Avoid these mistakes when you have a difficult conversation

​A few years back, I was involved in a ​sports club. There were teams at every age group as well as adult teams. In most cases, those who participated had great fun and were happy being part of the club. But there was one team where there was a major problem – the Under 14’s. Like the other teams, this team had a management team over them. One of the managers was an army man. He treated training like an army boot camp and he ran the boys into the ground. The army has its own way of doing things and I am not going to judge that but these 12-14-year-old boys signed up to play sports; not to join the army. To make matters worse, this manager had terrible communication skills. He had no idea how to have a difficult conversation with the boys when they stepped out of line and it was also apparent that nobody involved with managing the club was prepared to have a difficult conversation with him.

It didn’t take long before some of the boys started dropping out of the team. They stopped turning up for training and matches. A squad of over 30 quickly dropped towards 20. Eventually someone from the club approached a few of these boys to ask why they were leaving. They all pointed the finger at the trainer who treated them like they were in the army. They also stated that they didn’t enjoy themselves which was hardly surprising. The players who remained started to come forward and give the same story; making it clear that they were prepared to leave too. In the end, the remaining members of the management team and the board of the club managed to convince the army man that the team would get all the running they needed by playing games which was more fun for them. It seemed that everything had been sorted.

​Assertiveness Tactics Report

If you need to have a difficult conversation, assertiveness skills will allow you to do so in a confident and composed manner. My FREE Assertiveness Tactics report will give you some great strategies.


Get Your FREE Copy

Two years later, I was standing on the side of the pitch, watching a match featuring the same boys, who were now Under 16. I just happened to be standing next to the army trainer who was no longer involved with the team. To my surprise, he told me that he had applied to manage the team at the beginning of the year but had been told that his application was too late and the management team had already been decided. I realised that whatever conversation had taken place two years earlier had not been an honest conversation. He was completely unaware of the fact that the boys had threatened to give up the sport rather than work with him. I later learned that he had worked with other teams, in other clubs, and kept encountering the same problems.


He was pretending not to know that he had problems with his management style but nobody else was prepared to have a difficult conversation with him; to tell him that his management style was destroying every team he was involved with.


A few years back, I was involved in a local sports club. There were teams at every age group as well as adult teams. In most cases, those who participated had great fun and were happy being part of the club. But there was one team where there was a major problem – the Under 14’s. Like the other teams, this team had a management team over them. One of the managers was an army man. He treated training like an army boot camp and he ran the boys into the ground. The army has its own way of doing things and I am not going to judge that but these 12-14-year-old boys signed up to play sports; not to join the army. To make matters worse, this manager had terrible communication skills. He had no idea how to have a difficult conversation with the boys when they stepped out of line and it was also apparent that nobody involved with managing the club was prepared to have a difficult conversation with him.
It didn’t take long before some of the boys started dropping out of the team. They stopped turning up for training and matches. A squad of over 30 quickly dropped towards 20. Eventually someone from the club approached a few of these boys to ask why they were leaving. They all pointed the finger at the trainer who treated them like they were in the army. They also stated that they didn’t enjoy themselves which was hardly surprising. The players who remained started to come forward and give the same story; making it clear that they were prepared to leave too. In the end, the remaining members of the management team and the board of the club managed to convince the army man that the team would get all the running they needed by playing games which was more fun for them. It seemed that everything had been sorted.
Two years later, I was standing on the side of the pitch, watching a match featuring the same boys, who were now Under 16. I just happened to be standing next to the army trainer who was no longer involved with the team. To my surprise, he told me that he had applied to manage the team at the beginning of the year but had been told that his application was too late and the management team had already been decided. I realised that whatever conversation had taken place two years earlier had not been an honest conversation. He was completely unaware of the fact that the boys had threatened to give up the sport rather than work with him. I later learned that he had worked with other team, in other clubs, and kept encountering the same problems.  
He was pretending not to know that he had problems with his management style but nobody else was prepared to have a difficult conversation with him; to tell him that his management style was destroying every team he was involved with.

​Mistakes when you want to have a difficult conversation

Mistakes when you want to have a difficult conversation

​I don’t know the exact content of the conversation that was had with the army man when all the boys threatened to leave the team. However, I would be confident that some of the club's leadership were guilty of some of the most common mistakes made when trying to have a difficult conversation.

I cover some of these mistakes below:

I don’t know the exact content of the conversation that was had with the army man when all the boys threatened to leave the team. However, I would be confident that some of the club were guilty of some of the most common mistakes made when trying to have a difficult conversation.
I cover some of these mistakes below:

​1. Starting a chat

have-a-difficult-conversation-chat
1. Starting a chat

​If you want to have a difficult conversation; have a difficult conversation. Don’t try to fit it into the middle of a chat. You are only going to confuse the person you are trying to have the conversation with. They will see through any insincere nonsense such as ‘How is everything with you?’ If you are preparing to have a difficult conversation, your body language shows that you have something important to say and that you are anxious. It will be obvious to the other person that there is a difference between your language and your body language. As they don’t know what is going on (because you haven’t told them) they are likely to become defensive and closed to an honest conversation.

