Difficult Conversations: During The Talk

Updated: Dec 30, 2018


You've decided this conversation is important and you've prepared for it. Now, to the heart of the matter. How do you approach the conversation?


This is a 3-part series on handling difficult conversations. Please read Before the Talk first if you already haven't.


There's a tendency for you to decide to have the talk and then get cold feet.

You'll find excuses to back out of the conversation, and they will be logical to you. Try not to do that. If you really need to have the conversation, it is important you do so early before things get even more complicated. Go into the conversation with a strategy, a clear head and most importantly, a listening ear.


The tone and approach to conversations differ, depending on their relationship with you. Here's my personal approach:


Someone Who Reports To You: I'm firm, direct and constructive. Give rounded feedback — positive and negative. Give specific steps for them to improve. Tell them their strengths. Measure their progress and iterate. A structure for feedback I adopt is the sandwich approach: Positive - Negative - Positive Feedback.


Someone on Your Level: I ask them if they mind receiving some feedback. Giving people the option to refuse feedback disarms them and makes communication much easier. Focus on what they did, not who they are. Communicate clearly and say where exactly it was a problem for you. This group is likely to be very defensive. Expect it, keep your tone calm, but keep your voice firm.


Someone You Report To: Quite naturally, it's important that you are very selective about this group because you report to them and any dent on your relationship will likely affect both your professional life and personal life. Pick your battles on this one, but when you decide that it is important you have this conversation, then go for it.

The trick here is to first ask if you can give them feedback and request a separate time for the conversation. Timing is key. If you see they are flustered, angry or in a turbulent mood, postpone the conversation. If they say yes, that's half the job done. During the talk, I communicate how difficult this is, but I also mention I had to bring it up because I felt it would do more harm than good if I didn’t.


Again, start with their positives, what you admire and respect about them, and then you could ask questions to clarify why they took whatever action they did that calls for the conversation. When you have more context, explain how it came across to you. Here, it helps to think about it from their point of view and communicate how they may have seen it vs. how it came across to you and the impact it had on you.


In conclusion, mention other ways they could have approached it and how it could potentially have yielded a better outcome, and thank them for letting you share your feedback.This approach has worked for me over the years, and occasionally I adjust on the go. With practice it becomes an art but these principles have helped me have rounded, meaningful relationships with my peers, bosses and team.


That's not all; what happens after the talk? Find out here.

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