A Guide to Difficult Conversations


As educators we are, by the nature of our work, faced with many opportunities to have difficult conversations. These occur with students, with parents, and sometimes even with each other.  Our job is, at its core, to help people grow and learn. To do this we have to be able to address and talk about things that might be uncomfortable. In this article, we are going to explore the idea of having difficult conversations: It’s my hope that by the end of this you have some new tools to do so.

Let’s start with the big picture on tough conversations — they are part of life — and whether they are successful depends not on logic and not on how right you are, but on whether you can establish a successful dialogue that allows both people to feel heard and reach a resolution.

A conversation is a relationship: It is not a set of techniques or tricks you do to someone — it’s a shared experience — with a shared outcome. Having a conversation isn’t a battle; no one wins (that’s called an argument). The core aspect of having a good conversation with someone is to communicate.

A Good Conversation is:

  1. Safe: The conversation has to be “safe” and by that, I mean free from judgment, criticism or coercion. The number one goal for you is to establish a welcoming, open atmosphere that conveys you are there to help, and that you are willing to listen and work with the person. This is true even and especially when you are addressing a topic you and the other person might not agree on.
  2. Mutual: A conversation is two ways — you have to show your willingness to listen and a desire to understand the other person’s perspective because chances are, they have their own reasons for thinking, feeling and acting the way they do.
  3. Empathetic: Empathy means you understand not only what someone is saying, but you are picking up on the unspoken and non-verbal elements of the message. Being empathetic means listening to emotions as well as words and acknowledging them — often through our own non-verbal responses. This kind of resonance goes a long way to build trust.

At the end of the day, your chance of having a successful conversation with someone on a difficult topic isn’t determined by how hard the topic is but on how well you can create the right climate for a conversation.

What is a “Difficult Conversation”?

When I talk about a “difficult” conversation, I’m going to define it for our purposes as one in which you need to convey information that the other person may find hard to hear. The list of possibly difficult conversations is endless. Common conversations might include:

  • Discussing an area of academic weakness with a student or parent
  • Addressing an ongoing problem with a student, parent or co-worker
  • Letting a parent know you suspect their child has a disability
  • Discussing an incident that made you feel uncomfortable or was unsafe
  • Informing a parent about discipline their child will receive, such as suspension.

Step One: Decide if You Need to Have this Conversation

The first step in deciding how to approach a conversation is to decide if it is necessary to have this conversation at all. Some important questions to ask include:

  • Is the conversation something that can help both parties?
  • Does the conversation benefit the students and community you serve?
  • Are you the right person to have the conversation?  Is this within your role? Would the issue be better addressed by someone else (e.g. parent, supervisor)?
  • Could the conversation have an adverse effect that might make you think twice about having it?

If the conversation is only for you to “be heard” or “be right” or let someone know something that’s bugging you and isn’t helpful to the other person you might think twice about having it.   A difficult conversation isn’t self-serving. It is heroic, because although it’s hard for you, it is intended to serve the greater good.

Step Two: Have a Plan

It’s critical that you don’t go into a difficult conversation without thinking it through. You want to keep the conversation short and sweet but long enough to get things resolved. You don’t want to go on and on, which you might do if you don’t have a plan or are feeling nervous.  While you can’t plan everything, it helps to think about:

  • How will you introduce the conversation?
  • Rehearse it in your head: think about how you want to say it — both the words you will use and the intonation and non-verbal signals you might use as well. Get comfortable saying the words. Practicing can go a long way towards helping you feel comfortable and ready.
  • How will you respond if the other party reacts negatively? Think about what they might think or say. If you are ready for the “worst case” scenario reactions you will feel more confident.

Step Three: Check Yourself

If the conversation is about something that you are emotionally passionate about, or perhaps even angry about, you have to stop and make sure you are ready to have the conversation without wrecking it by broadcasting a lot of negative emotion. Your calmness and comfort with the subject is going to transfer to your conversation partner.  

Step Four: Introduction

The introduction to a conversation is the very important part. This is where you will introduce the topic and discuss why it’s important before going into specifics. You might start by saying what you have noticed and ask the person to help you understand it.

Step Five: Listen First

Listen FIRST!  You are probably going to be ready to discuss your point of view and want to say those important things, but it is helpful to get the other person’s perspective before you start on your own. After you’ve invited the person to talk on the subject, try to summarize their point of view and see where they might be coming from.

Step Six: Ask for Suggestions

Once you have the problem on the table, you can ask the person for suggestions on how to solve the problem. This is a lot better than telling your partner what you want, or what they should do. Ask how you can help and be part of the solution where appropriate. Think about and evaluate solutions and potential roadblocks.

Step Seven: Dealing with Resistance

What if the other person gets defensive or angry? It’s likely that they feel attacked or criticized by your actions. They might even do or say things that make you even more angry, shifting the blame onto you or someone else, making excuses or failing to see how the issue is a problem.   At times like this REMAIN CALM. You may not get to the solution today.

You may encounter people becoming defensive. Remember that people try to protect themselves in different ways and those ways aren’t always pleasant. When you see someone getting defensive, that’s a signal to you they are feeling attacked and you have to do what you can to help them feel more comfortable in the conversation.

Step Eight: Ending the Conversation

At the end of the conversation you can summarize what you both have agreed on as a solution.   You may NOT have gotten to a solution and sometimes you won’t. If this is the case, it’s important that you end the conversation with an agreement to keep talking about it and keep the lines of communication open. If the conversation is awkward or heated, try to end it on a pleasant note. Thank the person for talking with you and acknowledge that it is hard to discuss the topic. You may agree to disagree. In the end, if you have a better relationship and more trust with the other person, that is something you can feel good about.

The problem that prompted your conversation might not be solved. In fact, sometimes you may have to bring in a third party, take the issue to a supervisor, let the issue go or maybe even have another conversation.

I hope these tips will help you put difficult conversations into perspective and allow you to bravely go forward and talk about those things that improve the lives of the people you serve and work with.

Dr. Will Henson is a licensed clinical psychologist and an education consultant to school districts, and a co-founder of 321insight, provider of online video training for trauma-informed school staff and paraeducator effectiveness.  Dr. Henson consults, speaks and gives trainings on topics including paraeducator effectiveness, trauma-informed practices, threat management, functional assessment and best practices in supporting students with emotional and behavioral disorders. His first book “Behavior Support Strategies for Education Paraprofessionals” was published in 2008, and his 321insight content is used by schools and districts across the country.

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