This evening (from whenever I began writing this) my wife and I are going to have dinner with one of my best friends from college whom I haven’t spoken with in the past 5 years.  I haven’t spoken to this friend because we had what many might call a “falling out” 5 years ago from one of those conversations that I wish I could do over again.  We’ve all had those conversations.  They haunt us while we’re in the shower or trying to fall asleep at night.  Maybe you weren’t wrong, or maybe your heart was in the right place.  However as the conversation plays out, you could have articulated your message better.  Of course, it’s always possible you were just out of line.

            Because I’m not interested in blogging to make myself look bad (who is?), I’m going to spare you the details of my specific situation and instead offer you what I have learned from these difficult conversations.  It’s my hope that these pointers will help you check yourself before you give an intervention or express that you have been hurt by something.  Hopefully these ideas will empower you to love honestly yet minimize those falling outs we’ve all suffered before.

Think it through.

            A simple question to keep locked in the back of your mind is “Is what I’m saying critical or affirmative?”  If it is critical, ask yourself “How can I criticize constructively?”  If you aren’t creative enough to come up with a way to do so, you might as well shut up.

            Be prepared to have the conversation if your message isn’t well received.  Be able to defend your perspective, be ready to be calm and tactful, and be ready to suffer the consequences that your words may have on your life and relationship.  The most common worst-case scenario is you lose a friendship.  For this reason, it’s always important to assume that the words that leave your mouth can’t be unheard. 

Know your place.

            It’s best to ask yourself whether or not you are the person to be delivering the message that your friend is hearing.  One of my favorite proverbs is “Never take advice from someone you wouldn’t trade places with.”  People don’t tend to receive messages from those they don’t see as credible.  If credibility isn’t established, a difficult conversation runs the possibility of being an unheard waste of time that just burns a bridge.

            Another important question to ask is “Am I a consistent enough presence in this person’s life to be saying something this personal to him or her?”  Just because you have a history with someone doesn’t mean that you know where he or she is in life right now.  This is one of the easiest ways to over-step.  The more consistent you are in someone’s life, the easier it will be to have the conversation for you as well as your friend.  However, there may come a time when you feel the need to have one of those conversations out of responsibility (for example: “If I don’t say something, I’m afraid no one will.”).  Then, it always pays to come to the discussion with as much humility as you can muster.

If possible, listen first.

            The longer I live, the more I learn why a wise man is slow to speak.  It makes sense that all anyone ever wants is to be understood, but you will go further in life if you seek first to understand.  So when having a difficult conversation, ask as many questions as possible.  Be as compassionate and as loving as possible.  The words you speak will hold more value if they are carefully rationed, and they’ll be more relevant if you are listening closely. 

Be as objective as possible.

Whatever it is that needs to be expressed, it can wait.  The more serious it is, the more you want to be sure that you have not only thought it through but also checked yourself emotionally.  Be sure that you have given yourself a chance to cool down.  Make sure that you can have evidence or specific examples to enforce your position.  Your emotions are important, but the more you use them to communicate difficult ideas, the more you run the risk of coming across as irrational. 

Even if the conversation is centered on your feelings, it is possible to approach your feelings in an objective manor.  Simply make “I feel…” or “When you… it makes me feel…” statements.  No one is entitled to argue with how you feel but you.  However, in order to stay objective it is vital that you don’t speak for anyone else but you.  Avoid using “He said,” “She said,” or “A lot of people think” in your speech.

Ultimately you are in control of you, and that’s it.

            If something bothers you enough for you to feel the need to have a sit-down with someone, you’re going to have to find a means to get over it whether or not the person you speak with is able to correct anything to your satisfaction.  It is important that we have the freedom to express ourselves safely.  However, we will always come to a point when we have to take responsibility for the way we feel.

            This means that if you get to be free to choose how you feel in life, so are others.  A sociopath may try to take control over another person’s thoughts and feelings, but you shouldn’t.  So remember that if you feel bad and would like to be honest about it, your goal is to explain how you feel and not to make them feel how you feel.  Bypassing guilt and shame will lead to a more productive dialogue.