Lead the Team (Top 2% of Podcasts)

The bigger your company gets, the more polished reports can distort vital truth.

In this episode of Lead the Team, Ben Fanning sits down with John Case, CEO of Acumatica and former Microsoft executive who helped scale Office 365 into one of the most successful cloud businesses in the world.

John shares why one of the most important responsibilities of leadership is creating direct access to truth before critical information gets filtered on its way up the organization.

From customer conversations to strategic decision-making, he explains how great leaders stay connected to reality as...

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:

AI IS REBUILDING LEADERS

KK, 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.

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...

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...

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:

Getting AI Wrong

Arun 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 eno...

The Scaling Mistake

Hightouch 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

• automation

Yes, 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 th...

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 Leadership

What 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...

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 st...

They Said Don’t.

Andrew Brandman, COO of DailyPay and a former leader at the New York Stock Exchange, knows risk taking

When 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.

Fastest Tech Adoption in History.

Zoom COO Aparna Bawa was right in the middle of it...

helping lead the company as the entire world moved onto one platform in a matter of weeks.

For work.

For school.

Even for final goodbyes.

I sat down with Aparna to understand what leadership actually looked like in that moment.

One decision changed it all...

They turned Zoom on for K–12 schools across the U.S.—for free.

No perfect information.

No time to o...

Inside the Room.

Hayden E. Stafford, President & CRO at Seismic, had a front-row seat to Satya Nadella rebuilding Microsoft from the inside out.

The world saw the outcome.

Hayden saw the decisions.

The ones that got challenged.

The ones that got changed.

And the ones leaders refused to change.

He saw that alignment didn’t break all at once.

It broke when signals said something isn’t working…

and nothing changes.

That’s when teams drift.

Priorities split.<...

AI isn’t accountable. Leaders are.

Eileen Sweeney, PROS CRO, operates in a world where algorithms influence billions in airline revenue.

The scale and speed are staggering.

What a conversation on a big idea that leaders and teams are challenged by right now...

When algorithms shape decisions…

who owns the outcome when it goes wrong?

Not the system.

The leader.

You see it in high-stakes deals—everything points to “close it.”

The system says go.

But the real question becomes:<...

Looks Like Progress. It’s Not.

So I asked Adrian Stoch, CEO Americas at Hai Robotics:

What’s the mistake that looks right… but costs millions?

Why do “working” systems still fail?

What breaks first when you scale?

He’s led automation at massive scale.

Inside Target.

Inside GXO.

Now leading robotics.

He told me about one warehouse…Robots installed.

Systems live.

Dashboards green.

It looked like progress.

Until it didn’t.

30% of the pro...

After 10,000 Interviews...

Rod McDermott, CEO of McDermott + Bull and founder of Activate 180, has noticed that the executives who win interviews…

...aren’t always the ones who build results.

And that’s the trap.

It's so easy to fall for the wrong signals.

The leader who owns the room.

The polished answers.

The one who leaves everyone thinking, “That was impressive.”

But impressive DOESN'T SCALE.

Rod reminded me:Leadership isn’t performance.It’s followership.

The real test of a leader isn’t h...

Noise vs Focus.

Bob McCuin, Chief Revenue Officer and EVP at Clear Channel Outdoor, has spent decades inside the attention economy...radio, sports media, and literally the most valuable billboards on the planet.

When you live in that world long enough, you start to notice something about leadership.

What's shaping how organizations behave.Bob told me that attention determines priority.

Most leaders think priorities are set through goals, meetings, and KPIs.

But teams don’t really follow the slide deck.

They follow what the leader consistently pays at...

Leadership Blindspot

Adam Block, Chief Revenue Officer at Motive, who helped scale the company to serve 100,000+ customers and more than a million drivers, shared a real wake up call with me.

Early in his career, he spent a lot of energy trying to help struggling employees succeed. Then he realized something uncomfortable.

“The people that suffer the most in that situation are actually the best players.”

Because when leaders spend most of their attention fixing what’s broken… the people who are actually driving results start getting less attention.

Less coa...

My AI just joined the meeting...

I expected Abhijit Mitra, CEO of Outreach, a multi billion-dollar AI company, to tell me about their legendary tools and automation.

Instead, he it took a different direction.

When he’s in a meeting… his AI agents actually join the meeting and coach him in real time.

Not summarize it later.

Not send notes afterward.

They’re in the meeting, helping him think, respond, and prepare.

That’s when the real insight hit.

Myself and most leaders today ar...

Lives Depend.

Parker Burke, Group President at Fluke Corporation, leads an organization whose tools help technicians safely test electrical systems in power grids, hospitals, factories, data centers, and mines around the world.

So when a technician trusts the reading on a device…they’re trusting it with their life.

A 99% success rate isn’t success.

Because the remaining 1% can mean catastrophe.

That reality forces a different kind of leadership perspective.

Parker’s years in the Marines shaped how he approaches it.Not by carrying the weight alone…but by ser...

Details Define You.

Bob Hughes, President & CEO of Deltek, learned that in moments when the stakes were highest..

on a nuclear submarine…

in the middle of a $22B merger…

and during a ransomware attack.

He was inspired early in his career when a leader told him:

“The devil’s in the details… but so is salvation.”

I particularly appreciated his insight:

“Operational discipline scales trust.”

We’ve all seen the opposite play out too.

One meeting starts late.

Elite CEOs and athletes share a belief.

Usman Shuja, CEO of Bluebeam, learned it long before the boardroom, representing the USA national cricket team and becoming one of the top wicket-takers in U.S. history.

