Do’s and Don’ts with tough Conversations

Only seeing the hands and a table with two people across from each other and one pointing a pen down while holding a paper with writing on it in the other hand

A difficult conversation can be something that makes you anxious or gives you stress. Everyone has difficult conversations The question is, what should you not do and what should you do when faced with a tough conversation. This could be personnel matter, a conduct issue, a reprimand, a transfer, a termination, or any of a host of difficult conversations. As an author that specializes in conflict resolution and collaboration, here are some observations to help you.


What not to do


Do not assume.

Do not assume what the other party knows. Often parties think something is obvious, when in fact it is not. Make sure you both have a clear understanding of all of the relevant facts. Ask open ended questions to make sure you both have the same understanding of the facts. Once the facts have been determined, it may be possible to identify the issues so that they can be addressed timely.

Do not attack character.

Good character assumes wanting to do the right thing and do what it takes. When you attack someone else’s character by implying lying, that they are unethical, unprofessional, or wrong this does not help the situation. You may indeed be right, but if you want to have a conversation, this will not help.

Do not exaggerate.

Often you can make a more compelling case if you can embellish the facts or exaggerate the situation. However, this will sabotage the conversation. Again, do not use words like “always” and “never”. Stick to the true facts and do not make a situation sound worse than it is. You may feel that way, but to have a tough conversation you need to avoid the trap of exaggeration.

Do not insult.

This seems pretty obvious. However, using words form above like “never”, “always”, or other phrases like “without a doubt”, “clearly”, “obviously”, or “everyone knows” implies negative connotations on the other party. This can be hard when emotions are running high. Make a deliberate action to not insult the other party. Words matter. Be there to help.

Do not say “it’s not personal”.

Maybe that is true for you. It may be personal to the other party. This ties into the commentary from above not to assume. What may not be important to you, may be particularly important to the other party and vice versa. The other party may respond to you that it is not personal. Be ready for that too. You may be having a hard tie with this difficult conversation, and it may not be perceived that way by the other party.

Do not tell someone else what to do.

No one likes to be told what to do. Rather, ask the other person what they think would be a good way to address the concern. Incorporate them into the decision making. You can lead the other party asking questions like “Would you consider?”, “Have you thought of?”, “What if?”, or “How could we address this type of situation better together in the future?”

These tips are adapted in part from Words and Phrases to Avoid a Difficult Conversation by James R. Detert.


So, what should you do?



What to do



De-escalate the situation.

First, work to de-escalate yourself. Consider the ten points below taken from the book Peaceful Resolutions.


  1. Make sure you do not take it personally.
  2. Decide not to be angry
  3. Use active listening
  4. Slow down
  5. Be empathetic
  6. Be aware of emotional triggers and avoid them
  7. Do not pass judgment
  8. Always be courteous
  9. Work the other person to say yes
  10. Give yourself positive self-talk


By applying these 10 points to yourself you are likely to help the other party to be more reflective of your actions. This may help the other party to de-escalate as well. Work on centering yourself to be calm, confident, and competent with the conversation. Consider bouncing this off of a mentor and possibly practicing this ahead of time to help yourself de-escalate the situation.


Inform the other party beforehand.

Let the other party know the subject of the conversation ahead of time. This will set the stage. You do not have to label this as a transfer, reprimand, demotion, termination, or similar negative implication. You should indicate that it is about the “blank” project, a personnel matter, or similar commentary. This will allow the other party to understand the situation mentally, without clearly outlining the nature of the difficult conversation.


Make it timely.

Do not wait and postpone the inevitable. Timely quality feedback is best for you and for the other party. This will reduce your own stress about having the difficult conversation, and this will bring closure quicker. The other party too would rather have this conversation sooner rather than later.


Pick an appropriate location.

Think about this carefully. Should this be face to face and in a private room? Should you bring the other party to your location to emphasize the importance of the meeting? If you do consider the “what”, “when”, “where”, “why” and “how”. Consider how this may be viewed by the other party and by others observing or hearing about the conversation later.


Be tough on the problem and soft on the people.

Define the problem by focusing on the facts. This is probably the most important aspect of the process. When frustrated our minds like to make simple right wrong decisions. This may imply defining the problem to fit a preconceived solution. Often this is personal. By stepping back and defining the problem differently it may be possible to work with the other party to mutually focus on what you can do together to overcome a past event for example.


Consider the model “When you…”, “I think….” and “I feel…”

if you think this will help the other party to understand where you are coming from and this may help them to open up and share their concerns and feelings too, consider this model. By not attacking the other party and reaffirming your respect for them as a person you are sharing your respect for the other party as a person and an individual.



Other thoughts



For example, with a reprimand, use the techniques presented here, but realize once the reprimand is given, it is over. It is important for the other person to know that you are there to help. You are on their side. Reaffirm with the other party how much you value them. Remind them how much you appreciate them and their efforts. Affirming what we will do together going forward in a positive way is critical to your and their success.





About the author

Mike Gregory is a professional speaker, an author, and a mediator. You may contact Mike directly at and at (651) 633-5311. Mike has written 12 books (and co-authored two others) including his latest book, The Collaboration Effect: Overcoming Your Conflicts, and The Servant Manager, Business Valuations and the IRS, and Peaceful Resolutions that you may find helpful. [Michael Gregory, ASA, CVA, MBA, Qualified Mediator with the Minnesota Supreme Court]