Most of us know exactly which conversation we’ve been putting off. Maybe it’s a team member whose work has started to slip, a peer who keeps stepping on your toes, or some feedback for your own manager that you’ve been sitting on for weeks.
Have a read through the five below and see which one sounds most like you. Each one explains why it happens, gives you a line you can use, and suggests one small thing to try this week.
Jump to your reason:
- I don’t know how to start
- I’m worried about how they’ll react
- I don’t want to damage the relationship
- I soften it until the message gets lost
- I keep waiting for the right moment
REASON 1 OF 5
I don’t know how to start
Most leaders prepare the middle of a hard conversation: the examples, the evidence, the outcome they want. Very few plan the first 20 seconds. Without an opening, the conversation feels impossible to begin, so it slides to tomorrow, then to next week.
The opening doesn’t need to be perfect. It needs to name the topic, say why it matters, and make it clear you want to hear their side.
TRY SAYING
“I want to talk about how yesterday’s client meeting went. I’ve noticed something I think is getting in your way, and I’d like to work through it with you.”
ONE THING TO TRY THIS WEEK
Write your opening down before you walk in. Name the topic, say why it matters, and say you want their view. Three sentences, no more.
REASON 2 OF 5
I’m worried about how they’ll react
When you picture the conversation, you’re probably picturing the worst version of it: tears, anger, a resignation letter. That version rarely happens. Most people take feedback better than we expect, and when they don’t, it’s usually surprise rather than defiance.
The reaction you’re dreading is far easier to handle when you’ve already decided what you’ll do with it.
TRY SAYING
“I can see this has landed hard. Take a minute. I’m not going anywhere.”
ONE THING TO TRY THIS WEEK
Decide in advance what you’ll do if they get upset or defensive: pause, acknowledge it, and come back to the topic. Having a plan for the reaction makes it much easier to start.
REASON 3 OF 5
I don’t want to damage the relationship
Holding back feels like protecting the relationship. In reality, the relationship is already taking a hit. They can usually sense something is off, and you’re quietly losing confidence in them while they have no chance to fix it.
People can hear hard things from someone they trust. The work is making sure they know you’re on their side before you need to say something difficult.
TRY SAYING
“I’m raising this because I want you to do well here, and I think this is holding you back.”
ONE THING TO TRY THIS WEEK
Before you say anything critical, ask yourself whether they know you’re on their side. If you’re not sure, start there. Feedback lands when the trust is already built.
REASON 4 OF 5
I soften it until the message gets lost
You go in with a clear message and come out having said something so gentle it could mean anything. Kim Scott, author of Radical Candor, calls this ruinous empathy: caring about the person but not challenging them directly.
You leave feeling kind. They leave not knowing anything needs to change, and three months later they’re surprised it has become a bigger issue.
TRY SAYING
“To be clear, this needs to change by the end of the month. What support do you need from me?”
ONE THING TO TRY THIS WEEK
At the end of your next feedback conversation, ask them what they’re taking away, in their own words. If it isn’t what you meant, you softened it too much.
REASON 5 OF 5
I keep waiting for the right moment
After the big presentation. Once the project’s finished. When things are less busy. The right moment rarely arrives, and the longer you wait, the bigger the conversation gets. A quick comment this week becomes a formal performance conversation in three months.
The fix is to make feedback so regular that no single conversation needs a perfect moment.
TRY SAYING
“Got two minutes? Quick bit of feedback on this morning’s meeting.”
ONE THING TO TRY THIS WEEK
Give one small, specific piece of feedback every day this week, positive or corrective. When feedback is normal, hard conversations stop feeling like an event.
Start with the one you’ve been putting off longest
Hard conversations don’t get easier by waiting. They get easier with practice: a clear opening, a plan for the reaction, and enough trust that the message can be direct. Pick one conversation, use the line that fits, and have it this week.
LEADERSHIP COLLECTIVE · MELBOURNE
Courageous Conversations & Building Coaching Capability
Practise these conversations with leaders from other industries who are working through the same problems. Tuesday 10 November, 10:00am to 4:00pm, Melbourne CBD. $654.50 incl. GST.
Ruinous empathy is a term from Kim Scott’s Radical Candor.
Most leaders can name the conversation they’re avoiding. A team member whose work has slipped. A peer who keeps overstepping. Feedback for someone more senior that never quite gets said.
