defensiveness than using “you statements.”  Example.  “You never listen; you make me mad; you aren’t paying equal attention to your students” sounds a lot different than “I feel minimized, I am angry, I am concerned you aren’t giving your students equal treatment.”  It seems like the tiniest distinction, but it will make a huge difference.


Be specific about what you want.  In addition to communicating how you feel, communicate what you want.  And be specific.  “I’d like us to spend dinner without electronics on, I’d want to take the lead role on a proposal, I need you to let me vent without offering up advice.”  Even when people see your point, they don’t always know how to make it happen.  Being specific with what you want helps them take action towards your request.


Acknowledge the awkwardness or difficulty of the conversation.  (This is one of my favorite skills to practice!)  For some reason, when we think about having difficult or awkward conversations assertively, most of us think we have to turn into some hard ass, no nonsense communicator.  I don’t think this is necessary.  It is ok to acknowledge that you are slightly nervous to have this conversation; it is ok to acknowledge that talking about money makes you uncomfortable.  It is ok to acknowledge that you’re fearful you will be rejected.  Authenticity is my life buzzword, so I’m a firm believer than being real, even in difficult conversations, is important.  I try to have some restraint with this point though, sometimes toning down the intensity of my emotion.  Instead of saying, “I was up all night freaking out about what you might say,” I might say, “I am concerned about how you will hear this,” or “Difficult conversations can be a little anxiety provoking for me.”  Follow that up with, “And yet this is important.”  This point will help show you are a human, but a human that means business.


Think about what you want to say, how you want to say it, and how you want to look saying it. This point is frequently made, yet very rarely practiced.  Actually rehearse, out loud, what you want to say.  Practice with different tones and words; anticipate what the other person might say and how you want to react.  This will help you be comfortable with your side of the conversation.

Difficult conversations aren’t fun or easy, yet they are important.  They are an art form in many ways, with lots of variables to consider.  But with the right approach, tone, phrasing, and practice, they are absolutely manageable.


What difficult conversations are you preparing for, and what can you do to make having that conversation a little bit easier?


  1. Maggy

    This article was full of great advice. I find difficult conversations are the worse to have so I’ll be using your tips. Good luck on the new website, I signed up for your weekly inspiration too.

    1. Dr. Allison


      For some reason, I didn’t see your comment until this morning, so I apologize for my late reply! I am so glad you found this post helpful. Difficult conversation are certainly tough, and I don’t think any of us look forward to them. Yet, them are important, so I hope these tips will help you as you face these tough conversations head on. You can do it! Thanks for the encouragement on the site; I am grateful for your support! Have a great week!

      Dr. Allison

    1. Dr. Allison

      Wendi, Thanks for the feedback; I’m glad you found this post helpful. Remember that you can submit questions or topics you’d like to see addressed by clicking on the “Answers” tab and submitting a question. Thanks for your encouragement; I look forward to interacting on the site more!

    1. Dr. Allison

      Awesome; I’m glad the info is helpful! After years of using these tips, I’ve become pretty skilled at awkward, difficult conversations. I don’t “enjoy” them lol, but I can do them! 🙂

    1. Dr. Allison

      Thank you so much, Laura! That is so encouraging to hear; the feedback means a ton! Thanks for reading and supporting Dr. Allison, both now and during my Access days 🙂

      PS: Sorry for the late reply; my site was being funky with comments.

  2. Will

    Dr. Allison thanks for reposting this article! The hardest part of difficult conversations for me is “how you want to say it”. It’s hard to suppress the anxiety and emotions that I feel, and that I anticipate the other person would feel. Asking for time, using I, etc helps to reduce some of this. Great web site!!

    1. Dr. Allison

      You betcha, Will. Difficult conversations are tough, and while we can’t make them EASY, we can make them EASIER with some intention and planning. Thanks for reading and commenting!

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