Having that Difficult Conversation

See also: Communication in Difficult Situations


At the core of every successful conversation lies the free flow of relevant information.

Joseph Grenny (Crucial Conversations)

Confronting people on hard issues ranks right up there with having a root canal on our list of things we hate to do. Most people don't like to confront others and almost everyone dislikes being confronted. Just the very thought of confrontation may stir up childhood memories of unpleasant discipline by parents and teachers. We tend to fear going back to that little child who is being admonished (and even punished) for misdeeds.

Because we tend to fear these crucial conversations, which could potentially repair festering problems, we prefer to avoid them altogether.  We find other ways to settle the matter and avoid the necessary face to face conversation.

  • We send out emails
  • We leave voicemails
  • We send out text messages
  • We change the subject
  • We suddenly remember that we have forgotten to do something and excuse ourselves to take care of it.

Emotional intelligence does not mean merely "being nice". At the strategic moment, it may demand not "being nice", but rather, for example, bluntly confronting someone with an uncomfortable but consequential truth they've been avoiding.”

― Daniel Goleman, Working with Emotional Intelligence

Avoiding these necessary discussions may appear to bring relief and lower our anxiety levels, but all it really does is sweep the issue under the carpet and leave it there to resurface later with perhaps even more serious implications. Experience shows that those who regularly face issues head-on and confront them are more efficient at correcting problems, building healthy relationships and teams than those who fail to confront and are generally better at getting things done.

Where Do We Start, and How Do We Confront?

Steven Covey said, "The main thing is to keep the main thing the main thing." In his book, The Speed of Trust,  Behavior #8 (pp. 185-191) is:

Confront Reality

  • Take issues head on, even the "undiscussables"
  • Address the tough stuff directly.
  • Acknowledge the unsaid.
  • Lead out courageously in conversation
  • Remove the "sword from their hands."
  • Don't skirt the real issues
  • Don't bury your head in the sand

So our first job is to focus on the problem. Keep in mind, I am not suggesting that we go at the person with a (proverbial) baseball bat.  We need to look for mutual purpose and mutual respect. We should try to come alongside the other person (or people) and look at the situation from their side of the table. The goal should be to resolve the problem in a team spirit.

The key here is that we need to be "on their side", otherwise our words can come across as manipulative or artificial. It is not enough for us to believe that we are on their side; they actually need to feel that we are. The word "confrontation" means "to turn our face toward" and that is what we should do. We should strive to be authentic by letting them know that we are interested in looking at the problem together.

Prepare for Dialogue

Before having a crucial conversation, it is best to check our own motives first. Don't go into the conversation with emotional baggage. We should take ownership of our part in the situation and apologize for areas where we might have contributed to the problem and go in with a clean slate. It is good to take the proverbial "plank" out of our own eye before we can see well enough to help the person we are confronting get the "speck" out of their eye. Clearly, from this famous quote, we can see that the biggest share of the responsibility is on our shoulders.

"Don't confront someone if you owe that person an apology first".

Clarify the Problem and Stay on Focus

In their book How to Have that Difficult Conversation, authors Dr. Henry Cloud and Dr. John Townsend discuss the need to have a clear idea about the problem. They highlight three steps:

  1. Have a clear idea of what the problem is all about and then make it as clear as possible to the other person.
  2. Clarify how the problem affects you or any other people affected.
  3. Be clear about what changes need to happen

What is the focus of the crucial conversation and what is the goal? If need be, we can write out what we want to say to eliminate any non-issues and stay on track. Let's make sure that we know what we want to accomplish to avoid getting sucked into the minefields of emotional games and drama. There will always be the risk of being led off track into unrelated or unproductive arguments, so we need to be prepared to circle back around and redirect the conversation to the main focus.

Keep It Safe

We should do our very best to be gracious and understanding without giving in to emotional blackmail. Be prepared for such things as sarcasm, projecting, blaming others or situations, the silent treatment, sulking or withdrawing from the conversation. The more we do make sure that our approach is safe and not aggressive or emotional, the better the chances of a positive outcome. When in doubt, err on the side of grace rather than on the side of hammering them with the truth.

