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September 17, 2019
166: Having difficult conversations

Whether you are a freelancer who wants to get paid or just someone who wants to work better with a colleague, we will all experience the nerve wracking build up to a difficult conversation at multiple points in our careers. We are all humans, doing our best and with different working styles that is bound to cause conflict from time to time. In this episode we get vulnerable and speak candidly about the difficult conversations we have had in the past and how, with time and practice, we have been able to get the most out of them.

key takeaways

If you have a heads up that a difficult conversation is on the cards, it doesn’t necessarily make it any easier. Making notes can help you to focus on the information you want to get across. You don’t have to bring a notebook with you into the meeting but writing down your thoughts and feelings before the conversation can help you to gain clarity. Writing out what you intend to say can also help you to speak clearly.

As you are having a difficult conversation, listen to the other person. Ask questions to gather more information. Put your point across. If you feel that you might need to take some time to think about what the person has said, let them know that you would like to come back to the conversation once you’ve had some time to think.

Check in with someone you trust before you have the difficult conversation. It can be useful to have someone else’s perspective on the situation. They may offer a new point of view that you had not considered. A trusted friend or manager may give you further insight into the situation.

Cultivate your relationships with your colleagues and managers. Put time into the relationships so that there is a solid foundation from which difficult conversations can be approached.

Suggest to your team to read one of the books that we have mentioned above. It just takes one person to be brave, and make a suggestion like that to help better inform the entire team. You may be surprised at how having a toolkit and exploring the topic of difficult conversations will help everyone work together with more ease.

show timestamps

2.48 – Preparing for a difficult conversation

9.30 – Listening to the other person’s POV

16.00 – Avoiding difficult conversations (don’t!)

21.18 – Learning from others

26.25 – Reflecting on past conversations

29.15 – Choosing the right setting for difficult conversations

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