Six top tips for navigating challenging conversations in the workplace

"Preparation involves entering the conversation with the right mindset," says consultant Jon Horsley

For professionals working in HR, handling difficult conversations is a vital skill.

Whether conducting performance reviews, giving confronting feedback, or challenging a superior on a decision, these conversations need to be managed effectively to achieve the desired outcomes. 

Most people don’t relish the thought of having difficult conversations. Research from the Chartered Management Institute (CMI) also found that 57% of managers would do almost anything to avoid one. 


Read more: Acas launches guidance on ‘difficult conversations’ at work


The CMI highlights five main reasons: not knowing how the other person will respond; not being able to get a point across clearly; being in a confrontational situation; getting upset or emotional; and the other person getting upset or emotional.

This is where coaching skills can be incredibly valuable. The core skills of coaching, which are active listening, asking effective questions, and providing feedback or reflecting on what you have heard, are all useful in effectively navigating challenging conversations.

Here are my six top tips to ensure more positive outcomes:

Be prepared

The idea of ‘being prepared rather than having prepared’ is helpful. Preparation involves entering the conversation with the right mindset. The Human Systems Dynamics Institute suggests shifting from judgement to curiosity, turning assumptions into questions, defensiveness into self-reflection, and moving from conflict between the two parties into a shared enquiry into the issue or problem causing the conflict.

Acknowledge emotions

All challenging conversations are fundamentally about feelings, so it’s important to acknowledge what’s going on emotionally and create a little distance between who we are and what we’re feeling. For example, explore the difference between ‘I am angry’ and ‘I am feeling angry’. It can also be helpful to understand that, while thoughts and feelings come and go like the weather, our values are the bedrock from which we can choose to act.


Read more: How HR can help to detoxify language in workplace conversations


Focus on interests, not positions

It’s sometimes said that all conflict is the encounter of unmet needs. Consider reframing the upcoming challenging conversation as an exploration of underlying interests and needs, fostering empathy and collaboration around how they can be met. Seeking to defend a position may be understandable in the heat of the moment, but if winning means the other person losing, or vice versa, there will be very little room for compromise.

Disentangle intentions and impact

One of the common causes of misunderstanding, confusion and conflict in challenging conversations arises from the assumption that we know the other person’s intentions. We attribute their intentions based on their impact on us. Feeling hurt by what someone has said or done can lead people to assume that the person intended to hurt them. Focus on actions instead and what the other party actually said or did. Be clear on the impact this had and reflect on the assumptions made about the other person’s intention.


Read more: How to have positive conflict at work


Work on assertive communication

Clarity about impact, intentions and needs requires clear, concise and assertive communication. Don’t downplay what is important to you, take ownership by using a strong personal 'I' rather than a vague 'we' or 'you' and make explicit requests. Framing intention from the outset and not beating about the bush concerning the purpose of the conversation is the best approach. 

Work with a coach or colleague

Practice technique and tone with a coach or colleague to get a feel for what having a challenging conversation feels like. This can help prepare for the conversation to come and perhaps dispel the fear that the relationship with the other person will be irreparably damaged by it. 

By Jon Horsley, consultant coach-mentor for The OCM