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Navigating difficult conversations at work, here's what to do
26 Nov 20248 min read

Difficult Conversations at Work: Here's What To Do

 

Navigating difficult conversations at work might feel daunting, but they're essential for maintaining a healthy workplace.

Perhaps you're facing a team member who's consistently underperforming, or there's a need to discuss sensitive topics like pay disagreements or conflicts between colleagues. Ignoring these issues can lead to a toxic environment, lowering productivity and morale. It's crucial to handle these talks well to foster understanding and support within your team. So, how can you prepare effectively? Let's look at some practical steps to make these conversations more manageable and constructive.

1. Preparing for the Conversation

Understand the Importance

Recognising why these conversations matter is the first step. They help address misunderstandings, clarify expectations, and reduce stress in the workplace. Ignoring issues can lead to prolonged tension and inefficiency. By engaging in open dialogue, you not only resolve existing problems but also prevent future misunderstandings. Consider, for example, a team member not submitting reports on time. Addressing this matter promptly helps redefine timelines and expectations.

A healthy work environment thrives on transparency and honesty. When you openly address issues, it sets a precedent for future interactions, encouraging others to speak up, too. This sort of culture can transform how a team functions and leads to improved productivity. It's like Strengthify's approach of regularly assessing and utilising strengths, ensuring everyone's on the same page and working towards shared goals.

Pro-tip: Initiate regular feedback sessions with your team. This habit encourages continuous dialogue and eliminates the build-up of minor issues into full-blown conflicts.

Identify Your Goals

Define what you want to achieve before diving into the conversation. Clear objectives help guide the discussion and maintain focus. For example, if a team member constantly interrupts meetings, decide whether your goal is to curb interruptions, understand their source, or something else entirely. Be specific about your desired outcomes.

Keep these goals in mind as a reference point during the conversation. They act as a compass, ensuring that even if the discussion veers off, you can steer it back to what's crucial. Always ensure these objectives are measurable and realistic. It might involve reaching an agreement or simply gaining understanding. Compile a list of talking points to keep things structured and on topic.

Pro-tip: Visualise success by imagining post-conversation scenarios. This helps solidify what needs to happen for a positive outcome and boosts confidence as you approach the talk.

Plan Your Approach

A well-thought-out plan ensures you're prepared for various outcomes. Start by choosing the right setting — a private, neutral location is typically ideal. Planning involves considering the timing, your tone, and approach. Aim for a calm, respectful, and direct dialogue. Avoid blaming language that might escalate tension; instead, use “I” statements to keep the focus on your perspective.

Include anticipatory thinking in your preparations. Consider potential reactions and have strategies ready for addressing them. This might mean practising patience if the conversation doesn't initially go as planned. Strengthify's positive psychology methodologies can be an effective resource here, exploring how best to communicate and understand diverse perspectives within the team.

Pro-tip: Develop a conversation roadmap. Outline key points, potential responses, and gentle ways to steer conversations back on course if things drift off-topic.

2. Navigating Difficult Conversations

Start with the Right Tone

To set a constructive atmosphere, it's essential to start the conversation with an open and respectful tone. Address the person with empathy and acknowledge any emotions involved. This might include saying, "I understand this might be difficult" or "Your feelings are important to me." Aim to create a safe environment where both parties feel valued. Establishing this tone from the outset encourages openness and trust. Keeping your body language open and maintaining a calm demeanour also significantly contributes to setting the right mood.

Furthermore, it's beneficial to anticipate any potential emotional reactions. If the topic is sensitive, consider phrasing your points carefully or using neutral questions to ease into the discussion. For instance, ask, "How have you been feeling about this situation?" before diving deeper. This approach makes the other person more likely to engage positively and see the conversation as collaborative rather than confrontational.

Pro-tip: When discussing difficult topics, use "I" statements to express how certain actions affect you, rather than "you" statements, which can sound accusatory.

Listen Actively

Active listening is crucial for successful conversations. It involves more than just hearing words; it means understanding the emotions and intentions behind them. While the other person speaks, give them your full attention by maintaining eye contact and nodding to show understanding. Avoid interrupting, and instead, use prompts like "Can you tell me more about that?" to encourage them to elaborate. This not only demonstrates that you value their perspective but also helps clarify any misunderstandings.

An essential part of active listening is reflective feedback. After they have spoken, summarise what you've heard in your own words to ensure clarity and correctness. Phrases like "So what I'm hearing is..." or "It sounds like you're saying..." can confirm understanding or uncover any discrepancies. This technique helps mitigate miscommunications and keeps the dialogue constructive.

