JEM Management Training

How do I start a difficult conversation?

Sign Up To Our Newsletter

Share This:

Difficult Conversation

Unfortunately, many people deal with difficult situations by ignoring them and hoping they’ll go away. Among the reasons behind this are that they don’t know how to start a difficult conversation about it.

The workplace presents many situations that require us to have ‘difficult’ conversations. The topics or people involved may not be easy to discuss or approach. Difficult conversations may arise because of:

  • conflicting viewpoints
  • performance issues
  • behaviour in the workplace
  • complaints or grievances
  • tough business decisions

The difficulty of these conversations can then be exacerbated due to who the person is in terms of their level of seniority or how they typically do or could potentially react.

All of this can lead many managers to procrastinate about having the conversation.

  • “It’s not that big of a deal”
  • “Now’s not the time”

  • “It’ll just blow things up”

Instead of putting it off, learn how to start a conversation

Before you start a difficult conversation, it’s useful to get yourself prepared by getting into a constructive headspace, thinking about the structure you can use for the conversation, how you might phrase your communication, what outcome you’re looking for, what you will do if things go wrong etc. This preparation will help boost your confidence and provide focus for the conversation. You also need to consider where you’ll meet.

Then it’s time to start. One of the classic mistakes people make when starting a difficult conversation is beating around the bush with phrases like:

“How’s the family?”

“How do you think you’re doing?”

“It’s not a big deal but I just wanted to talk to you about something, do you know what it is?”

It’s best to be direct – tell them:

  • What the issue is
  • What the aim of having the conversation is
  • An outline of how the conversation might flow
  • Examples and specific evidence

By using this formula, you send the message that the focus is on finding a solution rather than blaming an individual. You also demonstrate an openness to a two-way dialogue rather than just laying down the law. Sharing the structure for the conversation will set the expectation with the other party.

For a performance issue you might say something like:Difficult Conversation

“Hi Angie, thanks for agreeing to see me. I want to discuss your performance as some elements aren’t up to scratch. The aim of highlighting these issues is so we can put in place some strategies to help you. Let me start by sharing what I’ve been seeing, then I’ll ask for your viewpoint and then we’ll brainstorm some ideas that might help. Sound good?

What I’ve been seeing recently is….(insert specific evidence/feedback) Talk me through the way you see things…”


For a complaint you might say something like:

“Hi Shahin we’ve had a complaint that I need to speak to you about. I want to share the feedback we’ve had so we can avoid it happening again. I’m going to share the specifics of the complaint and I’m interested in your take on things, why you think it happened, and then we’ll quickly move onto solutions and ways we can avoid the same thing occurring again. The complaint was about….”

Once you’re over the first hurdle and into the conversation, it should be easier to carry on. Remember to stick to a structure and focus on solutions not problems.

Additional working practices that can assist and reduce the need for ‘difficult’ conversations are:

  • having regular one-on-one meetings that allow a private setting to raise issues early, before they escalate.
  • being approachable and showing a willingness to listen. This means staff are more likely to come to you with problems before they escalate.
  • giving people a ‘heads up’ about upcoming changes and decisions so they can start to be more prepared
  • being clear about expectations regarding performance and behavior from the outset

If you need help with the skills needed or process to follow to start a difficult conversation, check out our training courses or contact

Share This:

JEM Management Training

JEM Management Training designs and delivers flexible, in-house management training courses to help  organisations in Perth engage their staff fully in the workplace.

As time is often limited, JEM Training offers flexible half-day management training courses which focus on a specific area of management expertise. These short courses build upon each other over a period of time, chosen by you, to provide ongoing management development.

Recent Posts