Instead, remember that there is a purpose to your conversation and stick to that purpose. You don’t have to be aggressive but you don’t have to be passive either. Be assertive, state your point and make the purpose of the conversation clear i.e. there is a problem which you need to work together to resolve. Cut the chit chat and have an honest, open and assertive discussion.

Resource: How to talk so others will listen

If you want to have a difficult conversation; have a difficult conversation. Don’t try to fit it into a middle of a chant. You are only going to confuse the person you are trying to have the conversation with. They will see through any insincere nonsense such as ‘How is everything with you?’ If you are preparing to have a difficult conversation, your body language shows that you have something important to say and that you are anxious. It will be obvious to the other person that there is a difference between your language and your body language. As they don’t know what is going on (because you haven’t told them) they are likely to become defensive and closed to an honest conversation.

Instead, remember that there is a purpose to your conversation and stick to that purpose. You don’t have to be aggressive but you don’t have to be passive either. Be assertive, state your point and make the purpose of the conversation clear i.e. there is a problem which you need to work together to resolve. Cut the chit chat and have an honest, open and assertive discussion.

Resource: How to talk so others will listen

​2. Not stating your expectations

have-a-difficult-conversation-not-state-expectations
2. Not stating your expectations

​Each of us enters a conversation with our own expectations. We know how we would like things to go and the outcome we want to achieve. Then, if your expectations are not met, we get annoyed, frustrated and angry. We blame the other person for not meeting our expectations. After all, it is easier to blame others.

Of course, when blaming others for failing to meet your expectations, you forget to ask yourself a couple of important questions:

Each of us enters a conversation with our own expectations. We know how we would like things to go and the outcome we want to achieve. Then, if your expectations are not met, we get annoyed, frustrated and angry. We blame the other person for not meeting our expectations. After all, it is easier to blame others.

Of course, when blaming others for failing to meet your expectations, you forget to as yourself a couple of important questions:
  • ​Did I clearly communicate my expectations?
  • Did I check to ensure that the other person clearly understood my expectations?
    Did I check to ensure that the other person clearly understood my expectations?

​The answer is usually No to both questions. So, how can you then blame the other person? How could they meet your expectations when they didn’t understand what those expectations were? So, if you need to have a difficult conversation, take the time to understand your expectations and ensure that you communicate them clearly and; double check to ensure the other person has a clear understanding of what you expect. It may seem like overkill but taking a little extra care up front prevents a great deal of stress and conflict further down the line.

Related article: What did you communicate? It probably wasn’t what you think

The answer is usually No to both questions. So, how can you then blame the other person? How could they meet your expectations when they didn’t understand what those expectations were? So, if you need to have a difficult conversation, take the time to understand your expectations and ensure that you communicate them clearly and; double check to ensure the other person has a clear understanding of what you expect. It may seem like overkill but taking a little extra care up front prevents a great deal of stress and conflict further down the line.
Related article: What did you communicate? It probably wasn’t what you think

Others cannot read your mind. State your expectations clearly

Click to Tweet

​3. Being too nice

3. Being too nice
have-a-difficult-conversation-too-nice

​Despite what some macho business people might tell you, being nice has a place in business. In fact, I believe it should be your default position, though I do occasionally struggle. But when you need to have a difficult conversation, being nice cannot be given top billing ahead of resolving the issue. You must strive to resolve the issue while being as nice, honest and sincere as you can be but resolving the issue must be the number one priority. Of course, if you are well prepared and you know your stuff, you will be able to remain calm, composed and in control throughout the conversation; all of which allows you to be nice.

Where being too nice becomes a problem is when you try to tone down the message or sugar coat it. The problem is the problem. You cannot resolve it if you are not prepared to discuss the full extent of the problem; warts and all. In the example I gave earlier, the nice thing would be to tell the army man that the kids would have more fun and do their running while playing games. The honest thing to say would be to tell him that his management style and communication style was driving a wedge between management and the team and the team were threatening to walk away.

​Only one of those conversations had any chance of resolving the real issue.  Being too nice doesn’t solve problems; it ignores them. That approach eventually leads to bigger problems.

