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

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.
 
When we’re the one who has to initiate it, we’re aware the other person is uncomfortable. We’re not exactly looking forward to it either. Two people in a conversation, neither of whom wants to be in it. That’s the emotional reality of a difficult conversation.

“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


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Done well, difficult conversations build stronger relationships, establish trust, and move teams forward. A clear framework and structured approach can change the dynamic considerably when navigating conversations that would otherwise stay stuck or get avoided altogether.

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.

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10 questions to consider as you prepare:

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?

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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 insights on effective communication in his book Never Split the Difference: Negotiating As If Your Life Depended On It. His practical tips on labelling and mirroring 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 demeanour, even if the conversation becomes tense. Sometimes a break may be the best course of action, returning to the conversation when both parties are calmer.

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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.

“The best time to build trust isn’t during or right before the difficult conversation, but in all your interactions on an ongoing basis.”

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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.
• 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, check in 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.

Think of one conversation you’ve been putting off. The one that’s sitting in the back of your mind, taking up more energy in avoidance than it would in the actual chat. Prepare for it using the questions above, set up the right time and place, and have it this week.

Difficult conversations are an inevitable part of professional life, and they get easier with practice and the right preparation. Prepare mentally, communicate with genuine empathy, and focus on solutions rather than positions, and even the toughest discussions can be navigated well. If this is a capability worth building, whether for leaders, managers, or whole teams, well… we need to talk.


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