The Reflection Series Part 6: The Necessity of Having Difficult Conversations

A Simple Method You Can Follow When A Difficult Conversation Is Needed and Necessary

Photo by Christina @ on Unsplash

When’s the last time you had a difficult conversation? If you are in a relationship with, well, anyone, it is likely you’ve had a difficult conversation recently. They are a part of being in a relationship with someone. Yes, difficult conversations are needed and necessary in the workplace, and they are also needed and necessary in our private lives.

It is through the most difficult conversations where growth for the people inside of the conversation becomes possible. When we avoid these conversations, nothing really happens. Actually, if anything, when we avoid difficult conversations, the relationships we have are built upon a shifting foundation.

Meaning, unstable, and unreliable. Why?

Because, we’re not being true to how we think and feel when we avoid things that are difficult; and, difficult conversations are not removed from this truth.

Many people struggle with having these conversations, just as I once did. Truth. And, yes, they are hard. I’ve had many in the past three years, and, yet, there is also something beautiful in the experience of being in that difficulty with another human being, and creating a way forward.

Alright, let’s first consider two concepts, which occur prior to the difficult conversation, and then a very simple, pun intended, as you will soon see, strategy, you can employ inside of a difficult conversation. Ready? Good. Here we go.

Photo by Pablo García Saldaña on Unsplash

Difficult Conversation Continuum

Even in the language, I’ve used thus far to describe a difficult conversation can appear binary. Meaning, either the conversation is in one way difficult, or the opposite, not difficult.

It is important to understand that difficult conversations, like all things in life, live along a continuum. This means that there are many types of difficult conversations, from, let’s say, conversations that are easier, yet still sensitive, to conversations, which are much more difficult.

We can think about them living along a straight line that continues forever, with sensitivity on the far left, and, in a workplace example, a corrective action conversation on the far right. In between?

Many types of conversations. Yet, regardless of the type of difficult conversation, there are several steps we can take to make sure we are ready. The first? Making sure you are clear and that what you understand about the context you are witnessing with the person you need to have a difficult conversation with is true.

Photo by Randy Jacob on Unsplash

Clear and True

What do I mean by clear and true? Let’s take a look.

  1. Clear – that you’ve done the pre-work necessary to understand the context you are witnessing, and that indeed a difficult conversation needs to take place. Again a working example may suffice. Maybe someone on your team is having difficulties at home, or with another coworker, and does not yet have the tools needed to know how to talk about the issue. However, if the employee does not talk with someone about the issue, their work will suffer. In this instance, I would classify this difficult conversation as a sensitive conversation, somewhere toward the left of the continuum. However, it also depends on how long the team has been together, and how long you’ve worked with the employee. If the team is new, and or the employee is new, the conversation will be more difficult. Either way, knowing that the conversation needs to take place and that you are clear on the reasoning is key.
  2. True – true meaning that we’ve taken time to watch the behavior, and reflected upon it. It is super important to avoid emotional reactions to situations as they arise. Taking time to witness behavior gives us a more three-dimensional view. Yes, there are times when we will need to have a difficult conversation at the moment. It happens. However, when we practice applying the clear and true principle, it helps us with planned and unplanned difficult conversations. Both.

Once you are clear and know that what you are seeing is true, you can deploy a very simple strategy to conduct a difficult conversation.

And, yes, I chose this acronym intentionally, as some people find themselves attracted to language. Meaning, they like to use a lot of language when in conversation with someone.

However, using more language than is necessary and needed in a difficult conversation will only make the conversation more difficult and less clear. It is very important to keep things simple.

Photo by Sarah Dorweiler on Unsplash


  • Strategy – having a strategy for how you are going to have the conversation is important. Here are some questions to ask yourself prior to the conversation.
    • What are you going to say?
    • How are you going to say it?
    • Where will the conversation take place?
    • What is your goal for the conversation?
    • What questions might the employee ask, and what are your answers?
    • How long will the conversation last?
  • Intentional – you want to, at all costs, make sure this conversation is created intentionally, once you know your strategy. Again, sometimes these conversations happen at the moment, however, I’ve found that most often, you can take the time needed to watch, learn, strategize, and then create the conversational context. And that is doing things intentionally.
  • Meaningful – the conversation needs to be meaningful. When you create the goal of the meeting, also create the takeaway for the employee. For instance, how is this conversation going to create the possibility of a developmental step forward for the employee? It is important that the conversation includes this developmental step. It is up to the employee to take a hold of that developmental opportunity and do something with it. Just as it is your job as the leader to create the developmental possibility in the first place.
  • Planned – we’ve covered having a plan for the most part. Here I will simply add that taking the time needed to create your strategy and plan accordingly is important. For instance, making sure to clear your calendar leading up to and after the conversation, so you have time to do the necessary pre-work and decompress after. Difficult conversations are called such because they are difficult for everyone, the leader included.
  • Learning – once you’ve created the possibility of a developmental step forward for the employee, it’s time to make sure the theoretical development is pulled into practice or reality. It is your job as the leader to ensure this possibility also exists. Now, the developmental work is for the employees to do, however, you can assist them by implementing a timeline and due dates, and a follow up 1W1 to ensure you are supporting them in their development.
  • Experience – it’s also the leader’s job to ensure that the conversational context is an experience that is safe, and includes both empathy and compassion. Meaning, that everyone is in a different developmental stage as a human being; and people, all people, need safe spaces where they can learn new strategies they can employ in their life to move them forward as human beings. For this to occur, the context needs to be safe, and include both empathy and compassion. Empathizing with someone, simply means understanding where they are free of judgment, and compassion? Means remembering you, as the leader, are a human being just like they are, and have had very similar situations arise in your life.

Wow. That was fun.

Alright, there are several strategies you can employ prior to, during, and after a difficult conversation.

Remember, these conversations are needed and necessary. Really and truly. When we take the time necessary to create safe contexts where difficult conversations can occur, we are paying forward a part of ourselves, and helping someone else move forward in their life. And guess what?

When you create these contexts, you also learn more about who you are as a human being. Always. In every difficult conversation, I’ve ever had, I have always learned more about myself and my own development.

And that, my friend, is movement, and it is beautiful.

#clearandtrue, #continuum, #difficultconversations, #experience, #keepingthingssimple, #meaningful, #planned, #strategy