Difficult conversations are inevitable in any career. Whether it’s pushing back on unrealistic deadlines, addressing a conflict with a colleague, or negotiating a raise, knowing how to navigate these discussions effectively is a crucial skill and is something I am asked often.
It really is a challenge for everyone and so often, training is not given and cultures can become spoiled and difficult and people leave.
There are lots of great resources out there but here are some of my favourites (which I've used more than I would have liked).
Approach them with clarity, composure, and confidence.
1. Prepare Before You Speak
💡 Why it matters: Walking into a conversation without preparation makes it harder to stay on track.
✔ Clarify your goal – Are you seeking a resolution, a commitment, or simply to be heard?
✔ Gather key facts – Stick to specifics instead of broad generalizations.
✔ Anticipate responses – Think about potential objections and plan how to respond.
📌 Example: If asking for a raise, bring data on your contributions and industry salary benchmarks.
2. Regulate Your Emotions & Stay Composed
💡 Why it matters: Emotions are natural, but managing them ensures the conversation stays constructive. Self regulation is key in this moment and is one of the few things you are able to control.
✔ Pause before reacting – Take a deep breath if emotions start rising; you lungs are the primary organs that you can have full control over to help regulate your nervous system
✔ Reframe the situation – Instead of assuming bad intent, focus on finding a resolution.
✔ Practice self-compassion – A difficult conversation does not define your worth.
📌 Example: If a colleague dismisses your idea, rather than shutting down, ask, “Can we explore your concerns further?”
3. Stick to Facts & Own Your Perspective
💡 Why it matters: Conversations become defensive when statements feel like accusations. Focus on your experience rather than assigning blame.
One powerful method is Nonviolent Communication (NVC):
✔ Observation: State facts without judgment
✔ Feeling: Express how the situation affects you (especially using 'I' not 'You' statements)
✔ Need: Identify what is important to you
✔ Request: Make a clear, actionable ask
📌 Example: Instead of “You never listen to me in meetings,” say, “I’ve noticed my input isn’t always acknowledged. I’d appreciate a chance to share my thoughts before moving to the next topic.”
4. Find Common Ground & Offer Solutions
💡 Why it matters: Conversations are more productive when they focus on collaboration, not blame.
✔ Acknowledge the other person’s perspective – “I understand this deadline is important for the team.”
✔ Suggest a compromise – Frame solutions instead of just pointing out problems.
✔ Keep the bigger goal in mind – How does resolving the issue benefit both sides?
📌 Example: If a manager rejects your promotion request, ask, “What specific skills or achievements would put me in the best position for this role in the next six months?”
5. Know When to Push & When to Pause
💡 Why it matters: Not every conversation will reach a resolution immediately and the key is to share your feelings and what you would like.
✔ If emotions run high, suggest a follow-up – “I appreciate your perspective. Let’s revisit this after we’ve both had time to think.”
✔ Recognize when to escalate – If discussions stall, involve a mentor or HR.
✔ Reflect afterward – What worked? What could be improved next time?
📌 Example: If a teammate keeps interrupting you and direct feedback doesn’t work, involve a manager to reinforce respectful communication norms.
How to have difficult conversations at work - it requires planning and intention
Difficult conversations aren’t just about addressing workplace issues—they’re about advocating for yourself, setting boundaries, and building confidence in your career. Every time you navigate one successfully, you strengthen your ability to communicate with clarity and assertiveness.
Remember, confidence isn’t about having all the answers—it’s about trusting yourself to handle challenges as they arise. If imposter syndrome or self-doubt is making it harder for you to speak up, I’ve got something that can help.
What else would you add here that has helped you in a difficult situation? Would love to hear from you in the comments.
Have a meeting coming up and struggling with confidence?
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