Difficult conversations are growing pains – here’s how to get them right.

Difficult conversations are growing pains – here’s how to get them right.


How brave do you think you are with having difficult conversations at work?  

Having to tell someone that they’re underperforming? Asking for a pay rise?  Delivering bad news in a project update?

If you dread having them, then join the club.  Very few people feel comfortable – or confident – when it comes to putting themselves in a potentially unpredictable situation where, in our imagination at least, there’s a high possibility of things ending up feeling at best awkward, or at worst out of control with the risk of an emotional response.

Ultimately, we really have to push ourselves out of ourcomfort zone to have successful difficult conversations.  It’s far easier and less risky to bury our heads in the sand a little bit and avoid anything that might be somewhat confrontational.  This however only makes things worse and perpetuates the problem – as the saying goes, unlike fine wine, problems do not get better with age!  They get worse.

It's well known that managers who are able to have difficult conversations with their line reports never have to fire anyone, because employees either improve following the negative feedback, or leave of their own accord.

By pushing ourselves to step into difficult conversations when needed, our skill set and confidence grows, because we know we can deal with any situation, say what needs to be said, and ultimately get things the important things done.

So how do you prepare for a difficult conversation?

Proactively managing your mindset in preparation for difficult conversations is key.   Rather than dreading them and imagining the worst, choose to have a mindset that looks for the opportunities.

An opportunity to get better at clear communication? An opportunity to understand more about the other person’s perspective? An opportunity to hit the reset button on a working relationship to gain alignment?

Approach the conversation with a sense of curiosity and always assume positive intent – this gets you in the right frame of mind for a positive, balanced and productive conversation.

To get the best out of you – and the other people involved – here are our Fearless tips for successfully managing difficult conversations:

Preparation is key

Prepare, practice and rehearse.  Think about what you want to say, think about what the other persons responses might be. Role play tricky conversations with a colleague.

Let the other attendees know what’s on the agenda in advance – surprises are a surefire way to derail the meeting and provoke an emotional, defensive response.

Time and venue

Never send an email – always talk in person.  And make sure you talk at a time and in a place that is appropriate to the conversation. Catching someone as they are rushing out of the door to catch their train is never a good idea.  Neither is having the conversation in the kitchen next to the busy kettle.  

Managing the conversation

Be wary of making assumptions or deliberately searching for evidence to support your internal hypothesis – what you think may not actually be true.  Move away from the notion of ‘blame’ or arguing about who’s right and focus on how to find a solution and move forward.  There will be emotions in the room – try not to disregard them as if they stay bottled up they are likely to explode at some point!  

Read the room

Listen twice as much as you speak – silences feel awkward but are critical to giving someone the space to say how they are feeling.  Listening also gives you time to read the room - feel free to suggest a quick tea break if you sense the level of emotion or frustration is reaching unmanageable levels. And if it gets really tough, it’s okay to pause the conversation for a while and reschedule later.  

Concluding the meeting

Be crystal clear at the end of the conversation that you are all agreed on the content of discussion and the outcome.  And follow this up by scheduling in a meeting date a few weeks later to review progress. There’s nothing worse than coming out of the meeting thinking you’ve resolved an issue only to find out later on that the other person doesn’t agree with this at all.

And just remember that assertiveness is a muscle to grow and build.   With preparation and practice, you’ll find that difficult conversations become something you can face calmly, confidently and fearlessly.

This article was written by Natalie Forkin, Communication Skills Coach at Fearless.