How to Raise a Difficult Issue in a 1-1 Meeting

August 4, 2025

Effective Strategies for Addressing Challenging Conversations at Work



Raising a difficult issue with your manager or colleague can feel daunting. However, approaching it effectively in a one-on-one meeting can lead to meaningful resolutions and stronger workplace relationships. Here’s how to address challenging topics thoughtfully and productively:


1. Prepare Thoroughly


Before the meeting, clearly define the issue. Identify specific examples, consider your emotions, and outline the outcomes you hope to achieve. Preparation helps you communicate clearly and calmly, making it easier for the other person to understand and engage constructively.


2. Set the Right Tone


Start the conversation positively by expressing gratitude for the opportunity to discuss openly. Emphasize your intent to find solutions rather than placing blame. For example, begin with, "I appreciate your time today. I'd like to discuss something that's been challenging for me so we can work together towards a solution."


3. Be Specific and Objective


Clearly state the issue, focusing on specific facts and behaviours, not personality or generalizations. Frame your points objectively to avoid triggering defensive responses. For instance, instead of saying, "You never listen," try "I felt overlooked during yesterday’s meeting when my input wasn’t acknowledged."


4. Invite Dialogue and Listen Actively


After presenting the issue, invite feedback with open-ended questions. Actively listen to the other person's perspective without interrupting. Reflect back what you hear to ensure mutual understanding. Phrases like, "How do you see this?" or "Can you share your perspective?" foster open dialogue.


5. Propose Constructive Solutions


Suggest potential solutions and be open to collaboration. Offering ideas shows your proactive stance and willingness to improve the situation. For example, "One solution might be setting clearer expectations before meetings. What are your thoughts on this approach?"


6. Agree on Next Steps


Conclude the meeting by agreeing on actionable steps. Confirm each person's responsibilities and set a timeline to revisit progress. Documenting these steps can provide clarity and accountability moving forward.


Final Thoughts



Approaching difficult conversations with clarity, empathy, and openness lays the groundwork for positive outcomes. Remember, addressing challenging issues proactively strengthens trust and fosters a healthier workplace culture.


How Artificial Intelligence Is Changing the Way Professionals Find Opportunities
September 17, 2025
The hidden job market in Canada is changing. Learn how AI is uncovering finance and accounting opportunities beyond job boards and helping employers hire smarter.
September 15, 2025
Why Managing Chaos May Be More Valuable Than Technical Expertise
September 12, 2025
Salary growth has not kept up with inflation in Canada. Learn how finance and accounting professionals can navigate rising costs, what employers are doing, and how to approach career growth in 2025.
September 5, 2025
Why Finance and Accounting Professionals in Canada Must Embrace Data and Tech Skills
September 2, 2025
Why Mid-Sized Firms Can Offer the Best of Both Worlds
August 28, 2025
Understanding Ontario’s Return-to-Office Plan and What It Means for Employees
Finance leader in Canada guiding a team meeting, demonstrating emotional intelligence and collaborat
August 20, 2025
Discover why emotional intelligence is the must-have skill for finance leaders in Canada in 2025, and how it helps drive stronger teams, smarter decisions, and lasting business results.
Canadian finance professional planning career progression, highlighting certifications, networking,
August 15, 2025
Discover the biggest career mistakes finance professionals make—like staying too long in one role, neglecting certifications, or forgetting to network—and learn how to avoid them, backed by Canadian data.
August 15, 2025
What Finance Professionals in Canada Value Most in 2025
Finance career path roadmap showing progression from Senior Financial Analyst to CFO, including mile
July 25, 2025
Want to move from SFA to CFO in Canada? Discover the key milestones, certifications, and skills every finance professional needs to build a career path to executive leadership.