top of page

7 Questions on Leadership with Jason Tan

Name: Jason Tan

Title: Founder

Organisation: Engage AI

Jason Tan is the Founder of Engage AI, a Conversation Copilot that remembers conversations across multiple channels to augment conversations in virtual and real-life. Since its release in Jan 2023, over 40,000 users worldwide have been using it to break the ice and engage with their prospects. Taking the learnings from implementing Engage AI, he also assists and shares the learnt lessons with enterprises to embrace and incorporate Generative AI and Large Language Models into their business.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Jason's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Being an introverted leader and founder presents its unique set of challenges. As someone who tends to thrive in focused, thoughtful work, stepping into a leadership role demands a different kind of engagement - active interaction, networking, and clear communication.

One of the hurdles I've faced is venturing beyond my comfort zone to build connections and network. Being an introvert means that social interactions, particularly in larger or unfamiliar settings, can be energy-draining. But over time, I've come to understand the importance of networking for personal and professional growth. I've also picked up strategies to preserve my energy while still forging valuable relationships.

Another obstacle has been mastering public speaking and addressing larger audiences. While introverts often lean toward one-on-one or small group interactions, leadership often involves presenting concepts, conveying visions, and motivating teams. Navigating the nervousness tied to public speaking and honing effective communication skills has been an enriching journey of growth for me.

2. How did you become a leader? Can you please briefly tell the story?

Back in 2003, I made my way to Australia from a quiet town in Malaysia. Armed with a one-way ticket and just a thousand dollars, my determination to thrive was my driving force. Juggling two jobs while navigating university life became my norm, a challenging journey that ultimately led me to a Bachelor's degree in Information Technology.

From a stint at a restaurant to relentless job hunting, a year passed before I secured a spot at Suncorp, marking the true beginning of my career. And the learning didn't stop – I simultaneously pursued a Master's in Business, determined to push my boundaries further. The Suncorp phase kicked off my career journey, donning the hat of a Senior Pricing Process Analyst from 2007 to 2010. 2010 was a turning point as I leaped into the world of entrepreneurship, founding two startups by 2014.

This led me to launch The Analytics Show in 2019 – a podcast where I engage with business leaders to uncover the role of data and analytics in high-performing organisations. This venture honed my communication skills and allowed me to connect with industry experts. In that same year, DDA Labs took shape, a venture focused on advanced analytics, generative AI, and OpenAI strategy.

Yet, my most recent endeavour, Engage AI, truly shines. Founded in 2023, Engage AI empowers individuals and businesses to harness Generative AI for more meaningful LinkedIn interactions. This platform embodies my vision for AI's potential in elevating relationships and conversations. Today, I reside in Brisbane with my amazing wife and two wonderful kids. If I had to define myself, it would be as a serial entrepreneur – some might say obsessed, but I prefer to call it a passionate pursuit.

3. How do you structure your work days from waking up to going to sleep?

My days are about finding that sweet spot between getting things done and spending quality time with loved ones. The day starts at 6 AM as I get the kids ready to drop off at childcare and kindergarten. Then, I’m hashing out a game plan for the day, setting up my to-do list, goals, and talking to customers and my team. We always aim to minimise the amount of meetings we have in the office so the team can focus on executing their work and still have enough time and energy to digest, think, and solve customer problems.

From there, it's heads down, and I'm in the zone, tackling work tasks and projects until 5 PM. After that, I head to pick up the kids and then prepare dinner and hang out with my family. I circle back to work after that, making the most of the quieter hours until about 11 PM. As many of our customers are from around the world, I sometimes need to jump into meetings with our European customers during these hours.

Then, it's time to reflect on the day and start planning for tomorrow. Somewhere around midnight, I call it a day and hit the hay, ready to recharge and do it all again tomorrow. It's all about finding that balance and making the most of every moment, especially when you work from home.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I've recently stumbled upon a leadership lesson that's become a real game-changer for me. Active listening isn't just about nodding along. It's about unravelling perspectives and painting a clearer picture of where someone is coming from.

This has become my secret sauce for building trust. People feel valued when they know they're being heard. When someone knows you're not just hearing their words but truly remembering what they say, that's when the real magic happens. People light up when they realise they're being heard and that their thoughts matter. But it's not just about empathy. It's about those hidden gems of insights that would've otherwise slipped through the cracks. I've been able to see problems from new angles, gather fresh ideas, and make decisions that are more spot-on.

Leadership Isn't just about calling the shots and doing the guiding dance. It's about showing up with your ears wide open, truly connecting, and letting those conversations shape the direction you take. It's a lesson that's made me realise the real magic happens when you take the time to listen, understand, remember, and genuinely appreciate the input of the people around you.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

One book that has shaken up my whole approach to leadership – "The Laws of Human Nature" by Robert Greene. This literary gem delves into the intricacies of human behaviour, allowing for a deeper understanding of what propels people to make their decisions.

As a leader, this book has provided me with an invaluable toolset to navigate complex interactions and inspire my team effectively. By grasping the underlying motivations and dynamics in human interactions, I've become more adept at building teamwork, smoothing over conflicts, and designing strategies that hit the right chords in people's hearts. This book has been a total game-changer for me.

It's completely shifted how I lead. I can now connect with my team on this whole new level and create an atmosphere where each individual's potential is maximised.

6. If you could only give one piece of advice to a young leader, what would you say to them?

If I could offer just one piece of advice to a young leader, it would be to prioritise continuous learning and adaptability. In the ever-evolving landscape of leadership and technology, the ability to learn, unlearn, and relearn is paramount. Embrace challenges as opportunities for growth, seek out new perspectives, and remain open to change.

Leadership is not about having all the answers but rather about being resourceful, curious, and resilient. As a young leader, your journey will be defined by your willingness to embrace change, learn from failures, and innovate. So, keep a growth mindset, invest in your personal and professional development, and remember that leadership is a journey of constant improvement and evolution.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

One meaningful story from my time as a leader stands out very vividly. It was during a critical project where our team faced unforeseen challenges that threatened our success. The pressure was high, and tensions were rising. Instead of succumbing to panic, I decided to gather the team for an open discussion.

I encouraged everyone to share their concerns, ideas, and potential solutions. Through this collaborative approach, we not only identified innovative solutions but also fostered a sense of unity and shared responsibility. As we worked together, we overcame the obstacles and achieved a success that exceeded our initial expectations.

This experience taught me the power of effective communication, teamwork, and the importance of maintaining a positive and solution-oriented mindset in times of adversity. It's a reminder that strong leadership is not just about making decisions but also about empowering the team and creating an environment where everyone's input is valued.

bottom of page