Handling Difficult Conversations: Four H’s That Will Help

Do you know why leadership training is important?  Because there is often a gap between what we know and what we do.  No matter how many books you have read, how experienced you are, or conferences you have attended, you can always learn something new, and/or be reminded to do what you know to do.  Such was the case for me on Friday.

There I was, someone who considers himself an expert on leadership.  As I listened to a training session on handling difficult conversations, a topic I have lectured on myself in the past, I realized I had violated some of the basic principles being taught within the last 24 hours, with other people in the room!  At the next break, I made my apologies, and it led to an immediate improvement in a couple of key work relationships.  That is a day well spent, in spite of the work piling up back at the office!

As usual I write about what I am learning or need to remind myself, so here is the lesson I learned about dealing with difficult conversations on Friday.  It can be summed up by remembering four H’s:


This is where I went wrong last week.  Someone approached me indirectly about a situation that they believed I should have been able to resolve.  From my perspective, I had gone above and beyond, and was incredulous that someone would not recognize my contribution, let alone ask me to do more!  In essence, it offended my pride.  That is the first lesson of having successful difficult conversations.  You have to be humble.  Whether you are initiating the conversation, or someone else is engaging you in one, if pride is not laid aside, you will get defensive, and things will go south in a hurry!


The next three H’s all go together.  Our facilitator for this session encouraged us to handle difficult situations with a three-step process… Heart, Head, Heart.  It is similar to something I have learned and practiced for years, the “sandwich methodology,” where you sandwich a negative message between two positive messages, but it has a subtle difference that I believe increases the likelihood of success.  Here is how it works:

Heart:  When you begin a conversation you expect to be difficult, start by letting the recipient know you care.  It is more than a mere positive statement taught in the sandwich methodology.  Find what you can say to demonstrate you know he or she has value and worth.  Connect with his/her heart by showing you truly care.  No matter what difficult conversation you have to engage in, if you are truly looking to help the person, you can show that, and connect with him/her.

Head:  Now is the time to apply your logic.  The recipient knows you’re on their side and you want them to succeed.  That will enable you to communicate what it is that needs to change, or be accomplished.  It is also time for you to TRULY listen to relevant concerns or questions, though not to deflecting arguments, and work through and gain agreement on a plan.

Above, of course, is the ideal situation.  Sometimes it will not happen.  Sometimes despite your best reasoning, the other person will not agree.  The best you can hope for then is that he or she will at least acquiesce to authority, if you are his/her leader, or to civility, if it is a peer-to-peer, or employee to superior situation.

Heart:  Whether or not you come to agreement, gain acquiescence, or it is just time to terminate a fruitless conversation, in the last step you should again try to connect to the heart by letting the recipient know you appreciate their willingness to agree, try it your way, or at least give you his/her time to discuss the matter.  During the “head” phase, if you keep in mind you will have to end with a “heart” message, it will help you not allow the conversation to devolve.


Difficult discussions are a frequent occurrence in leadership.  I believe this tool will help me close the gap on what I know versus what I do as I strive to be the best leader possible.  Every day we strive, we become better.  Every day we don’t, we don’t.

9 thoughts on “Handling Difficult Conversations: Four H’s That Will Help

  1. I really like the way you designed to deal the difficult conversation. Thanks a bunch for such good articles and topics.

  2. Thanks for sharing. I do believe that it is important to be able to handle difficult conversations effectively, especially when you are a leader.

  3. Great suggestions, difficult conversations are never easy. This is simple, true and should be very effective.

Leave a Reply