It's not mean, it's CLEAR - how to have challenging conversations

Updated: Nov 13, 2019

What is it about challenging conversations that makes it so hard for us to say what we really think?


In leadership roles I often see these conversations play out in two ways. The first - the leader is so worried about offending the team member that they beat around the bush, softening the message to the point where quite often the point they are making is SO diluted that they haven’t even really addressed the issue. They then wonder why nothing changes.


Second – the leader tips so far away from their natural communication style, that they become quite abrasive and too direct. They usually bulldoze their way through the conversation to the point that it is no longer a conversation, because they aren’t prepared to ask for the TM input and potentially change their perspective on the situation. There is no intention to offend or upset but they lose their empathy and don’t come across in a natural way. The Team Member is offended, and more than a little pissed off! They feel misunderstood and told off. The Manager then wonders why nothing changes, or the situation gets even worse!



Conversations like this typically involve people disagreeing about what really happened or what should have happened. It is based on the assumption that I am right, and you are wrong, and it often leads to arguing and debating. This is where people spend most of their time during difficult conversations. Who’s right? Who’s wrong? Who’s to blame? Who did their part and who did not? This conversation is often filled with many assumptions that are not true, which increases the complexity of the problem. People often get locked into their story being the right story and seeing the other person as “the problem.”


In my opinion, these situations come about from a lack of planning from the Leader on how they will structure the conversation. Of course, we don’t want these conversations to feel scripted, but we do want some confidence in our ability to lead the conversation constructively and get it back on track if for some reason it hasn’t gone to plan.


This is where many difficult conversations begin to fail. It is very hard to recover from a poorly crafted and poorly delivered opening statement. Your opening statement can be viewed as an honest invitation or it can be perceived as a threat that actually shuts down the other person. Your opening statement has the greatest chance to influence a positive result. It can also be the most stressful part of the conversation.


People who are very successful at difficult conversations achieve two things: one, problems are solved and two, relationships are maintained and improved.


In Kim Scott’s Radical Candour, she talks about strong leadership being defined as challenging directly, whilst showing that you care deeply. She describes this principle as having the willingness to say something that might piss someone off, but you are doing it for the greater good of that person. Her principle is summed up by “It’s not mean, it’s clear!” If you can show that you care for someone or a cause, but that something challenging needs to be said then you have a much greater chance of getting the result you want/need. (that isn't a green light to just say whatever you think! Constructive is the key word here!)


Taking time to develop in soft skills such as challenging conversations, mean clearer communication with your team and less time spent on team issues. The Talent Mill delivers workshops on this topic and many more.


To learn more about these workshops that are tailored to a workplace, or for dates for a group session please contact us directly!


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