handling difficult conversations


Having difficult conversations at work is, well, difficult.  

Considering just how much of our time is spent at work with our work colleagues, it’s not easy to sit down and talk about an uncomfortable topic with them. Whether that be performance related matters, behavioural/conduct issues or otherwise, these conversations aren’t ‘fun’, but they are oftentimes essential to nip any issues in the bud and help maintain a healthy & efficient workplace. 

Whilst avoiding or putting off these conversations can initially seem like the easier route to take, doing this can lead to a snowball effect. What might have been a minor issue ends up leading to stickier and more difficult issues to navigate. Suffice to say, this can be costly – on several fronts – for everyone involved and can severely interrupt both business operation and the work environment.  

So here are 7 tips on how to navigate handling a difficult conversation in the workplace – read till the end to find out where you can go for further assistance and support!


The key to effectively handling difficult conversations begins before you even have the conversation. The mindset you have when approaching the conversation will frame everything else that follows, so it’s essential that you’re going into a conversation with an open and neutral perspective.  

Preconceived judgements, hostile attitudes, or unnecessarily ascribing emotionally laden energy to the conversation from the get-go can result in unproductive, ineffective conversations which don’t solve the issue at hand. Your negative or unfavourable mindset can also influence or play on the other party and end up making the issue worse. Enter these conversations with the facts in hand but a mindset that is conducive to a healthy and open space, to ensure you’re able to resolve the issue effectively.  


Preparation is the other side of the coin to mindset in these situations. You need to ensure that you’ve got the facts and a plan as to what you want to communicate and ‘achieve’ by the end of the conversation. Consider doing the following ahead of having a conversation: 

  • Writing down what the issue is clearly and the relevant associated facts and evidence to use if needed 
  • Any questions you might need to ask  
  • Possible solutions/plans etc. 


Sometimes one word, phrase or sentence is enough to derail the entire conversation. It’s important to be mindful of exactly what you’re saying. Some common pitfalls in phrasing when it comes to difficult conversations include: 

  • Exaggerating and/or generalising. This most often happens using words like ‘always’, ‘never’. 
  • Blaming. This often turns the conversation defensive and at times, hostile. There’s clearly an issue that’s led to this conversation being had but the focus should not be on assigning blame, rather it should be on finding a resolution.  
  • Striking at personal character. Harvard Business Review (HBR) identifies this common issue beginning with the use of terms such as ‘unprofessional’, ‘wrong’ or ‘unethical’.1 These words, whilst they may be true, run the risk of making the other party defensive as it strikes at their character and integrity. Instead, consider ‘de-personalising’ these terms – for instance ‘unprofessional’ can instead be phrased as ‘not consistent with workplace values.  
  • Not Listening. A conversation is a two-way street and so, as important as it is for you to communicate the problem, it’s equally important to listen. It can help fill in the blanks, shine a light on things you weren’t previously aware of and give an insight into what’s been happening on the other end.  


Clarity is essential for handling difficult conversations. These conversations generate tricky environment that can be rife with opportunities for miscommunication and misunderstandings. Make sure you’re clear and concise in communicating exactly what the issue is, why it’s an issue and what the potential resolution might be.  


Always stick to facts – acting on hearsay, assumptions or otherwise can be disastrous and should be avoided. By sticking to the facts, you can ensure that clarity of communication is achieved and you’ll avoid things like blaming and generalising.  

TIP #6 ‘I’ VS ‘YOU’

The difference between using “I” statements and “You” statements when communicating the issue can sometimes be the defining factor in whether a conversation remains defused and conducive or charged and incendiary. “You do this” or “You do that” can come across somewhat akin to blaming. You can get the same message across in a more effective manner by shifting perspective and saying “I’ve noticed that..” or “I feel like... 


Difficult conversations are rarely a ‘one and done’ affair. To create effective change and really resolve an issue, following up is essential. It might also be beneficial to discuss with the other party what following up might look like, to get their involvement in finding a resolution and for it to seem more like you’re working together to find it instead of giving the impression of it being a solely punitive affair.  


These are not hard and fast tips – they’re largely general and there are several factors, specific to your unique situation and workplace dynamic, that can determine how to best approach a difficult conversation.  

We’ve got other blog posts looking at specific difficult conversations such as those centred around resignations & terminations and types of workplace conflicts & resolutions 

Workplace Wizards has a team of legally trained employment consultants who have worked with a variety of businesses to help resolve workplace issues. We provide a variety of different training packages to help find workplace solutions as well.  

 Reach out to find out what we can offer by way of workplace solutions for your business. You can call us on 03 9087 6949 or email support@workplacewizards.com.au 


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