If a friend had a small piece of spinach stuck in their teeth, would you tell them? What if they have bad breath? What if their body odour made it genuinely difficult to be around them, would you say something, or quietly start making yourself less available?
Most of us will admit to tolerating far more than we should before we speak up. And if that's true in our personal lives, where the relationship stakes feel lower, imagine what's playing out in your organisation every single day.
Jerry Seinfeld once observed that public speaking is most people's number one fear, ranked above death. His punchline: "This means to the average person, if you go to a funeral, you're better off in the casket than doing the eulogy." The parallel to leadership feedback is uncomfortably accurate. For many leaders, difficult conversations only happen when the situation becomes unavoidable, a matter of professional life or death. Everything short of that? Filed under too hard.
The irony is that most leaders are genuinely good at positive reinforcement. Recognising great work feels natural, low risk, and welcomed. But when the feedback is challenging, willingness evaporates and the team member who needed honest input six months ago remains none the wiser.
So why does it matter, and what can we actually do about it?
Building Trust Before Feedback
The foundation of effective feedback is trust. Before any difficult conversation, ask yourself: does this person genuinely believe I'm invested in their success? If the answer is uncertain, that's the first thing to work on. Feedback without relational credibility lands as criticism. Feedback within a trusting relationship lands as investment.
Principles for Delivering Tough Feedback
When the time comes, keep these principles front of mind:
Play the situation, not the person
The moment feedback becomes about character or identity, the conversation is lost. Focus on the circumstance, the behaviour, the outcome, never the individual's worth. "This outcome isn't where it needs to be" is a very different conversation from "you're not good enough."
Reframe the purpose
Rather than "you're letting me down," try "I feel like I'm letting you down", because if someone on your team is underperforming and you haven't addressed it, that's partially a leadership failure. Own that. It changes the entire dynamic.
Know that emotion will always beat logic off the start line
When someone receives difficult feedback, their emotional response will arrive well before their rational one. Acknowledge this. Don't rush to solutions. Take a breath, be clear, and leave genuine room for space and listening.
Frame feedback through questions, not verdicts
Some of the most powerful feedback conversations never involve direct criticism at all.
Try asking:
- How are you?
- Could you have been better supported?
- If you had your time again, what would you have done differently?
- What environmental factors may have contributed?
- Is this situation aligned with your own view of a quality outcome?
- What's the best way forward from here?
These questions invite self reflection rather than defensiveness, and often facilitate better insight than any statement you could make. The key is to listen deeply.
Drop the formula
The "compliment sandwich" (commend, recommend, commend) and other structured feedback scripts are well intentioned but widely recognised as being ineffective. The moment someone sees the structure, the message feels disingenuous. Be human, be direct, and be honest.
Follow up
A single conversation is rarely enough. Schedule a brief follow up, not to check up on someone, but to check in. Show that the conversation wasn't just a box ticking exercise. That moment is often where the real shift happens when thinking has had the opportunity to catch up once emotion has lessened.
Feedback as a Leadership Discipline
Like public speaking, delivering tough feedback is not a natural gift. It's a discipline, one that the best leaders practice deliberately and refine over time. The leaders who get it right aren't fearless; they've decided that both building trust and caring supersede the temporary comfort of staying quiet.
Here's a useful way to think about it, would you rather put out ten individually lit matches or one raging bushfire?
Make a start with the next difficult conversation, as all going well it's just become a little easier.
About the Author
As GYST's Managing Director, Steve Pettit helps leaders and teams build trust, navigate change, and create strong, high-performing cultures. Drawing on his experience leading teams across different markets, he coaches leaders and supports teams to grow, work more effectively and reach their full potential.
