Difficult conversations can cause anxiety because it is not always comfortable, at times the risks are high and we are not guaranteed what the outcome might be. The difficult conversation cannot be postponed into perpetuity; it can make the difference between success and failure in a relational or organizational context.

I am sure at some stage of your leadership journey you had to, or will in future have to deal with some of the following very difficult conversations:

  • business is down and you have to discuss with a staff member who had more than 20 years of loyal service, about unavoidable redundancy of his/her position
  • your teenage daughter whom you’ve invested in so much and had great plans for her future, in her matric year reports to you that she is pregnant
  • a business partner who is overextended in other activities and never available at critical moments to take collective responsibility for key business decisions
  • you discovered that your spouse is addicted to gambling or pornography
  • a very close friend betrayed your trust by discussing a personal and highly confidential matter about you, with other people in a malicious manner.

Wherever there is a high expectation environment, difficult conversations are inevitable. In relationships there is a constant need to have these difficult conversations; we avoid it at our peril. It is not a matter of me versus you but a matter of us versus a problem that might erode the cohesiveness of the relationship.


Mindful of the fact that engaging in difficult conversations are not that easy, we will be well advised to prepare ourselves appropriately for this important engagement. Our preparation however, should not only focus on the Head journey – what should I do? It requires more importantly, to focus on the Heart journey – who will I become? The net effect of the engagement should be to what extent it restored joy, a common purpose and cohesiveness of the relationship. I would like to recommend that you honestly reflect on the following key elements in your preparation:

1. What are my motives?

Is it to win a debate or engage in real and meaningful dialogue? Is my engagement punitive or restorative? Do I just want an audience or really solicit an honest opinion?

2. Write down the main points

No assumptions or generalizations; points should be factual and concise. Ascertain your own understanding and attitude about the situation or the individual involved. How would I have liked to be treated if I was on the other side of the equation?

3. Appropriate setting

Arrange for a place where you can have an unhindered engagement with sufficient time at your disposal. Email correspondence should never be a substitute for real engagement. Once confirmed, act; do not postpone indiscriminately

4. Prayer

Ask for God’s wisdom, guidance and responsive hearts.


I recently read an article of the American Management Association, termed the CANDID approach in difficult conversations which I found quite useful. It goes as follows:

Conceptualize the message to create a neutral opening

Ask questions based on the other person’s response

Normalize the situation

Discuss the details – factually and neutrally

Incentivize the outcome

Disengage from the discussion

We live in an era where people can so easily drift away from commitment. The success or failure in any relationship is dependent on how genuine and sincere we can engage in meaningful conversations, even the most difficult ones. If we do not walk in relational integrity by sometimes asking the hard questions, when challenges come our way – blaming, naming and shaming will be our default position.

‘’ When you are judging someone, you have no time to love them. “( Mother Theresa )

The key is to have a meeting with yourself, before you meet others. This will greatly assists in a mutually beneficial outcome and protect you from prejudice and being judgmental.  Let’s not shy away from speaking the truth in love – keeping our motives pure, content truthful, tone neutral and attitude gracious.

Let the discussions begin! 

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