monday.com CRO - Why Great Mentors Push You to Leave, Case George

AI is changing leadership faster than most executives realize, pushing teams to move at a speed that introduces multi-million dollar operational blindspots.In this episode of Lead The Team, Ben Fanning sits down with Radha Basu, Founder & CEO of iMerit, to break down why "right beats fast" when scaling technology.Discover how to navigate high-stakes AI disruption, structure true organizational ownership, and prevent executive burnout while leading a hyper-growth team.What You'll Learn in This Episode:How a missing piece of real-world context nearly triggered chaos in an autonomous vehicle model.The exact moment Radha risked losing an industry-leading client by refusing to drop her quality standards for speed.The 4 mission-critical AI roles leaders need to scale machine judgment safely.The Radical Feedback Loop: Overcoming executive burnout by building an organizational culture that talks back.The Slack Rule: Why data trainers must have a direct line to the CTO.-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

AI IS REBUILDING LEADERSKK, CEO of Ascendion, believes most companies are still thinking about AI too small-scale.The leaders pulling ahead are rebuilding how they operate.And that’s a very different conversation! KK walked away from one of the world’s largest IT services companies because he could already see the old model starting to crack:More headcount.More layers.More complexity.Meanwhile, AI was changing how decisions get made, how work gets executed, and what great leadership actually looks like going forward.One of my favorite moments was when he said the first move every CEO should make is building an AI agent for themselves first.Not for the company but for themselves.Because your team can tell pretty quickly whether leadership is truly embracing change… or just asking everyone else to do it.I think that’s the real shift happening right now.AI isn’t just changing technology. It’s rebuilding leaders.What’s one part of your workflow you’d trust an AI agent to help you with today?-----Follow KK here on LinkedInLearn more about Ascendion-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Comfort Stops Growth.Magen Buterbaugh, President & CEO of Greene Tweed, walked away from leading a billion-dollar business at DuPont because she realized something…Success can become a trap.Her role was secure.The path was clear.The reputation opened doors.But she knew she had stopped growing.So she left the corporate safety net to help build a startup with one employee, real payroll pressure, and no guarantee it would work.That decision completely changed how she leads.In this conversation, we get into questions every ambitious leader eventually has to face:• How do you know when your career has become too comfortable?• What happens to your leadership when the safety net disappears?• Are you actually growing… or just getting better at protecting what you’ve already built?She told me: “Until your back is against the wall, you really haven’t faced adversity.”I think a lot of leaders spend years trying to avoid discomfort.But discomfort is usually where the real growth starts.When has leading outside of your comfort zone helped you grow?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Most leaders are preparing for the wrong enemy.Matt Thompson, President and Chief Commercial Officer at Socure, is helping lead the fight—where machine identities already outnumber humans 80 to 1.And fraud isn’t just growing… it’s evolving faster than most businesses can keep up.Most leaders are still treating this like a tech problem.It’s not.It’s truly a strategy problem.The adversary is decentralized, fast-moving, and increasingly powered by AI.After spending over a decade in Army Special Operations under Stanley McChrystal, Matt is now applying those same battlefield-tested tactics to fight this new kind of enemy.Which means the old playbook—protect the front door and call it a day—is already outdated.In this conversation, we break down:Why fraud now behaves like a networked enemy.What leaders are getting wrong about defending their organizations.And how battlefield-tested thinking is being used to fight it at scale.So the real question for leaders is:Can your team and organization adapt faster than the threats evolving around it?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Pressure reveals leaders.Keval Hutheesing, CEO of Cygnet.One, was 25 when he suddenly became responsible for 900 people—in the middle of a crisis.No playbook.No certainty.And hundreds of people counting on his decisions.Most people think leadership in moments like that is about having the "right" answers.That’s the mistake.As Keval told me:“I didn’t have all the information… but I had our core goals and vision.”This raises a few uncomfortable questions for leaders in a crisis:- What do you do when you have to make an important decision with incomplete—or bad—data?- What if hesitating is higher risk than making the wrong call?- When the pressure is on what actually guides your decisions?Amateurs panic.Great leaders create direction. That’s how his team stayed aligned, customers stayed supported, and eventually they achieved success and became even stronger.What’s helps you stay calm under pressure?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Getting AI WrongArun Varadarajan, Chief Commercial Officer at Ascendion, reframed how I think about why so many AI initiatives are failing.“90% of projects fail because people don’t spend enough time defining the problem.”Not because the technology failed or the team wasn’t smart enough.It's because leaders started building BEFORE they got clear on what actually needed to change.So what looked like AI progress was really just motion without transformation.And once leaders DO identify the real problem, many still don’t move boldly enough to create meaningful change.They get stuck in pilots.Experiments.Incremental improvements.But never challenge the “untouchable” systems and ways of working that have existed for years.And when that happens, the real transformational impact of AI never materializes.The organization just falls further behind while thinking it’s making progress.Arun shares with us the leadership conviction and organizational courage to get AI right.Where do you think most organizations are still getting AI wrong?-----Follow Arun on LinkedinLearn more about Ascendion-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

