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Achieving a positive outcome from a difficult conversation

Management Overview

The most important part of having a difficult conversation how you approach it. It is better not to leave issues for too long, so tackling them whilst they are fresh in your mind is important. However, you don’t want to jump into a difficult conversation without some preparation first.  Without preparation the interaction my not achieve the outcomes you desire.  As a leader you will likely face difficult conversations regularly! (our Senior Associate Mim has shared with us a great framework for preparation).

This article by Fairwork Australia, Tips for Having Difficult Conversations in the Workplace, outlines some practical steps to take to make difficult conversations easier and more constructive:

  • State what the issue is straight away.
  • Stick to the facts, focus on the issue not the person.
  • LISTEN – this is absolutely key.
  • Be prepared for an emotional reaction.
  • Keep your own emotions in check.

Taking the emotion out of a difficult conversation will make it easier for you to achieve your desired outcome. The best way to do this is to stick to the facts and deliver your findings in a confident manner. This article, 9 Crucial Rules to Remember When Having Difficult Conversations with Employees, suggests that you should set a positive tone going into a meeting where you know the conversation will be difficult. If you have a negative approach, your employee is more likely to get defensive and argumentative. Use a tone that will help to coach your employee, rather than reprimand them, after all you want to motivate them to do better.

This insightful video Managing Difficult Conversations by Fred Kofman, PhD. in Economics, Professor of Leadership at UFM, offers some great tips.

“It is precisely at those times when communication is most vital to achieving your goals, that conversations break down most dramatically. That’s why difficult conversations are scary, the stakes are high. There’s a high cost to fail and yet that’s when failure is most likely”.

He goes on to describe a system for managing the process of having a difficult conversation.

The conversation needs to finish with an agreement on the course of action. What needs to change in the scenario that bought you to this conversation? Set a timeframe to review the progress of any performance or behavioural modifications that need to be addressed. As this article, The Top 6 Mistakes Managers Make When Having Difficult Conversations, points out, if you are rushing to get it over, you will forget to clarify what’s going to happen after the conversation which misses the point of the conversation in the first place.

Finally, make sure that you follow up to ensure issues are being resolved in the way that you agreed. It is important to keep the lines of communication open so that your employee feels that they can continue to speak to you about any issues that arise. The silent treatment is no good for morale!

If you’d like some further assistance with finding the courage to have difficult conversation in your role as a manager, or would like to run a workplace workshop, please contact us at


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