Some workplace conversations are easy. Others sit on the to-do list for days, weeks or even months.
- A performance issue needs addressing.
- Two colleagues are no longer working well together.
- A behaviour is affecting the team.
- A decision needs challenging.
- Someone needs feedback they may not want to hear.
- An expectation has not been met.
- A boundary needs to be made clear.
We often know the conversation needs to happen. The difficult part is having it well.
Courageous conversations are not about becoming confrontational, saying everything you think or proving that you are right.
They are about addressing an important issue clearly enough to make progress, while protecting the dignity of the people involved and keeping the purpose of the conversation in sight. Handled well, a difficult conversation can strengthen clarity, trust and accountability.
Handled badly, it can create defensiveness, resentment or another problem entirely. Avoided altogether, the issue often remains.
What is a courageous conversation?
A courageous conversation is an open and purposeful discussion about an issue that matters, even when raising it may feel uncomfortable.
The conversation may involve disagreement, feedback, performance, behaviour, expectations, conflict, change or a decision that needs to be challenged.
What makes the conversation courageous is not aggression. It is the willingness to address something important rather than avoiding it.
Good courageous communication combines clarity with respect. You need to be able to say what needs to be said. You also need to remain sufficiently open to hear information you may not yet have.
That balance matters.
When is a courageous conversation needed?
Not every disagreement requires a formal conversation. But delaying a conversation simply because it feels uncomfortable can allow relatively small issues to become harder to resolve.
A courageous workplace conversation may be useful when:
- someone’s behaviour is affecting other people
- performance is consistently below an agreed expectation
- roles or responsibilities are unclear
- a decision appears to have overlooked important information
- conflict is beginning to damage working relationships
- feedback has repeatedly been avoided
- a person feels unheard or excluded
- a leader needs to explain an unpopular decision
- an expectation or boundary needs clarifying
- a problem keeps returning despite previous discussions
The earlier a genuine issue can be discussed constructively, the more room there is to understand what is happening before positions become entrenched.
That does not mean every workplace issue should be managed informally.
Serious allegations, discrimination, harassment, safety concerns, misconduct or matters covered by formal organisational procedures may require HR advice or a formal process.
A courageous conversation should support good management practice, not replace it.
Why do leaders avoid difficult conversations?
Usually because something feels at risk. The relationship. The other person’s reaction. Our reputation. Our authority. Our own emotions. The possibility of conflict. Or simply the fear that we will not know what to say once the conversation begins.
Avoidance can feel safer in the short term. But unresolved issues do not disappear just because nobody mentions them. People notice inconsistent standards. Teams notice tension. Strong performers notice when poor behaviour is left unaddressed. Employees notice when expectations are unclear.
And leaders can find themselves having a much more difficult conversation later about an issue that could have been addressed earlier.
Courageous conversations are a capability. Like most capabilities, they improve through preparation, practice and reflection.
Start with purpose, not frustration
Before having a difficult conversation, ask: Why does this conversation need to happen?
That question sounds simple. It is remarkably useful.
If the answer is: “I want them to know how annoyed I am.” you may not yet be ready.
A stronger purpose might be: “I want us to clarify what is expected and agree how we move forward.” Or: “I want to understand what is contributing to the problem before we decide what happens next.” Or: “I need to make the impact of this behaviour clear and give the person an opportunity to respond.”
Purpose creates direction. Without it, a difficult conversation can quickly become a collection of complaints.
Prepare the facts before the story
Humans make meaning very quickly.
Someone misses two deadlines. We decide they are unreliable.
A colleague challenges us in a meeting. We decide they are disrespectful.
A manager does not respond. We decide they do not care.
The observation and the interpretation are not the same thing.
Before a courageous conversation, separate: What have I actually observed? from: What have I concluded from it?
For example:
Observation: The report was submitted after the agreed deadline on the last three occasions.
Interpretation: You do not take deadlines seriously.
The observation gives you something specific to discuss. The interpretation may or may not be correct.
The conversation gives you the opportunity to find out.
This is one reason Unbiased Thinking matters. Good conversations require enough distance from our initial reaction to test what we think we know.