The Scaling MistakeHightouch CRO, Josh Kanagy, showed me how companies scaling fastest right now are creating their biggest future leadership problem.Companies are obsessed with scaling:• systems• process• AI• automationYes, those things matter.BUT there’s a real danger when leaders start believing scaling the system automatically scales the company.Josh learned that the hard way in a humbling quarterly business review early in his career.Because systems don’t build judgment, create confidence, or develop leaders ready for the next level.People do.The best scaling companies aren’t just building better systems.They’re building people who can rise with the company.THE BEST SCALE PEOPLE.In this conversation Josh also shares:• The humbling QBR that changed how he leads.• Why great sales leaders think like community builders.• The AI battle most executives don’t realize they’re fighting.And once you hear where Josh learned that philosophy… it changes how you think about leadership.Are we scaling our systems faster than we’re scaling our people?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Do you know BRUCE?Andy Freed, Chairman of Virtual, Inc. has seen Bruce Springsteen nearly 100 times, and was so inspired by what he saw that he wrote a book about it.......Lead Like The Boss: The Bruce Springsteen Framework to Elevating Your LeadershipWhat Andy took from those shows completely changed how he leads.For instance at the end of every show, Bruce walks to the back of the stage……and personally acknowledges every single band member.For about 10 seconds each, he makes them feel like the most important person in the world.Andy saw that and thought:"Isn’t that the job of a leader?"But it raises bigger questions…Why can a rock concert hold attention for 3 hours…while an executive loses the room in 3 minutes?When did leadership become about slides…instead of connection?Most leaders are focused on:what they need to saywhat they need to get donewhat they need to presentBruce is focused on:what the audience feelshow the moment landshow people walk awayThat’s the difference.I’ve been in rooms where the strategy was right……but the leader lost the room in 60 seconds.And I’ve seen the opposite—where the message wasn’t perfect……but the leader had people leaning in, locked in, all the way through.That’s not an accident.That’s intentional.So here’s the real question:Are you trying to be heard…or are you trying to make people feel something?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

Why Leave Success?monday.com CRO Case George once got career advice he never expected.After decades at IBM a close mentor looked at him and said: “I’ll deny it if you tell anybody… but I think you should leave.”It was unexpected but that advice changed everything for Case.He went on to help scale billion-dollar revenue organizations and now leads global revenue at monday.com, a platform used by 200,000+ organizations worldwide.You'll also discover:• Why great mentors sometimes push you out of comfort• The strategy that grew monday.com into a $1.5B+ company• What happens when your response times drop from 24 hours to 2 minutes?----He shared with me that you don’t fully appreciate what you’ve learned… until you’re forced to use it somewhere new.Do you believe ambitious leaders leave successful companies earlier to grow faster,or can they do it where they are?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter

They Said Don’t.Andrew Brandman, COO of DailyPay and a former leader at the New York Stock Exchange, knows risk takingWhen he decided to join the NYSE back in the day, everyone told him he was making a mistake.“Everyone was saying to me, don’t do it!.”He did it anyway.That decision didn’t just work out — it actually put him at the center of transforming a 200+ year old institution and reshaped the trajectory of his entire career.But it wasn’t just the risk.It was why he took it.He saw a mission big enough to matter.A chance to impact not just a company…but the people behind it — the ones whose lives are affected by every decision.It's a call to action for leaders at every level...- How often are we evaluating opportunities based on comfort… instead of impact?- What if the best career decisions don’t feel safe at all?- What if consensus is actually a warning sign?And how do you know when to ignore smart people… and trust your instincts anyway?-----Connect with the Host, #1 bestselling author Ben FanningSpeaking and Training inquiresSubscribe to my Youtube channelLinkedInInstagramTwitter