The Dos and Don’ts of Handling Courageous Conversations

  • New York City, New York, United States

Author:  Dr Michelle Rozen

Short Description

The Dos and Don’ts of Handling Courageous Conversations 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 […]

The Dos and Don’ts of Handling Courageous Conversations 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.

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?

To 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.

The Dos and Don’ts of Handling Courageous Conversations

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 Conversationing.

When Communication Happens but Does Not REALLY Happen

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.

The Four Golden Rules for Getting 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 five 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 Dos and Don’ts

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:

  • 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:

  • 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 It All

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.  

Contact Us at WeSpeak Global and follow us on Twitter

The articles, video and images embedded on these pages are from various speakers and talent.

These remain the property of its owner and are not affiliated with or endorsed by WeSpeak Global.

Similar to The Dos and Don’ts of Handling Courageous Conversations

Lisa Orrell

Successful women in leadership roles manage their Personal Branding Benefits on a daily basis; and they started focusing on creating theirs early-on in their careers. Why do they focus on Personal Branding? And why has it become such a hot topic in the workforce today? Smart women in business understand the basic concept that every […]

  • Author: Lisa Orrell
Dr. Floyd Spence | Top Of Your Game

Power posing for success is a simple strategy that you can use to reduce anxiety, improve your ability to deal with stress, and boost your confidence. Besides, it takes less than two minutes and produces immediate results. Adopting a Wonder Woman’s pose might change your results or even your short and long-term success. Power Posing […]

  • Author: Dr Floyd Spence
David Avrin

Stop shoving Do-it-Yourself Options  technology on your customer that serve you, but not them!   I drop in to my local Wells Fargo branch to get a document notarized and the teller at the counter directs me to scan the QR code on the poster nearby to get on their “digital waiting list.” I say […]

  • Author: David Avrin
Dr. Darren Coleman

Defining great brand values: Five practical pointers A surprising number of brands have values that are about as useful as a chocolate fireguard. Seriously. They do. Unfortunately, this only becomes apparent when brands try to bring their values to life via the experiences they want to build. Things grind to a halt because their brand […]

  • Author: Dr. Darren Coleman
WS Logo 512

I have found that running gives me time to think, running give me time to introspect and running helps me heal so WHY ARE WE RUNNING?. I have embarked on all these journeys over the past 12 years for probably two main reasons. I suppose the first is the selfish side. It’s something I love […]

  • Author: David Grier

Extreme explorer, Cipla Foundation trustee and ambassador, David Grier, the First person to run The Great Wall of China in both directions and fellow extreme athlete, Andrew Stuart have passed the half-way mark of their gruelling 70-day, 4200 kilometre journey across the Great Wall of China.   This challenge is a feat that Grier already […]

  • Author: David Grier

When I am working from home, one of my favorite places to go when I need a break is my daughter’s apiary (bee yard). I am absolutely fascinated by these amazing creatures and WHAT YOU CAN LEARN. Between their work ethic and how they function together as a colony, I think I could sit and […]

  • Author: Jones Loflin
kelly swanson - Why Leaders Need To Be Good Storytellers

Me to My Husband, Bill:     Bill – look! My phone is blowing UP with all these stories about people getting this flesh-eating bacteria from getting into the ocean! Bill:    You’re kidding. (Not even breaking stride in his email checking) Me:     It’s true! It’s right here. A man who’s about to lose his arm. A 12-year old who is about […]

  • Author: Kelly Swanson

Our Mission

We are your partner creating memorable and engaging experiences that go beyond the event itself.

© All rights reserved 2025. Created using VOXEL THEME