Difficult Conversation Training for Leaders | Corporate Training Singapore

Equip your team with proven frameworks to navigate high-stakes dialogue, build psychological safety, and transform challenging workplace situations into breakthrough outcomes.

Featured In

Ignored Critical Conversations Come at a Cost

Evidence-based methodology | 5-step conversation framework | In-house & public workshops

Research shows 57% of managers avoid difficult conversations while 53% of employees simply ignore toxic situations. In Singapore’s workplace culture, only 80% of middle managers feel safe speaking up compared to 92% of senior leaders—creating a dangerous silence gap where problems fester.

When crucial conversations are postponed, your organization loses through escalating conflicts, reduced innovation, disengaged talent, and costly issues that could have been caught early. The ability to create a speak up culture where teams can voice concerns without fear isn’t optional—it’s essential for competitive advantage.

The Courageous Chat gives your leaders the communication skills training, frameworks, and courage capacity to turn uncomfortable silence into productive dialogue.

Joseph Wong speaking on stage

How One Courageous Chat Unlocks True Leadership

Addresses root psychological barriers

We tackle power dynamics, fear responses, and cultural conditioning around hierarchy—not just surface-level techniques. Our leadership development program combines behavioral science with practical application.

Proven 5-step conversation framework

Repeatable methodology (Prime → Set → Explain → Test → Explore) removes guesswork from any uncomfortable conversation—performance feedback, managing up, cross-cultural dialogue.

Personalized Courage Quotient assessment

Identify whether you're a "Maximizer" or "Minimizer" and get tailored strategies for your natural patterns and cultural context.

Precision Feedback system that builds trust

Stop delivering opinions that trigger defensiveness. Learn our feedback framework to facilitate perspective-sharing that creates mutual understanding.

Singapore-proven for hierarchical cultures

Designed specifically for cross-cultural communication in Asian workplace dynamics where traditional Western training often fails.

RiseUP Conference session 2023

Evidence-Based, Not Generic Communication Tips

Most training teaches what to say but ignores why people stay silent. We address the real barriers: power dynamics in hierarchical structures, willpower depletion under stress, survival instincts that treat tough conversations like physical threats, and cultural norms around preserving face.

Our corporate training program isn’t theory—it’s extensive role-play practice in real scenarios your teams face daily: giving feedback to underperforming direct reports, challenging authority respectfully, navigating multicultural team tensions, saying “no” strategically, and managing emotional reactions in the moment.

Result: Leaders who can conduct candid dialogue when it matters, middle managers who influence upward effectively, and teams that surface risks early instead of hiding problems.

The Guide – Why Train with Us

Led by TrainingGearAsia's senior facilitator Joseph Wong, The Courageous Chat™ blends behavioural research, proven conversation models, and engaging practice labs. We've helped regional giants and fast-growing SMEs alike build cultures where candour accelerates results.

The Foundations Behind His Work

Understanding Barriers

Examine power dynamics, learn strategies for managing up, and navigate cross-cultural communication patterns in Singapore's diverse workplace culture. Understand why fear and survival instincts subconsciously restrain honest dialogue.

Building Courage

Assess your personal Courage Quotient, identify Maximizer vs. Minimizer patterns, and develop sustainable habits for more frequent conversations without burning out. Learn the "Cage and Tiger Theory" of courage capacity.

Designing Conversations

Master our proprietary conversation framework with repeatable steps. Use the RSA Model for emotion management. Handle unexpected tough conversations with confidence and adapt your approach across different thinking styles.

Setting Boundaries

Learn the psychology of saying "no" strategically. Use Impact vs. Effort prioritization to protect your capacity while maintaining relationships. Script refusals that are clear, diplomatic, and relationship-preserving.

 

 

Precision Feedback

Stop giving feedback opinions. Master our feedback framework to facilitate perspectives. Cover performance feedback for direct reports, upward feedback to managers, and peer exchanges that build continuous feedback skills and trust.

Who This Professional Development Workshop Serves

  • Leaders & Managers:
    Senior leaders, middle managers, and team leaders who need to conduct performance feedback dialogues, build psychological safety training cultures, and model courageous behavior across their organizations.

 

  • HR & L&D Teams :
    HR professionals and learning teams architecting culture change initiatives, implementing speak-up programs, and developing leadership communication capabilities at scale.

 

  • Cross-Functional Teams:
    Project managers, technical leads, and teams in regulated sectors (finance, healthcare, tech) where speaking up prevents costly errors, addresses conflict resolution early, and drives innovation.
Joseph Wong with Ian Wong

Why Organizations Choose The Courageous Chat

Science-Backed Methodology

Grounded in research on psychological safety, courage, and human behavior under stress. Evidence-based strategies proven to overcome natural resistance to challenging conversations.

Culturally Adapted for Singapore

Explicitly designed for hierarchical workplace norms and multicultural teams. Addresses Asian cultural conditioning around authority, face-saving, and direct vs. indirect communication styles.

Practice-Rich, Not Theory-Heavy

Extensive scenario-based role-plays in contexts you face daily. Every concept immediately applied—not abstract principles but actionable conversation skills you use the next day.

Measurable Business Impact

Organizations report reduced conflict escalation, higher engagement scores, faster problem resolution, and retained talent within 30-90 days. Track behavioral evidence, not just good intentions.

What Sets Us Apart

5-Step Conversation Framework

Proprietary process that removes guesswork from any difficult dialogue.

What Sets Us Apart

Courage Quotient Assessment

Personalized strategies based on your Maximizer or Minimizer pattern.

What Sets Us Apart

Precision Feedback System

Facilitates perspectives, not opinions—reducing defensiveness and building trust.

How To Get Started

Our 3-step process:

Each step is guided by our leadership experts who bring career experience, strategic insights, and a passion for growing better leaders.

Schedule a Strategy Call

Schedule a conversation about your team's specific challenges and desired outcomes.

Receive a Custom Proposal

We design your program to address your actual scenarios, team dynamics, and culture.

Delivery & Support

Interactive training with toolkit and optional coaching—full-day, modular, or 2-day formats.

“The Courageous Chat™ equips your people with the art and science of brave conversation so every critical insight gets heard—and acted on.”

Stop Losing Talent and Ideas to Silence

When crucial conversations don't happen, your organization pays through disengagement, turnover, and problems that explode instead of getting solved early. Give your Singapore team the frameworks and courage to transform uncomfortable moments into breakthroughs.

Frequent Asked Questions:

What makes RISEUP different from other conference organising companies in Singapore?

Unlike typical event producers, RISEUP lets you run your own branded leadership summit using our proven format and speaker network — white-labeled under your brand.

Can we host a RISEUP-style summit within our own organisation?

Yes. Our internal summit model is perfect for companies that want to inspire and align teams through a branded leadership experience, managed end-to-end by us.

Is RISEUP only for corporate clients or can training providers use this too?

We partner with both. Many training and coaching companies work with RISEUP to deliver summits to their clients, without building internal event operations from scratch.

How long is a typical RISEUP conference?

Our leadership summits are designed to be short, sharp, and impactful — typically half-day sessions (3–4 hours) filled with honest conversations and high energy.

Do you provide conference event management for in-person, hybrid, or virtual events?

Yes. We offer full-service conference event management in Singapore for onsite, hybrid, and virtual formats — including speaker curation, production, and engagement tools.