How to Have Difficult Conversations at Work Without the Awkwardness

Few parts of being a people manager are as uncomfortable as having a difficult conversation. Whether it is addressing poor performance, giving challenging feedback, managing conflict between colleagues or raising concerns about someone’s behaviour, these conversations can be easy to put off.

For new and emerging managers in particular, the prospect of getting it wrong can be enough to avoid the conversation altogether. There can be a tendency to wait for the right moment, hope the issue resolves itself or tell ourselves that it is not quite serious enough to raise yet. In reality, avoiding a difficult conversation rarely makes the underlying issue easier to manage. More often, it allows frustration to build, expectations to become unclear and relatively minor issues to become more difficult to resolve.

Having difficult conversations is therefore less about finding the perfect words and more about developing the confidence and judgement to address issues when they need to be addressed. Done well, these conversations can strengthen relationships rather than damage them. They give people clarity, create an opportunity to be heard and establish a path forward.

Why Managers Avoid Difficult Conversations

There is a natural tension between wanting to maintain positive relationships with employees and needing to address behaviour or performance that is not meeting expectations. Managers may worry that being direct will make them seem unsympathetic, damage trust or create conflict where there was none before.

That concern is understandable. But good leadership is not about keeping every interaction comfortable. It is about creating an environment where people understand what is expected of them and feel able to have honest conversations when something is not working.

The Fair Work Ombudsman recommends addressing workplace issues early and having open discussions before problems escalate. Its guidance on difficult conversations highlights the importance of preparation, managing emotions and focusing on a constructive outcome rather than approaching the conversation as a confrontation.

This is particularly important when a manager notices a pattern emerging. One missed deadline may be an isolated issue. Repeated missed deadlines, unexplained changes in behaviour or ongoing tension between team members require a different response. The longer a manager waits, the more likely it is that the conversation becomes about accumulated frustration rather than the original issue.

Direct Doesn't Have to Mean Confrontational

One of the most important distinctions for a manager to understand is the difference between being assertive and being aggressive.

When managers are uncomfortable with confrontation, they can sometimes go too far in one direction or the other. They may soften the message so much that the employee leaves without understanding what needs to change, or they may approach the conversation with frustration and become unnecessarily blunt.

Neither approach is particularly effective.

Assertive communication allows a manager to be clear about what they have observed, explain why it matters and communicate what needs to happen next, while still giving the other person an opportunity to respond. It is direct without being dismissive.

Consider the difference between telling an employee, “You need to have a better attitude,” and explaining that “In the last two team meetings, you interrupted colleagues while they were speaking. It made it difficult for them to contribute and I need you to give others the opportunity to finish before responding.”

The second statement may still be uncomfortable to hear, but it gives the employee something specific to consider. It focuses on observable behaviour and its impact rather than making a judgement about their character.

This distinction becomes particularly important when managers are dealing with difficult or challenging behaviours. Labelling someone as a “difficult person” can make a situation feel personal and leave little room for a constructive response. Focusing instead on the behaviour, its impact and the expectations around it gives the conversation somewhere to go.

Preparation Matters, But So Does Listening

Being direct does not mean walking into a conversation with a predetermined outcome. Preparation is important, but managers should be careful not to prepare so extensively that they stop listening.

Before a difficult conversation, it helps to establish what you actually know. What happened? What have you observed? What impact has it had? Is there a pattern, or could this be an isolated incident? Most importantly, what outcome are you hoping to achieve?

Separating facts from assumptions is critical. A manager may believe an employee is disengaged, for example, when the observable issue is that they have missed several deadlines. The former is an interpretation; the latter is something that can be discussed.

Once the conversation begins, the employee should have an opportunity to explain their perspective. There may be circumstances the manager is unaware of, competing priorities that have not been communicated clearly or a misunderstanding that needs to be addressed.

Listening does not mean agreeing. It means making sure decisions are based on an understanding of the situation rather than assumptions.

This can be particularly challenging for new managers, who may feel that being in a leadership position means they need to have all the answers. In practice, effective people leadership often requires the opposite. Asking thoughtful questions, remaining curious and allowing people to explain their perspective can lead to better decisions and stronger working relationships.

The Conversation Should Be About What Happens Next

A difficult conversation becomes much more constructive when it moves beyond identifying a problem and towards agreeing on a way forward.

If an employee's performance is not meeting expectations, they need to understand what good performance looks like and what needs to change. If two colleagues are experiencing conflict, they need clarity around how they will work together going forward. If a behaviour is inappropriate, the expectation needs to be communicated clearly.

The aim is not necessarily to resolve everything in one conversation. Some issues will require ongoing discussion, support or formal processes. What matters is that the conversation creates clarity rather than leaving both parties wondering what was actually agreed.

This is where conflict resolution becomes an important management capability. Workplace conflict is not always negative; differences in perspective can lead to better ideas and decisions when they are managed constructively. Problems arise when conflict is allowed to become personal, entrenched or disruptive. For a new manager, developing this capability can provide a valuable foundation for handling disagreements before they escalate.

Difficult Conversations Don't End When the Meeting Does

One of the less obvious aspects of managing difficult conversations is what happens afterwards.

A manager may have addressed an issue clearly and reached an agreement with an employee, but that does not necessarily mean the matter is resolved. Following up demonstrates that the conversation was intended to create change rather than simply deliver criticism.

A short check-in can provide an opportunity to acknowledge improvement, clarify expectations or identify where further support is needed. It also gives the employee confidence that their manager is paying attention and is prepared to have the conversation again if necessary.

Consistency matters here. Employees are more likely to trust managers who are willing to address issues fairly and directly, rather than managers who avoid difficult conversations until frustration reaches a breaking point.

This is increasingly important as organisations consider the broader impact of workplace relationships and management capability. Research from the Australian HR Institute found that 38% of employers reported an increase in claims or complaints relating to psychosocial hazards in 2025, with workplace conflict identified among the leading causes. At the same time, only 28% reported investing in leadership and management capability to improve psychosocial health.

The findings highlight an important role for managers. While organisations have broader responsibilities for creating safe and productive workplaces, managers are often the people closest to the day-to-day relationships, behaviours and issues that shape an employee's experience.

Building the Confidence to Have the Conversation

Ultimately, becoming comfortable with difficult conversations is part of becoming a better people manager.

It is unlikely that any manager will reach a point where these conversations feel completely comfortable. The objective is not to remove the discomfort, but to develop the communication skills, emotional awareness and confidence to manage it.

For new and emerging managers, that development can make an important difference. Knowing how to communicate assertively, respond to difficult behaviours, manage conflict and listen effectively provides a stronger foundation for leading people, particularly when situations become challenging.

These are skills that can be developed through experience, reflection and targeted professional development.

AIM offers a range of courses designed to help managers build these capabilities, including Dealing with Difficult Behaviours, Conflict Resolution and Assertiveness Techniques. Managers looking to broaden their leadership capability can also explore Stakeholder Engagement, which develops skills for building relationships, communicating effectively and influencing others.

Ready to strengthen your leadership skills?

AIM is currently offering up to $300 in credit towards eligible Short Courses, Vocational Qualifications, Microcredentials and Mini MBA programs. It is an opportunity to invest in the skills that matter most to you and your team while making your professional development budget go further.