How To Have A Difficult Conversation 10 Practical Strategies

You’ve thought about it too much. It’s taken your time and attention. Perhaps you’ve lost sleep over it. Having THAT tricky conversation with a parent or co-worker or even your boss can be super uncomfortable.

Learning to have difficult conversations is an essential part of not only being a great teacher, but also a great person.

How do you handle tricky conversations?

Here are ten strategies to help you navigate through a difficult conversation:

1. Work on yourself first.

Preparing yourself for the conversation is one of the most important things you can do. Being ‘self aware’ is essential to the successful outcome of the conversation. Here are some questions you can ask yourself:

  • Why do I want/need to have this conversation?
  • What is my desired outcome?
  • What ‘buttons’ are being pressed for me?
  • What attitude do I have towards the other person?
  • What incorrect assumptions might I have made about the situation?
  • What am I afraid of?
  • Where have I contributed to the problem?
  • What previous experiences with this person/situation are influencing me?
  • Why have I delayed dealing with this issue/person?

2. Choose an appropriate time and place.

The timing of the conversation is incredibly important for the conversation to go well. The physical location is equally important. Think about when and where would be the best place for you to talk. It can be helpful to prepare the person for your conversation by saying, ‘I need to talk to you about something important. Can we make a time for 10am?’ That way, the person knows you want to talk about something specific and then you can choose a mutually suitable location.

3. Start positive.

Start your conversation with a few positive statements about the person/situation/relationship. I’ve written about the ‘feedback sandwich’ before and it applies equally here. For example, ‘I’ve really enjoyed working with you and I like the way we have…” Or, “I’ve been thankful that I have had this opportunity to grow in my role…” These positive statements are not designed to be controlling or manipulative but rather to help establish rapport with the person you’re meeting with and to help both of you relax at the start of the conversation.

4. Get to the point.

When you are actually in the meeting, you must get to the point. You must clearly and gently state exactly what the problem is (you will have already spent some time on this – refer to the first point). Be careful to be honest and also kind. Don’t spend too much time in small talk – get right to the point. For example, “My reason for us meeting together is to find a positive solution to the problem we’re having with _______.”

5. Use ‘I’ not ‘you’.

‘I’ statements show that you are taking personal responsibility to present your side of the issue. ‘You’ statements can cause the other person to get defensive because they usually come across as accusatory. For example, “I am finding it challenging when my shortcomings are announced in front of the whole staff and I would like to find a better way for us to talk about where I can improve.” Versus: “You always point out my failures and you make me feel insignificant.”

6. Include the other person.

After you have explained your side of the issue, you need to invite the other person to respond. You might ask them, ‘What do you think?’ Or, ‘What would you like to say?’ Including the other person (after all it is a two-way, two-sided conversation) shows you care and that you value their opinion, just like you expect them to value yours.

7. Listen.

When the person responds and shares their thoughts and opinions, listen. Really listen. And don’t interrupt them. What are they saying? What is being left unsaid? What is their body language telling you? How is their tone of voice giving you insight into how they feel? Let them talk until they are finished. This listening phase is all about you being curious and being genuinely interested in finding out what they think and how they feel.

8. Take personal responsibility.

Difficult conversations don’t always end the way you think they will. Be prepared to admit where you have gone wrong. I will say it again, be prepared to admit where you have gone wrong. Take personal responsibility and own your errors. And in all of this, remember to manage your emotions before, during and after the meeting. Your emotions are your responsibility.

9. Solve and Summarise.

After you have listened to each other, make a plan for moving forward in solving the situation. Be willing to find a different solution to what you have already planned for. Summarise what you’ve agreed upon (even if it is to keep talking about it at another time) and thank the person for listening. “I’m really glad we were able to have a chat about this.”

10. Reflect and Improve

Regardless of how the conversation actually finishes, reflect on what went well and what you could do better next time. What did you learn from the experience? What could you have done differently? How can you prevent a similar situation occurring again? I’ve written about the benefits of daily reflection, my most recent article is here.

Being able to have a difficult conversation is essential to your continued growth as a teacher and as a person. Use these ten strategies to help you.

This week’s assignment:

Identify THAT conversation that you need to have with a parent or with your boss or perhaps even a family member. Start with the first strategy and do some work on yourself to prepare you to actually have the conversation. Then let me know how you go! You can leave your comments here.

Enjoy the journey,

And more importantly,

Enjoy the moments.



P.S. Upcoming parent-teacher interviews? Gotta have some tricky conversations? Download the Parent Teacher Interview Proforma below to help you.

Parent Teacher Interview Proforma
Parent Teacher Interview Proforma
Want to be super-prepared for your interviews with parents? Download the Parent-Teacher Interview Preparation Proforma. It will really help you!

QUESTION: In what ways have you been successful in having difficult conversations? You can leave your comments here.