How to Make Courageous Conversations Less Difficult

March 30, 2023

Nigel Girling

Head of Professional Qualifications
Abstract image of two speech bubbles

Let’s begin by defining what is a “Courageous Conversation”?

It’s any conversation you know you are going to have to have that you are dreading: be it with a member of your team, a peer, your boss, or in your private life. A discussion that will involve a difficult topic, or has the potential for conflict. They are an accepted part of being a leader, but there are many ways you can make them easier. For a start….

Do they really need to be all that ‘courageous’?

If you have cultivated a trusting, open and honest relationship with your people, you should be able to talk about anything and they should be able to give honest feedback to you – so work on that first and all the time.

Think ‘Effective’ rather than ‘Courageous’ or ‘Difficult’

The point of the conversation is whatever happens as a result. The conversation could be ‘courageous’ for sure, but that’s no use if it makes things worse, severely damages the relationship or leads to no positive change in the relevant behaviour, attitude or performance. For such conversations to be effective, they must lead to the change you seek.

Secondly, attaching words like courageous and difficult to something makes it potentially too emotionally charged and may unhelpfully shift your mindset into ‘fight’ mode – and theirs too. If you only think about yourself and what you want, you’re missing a fundamental thing: it’s a two-way street and the change will only come if they choose to make it so.

Your point of view is often just that – a personal opinion and perspective

As a leader, you can sometimes mistake your own opinion for the factual truth. Unless there is irrefutable evidence of transgression against an absolute rule or boundary, this is really just you sharing your observations and perspective with another person in the hope of influencing them positively. Your respective job titles don’t make you the arbiter of all things.

In the best sense, this should become a meeting of minds and a shared set of beliefs about what is ‘right’ or ‘best’. That doesn’t mean that you fail to stand your corner or abandon your values! You just need to be aware that another person has their own point of view and that they may well be acting in accordance with what they truly believe to be right.

You can hold a position strongly without being angry or causing distress

There are a very many things I hold dear and believe to be absolutely true. Many of them have a basis in rational judgment and are factually correct. Some of them are almost certainly a bias which is rooted in habit, conditioning and my past experiences – even childhood and parental influence. It is very wise to know which is which.

If a colleague or significant other transgresses against one of my ‘red lines’ – perhaps for example by appearing to be unkind, lazy, stupid or illogical (according to me) – then I know it may ‘press my buttons’. I will typically experience a strong emotional reaction to this – and past experience shows me that immediately entering into a conversation with them about it is very unlikely to end well for either of us.

The best thing I can do to make that conversation ‘effective’ is to step back and reflect for long enough to check and challenge my thinking, and to know that I will stay calm, rational and positive when we speak. That may only require a pause of 45 seconds, or it may need a walk outside and a bit of self-coaching. I just know that I absolutely MUST let go of my emotional reactions and biases if the conversation is to have a positive impact.

An effective conversation is rooted in trust and reflection

It is unlikely that my feedback, advice or input will lead to a positive outcome unless the other party trusts me – and also thinks I have given sufficient intelligent thought to the matter. As such, my standing in the eyes of someone else is significant – not to my ego or any desire to be a hero, but to the positive impact I can have when giving feedback and advice to another. For optimum benefit, the other party must believe that:

a) I have their best interests at heart and have ‘honourable intentions’
b) I am offering my thoughts to help them – giving them the ‘gift of feedback’
c) I know what I’m talking about and have a valid viewpoint
d) I’ve reflected on the issues before formulating my views
e) I’m really listening to them and seeking to understand their perspective
f) I’m ready to accept that I might be wrong

This isn’t always easy – but it goes back to the very first point about developing trusting, open and honest relationships. Do that and everything gets much easier to talk about.