One excellent way that we can make the person feel safe is to ask open-ended questions and show an interest in them and their concerns. Questions, asked with the proper spirit and tone, can build bridges and reduce defensiveness.

Forget about "Should"

Although there is nothing wrong with the word "should", it can often be construed as an obligation or feel judgmental. Context is everything. If someone is asking for advice, using "should" might be better accepted than if we are being confronted for problematic behaviour. And using "should" in the past tense, "should have" for example, can make the person feel bad about themselves. There is nothing they can do about their past, so telling them what they should have done is counterproductive.

Be Specific

Being specific involves both what we need to avoid as well as what we should strive to do. Sweeping general statements using "always" and "never", in addition to probably being untrue, do nothing to help the person feel like they are part of a team with you. Labeling also is to be avoided for the same reasons. Both of these tactics steer us away from the focus of the conversation and do not give the person being confronted, any helpful information as to how to correct the problem.

Being specific also means being intentionally specific about how we perceive the problem and what changes we want to see happen. Clear expectations bring a clear understanding of what needs to be done and can provide the foundation for change.

Further Reading from Skills You Need

The Skills You Need Guide to Interpersonal Skills eBooks.

The Skills You Need Guide to Interpersonal Skills

Develop your interpersonal skills with our series of eBooks. Learn about and improve your communication skills, tackle conflict resolution, mediate in difficult situations, and develop your emotional intelligence.

About Forgiveness, Reconciliation, and Trust

It is important to understand the meaning and role of each so that we don't have unrealistic expectations or create further conflict.

The book "How to Have that Difficult Conversation" gives us some definitions (p. 75):

  • Forgiveness has to do with the past. Forgiveness is not holding something someone has done against them. It only takes one to offer forgiveness.
  • Reconciliation has to do with the present. It occurs when the other person apologizes and accepts forgiveness. It takes two to reconcile.
  • Trust has to do with the future. It deals with both with what you will risk happening again, and what you will open yourself up to. A person must show through their actions that they are trustworthy before you trust them again.

Delineating between forgiveness and trust prevents the other person from concluding that you are holding on to the offense and draws a line in the sand between the past and the future (with a new beginning):

Keep the future clearly differentiated from the past.

Forgiveness and reconciliation do not require that we continue in the relationship. Sometimes a problematic employee will have to be let go. Sometimes a friendship will have to be terminated. And, if we are to continue with the relationship, our trust will be dependant on the other person's commitment to change and our willingness to take the risk of trusting.

Sometimes It Doesn't Go As Hoped

Be aware though that not all crucial conversations will go as smoothly as hoped. Sometimes there are character issues that need to be dealt with before the main problem can be addressed. Sometimes there may be resistance. Cloud & Townsend in How to Have that Difficult Conversation (pp. 159-161) offer the following examples of resistance:

  • Attacking you for bringing up the problem
  • Justifying their behavior and reducing their own responsibility
  • Minimizing the problem
  • Blaming an external source
  • Denial (that the problem exists)
  • Failure to see that they are responsible for the problem

In these cases, it may be necessary to first address these (character) issues. Sometimes it will take several steps to get to step one. You will need to go back and, in love, confront the resistance behavior. Listen, but do not get sidetracked or sucked into the drama. Be ready to own your share of the responsibility, but don't own theirs. Several meetings may be required to get past this obstacle and persistence and patience will be your allies. It may be that you will need to apply consequences if no change is anticipated or seen. If you back down and give in, you will probably have to go back to square one.

The Takeaway

Confrontation is a necessary part of maintaining healthy relationships and should not be avoided. It all comes down to how we say what we need to say. Speaking truth in love and a spirit of reconciliation will increase the chances of a positive outcome. Patience, persistence, and focus should be your allies in any difficult conversation or series of difficult conversations.

Have a great day!

About the Author

Diana Lynne's passions are family, travel, self-improvement, pursuing a debt-free/financially free life. She also loves hanging out with family, friends and being with her dog Skye. Diana is a Quebec City girl who loves living life.