One of the least glamorous, but most essential skills in leadership is knowing how to have a difficult conversation. Whether it’s challenging a board decision, confronting underperformance, or pushing back on a superior’s judgment, hard conversations are part and parcel of the role. What separates strong leaders from the rest is not how to avoid these discussions—but how well they seek them out and navigate them.
Brett Himbury, former CEO of IFM Investors, recalls such a moment with his mentor. Faced with a significant decision, Brett chose to stand firm despite resistance. It wasn’t easy—but by staying purposeful and respectful, the conversation didn’t just protect the integrity of the decision; it strengthened the relationship between mentor and mentee. In hindsight, it became a defining moment of his leadership journey.
This story reveals an important truth: Difficult conversations—if handled well—don’t erode trust. They build it. So how can leaders engage in these moments constructively and with confidence?
Why Difficult Conversations Matter in Leadership
Leadership isn’t about consensus. It’s about actively seeking alternative views. Avoiding hard conversations might preserve surface-level harmony, but under the surface it creates costly fractures.
When leaders sidestep tough issues, they risk more than awkwardness. They risk:
- Lost opportunity. Teams stay stuck in underperformance or outdated strategies because no one wants to challenge the status quo.
- Cultural fractures. When candour is lacking, innovation stalls. People fear speaking up, and passive agreement replaces productive debate.
- Misalignment. Without clear expectations or accountability, priorities diverge and results suffer.
Great leaders, by contrast, lean into the tension. They use conflict, not to create division but to drive progress and clarity. Brett’s experience is a case in point. By confronting a major decision with honesty and courage, he earned not only respect but influence.
Strategies for Navigating Tough Discussions
Handling difficult conversations with compassion doesn’t mean avoiding emotion. It means preparing well, showing respect, and staying open to the unexpected.
1. Preparation is Key
Before entering any tough discussion, ask yourself:
- What am I really trying to achieve?
- How does my position align with the organisation’s purpose or values?
- What alternative views am I likely to encounter, and how will I respond?
This level of preparation grounds the conversation in strategy rather than ego. It helps you shift from “winning” to “aligning.”
2. Balance Confidence with Open-Mindedness
Confidence is essential—but so is humility. If you walk into the room unwilling to budge, the conversation becomes a dead end.
Instead, take a firm stance, but stay curious. The best leaders hold their views lightly enough to be persuaded by a better idea. It’s this balance—of conviction and flexibility—that builds credibility.
3. Timing and Tone Matter
Even the right message can fall flat if the delivery is poorly timed. Choose a moment where emotions are calm and distractions are minimal. Frame your points with empathy. A simple “Your perspective on this matter is important to me” or “I’m raising this because I care about the best outcomes for the team” can lower defences and shift the tone from confrontation to collaboration.
Turning Conflict into Growth
Difficult conversations don’t end when the meeting does. What happens afterwards matters just as much.
1. Follow Up Thoughtfully
A quick check-in after a hard conversation shows maturity and emotional intelligence. Ask, “How are you feeling about what we discussed?” or “Is there anything you want to revisit?” These gestures reinforce respect and prevent lingering misunderstandings.
2. Learn and Refine
Every tough conversation is a chance to grow. After the fact, debrief with yourself or a trusted colleague. What worked? What didn’t? What will you do differently next time?
Leadership is a continual process of adapting, and the more you reflect, the better your instincts become.
3. Long-Term Impact
While hard conversations can be uncomfortable in the moment, they leave a lasting impression. Over time, they contribute to a culture of transparency, resilience, and mutual respect. Employees learn that challenges are addressed head-on, not avoided. Trust deepens, and accountability becomes the norm—not the exception.
Much like empathy, the ability to have a difficult conversation is a skill—and it can be developed. It starts with intention: choosing to see discomfort not as something to be avoided, but as a signal that something important needs to be addressed.
It’s not about being confrontational. Nor is it about softening every blow. It’s about being real, honest, respectful, and aligned with a purpose bigger than the conversation itself.
Brett Himbury’s story is not unique, but it is instructive. When leaders bring clarity and conviction to their conversations—even the hard ones—they earn more than just compliance. They earn respect, trust, and the kind of influence that endures well beyond any single conversation.
The bottom line? Great leadership doesn’t sidestep discomfort. It walks directly into it—with purpose, and respect.
These insights into mentoring were part of a wide ranging conversation that MentorKey Founder and CEO, Maud Lindley, covered in conversation with Brett Himbury, on the Mentoring Unlocked podcast. Tune in for many more insights into how to unlock successful mentoring: https://mentorkey.com.au/podcast-mentoring-unlocked/