Four flowprofiler® dimensions that support courageous conversations
There is no single perfect style for a difficult conversation. Different circumstances require different behavioural choices.
Four flowprofiler® dimensions are particularly useful when thinking about courageous conversations at work:
- Assertiveness
- Unbiased Thinking
- Purpose
- Collaboration
The value lies not simply in having more of each. As with all flowprofiler® dimensions, effective behaviour depends on context and proportion.
1. Assertiveness: say what needs to be said
Assertiveness allows us to express a view, concern, expectation or boundary clearly.
Without enough assertiveness, people may soften the issue so much that the other person leaves without understanding what actually needs to change.
For example: “There have just been a couple of little things lately and I wondered if maybe we could perhaps keep an eye on them.”
That may feel polite. It may also be impossible to act on.
An assertive version is clearer: “I want to discuss the last three missed deadlines because they are affecting the wider team’s ability to complete its work.”
The issue is visible. The language is respectful. The conversation can begin.
But assertiveness can also be overused. Clarity can become force. Confidence can become certainty. A conversation can turn into a lecture.
The aim is not: I have said my piece.
The aim is: We have addressed the issue.
2. Unbiased Thinking: test your interpretation
Difficult conversations often begin after we have already formed a view. The risk is entering the discussion only looking for evidence that confirms it.
Unbiased Thinking creates enough distance to ask:
- What do I know?
- What am I assuming?
- What information might I be missing?
- What would change my view?
- How might the other person see this differently?
This does not mean becoming perfectly objective. None of us is. It means creating space between our immediate judgement and the conclusion we act on.
Overuse matters here too. Objectivity can become emotional detachment. A leader can become so focused on facts and logic that they fail to recognise the human impact of the conversation.
People and context still matter.
3. Purpose: keep the conversation pointed at an outcome
Difficult conversations can easily drift.
One missed deadline becomes a discussion about six months of frustrations.
One behaviour becomes a judgement about someone’s character.
One disagreement becomes a contest over who is right.
A clear purpose keeps the discussion anchored.
Ask:
- What needs to be different after this conversation?
- What needs to be understood?
- What decision needs to be made?
- What agreement do we need?
Purpose helps prevent the conversation becoming an emotional download.
But purpose can also be overused. An excessive focus on the desired outcome can become tunnel vision.
If the leader is determined to reach a particular conclusion regardless of what they hear, the conversation is not genuinely open.
4. Collaboration: solve the problem with the person
Collaboration changes the conversation from: I have a problem with you to: We have an issue we need to understand and address.
That does not remove accountability. Sometimes the leader still needs to set a clear expectation, make a decision or say no.
Collaboration means giving the other person meaningful space to contribute to the understanding and, where appropriate, the solution.
Questions such as these help:
- “How do you see the situation?”
- “What is contributing to this?”
- “What have I not understood?”
- “What do you think needs to change?”
- “What support would make a difference?”
- “What can we each do next?”
Collaboration can also be overused. Seeking agreement from everybody can become avoidance of a necessary decision.
A courageous conversation sometimes ends with: “I have listened to your view. The expectation is still this.”
Collaboration does not remove leadership responsibility.
Three supporting capabilities matter too
The four dimensions above provide a strong behavioural foundation. Other capabilities can make them much easier to use well.
Emotional Regulation
A difficult conversation becomes harder when our own emotional response takes over. Emotional Regulation helps us notice the reaction without allowing it to control every word, tone or decision.
That does not mean suppressing emotion. It means retaining enough choice to respond proportionately.
Social Awareness
What is happening in the conversation? Has the other person understood? Are they becoming defensive, confused or distressed? Is the discussion still productive?
Social Awareness helps us notice what is happening around the words without pretending we can read someone’s mind.
The useful response is curiosity. Not assumption.
Regard for Others
Courage is not permission to become careless with another person’s dignity. Regard for Others helps us challenge an issue without unnecessarily diminishing the person. You can be direct and respectful at the same time.
How to prepare for a courageous conversation
Good preparation does not mean scripting every sentence. It means becoming clear enough about the issue that you can stay present when the conversation takes an unexpected turn.
