How to Prepare for a Difficult Conversation

By Rachel Verlik, PCC

Let’s be real- NO ONE likes having difficult conversations.  They can be awkward and uncomfortable, with high stakes and little expertise in having them.   And because we don’t like them, we either botch the delivery, get angry, or avoid them altogether.   In any of those cases, the reason for the difficult conversation does not get solved, nor go away. We end up back at square one at best, degrading the relationship at worst.

Sound familiar?

So how do you know when you’re in a difficult conversation?  In the book “Crucial Conversations,” the authors describe a crucial conversation as having three components: high stakes, opposing opinions, and strong emotions.  With a cocktail of those three components, no wonder we may not do our best!   The good news is that with awareness and practice, we can become more adept at navigating these types of conversations.

You might ask -how can one best prepare to have a difficult conversation with someone? Below are a few tips to consider before you have the conversation.

  1. Understand your “powerful why”: What is the REAL reason that you need or want to have this conversation? What do you REALLY want?  For example, you may have a colleague with whom you continually don’t see eye to eye.    “Softer” discussions have not led to changes.  Take an inventory of what you really want from this colleague.  For example, is it about timely responses to your emails or is actually about feeling respected?
  2. Know Your Triggers: What makes you really mad?  What if someone pushes a hot button of yours? How will you react?  Deep down, we know ourselves better than anyone else does. Be honest with yourself about what angers you, how people know you are upset, and how you react.  This is a case where practicing and preparing is the best course of action – it will allow you to be armed with the proper exit ramp if emotions get high and you sense old patterns returning. The good news is that we CAN teach ourselves to react in different ways.
  3. Timing:  Know under what circumstances and time of day you’ll do your best . If you have a long and stressful commute, don’t have the conversation first thing when you get in.  Know your audience as well.  Create an environment and tone that will allow both you and the other person to have a productive, vulnerable and open dialogue.
  4. Physical Preparation: If possible, make sure physical needs are well attended to.  Be well rested, with an adequate amount of satiety and calm.  This is not an activity to undertake, if at all possible, when you are exhausted or “hangry!”
  5. Relationship as Primary: Last, but definitely not least, really embrace that the goal is to keep the relationship intact as primary throughout the conversation. This may mean being curious when you want to shut down, or realizing that both of you have high emotions that are not resulting in productive dialogue and may need to pause the conversation for another time.

It’s been said “If nothing changes, nothing changes.”  If you have attempted difficult conversations in the past and haven’t had much success, take an honest look at the overall approach.  Did you really know what you wanted?   Did you know what your triggers were?   Did you approach the other person when both you and s/he were ready to have a productive conversation?  Did you keep the relationship as primary?  If any of those were not at play, perhaps it means pausing and readjusting for your next difficult conversation.



One NOT difficult conversion is speaking with Rachel about your communication goals!