Remember that there is much they believe, do or say that you agree with or see as positive

When having a conversation or giving feedback and advice on something that you think may be unwelcome or lead to unhelpful conflict, it can cause you to focus entirely on the ‘negative’ issues. Balance is key. It may be that you feel positive about 80%, 90% or even 99% of what the other party does, says or believes. Don’t let the remaining few percent lead you to give the wrong impression and leave the person demotivated or demoralized and thinking that they’re worthless – or that you are. Equally, don’t avoid the issue and skirt round it to avoid causing upset.

Conflict is not, of itself, the enemy and it is a responsibility of leadership to help someone to hear and face the truth, get better and to learn.

Sometimes that can make you and/or them uncomfortable, especially if personal preferences or habits make one or both of you likely to find such honesty challenging. That doesn’t mean you should avoid it if there is reason to believe that it will move things forwards.

Unhelpful conflict is another matter entirely.

If the conversation leads to longer-term negative impacts for you, them, the team or the organization – then it can’t really be viewed as a success. The fact that someone reacts badly in the moment may not of itself be a negative, as long as they subsequently reflect and learn from the conversation. Choosing your words and moment sensitively is a wise first step.

You’re always acting on behalf of others

This isn’t just about you and how you feel. If someone’s behaviour, attitude or performance is having a negative impact on others – they will look to you to address it. You have a duty to do right by all stakeholders. You are often acting as an emissary from the rest of the team, internal and external customers and other stakeholders. Do the right thing.

Never forget the power of the pause

Many people, especially if nervous or uncomfortable with silence, will rush to fill any space with more talk. This is rarely helpful. For your feedback or advice to ‘land’ right and cause the other party to reflect, you have to leave time for your words to resonate.

A pause of even 2 or 3 seconds can add significant weight to whatever you have just said. It gives time for the other party to assimilate and consider the message and it gives time for them to formulate a considered response. If you gabble, they may either miss the point entirely or fire back an ill-considered response or an emotional outburst.

Equally, you need to give similar space to allow their words to land with you and to give them due consideration. It is crucial to listen ‘in order to understand’ not just ‘in order to reply’. Leaving pauses from time to time, especially early in the conversation, also subconsciously give the other party ‘permission’ to take their time in responding. It makes it ok for them to stop and think and shows them that you think this conversation is worthy of reflection.


The conversation itself isn’t actually the primary purpose of this process – it is simply the means to an end – the end of making things ‘better’ and making progress. Don’t let your need to ‘fix’ the situation quickly and ‘crack on’ cloud your judgement about what is fair, right and appropriate. This is not about you, or even really about ‘them’ – it’s about the ‘greater good’. As a leader, you have the power to influence and shape most things. Use it wisely.

A final thought
: the more challenging the subject matter of the conversation, the less likely it is that you will reach an effective point in just a few minutes.

It is often helpful in those circumstances to keep the conversation reasonably brief and arrange to follow it up at a subsequent time – even if only a few hours later.

This won’t always be feasible or indeed necessary, but be ready to draw the conversation to a temporary close if it is not proving helpful or you believe the other party – or you – to be too emotionally charged for a positive conclusion to be within immediate reach.

A hiatus of a few hours or even a day or two may provide both of you with the opportunity to reflect and to come up with some useful conclusions or ideas. In any event, following up the conversation at an appropriate point reinforces the importance of what was discussed and why. It also sends out the message that you feel the conversation – and the individual – worthy of further consideration and review.

This piece forms part of a whole library of guidance, training and thought on the challenges facing the modern leader. Topic areas include:

• Wellbeing & Mental Health • Cultural Change
• Resilience & Mental Toughness • Inclusive Leadership
• Thinking Skills • Coaching/ Mentoring
• Human Performance • Inspirational Leadership
• Emotional & Social Intelligence • Followership

Contact Matt Moore at IDG for more information or join our Continuing Professional Development forum group.

We have also discussed this topic in an episode of our podcast series≈, Leadership Learned. You can listen below, and then go to our Leadership Learned page to learn more about the podcast.

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+91 955 271 5800

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+44 (0) 1276 686644