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Chat the Chief

Author: Insight Global

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Your microdose of workplace culture and leadership insights—straight from a CEO of a multi-billion dollar global talent, consulting, and AI company. Bert Bean worked his way up to CEO after first joining Insight Global over 20 years ago. Now, he’s pulling back the curtain for a raw and unfiltered peek into how Insight Global operates and his take on leadership, resiliency, and the future of work.

Joining him are Culture and Tech expert Steve Wasik and Sales Executive Katie Hillary as they get to the root of what makes companies thrive. No fluff. No sugarcoating. Just real conversations from real leaders, reshaping the way we think about work.

17 Episodes
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If everyone has access to the same AI tools and information, what gives someone a competitive advantage? In this episode of Chat the Chief, Insight Global CEO Bert Bean is joined by Steve Wasik and Katie Hillary to explore why commitment might be the biggest differentiator in the age of AI. From the dangers of outsourcing our critical thinking to the power of curiosity, the conversation explores what separates people who simply use AI from those who are using it to push themselves further. Because having access to information is one thing. What you choose to do with it is another. Listen to the full episode as they dive into: Why commitment could be your greatest competitive advantage in the age of AI The difference between having access to information and actually turning it into knowledge How to use AI without losing your ability to think critically Why curiosity and a willingness to take risks matter more than ever What the entrepreneurial journeys of Bending Spoons and Nike teach us about commitment How leaders can build teams that embrace AI while maintaining ownership of their work Why experience and reflection are essential to personal growth About the Podcast: Chat the Chief is your microdose of leadership and culture, straight from a CEO navigating one of the fastest-changing markets today. Bert Bean became CEO of Insight Global after starting as an entry-level recruiter over 20 years ago. Now he’s giving listeners an unfiltered look into decision-making, purpose, resilience and modern leadership. Alongside Technology Solutions expert Steve Wasik and Strategic Accounts VP Katie Hillary, the show explores the principles that make teams thrive and companies grow. About the Hosts: Bert Bean is the Chief Executive Officer of Insight Global, one of the world’s leading talent, consulting and AI companies. He joined the company in 2005 as an entry-level recruiter and became CEO thirteen years later. Under his leadership, Insight Global has more than doubled revenue, from $1.9 billion in 2017 to $4.8 billion in 2025, and grown to 5,500 employees and 33,000 consultants worldwide. Steve Wasik is a technology and AI leader at Insight Global who brings his perspective on innovation, business and leadership to Chat the Chief. Katie Hillary is a sales veteran of Insight Global and now oversees the company’s Strategic Accounts division. A former standout sales executive, she specializes in building systems that accelerate development, growth and long-term success for some of Insight Global’s largest strategic partners. 📩 Have a question for Bert? Send it to [email protected]. It might be featured in the next episode!
What does it take to make a comeback? In this episode of Chat the Chief, Insight Global CEO Bert Bean is joined by Steve Wasik and Katie Hillary to count down Bert’s Top 10 comebacks of all time, from business and sports to entertainment and history. But behind each comeback is a bigger conversation about resilience, reinvention and what it takes to keep going when things don’t go according to plan. Listen to the full episode as they dive into: Why sometimes you have to say no to what made you successful to become something more Why investing in your people can transform an entire business What Kerri Strug’s iconic Olympic moment teaches about grit and perseverance Why timing can change whether someone is the right leader for the moment How setbacks can create the opportunity to reinvent what comes next Bonus: They also debate whether flip phones, Myspace and physical media are ready for their own comeback. You don't want to miss this one! About the Podcast: Chat the Chief is your microdose of leadership and culture, straight from a CEO navigating one of the fastest-changing markets today. Bert Bean became CEO of Insight Global after starting as an entry-level recruiter over 20 years ago. Now he’s giving listeners an unfiltered look into decision-making, purpose, resilience and modern leadership. Alongside Technology Solutions expert Steve Wasik and Strategic Accounts VP Katie Hillary, the show explores the principles that make teams thrive and companies grow. About the Hosts: Bert Bean is the Chief Executive Officer of Insight Global, one of the world’s leading talent, consulting and AI companies. He joined the company in 2005 as an entry-level recruiter and became CEO thirteen years later. Under his leadership, Insight Global has more than doubled revenue, from $1.9 billion in 2017 to $4.8 billion in 2025, and grown to 5,500 employees and 33,000 consultants worldwide. Steve Wasik is a technology and AI leader at Insight Global who brings his perspective on innovation, business and leadership to Chat the Chief. Katie Hillary is a sales veteran of Insight Global and now oversees the company’s Strategic Accounts division. A former standout sales executive, she specializes in building systems that accelerate development, growth and long-term success for some of Insight Global’s largest strategic partners. 📩 Have a question for Bert? Send it to [email protected]. It might be featured in the next episode!
