How to start a difficult conversation

Written by: Sonia Gill | Published:
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How should school leaders and managers start conversations when they have something difficult to discuss? Sonia Gill offers her advice

A question I am often asked when training is: “How do you start a difficult conversation?”

People find initiating the discussion quite stressful and I understand why. We are going to tell someone something they probably don’t want to hear and, even though we’re raising the issue to help them, we know they are likely to have a negative emotion. Most of us don’t want to upset someone because we care.

The opening of your difficult conversations is the only part I advise you to prepare for, to the point of having a script. There are several ways to open and I want to give you the most reliable one – I, issue, outcome (the commas demarcate the three sections of the sentence).

Start with ‘I’

Start with something like: I feel, I think, I’ve been told, I’ve observed, I’ve noticed, I’ve heard. Find the words that work for you. Starting with “I” is softer and less accusatory than starting with “you”. This opener lets you put across what you are thinking or feeling; you are not stating it as fact, you are saying this is what you believe to be the case and indicating that there is room to move if you are wrong. You are simply sharing your perspective.

The issue

Next you state the issue that has led you to have the conversation. Be as specific as possible and have examples to back it up if you need to.

The outcome

Finally, you state what you want the outcome to be – the end result of the positive change you are hoping to achieve with your colleague.

The mistake within the mistake

People often make a mistake here. When I train school leaders I will see them start with “I” and then say what the issue is. However, where they will fall down, time and time again, is failing to assert the desired the outcome. In Steven Covey’s popular book The 7 Habits of Highly Effective People (Covey, 2004), the second habit he talks about is to “begin with the end in mind”.This is “the outcome” in our opening sentence. School leaders often leave out the desired outcome because it can seem so obvious:

  • I’m talking to you about being late – so surely it’s clear I want you to be on time?
  • I’m talking to you about the lack of quality marking in your books – so surely you know what I want is better marking in your books?
  • I’m talking to you about looking disinterested in staff meetings – so surely you know I want you to be interested and engaged in staff meetings?

Maybe the other person does know what you want and you don’t need to say it. However, by articulating a clear outcome, even if it seems obvious, you can dramatically increase the chance of success and reduce the need for another conversation.

If you don’t focus on the outcome you will find yourself in the “swamp of issues”. This is where your conversation is all around the issue and doesn’t move onto the change you need to see.

This three-part opening sentence is your guiding star in a difficult conversation and will really help you keep on track and on topic.

Let’s take a look at what an opening sentence looks like across the spectrum of difficult conversations.

Low-level difficult conversations: “I notice you have been late four times over the last two weeks and the school needs you to be ready to work at 8:30am every day.”

Mid-level difficult conversations (performance issues): “I’ve seen from your data that your class is not making the expected level of progress and I need you to find a way to ensure that they all make at least expected progress by the end of the school year.”

High-level difficult conversations (staff conduct): “I feel you can come across as rude to parents at times and I would like you to express yourself in a positive manner throughout the school day, especially to parents.”

You can amend the wording to suit your personal style, and there are nuances as to how you word your opening sentence, but I hope you can see the three elements of “I, issue, outcome” at play.

If you cut “the outcome” from these sentences it reduces the clarity of what you require from the other person. Including a specific outcome makes success more likely because it reduces the margin of error in the other person guessing what they are meant to do.

  • Sonia Gill is founder of Heads Up and author of Journey to Outstanding. Her latest book, Successful Difficult Conversations: Improve your team’s performance, behaviour and attitude with kindness and success, has been published by John Catt Educational. For details, visit


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