What Is a Courageous Conversation?
There are times when we all need to have a serious conversation with someone, whether it’s a partner, a friend, or a work colleague. It’s one of those conversations where we need to be open and honest, not only with ourselves but also with the person in front of us. It could be about an incident, something they’ve said or done (or not done), non-performance, or non-delivery.
Many of us feel uncomfortable in situations like this. But avoiding these conversations doesn’t make the problem go away, it usually makes it worse. Unaddressed issues fester, trust erodes, and employee engagement drops as people lose confidence in leadership’s willingness to address problems.
A courageous conversation is a discussion that requires honesty, empathy, and the willingness to sit with discomfort, all in service of a positive outcome. And in the workplace, they’re essential for maintaining psychological safety and building work relationships that last.
Why Courageous Conversations Matter for Team Performance
When leaders and colleagues avoid difficult conversations, the cost is significant:
- Standards slip because underperformance goes unaddressed
- Resentment builds as high performers watch issues get ignored
- Psychological safety erodes because people learn that speaking up doesn’t lead to resolution
- Trust weakens because avoidance signals that the relationship can’t handle honesty
On the other hand, teams that normalise courageous conversations benefit from faster conflict resolution, clearer expectations, stronger trust, and higher engagement. The key is approaching these conversations with the right intent and the right techniques.
Preparing for a Courageous Conversation
Before diving into the techniques, preparation matters. A good manager or leader has two ears and one mouth, so they can really listen and hear what’s being said by the other person before reacting.
Here’s how to prepare:
- Gather the facts. Get as much information as you’ll need to support the objective of the discussion (e.g. a win-win resolution).
- Set a time. Don’t spring the conversation on someone unexpectedly. Make a set time to talk.
- Choose a neutral environment. Preferably somewhere with no underlying territorial energy (e.g. not your office or their office). A meeting room, a coffee shop, or a walk.
- Stick to the facts but deliver the message with compassion, empathy, and a willingness to seek understanding.
3 Techniques for Having a Courageous Conversation
1. The Awareness Effect
Make the person aware upfront that this is going to be an honest conversation by being honest yourself.
Example: “I realise this may be difficult to hear, but I need to be honest with you about…”
By telling someone that the conversation might make them feel defensive or uncomfortable, you often prevent them from becoming defensive. You’re naming the elephant in the room rather than pretending it isn’t there.
Key steps:
- Give them specific, real examples of their behaviour or non-delivery so they know exactly what you’re referring to
- State what it is you expect or need from them going forward so there’s no room for misunderstanding
- Be clear but kind, honesty without empathy is just bluntness
This approach builds psychological safety because the person knows where they stand. Uncertainty breeds anxiety; clarity breeds trust.
2. The Domino Effect
In this approach, you show how the person’s role plays an integral part in the bigger picture and the impact their non-delivery has on those around them, including you.
Example: “When the report wasn’t delivered on Friday as we agreed, I couldn’t complete my work, which resulted in me being late with my report to the client. That affected the team’s credibility.”
Key steps:
- Show the ripple effect, how their actions (or inaction) impact colleagues, clients, and the team
- Share your vision for where you see them playing an integral part, and get their buy-in
- Use practical, real examples so they have a clear picture of what you’re referring to
This technique works because it shifts the conversation from “you did something wrong” to “here’s how we’re connected, and why this matters to all of us.” It reinforces building work relationships by showing that everyone’s contributions matter.
3. The Enquiry Effect
In this approach, you enquire what’s going on for the person that they’re not delivering or meeting expectations. This is where active vs passive listening becomes critical, you need to genuinely hear their perspective, not just wait for your turn to speak.
Example: If they say “I’m so busy I can’t manage doing this too!”, step into their world and get specific: “What exactly is making things busy for you? Is it the workload, lack of resources, or something else?”
Key steps:
- Ask open questions to understand their reality
- Brainstorm solutions together – *”What needs to happen for it to be manageable so you can deliver on your tasks?”*
- Help them identify what they can do differently (e.g. if it’s skills they need, what needs to happen for them to acquire those skills?)
- Ask what you, as their manager or leader, can do to help in the areas they’ve identified
This way the individual takes ownership and responsibility for the part they play. They feel heard, supported, and part of the solution, which is the essence of employee engagement. The result is a collaborative situation rather than one that produces frustration for both sides.
What to Do When the Other Person Becomes Defensive
Even with the best preparation, the person you’re engaging with may become defensive, act negatively, or refuse to listen. Here’s how to handle it:
- Don’t let the situation escalate. Stick to the facts, keep your composure, and don’t get drawn into their emotional reaction.
- Restate the positive outcome you’re looking for a solution-based discussion, and ask if they’re willing to help find solutions.
- If the situation continues to spiral, end the discussion and reschedule for another time when you can both calmly look at the problem and find an agreeable way forward.
- If there’s no way forward, you may need to escalate to a third party who can mediate and help find middle ground.
This isn’t failure, it’s leadership skills in action. Knowing when to pause a conversation is just as important as knowing how to start one.
The Link Between Courageous Conversations and Psychological Safety
It might seem counterintuitive, but courageous conversations actually *build* psychological safety. When people see that difficult issues can be raised and resolved respectfully, they learn that honesty is safe in your team. They become more willing to speak up, share concerns, and admit mistakes, all of which drive performance and innovation.
The alternative, a culture where difficult things aren’t said, creates the illusion of safety while real problems compound silently underneath.
The Bottom Line
Courageous conversations aren’t about confrontation. They’re about care, caring enough about the person and the relationship to have the honest conversation that needs to happen.
When leaders develop the leadership skills to have these conversations well, the entire team benefits: trust deepens, engagement rises, and work relationships become stronger and more resilient.
The question isn’t whether you’ll need to have a courageous conversation. You will. The question is whether you’ll have the skills to handle it well.
Frequently Asked Questions
What is a courageous conversation?
A courageous conversation is an honest, direct discussion about a difficult topic such as underperformance, behaviour, or unmet expectations. The goal is always a positive, solution-focused outcome, approached with empathy and respect.
How do I prepare for a courageous conversation at work?
Gather the facts beforehand, set a specific time for the conversation, choose a neutral environment, and prepare to listen as much as you speak. Approach the conversation with compassion and a willingness to understand the other person’s perspective.
What are the three techniques for having a courageous conversation?
The Awareness Effect (being upfront about the nature of the conversation), the Domino Effect (showing how their actions impact the wider team), and the Enquiry Effect (asking questions to understand their situation and brainstorming solutions together).
How do courageous conversations improve psychological safety?
When difficult issues are raised and resolved respectfully, people learn that honesty is safe in the team. This builds trust, encourages people to speak up, and creates a culture where problems are addressed early rather than left to fester.
What if the person becomes defensive during the conversation?
Stay calm, stick to the facts, and don’t get drawn into their emotional reaction. Restate your goal of finding a solution together. If the conversation continues to escalate, end it and reschedule for a time when you can both approach the issue calmly.
Paula Quinsee is a Relationship Expert and engagement strategist. She helps organisations cultivate healthy workplace cultures through emotional intelligence, leadership development, and values-based implementation. Paula is the author of Embracing Conflict and Embracing No, and regularly speaks on workplace engagement, communication, and culture. Contact us to chat about how we can assist you with building engaged employees, engaged leaders and engaged organisations or book a discovery call here.