High Stakes Conversations: Turning Feedback Into Trust

Great leaders don’t avoid tough conversations—they master them.

High-Stakes Conversations: Turning Feedback Into Trust equips you to handle the moments that matter most: delivering feedback that lands, receiving it without defensiveness, and turning tension into opportunity. In this dynamic workshop, you’ll learn to navigate high-stakes conversations with clarity, empathy, and confidence - building stronger relationships and higher-performing teams in the process.

Grounded in the work of Kim Scott, Douglas Stone, and Amy Edmondson, this session provides actionable frameworks and real-world tools to help you transform feedback into a driver of trust, connection, and growth.

This isn’t about avoiding discomfort, it’s about leading with courage and creating a culture where people thrive.

2 levels available as well as an abridged “power hour” option
HIGH STAKES CONVERSATIONS: LEVEL 1

Foundations Of High Stakes Conversations

Building the Foundations of Giving and Receiving Feedback

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Great leaders know that feedback can either strengthen trust, or silently erode it. In this foundational workshop, you’ll learn how to approach high-stakes conversations with clarity, confidence, and empathy, turning what many fear into a powerful driver of growth and connection.

Drawing on the work of Kim Scott (Radical Candor), Douglas Stone & Sheila Heen (Difficult Conversations, Thanks for the Feedback), and Amy Edmondson (Psychological Safety), we’ll demystify what makes feedback land (or backfire) and give you a repeatable process for handling tough conversations without damaging relationships.

Through interactive exercises and real-world scenarios, you’ll practice the essential skills that make feedback feel less like confrontation and more like collaboration.

Outcomes:

  • Understand why most feedback conversations fail, and how to avoid the common traps

  • Learn a simple framework for delivering feedback that lands and inspires action

  • Develop skills for receiving feedback without defensiveness

  • Build confidence in initiating high-stakes conversations without fear or avoidance

  • Begin creating a team culture where feedback is normalized and welcomed

Soft Skills Developed:

  • Emotional intelligence and self-regulation

  • Clear, actionable communication

  • Trust-building and psychological safety

  • Active listening and curiosity

Workshop Length: 2-3 hours

high stakes conversations: LEVEL 2

Mastering High Stakes Conversations

Team Building, keynote, Trust, Training, Corporate teams, Psychological safety, team development, workshops, Teamwork, Motivation, community, Goal-setting, corporate keynote, team training, Toronto team building, Ottawa team building, keynote talk

Once you’ve built a foundation in giving and receiving feedback, it’s time to master the conversations that define leadership. Level 2 takes you deeper into navigating complex, emotionally charged, or high-consequence situations, where the stakes are high, and trust is on the line.

We’ll explore advanced tools from Radical Candor, Crucial Conversations, and adaptive leadership principles to help you lead through resistance, uncover the root of tension, and turn even the hardest moments into opportunities for alignment and growth. You’ll leave with practical strategies for shifting conversations from friction to forward momentum, all while building the kind of trust that drives long-term team performance.

Outcomes:

  • Confidently navigate complex feedback conversations with multiple layers of emotion or risk

  • Spot and address defensiveness, resistance, or tension in real time

  • Learn advanced techniques for creating psychological safety in high-pressure moments

  • Transform feedback into a two-way dialogue that strengthens trust and accountability

  • Integrate feedback practices into team culture for lasting impact

Soft Skills Developed:

  • Conflict resolution and de-escalation

  • Influence and emotional adaptability

  • Advanced trust-building

  • Courageous, clear communication under pressure

    Workshop Length: 2-3 hours

high stakes conversations: Power Hour

Power Hour: Feedback That Builds Trust

Team Building, keynote, Trust, Training, Corporate teams, Psychological safety, team development, workshops, Teamwork, Motivation, community, Goal-setting, corporate keynote, team training, Toronto team building, Ottawa team building, keynote talk

Even a single feedback conversation can make or break trust. In this fast-paced, high-impact Power Hour, you’ll learn the essential skills to navigate high-stakes conversations with clarity and confidence.

Expect a dynamic session packed with practical tools, real-world examples, and actionable takeaways you can implement immediately - perfect for leaders who need impact without the time commitment.

Outcomes:

Through expert frameworks inspired by Kim Scott’s Radical Candor, Douglas Stone & Sheila Heen’s Difficult Conversations, and Amy Edmondson’s research on psychological safety, you’ll discover how to:

  • Deliver feedback that lands without damaging relationships

  • Receive feedback without defensiveness

  • Turn even brief conversations into moments that build trust and drive performance

    Soft Skills Developed:

  • Active listening and clear communication

  • Emotional intelligence and self-awareness

  • Building trust quickly in high-stakes moments

Workshop Length: 1 hour