Managing Difficult Conversations At Work

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At Rise Up Women we believe there is power in women coming together. That is why last Wednesday we hosted our very first circle for Future Leaders.

Ten career driven women with a background in finance came together to connect and share their personal experiences on the topic of ‘Managing Difficult Conversations at Work’. They shared openly and honestly about the challenges they have faced in their career and shared tips with the group on how they overcame certain set backs.

This year in particular, there has been PLENTY of tough conversations and the reality is that communication is even more difficult in the virtual world. The emotions that come naturally in face-to-face communications is almost non existent. There is a lack of empathy and it is very easy for someone to take you up wrong.

What do we mean when we refer to difficult conversations? A disagreement with a peer. A team member not pulling their weight. An employee not exhibiting the values of their workplace, not showing respect to others. Approaching someone on your team who’s work is not up to expected standards. There are dozens!

How any manager or leader handles difficult conversations can have a huge impact on their relationship with their team. A poorly-handled conversation can erode trust and have a very negative longer term impact.



Focus on the facts and real examples – Before you start the conversation have a clear idea of what happened. Take responsibility for your role in the situation and focus on real life examples where you can clearly demonstrate your point.

Be empathetic –  Try and think about how the other person will feel when receiving this feedback. Will they get emotional? Be prepared for that. Could they have something going on that you are unaware of? Make sure to listen to what they have to say.

Acknowledge and control emotions – it is very normal to feel a mix of emotions at the thought of having these conversations. Take a step back, acknowledge these feelings and put them aside while you engage with the other person. Bringing them into the conversation will only make things worse, don’t let your emotions control your behaviour.

Think about possible solutions – You won’t achieve much by solely focusing on the problem. What are the possible solutions available to you both? What does a win look like for both of you? Be open to compromising.

Follow up to prevent a fall out – The reality is sometimes it takes more than one conversation to resolve an issue. People can have delayed feelings of embarrassment or resentment. Check in with the person, make sure they are doing ok. Suggest a coffee off site if things still seem off.


The most important tip of all is not to avoid having these difficult conversations and the sooner you address something the better. The worst thing you can do is wait for things to get worse. You will always be glad you plucked up the courage and nine times out of ten these things are always salvageable.


If you are interested in joining a peer to peer mentorship group for support as well as to build real connections with like minded women in your field, please message me on

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