Pro-tip: Take notes during the conversation to remember key points and follow up later, showing that you take the issue seriously.

Address the Issue Clearly

Clear communication is indispensable when tackling difficult issues. Avoid beating around the bush or using vague language. State the problem directly but diplomatically, focusing on specific behaviours or situations rather than personal attributes. For example, say, "I've noticed that deadlines have been missed," instead of "You're always late." This keeps the conversation objective and professional.

Along with clarity, be solution-focused. Present potential solutions and encourage the other person to contribute their ideas, fostering a sense of co-ownership in resolving the issue. By working together on a practical plan, you not only address immediate concerns but also build a stronger working relationship.

Pro-tip: Prior to the meeting, jot down the points you need to cover to stay on track and remain clear and concise during the discussion.

For information on leveraging strengths-based approaches in workplace communication, consider exploring Strengthify's services designed to empower teams and individuals through effective dialogues and positive psychology.

3. Follow Up

Follow-up after a difficult conversation is critical. It confirms that everyone is aligned and that there are no lingering misunderstandings. Start with a quick recap of points discussed and any agreed actions. This not only ensures clarity but also sets a tone of cooperation moving forward. Use tools like email recaps or follow-up meetings to track progress.

Consider setting deadlines for action items and checking in at these intervals. Platform tools such as Trello or Asana can help manage these tasks efficiently. Focus on maintaining a consistent dialogue, showing that the conversation was a step toward team growth and not an isolated event.

Pro-tip: Regular feedback loops can prevent issues from escalating. Consider initiating periodic check-ins to gauge team sentiment.

4. Reflect on the Outcome

Reflect on how the conversation unfolded and whether your goals were achieved. Consider aspects such as the tone, engagement level, and if differences were effectively managed. Reflection helps in recognising what worked well and what needs adjustment for future conversations.

Ask yourself critical questions:

  1. Was the issue resolved?

  2. Did both parties leave satisfied?

  3. What feedback could improve future discussions?

Utilise this reflection to refine your approach. You might begin to see patterns or recurring challenges that signal areas for growth within your team or organisation.

Pro-tip: Use reflection as a springboard for personal development. Keeping a journal of these reflections can mark your progress over time.

5. Use the Experience to Grow

Post-conversation analysis should not be a tick-box exercise but a path to growth. Review what the experience has taught you about managing similar scenarios. It might reveal needed skills like emotional intelligence or conflict resolution techniques you can undertake for personal enhancement.

Translate those learnings into practical applications by:

  • Engaging in related training.

  • Incorporating new strategies into team meetings.

  • Seeking mentorship or feedback from peers or leaders.

Partners like Strengthify offer workshops that help individuals amplify these learned strengths, building a more cohesive workplace culture. Consider enrolling for courses that nurture such skill expansions.

By following these steps, one can transform difficult conversations into developmental opportunities.

Do you want to develop your management skills further? Explore Strengthify’s Management Development Programme to harness your strengths effectively.


Concluding a challenging conversation at work requires more than just exchanging words. By following up, reflecting, and leveraging the insights gained, you not only resolve current issues but also prepare for future challenges. Embrace these strategies as integral tools in cultivating a positive and productive workplace environment. Ready for your next breakthrough? Engage with partners like Strengthify to enhance team dynamics and personal growth.


Frequently Asked Questions

How to deal with difficult conversations at work?

Start by preparing in advance, understanding both your perspective and the other person's. Set clear objectives, communicate openly, and actively listen. Ensure you address the specific issues and consider solutions collaboratively. Practice empathy and maintain a calm demeanour throughout the conversation.

What to do after a difficult conversation at work?

Follow up with review emails to summarise agreed actions. Reflect on the conversation's effectiveness, focusing on outcomes and personal growth. Consider feedback for improvement and use the insights gained to enhance communication and relationship-building strategies within the team.

What are the three C's to difficult conversations?

The three C's include:

  • Clarity: Address specific issues concisely.

  • Compassion: Understand perspectives and show empathy.

  • Commitment: Agree on action points and follow-up.

What are the four D's of difficult conversation?

The four D's are:

  • Directness: Be straightforward in your communication.

  • Dialogue: Encourage open discussion.

  • Data: Base conversations on facts and evidence.

  • Development: Use the conversation as a learning opportunity.

If you want to find out more about our approach, you can join one of our Events, or you can set up a meeting or call with us so we can help you with hands-on practical tools and actionable insights to support team development and dynamics with a strengths-based approach. 

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