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How to deliver those difficult conversations

Business leaders often have to make challenging and uncomfortable decisions for the wellbeing of their team and the ability to say no and deliver bad news with compassion and professionalism is a skill that everyone should learn

We all have a natural desire to be liked and accepted by others, for reasons which are deeply rooted in our evolutionary, psychological and social make-up. For these reasons, we can all find it difficult to face stressful situations and, as a result, prevaricate and put things off. However, this does us and the situation no favours.

Delivering bad news is an essential skill in both personal and professional life, so to help you navigate these difficult conversations, here are some effective ways to do it successfully.

“Make sure you keep your communication simple, as a lack of clarity and vague or unclear language can lead to misunderstandings and confusion”

The starting point when confronting any difficult situation is to spend adequate time preparing and planning. Failing to prepare can lead to a disjointed and unconvincing message. 

Take time to reflect on your own feelings, biases and goals for the conversation, ensuring you:

  • GATHER all the necessary information to ensure you have a complete understanding of the situation.

  • SPEAK to relevant subject matter experts to understand company policies and procedures.

  • PLAN what you want to say, keeping the message clear and concise.

  • ANTICIPATE any likely questions or concerns the recipient might have and prepare suitable answers in advance.

It’s vitally important to choose the right setting and timing to have the conversation. Selecting the wrong time and place can quickly lead to the discussion going awry and produce an outcome that suits neither party, so remember:

  • TRY to choose a time when the recipient is in a calm and receptive state of mind.

  • SELECT an appropriate, private, and comfortable setting for the conversation. Ensure there are minimal distractions, as these will only unsettle and heap more pressure on you.

  • CONSIDER the timing and schedule the discussion at a time when the recipient can give their full attention and has time to process the news.

Start by being direct but compassionate – after all, you’re dealing with another human being. Put yourself in their position; how would you like to be treated if you were in their situation? 

Make sure that you keep your communication simple, as a lack of clarity and vague or unclear language can lead to misunderstandings and confusion. Avoid using technical or complex language that the recipient may not understand. 

Always use plain language to ensure clear communication and make sure that you:

  • START the conversation by being direct and to the point. Avoid unnecessary preambles or beating around the bush.

  • EXPRESS empathy and understanding for the recipient’s emotions and reactions. Listen to them, acknowledge their feelings and show support. Failing to consider the emotions of the recipient can come across as cold and uncaring.

  • TRY to offer solutions or support, but don’t make unrehearsed commitments. If possible, provide potential solutions or a plan to address the situation. Offering help or resources demonstrates your commitment to assisting the recipient through the difficult situation.

  • BE HONEST about what you can and can’t do to help, and don’t make promises you can’t keep – this will only come back to bite you further down the line.

You really need to listen, and by that I mean actively listen to their words, body language, facial expressions and tonality, so you get a real sense of how they are feeling and reacting to your message. Also ensure you allow appropriate time for reaction, for example:

  • AFTER delivering bad news, give the recipient time to react and process the information. Avoid interrupting or immediately pushing for a response. Avoid assigning blame or making accusations when delivering bad news. Focus on the situation or the issue rather than making it personal. This will only antagonise the situation. 

  • BE MINDFUL not to overwhelm the recipient with too much information at once. Stick to the key points and allow them to ask questions if they want more details.

  • LISTEN to their concerns and respond calmly – this will help defuse the situation. In emotionally charged situations it can be very easy to become defensive, particularly if the recipient reacts negatively to your message, so avoid becoming defensive or argumentative.

  • ENCOURAGE the person to share their thoughts and feelings, and actively listen to what they have to say. Sometimes,just having someone to talk to can bea comfort.

After the event, take time to reflect, be honest with yourself and ask what went well and what could have gone better.

“Put yourself in their position; how would you like to be treated if you were in their situation?”

Remember, the key to delivering bad news effectively is to show empathy, honesty and a willingness to support the recipient through the difficult situation. 

It’s important to always maintain professionalism and respect throughout the conversation, even when dealing with emotionally charged topics. If you follow this process, then the likelihood of getting the desired outcome increases.

There are no winners in avoiding these difficult conversations, but it’s much better to prepare properly and follow this process than put it off. 


Paul McDevitt is Managing Director of McDevitt & Co, an experienced business consultancy that helps to inspire people, improve productivity and increase profits in the construction industry. Find out more and contact him at

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