How to Have a Challenging Conversation


Hands up if you like delivering
tough messages to people?

That’s what I thought. Not something that leaps to the top of the list for many people.

Whether you’re in a leadership role or not, we all, at some point, need to have conversations with others that we don’t relish, and don’t want to deliver.

  • Some of us may be concerned about the impact on the other person
  • Some of us may struggle to know what to say – how to even bring up the topic
  • Some of us may shy away from what feels like a conflict situation waiting to happen.

But there are ways we can make it easier on ourselves and those we need to land messages with.

It starts before it starts

What’s your overall relationship like with the person?

What are you thinking about the conversation? 

What you’re perceiving as a challenge may not be, if you have the right foundations to work on, and take a coaching approach.

Let’s take Paul as an example.

Paul has been managing Priya for around 2 years. He’s built up a great working relationship with her, getting to know Priya’s likes/dislikes, her family and personal circumstances, her strengths and her weaknesses. They have regular 1-1s and Paul shares broader context about the working environment, and shares the priorities of the team.

He knows that Priya is meticulous in her work and needs to speak to her now about her current project where a stakeholder has flagged an issue with a presentation Priya gave earlier in the week.

Paul decided to have a quick catch up with Priya to ask how she thought the presentation landed. He then gave some positive feedback on her thought processes and asked her to explain a little more about how she thought it had landed with her stakeholder. At that point, she said she didn’t know and looked uncomfortable and as if she’d been caught out.

Paul reassured her that she was thinking about a wide project which was new to her and not knowing wasn’t the end of the World. Then encouraged her to pick up a conversation with the stakeholder.

He then also asked her to talk through what the key deliverables were – and they jointly worked through the next steps of how she’d contact the stakeholder and make some changes.

Looking back at this example, we can see there are many reasons why Paul’s approach has landed well and avoided becoming a challenge:

  1. He’s taken the time to build a good foundation for their working relationship. When you have this in place, there’s automatically more ‘permission’ to have a more challenging conversation which is readily accepted and acted upon
  2. His approach is ‘joint’. He doesn’t place blame on Priya or accuse her of making a mistake. He checks in for her understanding and gives her recognition for what’s gone well. There’s always something which will have gone well, although sometimes our mindset about a person may lead us to think otherwise
  3. He’s suggested that she takes accountability for a follow up conversation with the stakeholder herself. This removes any element of him sharing second hand feedback, and builds her resources to make it successful, through coaching, sharing knowledge and giving guidance.

Having the right mindset

Having the right mindset

Your mindset will determine how you approach the conversation. Paul clearly has respect for Priya and her work, wanting her to be successful. This positive view of Priya means his words and actions are more likely to convey that to her, and she’ll perceive this conversation as less of a threat.

Typically, even though she may feel shame or disappointment for not living up to her high standards, she’s more likely to be receptive and take the messages on board.

Your mindset and approach to the conversation itself also plays a large part in how it will play out. When we think of anything as ‘challenging’ ‘difficult’ or ‘hard’ we are priming our brains to look out for danger. We become more anxious and likely to respond in one of two ways:

  • Pussyfooting around the conversation *
  • Clobbering people with direct messages

* phrase taken from John Heron’s ‘The Complete Facilitator’s Handbook’

When we focus on landing an honestly told message with the intent to help (as opposed to taking frustrations out on other people), we avoid the extremes above. This enables us to be clear, and direct whilst caring about the person, so our message is less distorted and more easily understood.

Using the right words

Using the right words

In a situation where there has been investment in the relationship ahead of the conversation, and you have a positive view of the person and the conversation, you can probably get away with using most words and phrases. That said, there are several ways you can reduce any excess emotion which only serves to help.

What to say

“I’m listening”

Why it works

People have a fundamental need to be seen, heard and recognised. When you say ‘I’m listening’ and actually listen, it has a powerfully calming effect. They are then able to state their case, and you have more information to work with.

What to say

“I’m curious about”

Why it works

This is a much more useful way to find out ‘why’. The word ‘why’ typically has connotations of childhood. “Why haven’t you done your homework?” and feels accusatory. Using the word curious suggests that you’re interested, but not judgemental.

What to say

“I see things a little differently”

Why it works

You’re being clear that you disagree, but it’s almost impossible to say these words in an aggressive way. It invites rational discussion, and opportunity for you both to speak and to listen.

Many studies have shown that when people have the words that make the conversation easier, they are less fearful and more inclined to just give it a go.

Choose your response  

Choose your response

THE most powerful piece of advice I ever received was this. We don’t have to be owned and driven by our emotions, we can always choose how to respond. For some of us, an emotional response or reaction is all we’ve known or experienced, so this concept may seem a little strange at first.

It starts by being aware of our emotions, and our triggers. So if you have a conversation coming up with someone who frustrates you, or knows how to push your hot buttons (spoiler alert – we don’t actually have hot buttons – they’re merely a psychological construct) you can plan ahead for how you’ll manage your reactions.

The most simple thing to control your response, if you can feel yourself getting angry or frustrated, is to say nothing. Take a deep breath, pause, and start counting to ten, breathing in and out slowly.

You could say something like “Let’s take a break for a few minutes and come back to this” and give yourself some physical and mental breathing space.

Just know that someone else’s actions or behaviours do not cause you to act in a certain way. You always make that choice, albeit often quickly and subconsciously. If you don’t like how you react, you can learn ways to control your emotions and thinking to respond in a different way.



Radical Candor:
Kim Scott

A practical book to help you land honest guidance, and so much more. Former silicon valley leader with plenty of advice and tips.



How to say anything to anyone:
Shari Harley

A 15 minute whirlwind of candid and funny feedback advice, with an 8 step process you can use for the really HARD stuff!



Have a go!

Start small with a lower risk conversation that you’ve been putting off. Try out some of the suggestions here, and then see what response you get.

If you don’t get a great outcome, reflect back on what you were doing, saying and thinking. What could you change for next time?

And if you:

  • Want to practise some of those challenging conversations
  • Need support and guidance to deal with the specific challenge that you’re having right now
  • Want to make sure as a new manager that you’re prepared for when you have to have one

Our Challenging Conversations workshop might be just the thing for you.

Alternatively, our coaches are skilled at working with people who find conflict and confrontation difficult, and can work with you 1-1 to overcome your fears or alter your unhelpful thinking patterns.

Leave a Comment

Your email address will not be published. Required fields are marked *

We have a range of virtual training and coaching options and would be happy to speak with you for bespoke or project work too

Scroll to Top