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How to have Brave Conversations at Work

How to have Brave Conversations at Work

ted Learning Theatre of Learning drama based training
Do you have to frequently dodge difficult conversations in the workplace? You’re not alone! Most of us find it daunting to bring up those “undiscussables” – uncomfortable topics or challenges that could cause friction. But what if we told you that brave conversations at work are possible and absolutely essential for success? It might sound intimidating, but with the right mindset, approach and tactics, these awkward conversations can become easier.
In this blog post, we will uncover how c-suite directors, managers and team leaders can make brave conversations happen at work: from preparing yourself mentally to understanding when enough is enough. We’re also going to add a little humour into the mix – because every workplace needs a little bit of fun once in awhile!

Preparing for Brave Conversations – Identifying the Problem, Setting Goals and Choosing an Appropriate Time and Place

Preparing for brave conversations is critical in order to ensure they are successful. Firstly, identify the problem you want to discuss and try to form a solution that both parties can agree on. Once you have identified this, it may help to write down your thoughts so that you have a better understanding of what the issue is, what solutions are possible, and so forth. Setting achievable goals for the conversation will also help structure the dialogue and keep your discussion on track. Finally, choose the right time and place where both parties can be comfortable and assured that there won’t be any distractions or interruptions – no surprises here! With these steps in mind, you’re guaranteed to make brave conversations go more smoothly and work out better for everyone involved.


Establishing Trust – Being Open and Honest, Asking Questions and Showing Empathy

Establishing trust through open and honest communication, asking the right questions and showing empathy can be the difference between success and failure when conducting a difficult conversation. Creating an environment where both parties feel safe to express their thoughts, feelings and opinions will lead to productive dialogue that all parties can benefit from. Courage, rather than avoidance plays a key role in assessing any situation – identify the facts to deal with it, take ownership for any mistakes or confusion that may have occurred but ultimately try to focus on solutions and moving forward constructively. If all else fails, try adding a bit of humour – not only will it lighten the mood but there is no denying that it makes almost anything more enjoyable!


Owning Your Part – Taking Responsibility and Acknowledging Feelings

When it comes to facing the ‘undiscussable,’ brave conversations can provide us with an opportunity to take ownership of our part, and explore, acknowledge and work through our own feelings – as well as those of others. Breaking down walls and being open to learning from difficult discussions will help redirect energy towards a mutual goal; a step in the right direction! Although having the courage to start these sometimes-uncomfortable conversations can be hard, listening actively and staying mindful are the key elements needed to bring about positive results.


Speaking Your Truth – Using “I” Statements and Staying Calm

Having brave conversations can be difficult, especially when you need to speak your truth. It can take time to master the art of using “I” statements without adding accusations or blame. When partaking in a conversation like this, it is important to remain calm and use non-aggressive language. This way you would still be able to really get your point across without fear of offending someone else or seeming hostile! However, learning how speak up is worth setting aside the time for as you will develop better communication and social skills throughout which will help you voice your thoughts in the best way possible.

Reaching a Resolution – Exploring Solutions and Agreeing on Next Steps

Initiating a brave conversation can sometimes be the hardest part. But, know that by doing so, you are creating a pathway for exploring successful solutions and agreeing on next steps to reach a resolution. Humour can help make the journey easier, lightening the atmosphere and allowing you to weigh up suggested options with courage and clarity. Together, these steps will help your team move forward in unity and confidence; while building relationship trust. Remember to take an open-minded approach – this is how effective collaboration is effortlessly gained!


Reflecting on the Conversation – Learning from Mistakes and Celebrating Successes

Having a brave conversation can be a daunting task but is an important step to open up dialogue which may have been avoided. It can give us the opportunity to learn from our mistakes and also celebrate successes that have been achieved as a result of our discussions. Reflection on a brave conversation may be difficult in the moment, however, understanding what went well, what could have been done better and how to continue the dialogue will all help lead us to successful outcomes going forward.


Having hard conversations is not easy, but having them is often far better than not talking about something. Preparing for such brave conversations requires you to identify the problem at hand, set a goal for resolution, and choose an appropriate time and place in which to discuss the topic. Establishing trust amongst those involved is key through being honest, asking questions and showing empathy. Talking about your part of a situation can be uncomfortable – as can speaking your truth by using “I” statements whilst maintaining calmness – yet these are both important if any meaningful resolution is to be reached. Once a solution has been settled on, it’s important to reflect upon what was learnt during the conversation, including how it went wrong and celebrating successes along the way. Therefore, although going into difficult conversations with loved ones can seem daunting, approaching them with an open mind, coupled with an understanding of how to participate effectively will help to ensure they don’t lead to hurt feelings or regret and may even strengthen future relationships.

Justin Smith Essex - ted Learning Theatre of Learning drama based training
Justin Smith-Essex

Justin is the Group MD of Squaricle Group & one of the co-founders & Managing Director of ted Learning.