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Tough Discussions

June 9, 2026 by
Christian Sellars

 

Earlier this month I asked a group of HR leaders which discussions they found most difficult.  Their top four were: 


• speaking up to senior leaders

• dealing with resistance to change

• delivering bad news and 

• giving difficult feedback to talented employees


What these discussions have in common is risk. The person you’re talking to might react badly, your relationship may suffer, or you may fail to achieve the outcome you were hoping for.

Yet the HR leaders also shared examples where avoiding a discussion caused much bigger problems. In some cases, delayed feedback resulted in resignations, financial setbacks and unnecessary frustration, outcomes that could have been avoided by a simple conversation at the right time.

The good news is that tough discussions become much easier when approached systematically. The following six steps can help:


1. Recognise when a discussion is needed

Tough discussions are most useful when there is a repeated pattern of behaviour or an issue that is affecting results, relationships or wellbeing. Once it becomes clear that a discussion is needed, schedule it. The longer people engage in problematic behaviour, the more entrenched it becomes, reducing the likelihood of a productive outcome when a discussion finally occurs.


2. Prepare
Once the meeting is scheduled, think carefully about what you have observed, how it affects you and what outcome you would like to achieve from the discussion. Also spend time considering how the other person might see the situation. What information might they have that you don’t? What pressures or concerns could be influencing their behaviour?

Next, give the person a heads-up that you would like to have this conversation. A simple message such as “Could we spend some time tomorrow discussing something important?” gives them an opportunity to prepare their thoughts and arrive ready for a constructive discussion.


3. Create the conditions for a constructive discussion
Before discussing the issue, talk about the objectives and interests that you share.  Most discussions go better when people can see that they are working towards a common goal rather than fighting to win an argument.

It can also help to acknowledge the other person’s strengths or contributions. This technique, known as contrasting, helps people see that the discussion is intended to improve a situation, not diminish their value.


Once you’ve established a shared purpose and reassured the other person that you value their contribution, you can turn your attention to the issue itself.


4. Share your facts, feelings and story
Describe what you have observed, how it has affected you and the conclusions you have reached. This can feel vulnerable because you are giving the other person an opportunity to challenge your observations and interpretations with information that you might not know. 

Yet that vulnerability often improves the quality of the discussion. By acknowledging that your perspective may be incomplete, you create space for a more accurate understanding of the situation.


5. Listen carefully
Once you have shared your facts, feelings and story, ask the other person to share theirs. Resist the temptation to interrupt. Instead, ask clarifying questions and summarise what you have heard.

You may discover information that changes your interpretation of the situation completely. Once both perspectives are on the table, it becomes much easier to identify a way forward.


6. Agree on what happens next

Finally, agree on the actions that will be taken, who is responsible for what and when progress will be reviewed. Put the review session in the calendar before the meeting ends so there is a clear commitment to follow-through.


These six steps help people move beyond assumptions and develop a shared understanding of a situation. They also increase the likelihood that discussions will result in practical action and improvement.

Handled well, these conversations strengthen relationships, improve performance and prevent small problems from becoming large ones.


If you would like to build this capability within your team, Transforming Engagements Ltd (TES) delivers practical workshops that help leaders and employees navigate difficult conversations with greater confidence and skill.


Christian Sellars June 9, 2026
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