How to Have a Difficult Conversation

Set the Time, Place, and Length of Time for the Conversation

Call the other person on the phone to schedule a block of time to speak at a neutral and public place where two people can talk with a degree of privacy.  Parks, coffee shops, and food courts work well.  Do not pick a location where it is difficult for one of you to leave.  For example, restaurants are NOT an ideal place because you will be interrupted by the waiter and (theoretically) can’t leave until you’ve paid for your meal if one of you decides to order.  Choosing a neutral place is important so neither of you is uncomfortable or defensive.


The goal of the phone conversation is to get the other person to agree to meet you at a specific place at a specific time and for a specific amount of time.  That’s it.  Nothing else should be discussed during the phone call.  This should be a phone call, not a text or an in-person request, because texts can be read the wrong way and if you do this in person you may not be able to limit the conversation to just scheduling the meeting.  Doing this over the phone enables you to end the conversation quickly.


Generally, it’s preferable to not discuss what you will talking about.  This prevents the development of any misunderstandings before you have a chance to talk with the person at length.  However, if you think the person will meet you even if they know you will be having a difficult conversation say something like this:


“Hi __(insert name of person)__.  I’d like to spend some time with you to talk about __(e.g., our relationship, our conversation the other day, etc.)__.  When would you have __(15 minutes, 30 minutes, one hour, etc.)__ for us to chat at __(insert location here)__? Great.  Thanks.  I’ll see you then.” Hang up the phone.


If you don’t think the person will come to the meeting if you tell him or her what it’s about then say something like this:


“Hi __(insert name of person)__.  Can we set aside some time to talk about a few things? When would you have __(15 minutes, 30 minutes, one hour, etc.)__ for us to chat at __(insert location here)__?”


If the person presses you to find out what you want to talk about do not deviate from your goal of getting them to agree to meet you at a specific place and time.  Respond with something like:


“We’ll talk about it more when we meet.  I’m free __(list a few periods of times)__.  Do any of those times work for you to meet at __(insert location here)__?”


If they keep asking you what it’s about respond with something like this:


“It’s not something I’m going to discuss over the phone.  Can you meet me at __(insert location here)__ at __(list a few periods of times)__?”


If they refuse to meet with you unless they know what you will discuss this is not a person you want in your life.  If they won’t give you the time of day without getting an agenda they can use to prepare their defenses find someone who will to take their place in your life.


How Much Time Should I Ask For?


Allow for twice the amount of time you think you will need for the conversation.  Generally, half an hour is a good minimum.  For a difficult conversation to be meaningful, there has to be enough time for both sides to listen and express their feelings and thoughts.  Additionally, if the conversation goes well and takes less time than expected, the two of you can spend that extra time reconnecting with each other on a positive note.


Prepare in Advance


Write out and read what you want to say BEFORE you meet with the other person.  Seeing your thoughts on paper is very different form seeing them in your head.  Reading your thoughts may change how you feel.  This is especially true if what you really needed was to vent.  If, after reading your thoughts, you feel better you can always call the person and let them know that you were just angry but have gotten over it and everything is okay.  If you still feel you need to have the conversation, writing your thoughts down will remove a layer of emotion which will help you express yourself in a non-confrontational manner.


Once you have your thoughts written down on paper, revise them so you are owning own feelings rather than attacking the other person or telling them what you think.  For example, instead of saying “You need to stop making fun of me!” or “I think you should treat me better!” say something like “When you make jokes at my expense it makes me feel bad about myself.  It also makes me feel like you don’t value me as a person or a friend.”


If you tell someone what to do they will get defensive.  They won’t be able to hear what you are saying because 1) a different part of their brain has been engaged and 2) they will be working on their response to what you’re saying rather than understanding your situation.  Plus, if you speak in terms of what you “think” rather than what you “feel” you will get stuck in a pointless argument of logic.  The way a person thinks or an opinion can be changed by reason.  Unless the person you are speaking with is an adept listener with a high level of emotional intelligence, he or she will start to convince you as to why you should “think” a different way about the subject.  No one can dispute how another person feels.  It is a reality and, when stated as a fact without accusation, can’t be refuted.  So make sure you say whatever it is you are going to say in terms of how you feel without passing blame.


The Conversation


Show up ten to fifteen minutes early so you can choose a good spot for the conversation.  You may need to change locations and you want to avoid any awkward periods where you and the other person are anxiously waiting (and possibly avoiding) the inevitable.  You also want to choose a place where you feel comfortable and can mentally prepare.


When the other person arrives have his or her place to sit ready.  Once he or she sits down, DO NOT start engaging in small talk. Be pleasant, thank him or her for coming, and get right into it.  You both know you are there to talk about something serious and delaying the inevitable just makes the other person more nervous.  Studies show time and time again that people who are coming to a difficult conversation (e.g., being fired) prefer and appreciate when the other person is honest and direct.  So be nice to the other person and get straight to it.


After thanking them for coming, you will use what’s known as the “sandwich technique.”  This is where you sandwich something negative between two positives.


If you care enough about this person to have a difficult conversation with them then you can find two nice things to say about them, your relationship, etc.  An easy thing to lead with is something like this:


“Thanks for coming. I really appreciate it.  I really value our relationship which is why I wanted to talk to you about __________.”


This is when you express how your relationship with the other person is affecting you or your life.  Remember, do not accuse, don’t blame, and own your own feelings.  We can’t control or change other people.  We can only try to help them understand how we feel and then make our own decisions about who we allow into our lives.


It’s also important that you get through everything you came to say.  If you think the other person will jump in or interrupt before you are finished, when you start the conversation say something like this:


“Thanks for coming. I really appreciate it.  I value our relationship which is why I wanted to talk to you about __________.  I’ve prepared some thoughts so I’m going to ask that you wait and let me get through them so I’m able to listen to anything you might want to talk about when I’m done.”


After you’ve finished sharing with the other person, make sure you end with something positive.  Tell the person why you value them as a friend, something you love about them, something you admire about them, etc.  If you care enough to have this conversation you should be able to find something but if you can’t you can always fall back on:


“I value our relationship and I appreciate you listening.”


Once you’ve said what you need to say you then need to allow the other person a chance to express themselves.  Sit quietly, actively listen (which means looking at the person while he or she is talking and think about what they are saying), and don’t interrupt.  At this point the other person will either:


1) be defensive

2) ask you questions to understand more about what you said or

3) empathize, apologize, and thank you for sharing with them


If No. 1 happens, there is not much else you can do.  If the conversation is to help fix a romantic relationship, you may need to seek professional help to learn how to communicate.  If No. 2 happens, answer his or her questions in the same way you shared your thoughts and feelings.  If No. 3 happens congratulations!  You’ve taken your relationship with that person to a new level.