The Dos and Don’ts of Handling Courageous Conversations


Is there a challenging conversation at work or in your personal life that needs to happen that you keep putting off? We all face difficult conversations that need to be handled, but we all dread them. We can call these ‘Courageous Conversations’ because they oftentimes require so much courage to handle. In your personal life, this can be a conversation with a spouse, parent, sibling, or friend. In your work environment, this can be a much-dreaded conversation with your boss, your colleague, your client.

Table of Contents

What IS The Conversation Gap?

 Seven out of ten American employees would rather avoid discussion on an important work issue than tackle it head-on, according to a new study by Bravely.

This gap – of conversations that need to happen but are being avoided – negatively impacts the engagement levels and the productivity of those involved. It can also serve as the foundation behind passive-aggressive behaviors in the workplace that lead to high turnover numbers, as employees end up quitting instead of speaking up.

So, Courageous Conversations: We know that we need to have them. Some issues need to be addressed. We also know that sometimes, by initiating these courageous conversations, we are taking a risk. A big risk. Who knows what the reaction may be, and how the conversation may end? Whether at work or home, the implications and the concerns of having a Courageous Conversation are quite similar: hostility, detachment, loss of interest altogether, highly emotional reactions that are hard to manage, anger, etc.

Should I Have the Conversation – Or Avoid It?

 For many people, the option of avoidance is tempting. We may be anxious about the ramifications of these conversations and not want to deal with them. After all, our mind prefers pleasure to pain, and if we can avoid an unpleasant or potentially painful situation, it will always pull us in that direction. The problem is that through avoidance, we simply do not accomplish anything. When a Courageous Conversation needs to take place, avoidance will only lead to a deterioration of the situation as we grow angrier and more frustrated. Sound like a productive work environment or a happy personal life? Not really.

On the other hand, you should avoid making a hasty decision when it comes to having a courageous conversation, simply because of the possibility that it may not be justified; perhaps it was a single incident that you have blown out of proportion and overreacted towards. In such a case, headstrong confrontation may not be the smartest move.

So if it’s important to initiate these conversations quickly in order to take care of situations before it gets worse, and it’s also important to not be too hasty in your decision to initiate one, how are you supposed to know when it’s appropriate to have a Courageous Conversation?

Here are three questions to ask yourself if you are considering initiating a Courageous Conversation:

  1. Is this important?
  2. Is this a pattern?
  3. What can I gain out of this conversation?

If it is important if it is a pattern and if having the conversation is about making real progress along with a genuine effort to also hear what the other person has to say (as opposed to initiating the conversation in order to blow off steam), then you have a green light for Courageous Conversing.

What is Avoidant Communication

When it comes to actually carry out a Courageous Conversation, some people are so concerned about the consequences of confrontation that they end up delivering the message in a foggy, obscured manner. This behavior is Avoidant Communication. What had to be said was not really said clearly, and the recipient is quite likely not to really get it. This is probably the worst place to be in terms of interpersonal dynamics because the conversation had supposedly happened where in fact it did not, the other person has no idea what you had actually meant to say and nothing was accomplished.

4 Tips to Get Your Message Across

It is so important to be clear in what you say when you decide to have a Courageous Conversation with someone. Here are your four golden rules to make sure that your message comes across, and in the clearest and most effective way:

  1. Make sure everything you say is accurate and backed up by facts
  2. Avoid unnecessary repetitions and expanding your message with an excess of adjectives, to prevent lack of accuracy. Stick to the facts and make sure that they are accurate.
  3. Practice ahead of time, many times, as preparation for your meeting
  4. Prepare to receive feedback from the recipient as well. They must have their own perspective on the situation at hand, and may even have some feedback on your behavior as well. As much as you want to be listened to and respected, your recipient may have some feedback and perspective that you might not have thought of. Be prepared to not only convey your own messages, but also to be an attentive recipient.

Courageous Conversations Cheat Sheet

 As a quick cheat sheet, here is how you have a courageous conversation. Here is what to do, and here is what to avoid:

Courageous Conversations Don’ts

 Here is a list of things you shouldn’t do:
  • Don’t blame
  • Don’t get stuck in the past
  • Don’t use examples for finger-pointing
  • Don’t turn subject into a hallway talk
  • Don’t be combative
  • Don’t make it personal

Courageous Conversations Do’s:

Here is a list of things that you should do:

  • DO notice and compliment change
  • DO say what needs to be said clearly
  • DO stick to the point and be consistent
  • DO create a collaborative, brainstorm atmosphere
  • DO show optimism about a positive outcome

Courageous Conversations are the Key to Productive Relationships

I cannot stress this enough. The ability to be a clear, courageous and productive communicator is at the heart of success. You cannot lead effectively unless you are a solid communicator. You cannot have productive relationships at home and at work if you are avoiding conversations that need to happen. If it is important, if it is a pattern and if you can gain progress, productivity or a better relationship with the other person by having the conversation. Get to the point and have it. You so often have so much more to lose by avoiding courageous conversations than by having them.  

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Dr. Michelle Rozen

Dr. Michelle Rozen, Ph.D., is a highly respected authority on the psychology of change. She is one of the most booked motivational speakers nationwide as well as internationally, and a frequent guest on media outlets such as NBC, ABC, FOX News, and CNN on topics related to dealing with change in our world and in every aspect of our lives, so that we can do better and feel better.

Her most recent book, 2 Second Decisions helps people power through with their most challenging decisions through turbulent times.

Dr. Michelle Rozen consistently speaks for Fortune 500 companies and her clients include some of the most recognizable companies in the world including Johnson & Johnson, Merrill Lynch, Pfizer, and The U.S. Navy. She holds a master’s degree and a Ph.D. in Psychology and resides in the greater NYC area.

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