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How to have Difficult Conversations

  • Writer: Wendy Marshall
    Wendy Marshall
  • Mar 15, 2023
  • 4 min read

Do you find yourself avoiding conversations because you think they may be difficult?

I know I do, that is until I give myself a good talking to, outline my plan and embrace helping another human.


"The way we see the problem is the problem".

The problem is that avoiding them does not make them go away or solve the problem that occurred creating the need for a conversation that may be difficult. As Stephen R. Covey says, "the way we see the problem is the problem".

What is in the way is the way because what we avoid becomes bigger in our minds and we then give situations a meaning that may not be real or truthful. We are meaning-making machines and our amazing minds can create all sorts of stories and scenarios on how situations may turn out.

The fact is that some conversations can be difficult, but that does not make them impossible, they may just be uncomfortable. 'I'm-possible' is a different way to look at the word 'impossible' because when it is important it is possible, it is about finding the way. Having conversations that may be difficult is a part of life and is particularly important in business as well.

The truth is that when we stretch our comfort zone and jump into that fear zone of facing what is uncomfortable we often find out that what we feared or avoided is not as bad as we perceived it to be. So when you can face that fear of having difficult conversations, you stretch your comfort zone even more and you move into your learning zone.

Your learning zone is where you have moved out of your way, embraced the opportunity and gained knowledge of how you can approach difficult conversations. When you put that knowledge into practice and have difficult conversations you will realise you have grown as a leader. This growth comes from how you think and embrace being comfortable with being uncomfortable. Your comfort zone has now stretched to include the growth zone.

This constant stretching of your comfort zone is about embracing being comfortable with being uncomfortable and when you do this new growth opportunities exist because you have created your opportunities to learn.


It is that simple! Yes, I know you are probably thinking but it is not simple and I know I need to do it, I need to learn. Like any skill, we want to learn it starts with being aware of the need or desire to learn. As humans we have the capability to learn anything we put our minds to, you just have to want to do it.

Having difficult conversations is a skill to learn as a leader in life, relationships and business. When you do there exists the ability to help others be the best they can be and isn't this what being a leader is all about?

Here are a few tips for approaching difficult conversations

Listen to understand

Focus on the conversation being about the other person, not about you. Put aside your doubts and uncertainties to focus on listening to what the other person has to say. Give them a safe space to share their thoughts, feelings and experiences of what is contributing to the need for the conversation to take place. Listen with patience, empathy and humility. Avoid the temptation to interrupt, defend or judge. Every human being has a map of their world and of situations, so be present and allow them to share their view (their map) of the situation so that you can understand before you try to put your view forward. Being willing to listen and having difficulty is a reflection of your character and therefore about trust. Trust in yourself to have the conversation and build trust with the other person.

Respond with intent and integrity

Responding with intent is about your motive for the conversation, and being transparent about your agenda and what is to be achieved. When you have an understanding of the other person's perspective on the situation, share your views with clarity and confidence, even if you are not feeling confident. Behave like to leader you want to be and you will become that person, whether that is a leader in business, family or relationships. Prepare your notes before, be sure you are clear on your perspective and have the willingness, to be honest, authentic and fair. This is how you can embrace uncertainty and share your map of the situation, your view of how it is or how you think it needs to be. Embracing the uncertainty of not knowing where the conversation will go, is the pathway to finding a solution.

Aim for a win/win outcome

There is always a need to be flexible in your thinking, bringing humility to the conversation that demonstrates your understanding of the situation. If you are rigid in your viewpoint and not open to other ways of thinking, you will always find it difficult to approach having effective conversations, difficult or otherwise. Being flexible does not mean you have to agree, it is about being able to discuss with each other, clarify and explore options to find an outcome that is a win for all. If the other person is rigid, that is on them, if you are rigid, that is on you. As in all situations we only have control over ourselves, not other people. Everything is a choice and as the one who is leading the conversation you have a choice to aim for a win/win. The outcome to aim for is to have the conversation and move forward with a solution that is good for all. Doing this in a way that is congruent and aligned with your character as a leader is the way to do it!


Practice these tips in any conversations you are having, not just the difficult ones. We have two ears and one mouth and only one of them can shut. When you can listen to understand and respond with great intent, there is a way to navigate to a great outcome for all involved. Give it a go, you will be amazed at the difference.


If you would like to learn more, book a Free Strategy Session with a lead coach at Leaders Network.








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