Riaz Meghji

Human Connection Expert | Author of Every Conversation Counts

Why do we avoid difficult conversations at work? The common response I hear from leaders is “Because we’re afraid of conflict.” I don’t think that’s true. I think the real fear is uncertainty.

We don’t know how the other person will respond. We wonder if we’ll say the wrong thing, make things worse, or damage a relationship we care about. So we wait. We rehearse. We convince ourselves it’s better to say nothing. Yet what’s left unsaid rarely disappears. Instead, it slowly becomes resentment, assumptions, or relational distance.

I’ve learned that meaningful connection isn’t built by avoiding uncertainty. It’s built by walking into it together.

Before your next difficult conversation, pause and ask yourself one question: “What is this person carrying that I can’t see?”

Maybe it’s pressure at home. Maybe it’s self-doubt. Maybe they’re grieving, overwhelmed, or simply trying their best with limited capacity. You may never know the full story, but that question shifts your mindset from judgment to curiosity and from reaction to empathy.

The strongest relationships at work are the ones where people are willing to face uncertainty and each other with empathetic curiosity.

Riaz Meghji is an accomplished broadcaster. After one conversation led him to take a dramatically different career path, he became dedicated to exploring the ways that authentic human connection can change lives and organizations. A natural storyteller, he shows audiences how to create engaged and connected cultures through the power of candid conversation.

Randy Boyagoda

Writer, Critic, and Scholar | Advisor on Civil Discourse

Civil discourse is important, but it’s not the ultimate priority. The mission of the organization is. Civil discourse matters because it advances that priority. It creates the best possible conditions for people to think out loud together, to reckon with difference and disagreement, and to see them as good things that can lead to greater understanding of others’ perspectives and strengthen shared efforts toward an organization’s goals.

Leaders should always keep first principles in mind: we’re not civil to each other simply because it’s good to be civil. That’s true, but there’s more to workplace interactions than just making sure they stay civil. Leaders who aren’t willing and able to create and sustain conditions for difficult, demanding conversations risk coming across as mere managers — or even tone-police — rather than leaders. Done well, those conversations leave people feeling taken seriously and knowing their views matter.

At the same time, leaders need to make clear that as much as they welcome divergent views, they are ultimately the decision-makers — and that those decisions benefit most from the lively workplace conversations that advance the organization’s mission.

The University of Toronto’s first-ever Advisor on Civil Discourse, Randy Boyagoda has spent years studying and advancing what it means to disagree well. A CBC Radio national columnist and prolific novelist, he explores why civil discourse — how we disagree, debate, and think out loud together — is the foundation of how we build trust, advance knowledge, and strengthen our teams and organizations.

Liane Davey

Expert on Building Effective Teams, Improving Communication, and Increasing Leadership Effectiveness

When faced with a challenging conversation at work, one mindset shift makes all the difference. Stop thinking of teamwork like rowing a boat, where you’re all pulling in the same direction and trying not to rock it. Instead, imagine positioning a tarp to protect your tent from the rain. Each person is pulling in a different direction (based on their unique roles, expertise, and stakeholders).

In this scenario, you need to pull your rope hard enough to make the tarp taut, but not so hard that you pull it off centre, and you can’t let go because that would leave something exposed. Most importantly, you need to give and take to reach the optimal conclusion based on how the wind is blowing. If you get it right, everyone sleeps dry.

Next time you’re facing a contentious discussion, consider how to contribute in a way that optimizes the decision overall, rather than trying to win in a way where the business ultimately loses.

Known as the “teamwork doctor,” Liane Davey has worked with businesses, including Fortune 500 companies, from across the globe, helping them transform the way their people communicate, connect, and contribute for maximum results.

Jennifer Barroll

Leadership and Engagement Expert | Communication Strategist | Professional Host and Entertainer

The success or failure of a challenging conversation begins long before the conversation itself. Preparation is key.

In all communication, understanding above-the-line and below-the-line behaviour, a concept popularized by the book The 15 Commitments of Conscious Leadership, helps you approach conversations with greater self-awareness and intention. Above the line, we are curious, open, and responsive. Below the line, we become defensive, reactive, and quick to blame. Make a commitment to stay above the line.

Before the conversation, consider the emotional bank account. Every interaction is either a deposit or a withdrawal. Relationships with healthy reserves can withstand difficult conversations, while those running low often slip below the line before meaningful dialogue can happen. Know where you stand before you begin. If the account is overdrawn, it may be wiser to rebuild trust before having the conversation.

Finally, remember Stephen Covey’s principle: begin with the end in mind. Get clear on the outcome you want, then begin the conversation by inviting them to participate in the solution. That could sound like, “I’d like to spend a few minutes talking about where we are today and what we need to move forward. My hope is that we leave this conversation with a clear path forward on the timeline. How does that sound to you?” When people feel respected rather than threatened, difficult conversations become opportunities to strengthen trust rather than damage it.

With decades of corporate leadership experience across multiple industries and a background in leadership psychology, Jennifer Barroll brings a refreshing, human-centred strategy to developing stronger leaders and more connected cultures.

Dr. JP Pawliw

Leadership and Performance Expert | New York Times Bestselling Author

There’s often a gap between what we feel we should say and what we actually say when things get tough. In a recent study of 34,000 people published in Harvard Business Review, we found that this gap is 7.56%. Rounded up, we call this the Last 8%.

People don’t avoid the Last 8% because they lack the right words. They avoid it because staying silent feels safer at the time.

There are three ways to move past this. First, ask yourself: Who do I want to be today? Identity shapes our actions more than goals do. For example, telling yourself, “I’m someone who handles hard moments well” doesn’t rely on motivation. It’s about how you see yourself, and we don’t like to act in a way that is inconsistent with how we see ourselves.

Second, try to see the conversation as an act of care, not confrontation. Delaying a hard truth isn’t kind; in fact, you could call it selfish. It protects your own comfort but comes at someone else’s expense. Third, focus on the first step. You don’t need a full script, just the first sentence. That’s something I help leaders craft.

Leaders who handle this well aren’t fearless. They’ve simply learned to accept discomfort as part of building trust and a high-performance team.

As organizations face big challenges, whether it is an accelerated rate of change, the threat of disruption, ambitious targets, or aggressive competition, Dr. JP Pawliw’s curiosity and passion for helping people manage their emotions has driven his research into the skills and tools required to build a culture of exceptional leadership.