We weren’t born people pleasers. So what happened?

Over the past two decades, one of the greatest privileges of my work has been facilitating Assertive Communication programs for organisations across Australia, Asia and, more recently, through the University of Sydney Centre for Continuing Education.

Every program teaches me something new.

Not simply about communication.

But about people.

Over the years, I’ve come to realise something.

Most people don’t actually struggle with communication.

They struggle with permission.

Permission to disagree.

Permission to say no.

Permission to ask for help.

Permission to express a different opinion.

Permission to set healthy boundaries.

For much of my own life, I was a people pleaser.

I avoided conflict. I worried about disappointing others. Somewhere along the way, I’d confused being agreeable with being kind.

Looking back now, I realise they aren’t the same thing.

Too often, I was trading authenticity for approval.

The irony is that none of us were born this way.

As infants, we didn’t apologise for being hungry. We didn’t hesitate to let the world know when we were uncomfortable. We simply expressed our needs.

Somewhere along the journey, many of us learnt different patterns.

Some became passive.

Others became aggressive.

Some mastered passive-aggressive behaviour.

Only a few learnt the delicate balance of assertiveness.

One participant shared something recently that has stayed with me.

She was relatively new to a management role and spoke with remarkable honesty.

“Everyone keeps telling me I need to communicate more. I’m overwhelmed. I’m still learning the role. I’ve started losing sleep, and now every time my phone buzzes with another work message, I feel stressed.”

Her challenge wasn’t really communication.

Nor was it competence.

It was emotional bandwidth.

It reminded me that before we can communicate effectively with others, we often need to understand what’s happening within ourselves.

That’s why I’ve come to believe that assertiveness isn’t simply a communication technique.

It’s an expression of self-respect and respect for others.

It begins long before the conversation itself.

It begins with our beliefs.

Do I genuinely believe my needs matter?

Do I believe other people’s needs matter equally?

Do I believe disagreement can strengthen a relationship rather than damage it?

When those beliefs are in place, the skills become much easier to develop.

Self-awareness.

Emotional regulation.

Empathy.

Listening.

Influencing.

Negotiating.

Giving and receiving feedback.

Navigating manipulative behaviour.

Setting healthy boundaries.

None of these are really about “winning”.

They’re about creating the conditions for both people to flourish.

One of the most rewarding parts of facilitating these workshops isn’t watching people become more confident communicators.

It’s watching them become more authentic versions of themselves.

They discover they can say “no” without feeling guilty.

Give feedback without attacking.

Receive feedback without becoming defensive.

Hold difficult conversations without sacrificing compassion.

Just two weeks ago, I had the privilege of facilitating another wonderful group through the University of Sydney Centre for Continuing Education. Here’s the wonderful group I had the privilege of learning alongside.

Thank you to this wonderful group for your openness, trust and willingness to learn from one another. You taught me as much as I hope I contributed to you.

What struck me most wasn’t the role plays.

It was what happened between them.

Over two days, complete strangers became a team.

They encouraged one another.

Shared vulnerabilities.

Practised difficult conversations.

Celebrated one another’s growth.

It reminded me that psychological safety isn’t created by avoiding difficult conversations.

It’s created by learning how to have them well.

Perhaps that’s why I no longer see assertiveness as simply a workplace skill.

I see it as a life skill.

Because the way we advocate for ourselves shapes every relationship we have.

At work.

At home.

With friends.

With family.

Even the relationship we have with ourselves.

How we communicate ultimately shapes not only what we achieve…

…but who we become.

Perhaps assertiveness isn’t about finding our voice at all.

Perhaps it’s about giving ourselves permission to use it.

I’d love to hear your thoughts.

When in your own life have you found it hardest to be assertive?

Andrew Davey

Andrew is a Master Trainer and Executive Coach known for helping organisations shift from transactional leadership to emotionally intelligent cultures. A Tony Robbins Mastery graduate, Certified Life Coach, and MBA holder, he empowers leaders to unlock clarity, resilience, and purpose.

Dominic Siow

Co-founder and EQ Alchemist at EQ Strategist, Dom has inspired leaders and transformed cultures across 260+ organisations in 10 countries. He is the author of the Amazon best-seller *What’s GREAT About This?* and host of the *Inspiring Leadership* podcast.

Sue Siow

Co-founder and Director of EQ Strategist, Sue is known for her calm presence, strategic clarity, and deep empathy. With a background in information systems and advanced leadership training, she has supported leadership journeys for global clients across Asia-Pacific.

Caroline Crosbie

Caroline is a sought-after trainer and psychologist based in Perth, delivering experiential leadership and wellbeing programs. With expertise in resilience, work-life integration, and communication, she helps leaders sustain performance while leading with care, clarity, and balance.

Vivien Ong

Vivien is a seasoned facilitator and coach with 20+ years of corporate leadership experience. She specialises in mindful leadership, communication, and team dynamics, creating vibrant, high-trust learning environments where individuals step into leadership with clarity and voice.

Dale White

Dale is a high-impact leadership and performance coach with 19+ years of experience across government, corporate, and education. Known for his energy and practical insight, he helps leaders align strengths with strategy to drive sustainable, high-performance outcomes.