What does it actually cost to become the person you want to be?   In this episode of Chat the Chief, Insight Global CEO Bert Bean is joined by Katie Hillary and special guest Ryan Hawk, executive coach, podcast host and bestselling author of his new book, The Price of Becoming, for a conversation about what it really takes to pursue excellence in work, leadership and life.   After interviewing hundreds of leaders and coaching executives across some of the world’s most impactful companies, Ryan has seen the same pattern again and again: meaningful growth doesn’t come from a quick hack. It comes from doing the work, pushing yourself outside of your comfort zone and consistently getting a little better over time.   They dive into: Why writing can make you a clearer thinker, communicator and leader How curiosity and asking better questions can change the way you lead Why being uncomfortable can be a sign that you’re exactly where you need to be Why commitment can be a competitive advantage How to know when to stay the course and when it’s time to pivot Why consistency matters, especially when you aren’t seeing immediate results How doing hard things creates evidence that builds real confidence Why great leaders push people to see more in themselves than they see on their own How small actions and daily habits compound into meaningful growth over time Why the best leaders stay close to their people and the work One of Ryan’s biggest lessons? Confidence needs evidence. You build it by keeping promises to yourself, choosing hard things and proving, one day at a time, that you can handle what comes next.   You don't want to miss this one!    About the Podcast: Chat the Chief is your microdose of leadership and culture, straight from a CEO navigating one of the fastest-changing markets today. Bert Bean became CEO of Insight Global after starting as an entry-level recruiter over 20 years ago. Now he’s giving listeners an unfiltered look into decision-making, purpose, resilience and modern leadership. Alongside Technology Solutions expert Steve Wasik and Strategic Accounts VP Katie Hillary, the show explores the principles that make teams thrive and companies grow.   About the Guests and Hosts: Bert Bean is the Chief Executive Officer of Insight Global, one of the world’s leading talent, consulting and AI companies. He joined the company in 2005 as an entry-level recruiter and became CEO thirteen years later. Under his leadership, Insight Global has more than doubled revenue, from $1.9 billion in 2017 to $4.8 billion in 2025, and grown to 5,500 employees and 33,000 consultants worldwide.   Katie Hillary is a sales veteran of Insight Global and now oversees the company’s Strategic Accounts division. A former standout sales executive, she specializes in building systems that accelerate development, growth and long-term success for some of Insight Global’s largest strategic partners.   Ryan Hawk is an executive coach, bestselling author and host of The Learning Leader Show. He has interviewed hundreds of accomplished leaders and works with executives and leadership teams to help them perform at their best. His new book, The Price of Becoming, explores the habits, choices and commitments required to pursue excellence in both work and life.   📩 Have a question for Bert? Send it to [email protected]. It might be featured in the next episode!
What if the best thing you can do early in your career is stop trying to get everything right? In this episode of Chat the Chief, Insight Global CEO Bert Bean is joined by Steve Wasik, Vice President of Technology Solutions, and Katie Hillary, Vice President of Strategic Accounts, to talk about what it really takes to build a successful career — especially when you’re just getting started. From taking risks and finding the right mentors to navigating failure and figuring out what you’re actually good at, Bert, Steve, and Katie share the advice they wish they had at 22. They dive into: Why getting reps early in your career can matter more than getting everything perfect Why work ethic and adaptability can take you further than talent alone How taking risks helps you figure out what you’re good at — and what you actually enjoy Why the people you work for and with can matter just as much as the job itself How to seek out mentors, relationships, and opportunities instead of waiting for them to find you Why AI could make communication, creativity, relationships, and other “intangible” skills even more valuable The career advice they’d give anyone walking into their first day of work Their biggest advice? Put yourself out there. Take the risk. Ask the question. Get the reps. You’re going to learn either way. About the Podcast: Chat the Chief is your microdose of leadership and culture — straight from a CEO navigating one of the fastest-changing markets today. Bert Bean became CEO of Insight Global after starting as an entry-level recruiter over 20 years ago. Now he’s giving listeners an unfiltered look into decision-making, purpose, resilience, and modern leadership. Alongside Technology Solutions expert Steve Wasik and Strategic Accounts VP Katie Hillary, this trio explores the principles that make teams thrive and companies grow. About the Hosts: Bert Bean is the Chief Executive Officer of Insight Global, one of the world’s leading talent, consulting, and AI companies. He joined the company in 2005 as an entry-level recruiter and became CEO thirteen years later. Under his leadership, Insight Global has more than doubled revenue — from $1.9 billion in 2017 to $4.8 billion in 2025 — and grown to 5,500 employees and 33,000 consultants worldwide. Steve Wasik is VP of Technology Solutions for Insight Global’s Consulting division, where he partners with IG Labs, the company’s AI services and software practice, to bring scalable enterprise agentic solutions to customers across the world. Katie Hillary is a sales veteran of Insight Global and now oversees the company’s Strategic Accounts division. A former standout sales executive, she specializes in building systems that accelerate development, growth, and long-term success for some of IG’s largest strategic partners. 📩 Have a question for Bert? Send it to [email protected] — it might be featured in the next episode!
Most of us spend 100% of our waking moments trying not to fail. But that that mindset may be holding us back from our full potential. In this episode, Bert, Katie, and Steve discuss their personal relationship with failure and unpack how failure exposes truth, builds resilience, and often becomes the catalyst for our biggest breakthroughs.  You'll here why:  Failure is never what we want, but sometimes it's exactly what we need What failure teaches us that success never will Great leaders don't play not to fail. They play to win    Whether you're in a leadership position, just getting started building your career, or are navigating a challenge, this conversation offers real stories and advice to embrace failure and not only survive it, but use it as fuel. 
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