Hi {{first name | friend}}
Most of us have a conversation we’ve been putting off.
It might be news you haven’t delivered, a problem with a coworker you still haven’t addressed, or feedback you haven’t given.
This week, I cover:
Why avoiding and softening difficult conversations makes things worse
A four-step framework for having them well
Ideas on what to say at each stage
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Difficult conversations often involve delivering bad news, giving negative feedback, or addressing a sensitive topic. We tend to put them off, hoping that time will make them unnecessary, but it rarely does.
I’ve analysed the difficult conversations I’ve been involved in throughout my career and have used my observations to create a framework that helps make these conversations as productive and as easy as they can be.
I’ll walk you through the framework, then I’ll give you a task for this week so you can practise.
Step 1: Set time aside for the conversation
One of the biggest mistakes I see is someone trying to squeeze a difficult conversation into something else that’s already happening. Think tagging it onto the end of a meeting that was about a different topic entirely, or walking past someone in the office and trying to make it a passing comment. It catches people off guard, and it doesn’t work.
When starting a difficult conversation, the most important thing you can do is create space for it.
You can say:
When you have a moment, can we talk about something?
When’s a good time for us to talk? We’ll need around 20 minutes.
Step 2: Open the conversation
I used to have a manager who would try to soften difficult conversations by starting off with How are you? Did you have a good weekend? Oh, you went to the cinema. What film did you see? He saw it too so we’d start discussing the plot, we’d laugh, we’d joke. Then he’d say, “I need to talk to you about something tricky”.
I’d sense what was happening. He’d try to soften the blow but make it ten times worse by taking me on a five-minute detour while I sensed something was off.
Taking someone around the houses before having a difficult conversation confuses the other person and makes them panic. They know something’s coming but they don’t know what. My manager had me reflecting on my weekend, laughing about the film, then BOOM!
Instead, say:
Thank you for making the time to talk with me.
I appreciate you setting time aside for this.
The faster you deliver tough news, the smoother the conversation will go. Once you’ve opened the conversation, get to the point as quickly as possible by saying:
I have some bad news.
This might be difficult to hear.
This is going to be a difficult conversation.
When you set time aside for the conversation and open it quickly, you’re doing two things:
Signalling to the person that you think they can handle this (so there’s no need to overly soften the blow).
Showing the person the conversation deserves its own space because it’s important (so there’s no need to tag it onto something else, reducing its importance).
Step 3: Maintain a collaborative tone
When you’re in the conversation, set a tone that’s collaborative, not combative. You’re not having the conversation to win you’re having it to work through something together.
You can say:
I need your help understanding this (helpful when addressing a questionable comment or behaviour)
I need your help making this the best report it can be (useful when giving constructive feedback)
I need your help knowing what to do about this (good for navigating a complex or shared problem)
Step 4: Close the conversation
As you come to the end of the conversation, it’s a good idea to label where you’ve landed and agree on the next steps. This helps you both acknowledge progress made during the conversation and decide what comes next.
You can say:
I feel better after talking this through. What’s the next step? (ideal if you’ve had an argument)
I feel better understanding where you’re coming from. Shall we next check in on X date? (good for clearing up a misunderstanding)
There’s no rush to respond to any of this right now. Shall we talk it through more tomorrow? (helpful after giving someone difficult feedback they need to digest)
Of course, discernment is important here. When you’ve delivered unpleasant or disruptive news it’s not appropriate to say, “I feel better after talking this through”. Could you imagine?! Think about conversation you’re having, consider how the other person feels, and say something that’s appropriate for the situation you’re in.
When handled well, a difficult conversation doesn’t have to upset anyone or damage relationships. In fact, it might be exactly what’s needed to repair a coworker relationship.
✍️ Your task for this week
Use the difficult conversation framework to plan a conversation you need to have at work.
Being prepared is always best, so come up with a starting phrase for each stage of the conversation to help guide you:
Set time aside for the conversation:
Open the conversation:
Three phrases to maintain a collaborative tone:
Close the conversation:
Now go and have the conversation. There’s no time like the present!
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See you next Monday!
Hayley