Related article: 4 Reasons why avoidance is not an effective problem-solving skill

Despite what some macho business people might tell you, being nice has a place in business. In fact, I believe it should be your default position, though I do occasionally struggle. But when you need to have a difficult conversation, being nice cannot be given top billing ahead of resolving the issue. You must strive to resolve the issue while being as nice, honest and sincere as you can be but resolving the issue must be the number one priority. Of course, if you are well prepared and you know your stuff, you will be able to remain calm, composed and in control throughout the conversation; all of which allows you to be nice.

Where being too nice becomes a problem is when you try to tone down the message or sugar coat it. The problem is the problem and you cannot resolve it if you are not prepared to discuss the full extent of the problem; warts and all. In the example I gave earlier, the nice thing would be to tell the army man that the kids would have more fun and do their running while playing games. The honest thing to say would be to tell him that his management style and communication style was driving a wedge between management and the team and the team were threatening to walk away.
The issue was his management and communication style and only one of those conversations had any chance of resolving the issue.  Being too nice doesn’t solve problems; it ignores them. That approach eventually leads to bigger problems.

Related article: 4 Reasons why avoidance is not an effective problem-solving skill

​4. Forgetting to save the sandwich for lunch

have-a-difficult-conversation-sandwich
4. Forgetting to save the sandwich for lunch

​One of the most common feedback techniques is the feedback sandwich where you start with a compliment to soften the blow. You then deliver the negative feedback and finally, you follow up with another compliment to ensure that the conversation ends on a good note. I have come to believe that this is a cowardly way to deliver negative feedback and it is certainly another way that being too nice gets in the way of a difficult conversation.

Let’s use a little exaggeration to emphasise just how ridiculous the feedback sandwich is. Take the following example:

One of the most common feedback techniques is the feedback sandwich where you start with a compliment to soften the blow. You then deliver the negative feedback and finally, you follow up with another compliment to ensure that the conversation ends on a good note. I have come to believe that this is a cowardly way to deliver negative feedback and it is certainly another way that being too nice gets in the way of a difficult conversation.

Let’s use a little exaggeration to emphasise just how ridiculous the feedback sandwich is. Take the following example:
  • Compliment - John, you’re such a nice guy and you are always happy and positive in work
    John, you’re such a nice guy and you are always happy and positive in work
  • ​Negative feedback - But the entire workforce hates you and are threatening to walk out
    But the entire workforce hates you and are threatening to walk out
  • Compliment - By the way, I love the job you did on the Anderson project
    By the way, I love the job you did on the Anderson project

​Obviously, that’s a bit extreme but it highlights an obvious question; is the purpose of the conversation to praise John or to the deliver negative feedback which tells him that changes need to happen?  A difficult conversation which attempts to serve two different purposes ends up serving neither.  You usually end up with one of a couple of scenarios:

  • ​ ​The person gets wrapped up in the compliments and fails to comprehend what is at stake with the negative feedback so, no real change takes place.​​​​
    The person gets wrapped up in the compliments and fails to comprehend what is at stake with the negative feedback so, no real change takes place.
    John, you’re such a nice guy and you are always happy and positive in work
  • ​​They only hear the negative feedback and think you are a fake, insincere [insert expletive of choice here] for your attemps at sugar coating; which damages the trust between you.​
    They only hear the negative feedback and think you are a fake, insincere [insert expletive of choice here] which damages the trust between you.
    But the entire workforce hates you and are threatening to walk out
Obviously, that’s a bit extreme but it highlights an obvious question; is the purpose of the conversation to praise John or to deliver negative feedback which tells him that changes need to happen.  A difficult conversation which attempts to serve two different purposes ends up serving neither.  You usually end up with one of a couple of scenarios:

​There is a need in life for both positive and negative/constructive feedback but both should be delivered separately. Have one clear purpose for each conversation and stick to that.

Related articles: Positive feedback and constructive feedback


There is a need in life for both positive and negative/constructive feedback but both should be delivered separately. Have one clear purpose for each conversation and stick to that.
Related articles: Positive feedback and constructive feedback

​5. Being volcanic

have-a-difficult-conversation-volcanic
5. Being volcanic

​When I was younger, I struggled with anxiety. When I needed to have a difficult conversation, I would play it over and over in my mind. Unfortunately, I would always assume the worst and I would get very worked up. Then when the time for the conversation arrived, I would be too worked up and at the point of erupting like a volcano. If I did erupt, I would be loud, argumentative and sadly, on occasion. I would be abusive. Instead of dealing with what I thought was a difficult person, I became the difficult person.

When you assume the worst, you do get anxious and stressed. If you fall to control it, you can become aggressive. The truth is that you have no idea how it is going to work out so instead of assuming the worst, assume the best. Prepare yourself for the conversation and leave it at that. Once you have your facts and figures ready, you can be determined that you will do everything possible to resolve the issue in the most amicable way you can manage.

