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Leaders – Stop Putting Off Difficult Conversations

Have you ever gotten out of a difficult task?  A meeting you just didn’t want to attend? Decided against scheduling in that difficult conversation with a direct report because it just felt too awkward?

When we think about what makes a great leader, unfortunately, avoidance, procrastination and burying one’s head in the sand, are not the great character traits that sing out to us.  Instead, we think of accountable leaders, ones who tackle challenging issues head on. In many of my coaching conversations with leaders, I am asked about how to approach difficult or awkward conversations, often working with a leader who has avoided the conversation to date and in doing so is now facing a much more difficult task.

A key concept I try to start the ball rolling with, is that for leaders, having difficult conversations is part of their job. If you want to be a success in any role, it is about mastering all facets of the job and not just picking and choosing the ones that are easier, or the ones that appeal most to you. Where individuals harness this self-awareness and understand that avoidance is not an option, it is then possible to explore some of the elements to mastering a difficult conversation:

Not all difficult conversations are born equal

There are difficult conversations and then there are difficult conversations.  It’s important to fully understand the specific issues you are seeking to raise with someone.  Is this an informal chat? Is this a disciplinary issue? Is this an issue of serious misconduct? Refer to your organisation’s policies and procedures to understand if there is a process that you should be aligning to.


Difficult conversations are not ones for the corridor or staff lunch room.  Book a room that is quiet and discreet; this is true even for informal difficult conversations. You can’t guarantee the response of the person you are talking to, and they might appreciate the fact you have booked a private space.

Consider exactly what it is you would like to raise with the employee and be specific. Using examples is a great way to provide feedback, helping the receiver of the feedback to understand the exact issue. If you are nervous, try writing yourself a short script or some bullet points so that you definitely get across the points you need to raise.

It’s all in the delivery

Direct communication works well here; wrapping up negative feedback, sandwiched between good feedback can get confusing. I once worked with a leader who terminated someone but unfortunately the direct message of the termination got lost in translation when sandwiched between what an awesome person they are, and how much they enjoyed working with that person. You don’t need to be blunt, but honest, direct communication will be appreciated by the receiver and support their understanding of the key message.

If the conversation has been a long one or if you want to be extra sure that your message did get across, consider also sending a short email summary after the meeting that reiterates the key points addressed.

End game

What are you hoping will happen as a result of this difficult conversation? Are you seeking a performance uplift?  Are you seeking a change in behaviour? Are you hoping they will stop doing something? Be clear on your expectations before you go into the conversation?  If you aren’t clear on the outcomes, the likelihood is that your difficult conversation will feel like a ‘telling off’ rather than focuses on what could and should be achieved post conversation.

By focusing on outcomes and future expectations you are minimising the risk of the same poor performance/conduct happening again.


The final tip for a difficult conversation is making sure you build in meaningful space to listen to the other person.  Anyone who enters a difficult conversation is doing so based on their own perspective of a situation. There is always the opportunity that your perspective is incorrect, fuelled by others or simply misguided.  By approaching a difficult conversation with an open mind, you are then able to listen to other perspectives which will support more impactful decision making.

 Helen O’Connor, Managing Consultant

Posted in ANSON news