Before the meeting, consider:
Purpose: Why does this conversation matter?
Evidence: What have I directly observed?
Assumptions: What am I interpreting rather than knowing?
Impact: What effect is the issue having?
Perspective: What might I not yet understand?
Outcome: What would useful progress look like?
Responsibility: What part of the issue belongs to me?
Environment: Is this the right time, place and setting for the discussion?
That last question matters. A courageous conversation does not need an audience. Privacy usually helps. So does enough time to have the conversation without rushing towards the door.
How do you start a courageous conversation?
The opening matters because it tells the other person whether they are entering a discussion or an ambush. You do not need a complicated script.
Try something like: “I’d like to talk about X because Y matters. I’ve noticed Z, and I’d like to understand how you see it before we agree what happens next.”
For example: “I’d like to talk about the handover process because the delays are affecting the next team in the workflow. The last three handovers have arrived after the agreed time. I’d like to understand what is happening from your perspective and work out what needs to change.”
That opening does several useful things. It explains the purpose. It identifies observable information. It explains the impact. And it invites the other person’s perspective.
Compare that with: “We need to talk about your attitude.”
The second opening may be courageous. It is not particularly useful.
During the conversation: stay curious for longer
Many difficult conversations fail because both people spend their time preparing their next response. Listening is not waiting for your turn to speak.
Ask questions. Check your understanding. Reflect back what you heard. Look for information that changes the picture.
You can still disagree. You can still hold someone accountable. But disagreement based on understanding is usually more useful than disagreement based on assumption.
Try:
- “What makes you see it that way?”
- “Can you give me an example?”
- “Help me understand what was happening at that point.”
- “What do you think I am missing?”
- “What would a workable solution look like from your perspective?”
Curiosity is not weakness. It is information gathering.
Keep behaviour separate from identity
One of the quickest ways to create defensiveness is to turn a specific behaviour into a judgement about character.
Compare: “You’re unreliable.”
with: “The last three reports were submitted after the agreed deadline.”
Compare: “You don’t care about the team.”
with: “When the decision was changed without telling the team, three people had to redo their work.”
Specific behaviour can be discussed. Identity judgements invite people to defend who they are.
This distinction is central to the way we think about behaviour at flowprofiler®. Behaviour is not identity.
People can understand behavioural patterns, make choices and develop capability.
What if the other person becomes defensive?
Defensiveness does not automatically mean the conversation has failed. You are discussing something difficult. A response is likely. The question is what you do next.
- You can slow the conversation.
- Acknowledge what you are hearing.
- Restate the purpose.
- Return to specific information.
- Ask a genuine question.
If emotions are escalating beyond the point where productive discussion is possible, it may be appropriate to pause and agree when to continue.
Courage does not require pushing forward at any cost. Sometimes the most effective choice is: “This is clearly important and I don’t think continuing in this moment will help either of us. Let’s pause and come back to it at 2pm.”
Seven common mistakes in courageous conversations
The conversation becomes much harder when we:
- wait until frustration has accumulated
- go in determined to win
- use vague language rather than naming the issue
- arrive with conclusions but no evidence
- attribute motives we cannot know
- talk far more than we listen
- leave without agreeing what happens next
None of these makes somebody a poor leader. They are behavioural choices. And choices can change.
Psychological safety does not mean avoiding difficult conversations
Psychological safety is sometimes misunderstood as making sure nobody feels uncomfortable. That is not its purpose.
A psychologically safe team is one where people are more able to raise questions, concerns, mistakes and difficult issues without expecting humiliation or punishment simply for speaking. That can involve uncomfortable conversations.
In fact, a team in which nobody challenges a decision, raises a problem or discusses a mistake may look harmonious while important information remains hidden.
Courageous conversations and psychological safety can reinforce each other.People are more likely to speak when they believe their contribution will be treated seriously.
Leaders strengthen that environment when they listen, respond proportionately, admit their own mistakes and make it possible to disagree without turning disagreement into disloyalty.
Courageous conversations are not only about individual skill
Sometimes organisations send managers to communication training when the system itself is making good conversations unnecessarily difficult. That is worth checking.