If you are really worried about losing your cool, you can make plans for what you will do should the situation arise. That way you can set your mind at rest knowing that you have it under control.

Related article: Avoiding conflict while dealing with difficult people

​Assertiveness Tactics Report

If you need to have a difficult conversation, assertiveness skills will allow you to do so in a confident and composed manner. My FREE Assertiveness Tactics report will give you some great strategies.


Get Your FREE Copy

When I was younger, I struggled with anxiety. When I needed to have a difficult conversation, I would play it over and over in my mind. Unfortunately, I would always assume the worst and I would get very worked up. Then when the time for the conversation arrived, I would be too worked up and at the point of erupting like a volcano. If I did erupt, I would be loud, argumentative and sadly, on occasion. I would be abusive. Instead of dealing with what I thought was a difficult person, I became the difficult person.

When you assume the worst, you do get anxious and stressed. If you fall to control it, you can become aggressive. The truth is that you have no idea how it is going to work out so instead of assuming the worst, assume the best. Prepare yourself for the conversation and leave it at that. Once you have your facts and figures ready, you can be determined that you will do everything possible to resolve the issue in the most amicable way you can manage.

If you are really worried about losing your cool, you can make plans for what you will do should the situation arise. That way you can set your mind at rest knowing that you have it under control.

Related article: Avoiding conflict while dealing with difficult people

​6. Scripting

6. Scripting
have-a-difficult-conversation-script

​Of course, you should prepare when you are going to have a difficult conversation. But you can’t be over prepared. If you try to script every word of a conversation, you are being both unrealistic and disrespectful to the other person.

You are being unrealistic because you can’t control every aspect of a conversation which involves other people. They are free to think for themselves and choose their own responses. They will most likely have some responses which will take you down a route you were not anticipating. You can’t script that.

You are being disrespectful because you are not allowing for the other person having their own free will and freedom of expression. When you over script the conversation beforehand, you know what your arguments and you are determined to fit them in. You are so determined that you will often fit them in where they don’t belong. You may even misinterpret the other person’s words so that you can fit your argument in.  This isn’t necessarily a conscious action. It’s just that you are not fully open to the conversation which is currently happening as you are more focused on the conversation you were expecting to happen. Problems are resolved in the real world, not the imaginary world.

So, instead of scripting the entire conversation; script your introduction and note some key points that you want to cover but once you have started the conversation, afford the other person the respect needed to speak openly, honestly and freely.

If you struggle to have a difficult conversation, How to Talk So Others Listen will help you make some key changes to your conversation style.

Of course, you should prepare when you are going to have a difficult conversation. But you can’t be over prepared. If you try to script every word of a conversation, you are being both unrealistic and disrespectful to the other person.

You are being unrealistic because you can’t control every aspect of a conversation which involves other people. There are free to think for themselves and choose their own responses. They will most likely have some responses which will take you down a route you were not anticipating. You can’t script that.

You are being disrespectful because you are not allowing for the other person having their own free will and freedom of expression. When you over script the conversation beforehand, you know what your arguments and you are determined to fit them in. You are so determined that you will often fit them in where they don’t belong. You may even misinterpret the other person’s words so that you can fit your argument in.  This isn’t necessarily a conscious action. It’s just that you are not fully open to the conversation which is currently happening as you are more focused on the conversation you were expecting to happen. Problems are resolved in the real world, not the imaginary world.

So, instead of scripting the entire conversation; script your introduction and note some key points that you want to cover but once you have started the conversation, afford the other person the respect needed to speak openly, honestly and freely.

If you struggle to have a difficult conversation, How to Talk So Others Listen will help you make some key changes to your conversation style.

​Conclusion

Conclusion

​When a problem has been persisting for some time, it clearly hasn’t been dealt it. In many instances, people will tell you that they have dealt with the problem; that they have spoken with the relevant person. But the fact remains that if the problem had been dealt with; it wouldn’t still be happening. Experience has told me that most people don’t know how to have a difficult conversation. They get themselves psyched up and they have a conversation but that conversation is anything but a difficult conversation. There are any number of mistakes you can make which will diminish the effectiveness of a difficult conversation. This article has given you six of the biggest mistakes so why not tackle them and learn to have a difficult conversation that produces positive results.

When a problem has been persisting for some time, it clearly hasn’t been dealt it. In many instances, people will tell you that they have dealt with the problem; that they have spoken with the relevant person. But the fact remains that if the problem had been dealt with; it wouldn’t still be happening. Experience has told me that most people don’t know how to have a difficult conversation. They get themselves psyched up and they have a conversation but that conversation is anything but a difficult conversation. There are any number of mistakes you can make which will diminish the effectiveness of a difficult conversation. This article has given you six of the biggest mistakes so why not tackle them and learn to have a difficult conversation that produces positive results.