Vivien Ong

Vivien Ong is a seasoned leadership facilitator, coach, and trainer known for helping professionals grow into self-aware, courageous and impactful leaders. With over 20 years of corporate experience in sectors such as banking, telecommunications, BPO, and media,

Vivien brings a strategic yet deeply human lens to leadership development. At EQ Strategist, she facilitates programmes in mindful leadership, communication, psychological safety and team dynamics. Celebrated for her vibrant facilitation style, she combines energy, empathy, and practical insight to spark meaningful dialogue where learning and growth happen. She also mentors youth through a social enterprise and serves in the leadership team at the

Contact Centre Association of Singapore, where she advocates for better leadership and service standards. Her work is rooted in the belief that better leadership builds a better world. Through storytelling, behavioural tools, and reflective practice, she helps individuals step into leadership with presence, clarity, and voice. Vivien’s clients value her ability to create high-trust environments where people feel seen, heard, and empowered to lead from within.

Caroline Crosbie

Caroline is a sought-after trainer and psychologist who brings warmth, depth, and structure to leadership and wellbeing programmes. At EQ Strategist, she delivers experiential learning focused on resilience, work-life integration, and effective communication. Her academic background includes a Master of Clinical Psychology and certifications in Extended DISC, NLP, and EFT. Caroline’s clients appreciate her thoughtful approach to coaching and her ability to simplify complex psychological principles into actionable steps. With professional experience in five countries, she brings a culturally attuned perspective to her facilitation. Her goal is to help individuals and teams sustain performance without burning out—leading with insight, care, and clarity.

Dale White

“Real transformation doesn’t come from more information—it comes from aligned action.”

Dale White is a high-impact, outcome-focused leadership and performance coach, known for his energy, strategy and ability to drive real change. With 19+ years of experience helping professionals perform at their highest potential & a background in business, behavioural psychology, and high-performance coaching, Dale supports leaders to build clarity, confidence, and resilience in both work and life. At EQ Strategist, Dale facilitates training & coaching that blend behavioural insight, personal mastery, and practical implementation. His sessions are known for being dynamic, personalised, and results-focused – ensuring participants take real-world action that sticks. Dale holds degrees in Business and Exercise Science, and certifications in NLP, PCM, and Robbins Leadership Mastery. Whether supporting government departments, corporate leaders, guiding frontline teams or values-driven founders, Dale’s mission is to help people cut through theory and lead with purpose.

Jack Rankin

Jack Rankin is a high-impact trainer, executive coach, and culture catalyst with over 1,500 workshops delivered globally. His client portfolio includes leading names across government, finance, insurance, construction, and retail. At EQ Strategist, Jack helps organisations strengthen leadership capability, stakeholder alignment, and communication excellence. He is known for making learning engaging and actionable—tailoring each session to drive meaningful outcomes. His past clients include Singapore Airlines, Rio Tinto, Visa Westfield, Nike, Schneider Electric, and City of Parramatta Council. Jack is a Tony Robbins Leadership Mastery graduate and serves on the Synergistic Results Leadership team. Through each programme, he inspires individuals to elevate how they speak, lead, and influence.

Sue Siow

With a heart for people and a sharp strategic lens, Sue Siow co-founded EQ Strategist to help individuals and organisations flourish from the inside out. As Operations Director, she ensures the seamless delivery of high-impact programs while supporting clients with insight, empathy, and practical wisdom.

In addition to leading operations and client experience, Sue is also a skilled Facilitator and Participant Coach—contributing to larger workshops through 1-on-1 coaching, small group facilitation, and experiential team-building segments. Her calm, grounding presence invites reflection, trust, and personal growth.

With a background in Information Systems and advanced training from Tony Robbins’ Mastery University, Sue has supported programs across Singapore, Australia, Malaysia, China, and Indonesia for clients including Sembcorp, Esker, DBS Bank, Changi Airport Group, FedEx, Yokogawa, and AirAsia.

Dominic Siow

“Be the light or the mirror that reflects it.”

These words define Dominic Siow’s approach to life and leadership. As a globally recognised leadership facilitator, keynote speaker, coach, and co-founder of EQ Strategist, Dom is known for helping people reconnect with their purpose, lead with heart, and create cultures where everyone can thrive.

Drawing on senior leadership experience from IBM and Grapevine Technologies, he has spent the past two decades empowering over 260 organisations across 10 countries—from multinational corporations to public sector agencies and values-driven startups.

Dom’s facilitation style is equal parts insight, empathy, and inspiration. Whether leading a leadership retreat, designing a culture transformation program, or coaching executives through complexity, he helps people become not just better leaders, but better human beings.

He is the author of the Amazon bestselling book What’s GREAT About This?—a guide to building resilience through disruption—and the host of the Inspiring Leadership Podcast, where he shares real stories of growth and grit.

For Dom, leadership is not about titles. It’s about helping others find their light—and reflecting it back so they can shine.

Andrew Davey

At EQ Strategist, Andrew Davey is known for helping organisations move from transactional leadership to purposeful, emotionally intelligent cultures. As a master trainer and trusted coach, he brings a rare blend of business insight, coaching expertise, and facilitation mastery. Andrew’s clients span industries from logistics and software to government and education. He is a Tony Robbins Mastery University graduate, a Certified Life Coach, NLP Master Practitioner, and MBA holder. His mission is to empower leaders to unlock clarity, strengthen resilience, and lead inspired teams that drive results. Andrew delivers programs that are practical, energising, and deeply human—enabling sustained transformation at both the individual and organisational level.