Our Triple A Framework provides one way to think about individual readiness.
Aptitude
Does the person have the knowledge and skill to conduct the conversation well?
Attitude
Are they willing to address the issue, hear another perspective and take responsibility for their part?
Approach
Are they choosing a method that fits the situation?
The organisational environment matters as well. The Enabling Four provide a second check.
Rules
Are expectations, standards and policies clear?
Roles
Is it clear who should have this conversation?
Responsibilities
Does everyone understand what they are accountable for?
Resources
Do people have the time, information, support and authority needed to resolve the issue?
A manager cannot communicate their way out of every system problem.
Sometimes the courageous conversation reveals that the real issue is unclear roles, contradictory expectations or insufficient resources.
That is useful information.
What changes under pressure?
Many people know how they would like to behave in a difficult conversation. Then the conversation begins. Pressure changes things.
A naturally collaborative leader may become unusually controlling. A confident person may avoid the issue. A measured manager may become blunt. Someone who values evidence may become emotionally attached to being right. Another person may become so detached that the conversation loses its human quality.
flowprofiler® assessments examine behaviour in two states: day to day and under pressure.
That distinction can help people understand not just what their preferred behaviour looks like, but how it may shift when the conversation matters most.
It also helps us move beyond simplistic advice such as “be more assertive”. More is not always better. The aim is to use the right behaviour, in the right amount, for the situation.
A quick courageous conversation check
Before your next difficult workplace conversation, ask:
- What is the purpose?
- What have I actually observed?
- What am I assuming?
- What does the other person need to understand?
- What might I need to understand?
- Which behaviour am I most likely to underuse?
- Which strength might I overuse under pressure?
- What outcome am I hoping for?
- What will we agree before the conversation ends?
If you can answer those questions clearly, you are already better prepared.
Build capability, not avoidance
Courageous conversations are part of leadership.
Managers cannot motivate people, address performance, build accountability, resolve disagreement or lead change without sometimes discussing things that feel uncomfortable.
The objective is not to make every difficult conversation comfortable. It is to make it constructive. Clear enough to address the issue. Open enough to hear new information. Respectful enough to protect dignity. Focused enough to reach an outcome.
And courageous enough to happen in the first place.
Want your managers to become more confident with difficult conversations?
Our one-day Courageous Conversations workshop helps managers build the behavioural capability to prepare for, conduct and follow through on difficult workplace conversations.
The programme connects practical conversation skills with behavioural insight, helping participants explore how Assertiveness, Unbiased Thinking, Purpose, Collaboration and supporting emotional and social capabilities influence the way they communicate, particularly under pressure.
Talk to us about a Courageous Conversations workshop for your leadership team.
Understand the behaviour behind the conversation
flowprofiler® helps individuals and teams understand workplace behavioural patterns across emotional intelligence, resilience and motivation, including how behaviour may shift under pressure.
Behavioural insight can help leaders identify where they may avoid difficult conversations, become overly forceful, lose objectivity, seek too much agreement or become overly focused on the desired outcome.
Because knowing what to say is useful.
Understanding how you are likely to behave when the conversation becomes difficult is better.
References
Acas. (2025). Informal conversations: The key to reducing workplace conflict?
Acas. (2025). The power of informal conflict resolution at work.
Bradley, B. H., Postlethwaite, B. E., Klotz, A. C., Hamdani, M. R., & Brown, K. G. (2012). Reaping the benefits of task conflict in teams: The critical role of team psychological safety climate. Journal of Applied Psychology, 97(1), 151–158.
Edmondson, A. (1999). Psychological safety and learning behavior in work teams. Administrative Science Quarterly, 44(2), 350–383.
O’Donovan, R., & McAuliffe, E. (2020). A systematic review exploring the content and outcomes of interventions to improve psychological safety, speaking up and voice behaviour. BMC Health Services Research, 20, 101.
Ou, Z., Chen, T., Li, F., & Tang, P. (2018). Constructive controversy and creative process engagement: The roles of positive conflict value, cognitive flexibility, and psychological safety. Journal of Applied Social Psychology, 48(2), 101–113.
