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WE NEED TO TALK: Practical Approach to Handling Difficult Conversations in the Workplace

Handling Difficult Conversations in the Workplace

Recently, our team led a session on Handling Difficult Conversations for members of one of the major Australasian Institutes in the financial space.

In today's business landscape, tricky discussions are commonplace. Whether it's negotiating contracts, addressing performance issues, navigating sensitive client concerns, or delivering unfortunate news, we're no strangers to the heat of the moment. As leaders, often our time goes into having and handling difficult conversations.

And let's be real: ignoring these conversations only amplifies the problem. 

When we’re on the receiving end of a difficult conversation, it doesn’t feel great. It’s uncomfortable, and when we know it’s going to happen. When someone says, “We need to talk”, we can feel anxious in the lead-up, perhaps having a rough sleep the night before. We instinctively know that “we need to talk” can’t possibly be good.

On the other hand, when we are the one having to handle a difficult conversation, maybe discuss something that's a sensitive topic, we probably know the other person is uncomfortable. And we don’t look forward to it.

In other words, we have two people in a conversation, who don't really want to be in that conversation. It’s a difficult emotional space.


By avoiding discomfort, we miss out on opportunities for growth and collaboration.

💡 Insights from the session found three top key areas in which conflict is useful:

  • Brainstorming for Solutions

  • Gaining Buy-In for Change

  • Challenging Preconceptions

Dale Carnegie x Handling Difficult Conversations

Difficult conversations are not just about addressing problems; they are about building stronger relationships, fostering trust, and driving positive change within your organisation.

That's why we're so passionate about equipping your teams with the tools to tackle tough talks head-on. Embracing difficult conversations demonstrates leadership, integrity, and a commitment to excellence.

A clear framework and structured approach can help us immensely when navigating difficult conversations.

Prepare, Engage, Resolve: A Simple, yet effective Framework to Approach Difficult Conversations

1. Prepare

Before diving into a difficult conversation, take the time to prepare yourself mentally and emotionally. Ensure you’ve given thought and preparation to the following areas:

  • Clarify your objectives: What do you hope to achieve from this conversation? Whether it’s providing feedback, resolving a conflict, or setting expectations, be clear about your goals.

  • Gather information: Collect relevant facts, examples, and data to support your points. This will help you convey your message with clarity and credibility.

  • Anticipate reactions: Consider how the other party might respond and prepare yourself to address their concerns or emotions.

Questions to ask

10 Questions to consider as you prepare for a difficult conversation:

1.     What are you trying to achieve?

2.     How will you know if the conversation was successful?

3.     What does the situation currently look like?

4.     What are the facts, examples, or data supporting my perspective?

5.     What is the impact of the situation?

6.     What is my emotional state going into this conversation?

7.     How do I anticipate the other person might react?

8.     Has the problem been addressed before?

9.     What message is working for the other person?

10.   Do you or the other person have a hidden agenda?

2. Engage

Once you’re prepared, it’s time to engage in the conversation. Here are some tips for effective communication:

  • Choose the right time and place: Find a neutral and private setting where both parties can speak freely without interruptions.

  • Start with empathy: Show empathy and understanding towards the other person’s perspective. This sets a positive tone and encourages open dialogue.

  • Use active listening: Listen attentively to what the other person is saying without interrupting or judging. Reflect back their emotions and concerns to demonstrate understanding. Chris Voss, a former FBI hostage negotiator, shares his insights on effective communication and negotiation strategies in his book "Never Split the Difference: Negotiating As If Your Life Depended On It." In the book, he offers practical tips in labeling and mirroring which can help the other person feel heard and elevate your listening skills.

  • Stay calm and composed: Keep your emotions in check and maintain a professional demeanor, even if the conversation becomes tense or emotional. Sometimes, a break may be the best course of action, to them return to the conversation when parties are calmer.

Susan Scott, author of "Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time," emphasises the importance of honest, authentic communication in both personal and professional relationships. Difficult conversations tend to be a lot easier when we already have some rapport and trust with the person – meaning the best time to build trust isn’t during or right before the difficult conversation, but in all your interactions on an ongoing basis.


[Webinar] Win-Win Negotiations: The Art of Collaborative Success

[Webinar] Win-Win Negotiations: The Art of Collaborative Success

Join us for an engaging 45-minute webinar, where we gain insights into:

  • Understanding how and where we negotiate in our roles

  • Building trust and rapport with your counterparts

  • Identifying common interests for collaborative solutions

  • Explore a structured approach to win-win outcomes                                                                                                                                                              Watch Now!


3. Resolve

The ultimate goal of a difficult conversation is to reach a resolution or agreement. Here’s how to bring the conversation to a productive conclusion:

  • Focus on solutions: Shift the conversation towards finding solutions rather than dwelling on problems. Brainstorm together to explore possible alternatives. As Dale Carnegie said “Ask questions instead of giving direct orders.” When we ask questions of others, they are required to look inward for solutions and are more likely to commit to a resolution that they had a part in creating.

  • Seek common ground: Look for areas of agreement or shared interests that can serve as a basis for compromise. Nonviolent Communication by Marshall B. Rosenberg shares a communication model based on empathy, authenticity, and mutual respect, which can transform challenging conversations into opportunities for connection and understanding. When we’re able to find common ground, even a smaller area of agreeance, what feels like a stalemate conversation can be moved forward productively.

  • Clarify next steps: Clearly outline any action steps or follow-up tasks that need to be taken to address the issue and prevent recurrence. Document what your next steps are to ensure everyone is clear with expectations.

  • Follow up: After the conversation, follow up with the other party to ensure that any agreements or commitments are being upheld. This reinforces accountability and demonstrates your commitment to resolving the issue.

Difficult conversations are an inevitable part of professional life, but they don’t have to be daunting. By preparing yourself mentally, engaging in open and empathetic communication, and focusing on collaborative solutions, you can navigate through even the most challenging discussions with confidence and grace. If it’s competency skill-building you’re exploring for yourself or your teams, whether that be in maintaining composure under pressure, actively listening and finding common ground, well...

We need to talk.

For more insights on professional development and industry trends, stay tuned and connect with us on LinkedIn. Let's shape the future together.

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