The difficult convo!

The Difficult Convo

One of the most important skills to develop as a leader, must be that of being able to hold a difficult conversation. I have witnessed schools that are crippled because the leaders are unable to exercise this skill, leaving employees to do as they please, or act without guidance that will help  them to improve and develop. Practising a conversation, and perfecting the skill of being able to hold one, may seem like a small element of leadership but being able to hold a powerful conversation lies at the heart of communication, and therefore, of leadership. 

As Ken Blanchard said in the foreword to Susan Scott’s book, Fierce Conversations, “…no single conversation is guaranteed to change the trajectory of a career, a company, a relationship, or a life, but any single conversation can.”

As a leader, with or without a title, your conversations count. I have no doubt that we all have experienced that nagging feeling after a conversation which we felt could have gone better, as well as that light airy feeling after one that has gone well. So what is it that makes the difference? Well, this is a question that you will probably already have some of the answer to, but a lot of it comes down to clarity and purpose. In other words conversations that are clear and purposeful, and that result in positive outcomes for both parties, can be considered successful. 

In this module I will provide you with a 7 step conversation planning model that will help you structure a difficult conversation so that it meets these objectives. This model is ostensibly for use where you as the leader are having to raise an issue with one of your team, regarding things that they are doing or not doing when they should or should not be. If you follow the model closely you should find, with practice, that both you and the other person will be able to walk away from the conversation more aligned with each other.  

Let’s start off by thinking about the definition of a difficult conversation. In this context it could most accurately be defined as a conversation that needs to happen because those involved are, most likely, in some level of disagreement, whether spoken or not. The purpose of the conversation is to align the thoughts of those involved and to re-establish expectations and outcomes. The structure of the conversation that I have outlined below is based loosely on that outlined by Susan Scott in her book “Fierce Conversations” and it is a model that is highly effective if implemented properly. 

It is a 7 step recipe for a conversation, and from experience, it should really be followed as closely as possible without leaving any of the steps out. Each step has an important role to play in the course of the conversation.

Step 1 is Name the problem. This step requires you as the initiator of the convo to make the reason why the conversation is happening in the first place, very clear. The purpose of this step is to outline the issue as clearly and unambiguously as possible. Try to resist the temptation to use flowery language, or bring up irrelevant or unrelated topics. Just say the issue as it is.

Step 2 is Provide an example. There must be an example of the behaviour that you are challenging to bring up. If you have no example, don’t hold the conversation because this will just be construed as victimisation by the person.

Step 3 is Describe how it makes you feel. There is no shame in outlining how their behaviour has impacted on you personally. Of course you don’t need to go to town on this one but saying something like, “your behaviour has left me feeling disappointed in / worried about / saddened…”. This puts the issue into perspective for the other person and may bring about a different angle to talk about.

Step 4 is where you outline what is at stake. Identifying how that particular pattern of behaviour will play out is important to paint a picture of reality for the person. They may not have, after all, considered what their behaviour might have come across as, or they may not be aware of the impact that their behaviour is having on others. In my experience the vast majority of people don’t like to have a negative impact on those around them.

Step 5 is your opportunity to acknowledge your part in the issue. If you have inadvertently contributed to the issue arising in the first place it is important that you acknowledge and take responsibility for it.

In step 6 you outline your expectations of what you want to see happen next. Make this very clear so that there is no ambiguity in your statements, and so that the person is left with a clear roadmap forward of what needs to happen for the issue to become resolved.

And finally, in step 7 open the door for them to comment by inviting them to add anything that they want to. 

This is the process but like all things it takes time to perfect and craft these conversations. Make sure that you plan your conversations, even writing them down in the first place so that they are almost scripted. All 7 steps should take no more than 1 minute to say and you should expect that you can say them all before the other person responds. Do make this clear at the beginning of the conversation so that they know to listen, hear and digest what it is you are trying to get across to them before they have a chance to speak. For the most part if you go through this process you should find that the responses are far more positive than you were expecting. The main reason for this is that you have been clear and articulate with your conversation, and you have also given a clear road forward for the other person to follow.  

Point of Reflection

Quite often what puts us off guard in a conversation has nothing to do with the content of the conversation at all, and can often be far more to do with our relationship with the person we are holding the conversation with. Think about the different people in your team. Which ones do you feel less comfortable conversing with, and why do you think this is the case?

Personal Development Activity

Planning a conversation (30 mins)

This activity could either be done as a real opportunity, or it could be done hypothetically. The idea is that you get to grips with the process of planning a conversation, and running it through in your head. 


It is very likely that there will be a conversation that you are not looking forward to having, especially if you are already occupying a leadership role. In your leadership journal, plan your next awkward conversation in detail, making sure that you script exactly what you are going to say to the person at the start of your difficult convo. Be sure to follow the steps as they are laid out in the modular material. 

Practice at your whole script so that you know it word for word.