How to Approach Difficult Conversations in the Workplace 

When we think about difficult or sensitive conversations in the workplace, we often think of those centred around poor performance or conflict resolution. Perhaps someone has dropped the ball on an important job, or maybe two opposing personalities have clashed over a recent project.

While these scenarios are common, difficult discussions are not always work-related – some hard-to-navigate conversations may centre on a colleague or employee’s personal challenges, like illness or loss, and the impact these challenges can have on someone’s work life.

Approaching difficult or sensitive conversations at work can feel daunting and uncomfortable, but they’re a crucial part of any supportive, healthy, and high-performing workplace culture.

Whether you’re raising a personal issue with your boss or expressing concern for a struggling colleague, the secret to a successful and productive chat lies in approaching the situation with empathy and openness and coming from a place of genuine connection.

8 steps to approaching difficult conversations with empathy and openness

Be prepared: Before entering a difficult conversation, make sure you’re clear on what you want to achieve, and approach the dialogue with a mindset of empathy, understanding, and a genuine desire to find mutually beneficial solutions.

Choose the right time and place: Find a quiet and private space where you can have the conversation without interruptions. Make sure the timing is appropriate and that both parties are in a calm and receptive state of mind.

Use clear and direct communication: Be specific about your concerns and avoid making generalisations or accusations. Focus on the behaviour or actions that are of concern. For example, if you’re worried about a colleague’s health or wellbeing, you will need to express your concerns in a neutral, non-judgemental way and offer your support.

Listen actively: Give the other person a chance to share their perspective and actively listen to what they have to say. Importantly, listen to understand—not just to reply. Make a genuine effort to understand the situation from their perspective.

Stay calm and in control: It’s important to remain calm and composed during difficult conversations, even if the other person becomes emotional. Engage in active listening, validate their feelings, and refrain from reacting impulsively. Take deep breaths to centre yourself and maintain a respectful tone and body language throughout the discussion.

Focus on finding a solution: Instead of dwelling on the problem, focus on finding a resolution that is acceptable to both parties. Discuss possible solutions together and work towards a mutually beneficial outcome.

Follow up: After the conversation, follow up with any agreed-upon actions or next steps. Keep the lines of communication open and check in periodically.

Seek support if needed: If you feel overwhelmed or unsure about how to handle a difficult conversation, don’t hesitate to seek guidance or support from a supervisor, HR representative, or a trusted co-worker. They may be able to provide valuable insights or advice on how to navigate the situation effectively.

However, respecting confidentiality is also crucial in maintaining professionalism within the workplace, so be mindful of who you approach for support to ensure you aren’t breaching trust.

The importance of strong connections in the workplace

While difficult conversations are never enjoyable, coming from a place of genuine connection can make them a little easier. A survey by job site Indeed found that 70% of Australian workers say having at least one close or best friend at work positively impacts their overall sense of happiness and wellbeing. However, despite this, only around one-third (36%) of workers admit to having a close workplace friend, and this number is even lower among remote workers (25%).

Having strong, positive relationships in the workplace can go a long way when it comes to approaching difficult conversations, and these findings highlight a clear opportunity for employers to create an environment that encourages these more meaningful connections.

In fact, according to further Indeed findings, one-in-five workers (20%) would turn to a colleague for support when facing mental health challenges, while only 7% would approach HR—meaning the relationships we have with our colleagues are arguably some of the most significant.

Employers who encourage stronger and more positive relationships amongst staff—for example, via team building activities or a collaborative culture—are likely to find navigating difficult conversations easier.

Difficult and sensitive conversations are a part of every workplace, and while they’re bound to feel uncomfortable, they’re vital for the overall success and wellbeing of any team. Whether it’s discussing poor performance or sharing your concerns about a colleague, approaching these conversations with empathy, openness, and a willingness to find mutually beneficial solutions is key. By utilising these techniques, you can offer meaningful support while maintaining positive relationships.

About Author

Peta Sigley is the CEO and Co-founder of Springfox, Australia’s leading providers of evidence-based resilience training for individuals and organisations. Peta has a background in psychology and education, and works extensively with individuals, teams and organisations to help build resilience and enhance performance and wellbeing – both in the workplace and outside it.