difficult conversation example
Picture of Oscar Romano

Oscar Romano

How to Have a Difficult Conversation

Difficult conversations are never easy to have, hence the use of “difficult” in the phrase. Ideally, we’d all be working in schools where everything was so perfect that we never had to have a difficult conversation with anybody. Our lives would be harmonious and we’d always enjoy working alongside everybody at school.

Unfortunately, this is rarely the case, as a school is one area where you are bound to have issues with at least one individual. This is inevitable, as nobody is perfect and everybody makes mistakes. Sometimes, these mistakes leave a greater negative impact on us than others and cause us to have ill feelings toward the individual who made those mistakes.

There are times when that individual knows they negatively impacted others, but there are also other times when that individual isn’t sure they did anything wrong. Difficult conversations can help remedy situations like the latter. One individual has been negatively impacted, while the other individual might not be too clear as to their role in the situation or is completely unaware. Due to this lack of awareness, the negative interactions between the two individuals continue to occur and the ill feelings begin to compound.

It is important for the individual with those ill feelings to initiate a conversation where they can talk about what has happened. Ignoring this conversation could have dire consequences on the relationship, overall productivity, and the culture of the school. Difficult conversations usually aren’t too comfortable to have, but are extremely important.

Strategies on How to Have a Difficult Conversation

Here are some strategies to help you get ready for a difficult conversation:

Write a script

Plan out what you are going to say ahead of time. This will help you be more present in the conversation, allowing you to engage with the other individual rather than think about what to say next.

Role play

Practice your conversation with another individual so that you can get more comfortable with the flow of the conversations.

Neutralize power dynamics

You may also want to do this off-site or in a common space to neutralize power dynamics of being in one person’s office or the other.

How to Have a Difficult Conversation Sentence Stems

Here are some sentence stems and tips I have found to be helpful when having difficult conversations:

“Thanks for talking with me today. I’ve noticed some tension…”

Don’t beat around the bush. Immediately bring up the purpose behind the conversation, whether it be a specific interaction or an overall feeling.

“I want to work well and help kids…”

Connect the conversation to your purpose and/or the purpose of the organization. There is a greater reason behind talking to him/her today.

“Is there anything I’ve done? Could I do something different?”

There are two sides to every story, so show the other individual that you are willing to own your part in the situation.

How to Have a Difficult Conversation: Final Tip

Be quiet and LISTEN.

Take care to hear the other person out. Be mindful about not focusing your thoughts on your next words, but on what they are saying in the moment.

Have a Difficult Conversation for Better Relationships

The best possible outcome from a difficult conversation is that trust is established because the individuals were vulnerable enough with one another to engage in the conversation. The worst possible outcome is that the relationship is further damaged. When considering the fact that the relationship was already damaged before entering the conversation, it’s safe to say that the potential benefits resulting from a difficult conversation far exceed the possible costs.

Oscar is an Executive Leadership Coach and Founder of Romano Leadership. Interested in learning more? Sign up for a complimentary coaching call at this link.