How To Have Difficult Conversations


Whether we delay or avoid them, there comes a time, a moment of truth when we realize that we must a have conversation, with a family member, a friend, a team member, an employee, a work colleague, or even a leader. Typically, by the time we pluck up the courage to have this essential conversation, the troubling speech, action, or behaviour that began as the proverbial “molehill” would have mushroomed into a “mountain”. You see, by avoiding the issue, trivializing it, excusing it away, or ignoring it all together, it will not magically disappear. What will most likely happen is that it will grow exponentially when it is left unchecked. The key to avoid this is to have a conversation that will break through barriers, especially lack of awareness and understanding about the impact of our behaviour on others.



Whether we are part of a family, work, or any other type of social group or team, each of us has the potential to offend others in words or actions. The reality is that offences will come:

  • There are some persons who display offensive speech, body language, actions, and behaviours so infrequently that their family members or peers may not even think about addressing the issue, or may just chalk it up to the “the pressures of life”.
  • There are other persons who exhibit these issues so frequently that they have become a pattern that others have come to expect, and sadly, even accept over time.

Let us face it, we will offend others and others will offend us. Whether our offensive behaviour is normal or abnormal, affected persons have the right to address it and seek a resolution. Where warranted, we should have a conversation.



There are many reasons why we should take any concerns that we may have about the difficult nature of the conversation very seriously:

  • The subject matter is often of a sensitive nature.
  • This type of discussion requires great tact.
  • The conversation may stir up negative emotions and memories for both parties.
  • The discussion can take us into unknown territory because we cannot accurately predict how any of us will respond.
  • The outcome is essentially unpredictable and may even worsen the situation.

Notwithstanding these valid issues, we should not let them paralyze us into inaction. Instead, we must counteract them through proper planning and preparation.




Here are some critical first steps that we should take before venturing forward:

  • Observe the frequency of the troubling behaviour to determine whether it is isolated or a pattern.
  • Evaluate the impact of the issue, especially how it is affecting relationships, performance, and productivity.
  • Identify what must be addressed, how quickly, and by what means, for example a meet up in a social space or a structured meeting in a private setting.
  • Identify the motive for addressing the issue, for example, genuine concern for the individual, improving relationships, correction, or driving team or group success. Ensure that the motive is pure and free of the desire to blame, shame, or avenge.



We should try to discuss challenging issues as they occur and not allow them to pile up. Here are some must dos when planning and preparing to host the conversation:


Request a meeting with the person and mutually agree on a time and place. State the reason for the meeting clearly in a non-threatening, unemotional way, for example, “I would like us to meet to talk about the disagreement we had this morning”.


Prepare yourself physically and mentally by doing the following:

  • Set aside a block of uninterrupted time for the meeting.
  • Clear your mind of preoccupation with other matters, and preconceived notions and assumptions about the incident to be discussed.
  • Adopt an attitude of open-mindedness, humility, empathy, and problem solving.
  • Believe that you are going to get either an immediate solution or a breakthrough.



Here are some tips for effectively managing the difficult conversation:


Set The Tone

  • Welcome the person and enquire about his/her wellbeing.
  • State the motive in simple, clear language, and ask the person to share concerns.


Stick To The Facts

  • Stick to the topic, using factual examples rather than opinions or guesswork.


Avoid Threatening Or Accusatory Body Language

  • Use non-threatening body language and avoid finger pointing, shaking of the head,” steupsing”, or rolling of the eyes.


Speak In A Matter-Of-Fact Way

  • Speak in a straightforward, non-accusatory, non-judgmental manner, free of labelling or name-calling.
  • Avoid phrases like “you always/never…”, or “you do that every time”, which are essentially inaccurate generalizations.


Give The Other Person The Opportunity To Speak Freely

  • Allow the other person to speak without interrupting or criticizing him/her, devaluing his/her opinions and feelings, or making excuses.


Be Accountable For Our Actions

  • Take responsibility for our part in contributing to the issue, admit any wrongdoing on our part, and apologize sincerely.


Collaborate On A Solution

  • Ask the other person to identify what we can do better next time.
  • Ask the other person to identify what he/she can do better next time.


End On A Pleasant Note

  • End on a pleasant note even if we did not get the result we desired.



We must trust the process as change is usually gradual rather than instantaneous. Although we may not immediately see the change we desire, we must choose to believe that there was a breakthrough. We should continue to monitor the individual’s behaviour or performance, encourage him/her, or escalate to another person or another type of intervention as required.