Knowing isn’t the problem. Something stops the conversation from happening, and it’s usually one of five things. Only one in four managers has been properly trained to have hard conversations (Achievers Workforce Institute, 2024), so if this sounds familiar, you’re far from alone.
Find the reason that sounds most like you. Each one comes with why it happens, a line you can use, and one thing to try this week.
Jump to your reason:
- I don’t know how to start
- I’m worried about how they’ll react
- I don’t want to damage the relationship
- I soften it until the message gets lost
- I keep waiting for the right moment
REASON 1 OF 5
I don’t know how to start
Most leaders prepare the middle of a hard conversation: the examples, the evidence, the outcome they want. Very few plan the first 20 seconds. Without an opening, the conversation feels impossible to begin, so it slides to tomorrow, then to next week.
The opening doesn’t need to be perfect. It needs to name the topic, say why it matters, and make it clear you want to hear their side.
TRY SAYING
“I want to talk about how yesterday’s client meeting went. I’ve noticed something I think is getting in your way, and I’d like to work through it with you.”
ONE THING TO TRY THIS WEEK
Write your opening down before you walk in. Name the topic, say why it matters, and say you want their view. Three sentences, no more.
REASON 2 OF 5
I’m worried about how they’ll react
When you picture the conversation, you’re probably picturing the worst version of it: tears, anger, a resignation letter. That version rarely happens. Most people take feedback better than we expect, and when they don’t, it’s usually surprise rather than defiance.
The reaction you’re dreading is far easier to handle when you’ve already decided what you’ll do with it.
TRY SAYING
“I can see this has landed hard. Take a minute. I’m not going anywhere.”
ONE THING TO TRY THIS WEEK
Decide in advance what you’ll do if they get upset or defensive: pause, acknowledge it, and come back to the topic. Having a plan for the reaction makes it much easier to start.
REASON 3 OF 5
I don’t want to damage the relationship
Holding back feels like protecting the relationship. In reality, the relationship is already taking a hit. They can usually sense something is off, and you’re quietly losing confidence in them while they have no chance to fix it.
People can hear hard things from someone they trust. The work is making sure they know you’re on their side before you need to say something difficult.
TRY SAYING
“I’m raising this because I want you to do well here, and I think this is holding you back.”
ONE THING TO TRY THIS WEEK
Before you say anything critical, ask yourself whether they know you’re on their side. If you’re not sure, start there. Feedback lands when the trust is already built.
REASON 4 OF 5
I soften it until the message gets lost
You go in with a clear message and come out having said something so gentle it could mean anything. Kim Scott, author of Radical Candor, calls this ruinous empathy: caring about the person but not challenging them directly.
You leave feeling kind. They leave not knowing anything needs to change, and three months later they’re surprised it has become a bigger issue.
TRY SAYING
“To be clear, this needs to change by the end of the month. What support do you need from me?”
ONE THING TO TRY THIS WEEK
At the end of your next feedback conversation, ask them what they’re taking away, in their own words. If it isn’t what you meant, you softened it too much.
REASON 5 OF 5
I keep waiting for the right moment
After the big presentation. Once the project’s finished. When things are less busy. The right moment rarely arrives, and the longer you wait, the bigger the conversation gets. A quick comment this week becomes a formal performance conversation in three months.
The fix is to make feedback so regular that no single conversation needs a perfect moment.
TRY SAYING
“Got two minutes? Quick bit of feedback on this morning’s meeting.”
ONE THING TO TRY THIS WEEK
Give one small, specific piece of feedback every day this week, positive or corrective. When feedback is normal, hard conversations stop feeling like an event.
Start with the one you’ve been putting off longest
Hard conversations don’t get easier by waiting. They get easier with practice: a clear opening, a plan for the reaction, and enough trust that the message can be direct. Pick one conversation, use the line that fits, and have it this week.
LEADERSHIP COLLECTIVE · MELBOURNE
Courageous Conversations & Building Coaching Capability
Practise these conversations with leaders from other industries who are working through the same problems. Tuesday 10 November, 10:00am to 4:00pm, Melbourne CBD. $654.50 incl. GST.
Source: Achievers Workforce Institute, Workplace Conversations research, 2024 (survey of 1,500 employees in the US and Canada). Ruinous empathy is a term from Kim Scott’s Radical Candor.
