How To Have a Promising Courageous Conversation


How often have you heard someone say, “Sounds like it’s time for a courageous conversation!”?

I have to admit, hearing those words sends a series of thought-reactions through me.

First of all, when you need to have a “courageous conversation” with someone then the issue must be something significant and sensitive, otherwise you would not need to label it thus.

Secondly, when you need the word “courageous” to describe it then it is sure to take you and/or your conversation-partner out of your comfort zone.

Third, labeling it a “courageous conversation” implies the desire for shifts in thinking, being, doing.

Fourth, initiating a courageous conversation suggests that you are ready and willing to challenge the status quo.

Finally, participating in a courageous conversation indicates the belief that two parties can have an open, honest discussion that will benefit the outcome, rather than an individual.


A courageous conversation is one in which you take the opportunity to address things that are weighing you down by speaking up and expressing your feelings.


Courageous conversations occur in all settings and relationships.


They are necessary:

  • in the work-place, between colleagues and between employers and employees
  • in family relationships, between parents and children, siblings, extended family
  • in friendships
  • in partnerships


I know, the conversation may not be comfortable, and it may not be easy, but it is necessary if the ignored situation is unhealthy for those involved.

I also know that sometimes it takes a while before we are ready to initiate this particular type of conversation.

For example, we may like to give others the benefit of the doubt, that this conflicting feeling associated with the situation is just temporary and it will work itself out.

We may consciously choose to ignore the situation for a while, or live with it because it is not “that bad”.

We may hold out hopes that those involved in the situation will take some cues from us as to how to shift the circumstances rather than having to spell it out for them.

These are all valid reasons to hold off on a courageous conversation.


But one day, one moment, you will just know that it is time to address whatever elephant is in the room, and you will know that not doing so is no longer a possibility.

Holding these conversations from a space of authenticity, and seeking understanding and the highest good for all from them allows you to navigate your courageous conversations with grace and clarity.


Here are a few tips to consider when embarking on your courageous conversations:


Be confident

Yes, it is a challenging spot to be in, but you know that the only way forward is to have the conversation.

When you overcome your fear of all the “what-ifs” and replace it with your certainty of the “what-can-be’s”, you are setting the intention for a new and improved conversation to occur. Shifting your mindset away from fear and into confidence in your decision and vision is the first step.


Be clear

Your confidence comes from your clarity.

When you make the decision to embark on a courageous conversation, the clearer you are in your purpose, the more smoothly the conversation goes. Knowing why you are holding the conversation and what you hope it will achieve are key to its success. If you are unclear in your purpose, the other participants are unclear also, which leads to confusion and unresolved situations.


Be comfortable with the uncomfortable

This is not an easy task, holding courageous conversations.

Expect to be uncomfortable. There are many aspects of this process which can cause discomfort: the topic or situation itself, the person you need to talk with, the role you need to play in the conversation, the reactions from the other person, even the timing can be uncomfortable. Going into the conversation with awareness that it may not be your dream discussion is huge. Do your best to embrace the discomfort of the process, knowing that it will pass as you let go of it.


Be curious

Courageous conversations award us the opportunity to question and reflect upon our own beliefs as well as getting to understand others’.

When a situation merits a courageous conversation, listening to others provides a window into their soul and motivations. Ask questions. Hear their views and intentions. Understanding where they are coming from allows you to steer the conversation most productively.


Be collaborative

By opening yourself to their perspective you create opportunities for collaboration.

Your conversation has a purpose. Something that is happening (or not happening) needs to change. When you listen to others in the conversation, they feel that they have been heard and they feel like they have an opportunity to be a part of the outcome. You co-create the trajectory.

Can this always happen? Does every courageous conversation lend itself to collaboration? Maybe not always, but when it does, it is quite a powerful component.


Be compassionate

The most important thing to remember is that you are both human beings.

Courageous conversations are yucky, and difficult, and do not always feel like a win-win outcome in the moment. Always remember that everyone involved has feelings and hopes and dreams. Honor the emotions. Sometimes resistance is fear-based, sometimes actions and words reflect passion for the situation. Be kind - to yourself and the others in the conversation with you.


Once you break through your fears, clarify your purpose, embrace the discomfort, open up to others, all while honoring your true authentic self and theirs, the possibilities are endless.


True, courageous conversations can be uncomfortable, but without them you may wallow in confusion, resentment or anger, which only makes any situation worse.

Dare to take the leap!

Courageous conversations are healing and propel you forward.

Once you have one, your mind is eased and the load you are carrying grows lighter.

Courageous conversations are what shift the world.

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If the sun is shining, my Crosstrek is calling me to fill up her tank, throw open her sunroof, and head for the back-roads. With wind in my hair, I smile at everyone I see. Grace smiles back at me (even through the trees).