Managing Difficult Conversations

A recent survey by the Chartered Management Institute revealed some startling insights about workplace management in the UK. One statistic that stood out was that 45% of underperforming managers still receive a bonus. Why? Because senior leadership often avoids having the "difficult conversations" necessary to drive real change.

Difficult conversations are frequently entangled with conflict management and are one of the biggest challenges managers face at all levels. These discussions often centre around poor performance, bullying, appearance, redundancy, lateness, or dismissal. There is no shortage of "do’s and don’ts" available to managers, but based on over 30 years of experience, here are my key recommendations for handling them effectively:

1. Focus – Be Clear About the Issue

Before initiating the conversation, ask yourself two crucial questions: What specific behaviour is causing the issue? and What impact is it having? Clarity allows you to communicate effectively in just a few succinct statements. Without it, you risk losing focus and derailing the conversation.

2. Define Your Desired Outcomes

Theodore Zeldin once said, "A successful conversation doesn't just reshuffle the cards; it creates new cards." What do you want to achieve? What is negotiable, and what isn’t? Plan how to close the conversation with clear action steps, agreed-upon solutions, and scheduled follow-ups.

3. Choose the Right Setting

Where you hold the conversation matters. Inviting someone into your office may feel authoritative or intimidating. A neutral meeting room, where you can sit side by side without a desk as a barrier, can create a more collaborative atmosphere. Even a casual coffee shop setting can help ease tension.

4. Adopt a Mindset of Inquiry

Your attitude can shape the entire conversation. Approach it with curiosity rather than judgment. As the Taoists say, "Nature gave us two ears and one mouth because listening is twice as important as speaking." Before drawing conclusions, allow the other person to share their perspective - you may be surprised by what you learn.

5. Acknowledge and Manage Emotions

Emotions are inevitable. Instead of dismissing them, acknowledge and manage them. Maintaining respect and preserving the other person’s dignity - regardless of your personal views on their emotional response - can prevent escalation and facilitate resolution.

6. Be Comfortable with Silence

Silence can feel uncomfortable, but it serves a purpose. While extroverts may rush to fill gaps in conversation, introverts often need silence to process information. Allow any pauses to unfold naturally - they can lead to more thoughtful responses and better outcomes.

7. Preserve Relationships

Strong relationships are invaluable. A single mishandled conversation can damage trust built over years. Keep your focus on resolving the issue, not tearing down the person. As Hugh Mackay wisely said, "Nothing is perfect. Life is messy. Relationships are complex. Outcomes are uncertain. People are irrational." Seek to understand and accept this and embody it in what you do.

8. Be Consistent

Nothing undermines trust faster than perceived favouritism. Ensure fairness in your approach. Employees remember how past situations were handled, and inconsistencies can erode trust in leadership.

9. Develop Conflict Resolution Skills

Conflict is a natural part of human interaction. Having a few proven de-escalation techniques at your disposal can help keep the conversation constructive rather than confrontational. If you don't know any find a good coach to help you develop them.

10. Address Defensive Behaviour Directly

People may resort to stonewalling, sarcasm, or deflection. A simple and open acknowledgment of such tactics can disarm them. As Sarah Green of Harvard Business Review suggests, saying something like "I don’t know how to interpret your silence" can bring defensiveness to the surface and allow for a more honest discussion.

11. Start with a Direct but Gentle Approach

Many managers avoid these conversations because they don’t know how to begin. A straightforward yet non-threatening opening can set the right tone: "Jane, I’d like to talk about what happened in the meeting this morning when Fred asked about the missed deadline. Let’s grab a coffee tomorrow morning to chat." This removes the element of surprise and signals a willingness to discuss rather than reprimand.

12. Prevention is Better Than Cure – Train Others In These Skills

Difficult conversations happen at all levels, often informally. Equipping your team with conflict management skills can prevent minor misunderstandings from escalating into major issues.

Mastering the art of difficult conversations can transform workplace dynamics, improve team performance, and enhance leadership credibility. The question is - are you ready to start having them?