Talking with him made me think about how differently pressure shows up across seasons of life.

In sports, the pressure is loud and public.

In leadership, it even heavier....Board expectations. Team decisions.

Real consequences.

For most of my career, I thought confidence was what carried leaders through those moments.

...

Google’s “Wolverine” is now a $100M+ CEO

Keith Rabkin, CEO of PandaDoc, is one of the few leaders I’ve met who can bridge the gap between "big-tech discipline and scrappy underdog grit".

At Google, Keith was one of only 25 people (out of thousands of geniuses) to win the "Great Manager Award."

His secret isn't just a high IQ; it's what he calls the "Wolverine Mindset" .

It’s a relentless, "never-give-up" grit that focuses on one thing: obliterating roadblocks so the team can win.

Our conversation forced me to rethink...

THE TRANSFORMATION WALL

Randall Troutman, Winpak's, Chief Operational Excellence Officer leads a massive $1.1 billion transformation, tasked with turning 13 independent "kingdoms" into one efficient operating system.

But there’s a moment in every change effort where leaders mistake resistance for failure, and that’s when teams stop following.

Randall discovered that project success is never about the initial launch; it’s about what you do when the "physics of people" takes over.

We went deep into the "Valley of Despair" in this interview... ...that predictable, dangerous phase where the initial hype dies and th...

Leaders Are Built in the Blur.

Jed Ayres, CEO of ControlUp, told me something most leaders won’t say out loud:

Clarity usually comes after you move, not before.

If you’re waiting for the perfect signal…You’re already late.

That “responsible” decision you’re about to make?

It might be the very thing slowing your flywheel before it ever turns.

We talked about what it really takes to move when things aren’t clear:

- When the leader (who drove 600% revenue growth in three years and...

That first all-hands.

Patrick Dennis, CEO of Avaya, walked in expecting nerves and optimism.

Instead, one question he was asked changed the room.

It wasn’t dramatic or confrontational.

But it was revealing.

It showed to him that the organization wasn’t aligned on reality.

And misalignment at that level doesn’t stay neutral. It compounds.

I’ve seen this pattern more times than I can count.

Leaders hear a question and assume pushback.

But sometimes the question asked IS THE DATA.

The Hard Season

Matt Zilli, CEO of Planview, told me the hardest years of leading a company through billion-dollar growth (including restructures, tough people decisions, and uncertainty) became the most valuable leadership training of his career.

That really resonated for me. Some of the most uncomfortable stretches building my podcasts and business were the exact moments I wondered if I should pivot, slow down, or walk away. The audience wasn’t growing yet.

The results weren’t obvious. The path felt uncertain.

Ever had the "uncomfortable stretch"?

You know, thos...

Is obsession with "The Win" actually preventing it?

John Leach CEO of FLS Transportation shared with me that fixating on the win is the fastest way to lose control.

He breaks down what happens when he walked away from "personality-first" leadership to build a system where success isn’t a roll of the dice.

It made me reflect on some of my own team's results where we delivered short term but they weren't always sustainable. Wish I'd chatted with John years ago!

We discuss:

Missed Opportunity.

Greg Smith, Founder of Thinkific, shared with me how most leaders are sitting on their most undervalued asset: their own expertise.

And I’ve been guilty of this too.

For years, I thought growth meant building something new (a new product, new offering, new initiative).

BUT some of the biggest growth I’ve seen (in my own business and with companies I work with) came from teaching what they already knew.

Not as marketing.

Not as training.

As a product.

When lead...

High performance deceives.

Alain Dias, CEO of Nortal Americas, knows a thing or two about building at scale..after all his team helped build the world’s very first "digital nation."

When a leader with his kind of track record speaks about growth, I'm in!

His interview is a gut-check for most organizations:

If your expansion depends on a "Hero," you aren't ready to scale.

In many cultures, we celebrate the "firefighter" who pulls the all-nighter to save the project. We give them the shout-outs and the awards.

...

Scale deceives.

Barry Mainz, CEO of Forescout Technologies Inc., reveals how leaders unknowingly become responsible for massive risks they never personally approved.

As your organization grows, leadership doesn’t just get harder, the real issues become harder to see.

More effort stops producing better outcomes.

And more hustle just starts masking risk.

Barry’s work shows something unsettling:

even elite tech leaders are often blind to 30–50% of the devices actually connected to their networks inside their own organizations.

But that’s not a technology failure; it’s a l...

Vikram Savkar, CEO of VitalEdge Technologies, shares how a demanding moment pushed him to rethink how he was operating...

AND why choosing to reset earlier than most leaders do changed how he showed up as a leader, at work, and at home.

The business here wasn’t the problem.

But time at home was shrinking.

And the way work followed him everywhere wasn’t something he wanted to normalize.

Instead of waiting for a breaking point, Vikram created deliberate daily reset—and what happened next accelerated his results.

We t...

Pressure doesn't change the game...it reveals the leader.

Mitch Stevison, President & CEO of Frontgrade Technologies, recently shared how a high-stakes missile test forced a decision no textbook could prepare him for.

In this conversation, we break down the one skill he leaned on when the eyes of two nations—and a Senior Admiral—were watching.

If you've ever had to make a high-stakes call under a microscope, Mitch’s insight on trust is a masterclass in leadership.

What is the most important trait for a leader to have during a crisis...

Questioning unlocks elite performance.

Pete Harris, President of Pipedrive, was at the pinnacle of his previous profession (one that he’d spent his entire career pursuing).

Everything was on track... the prestige and the rank. But while many founders and leaders might push uncomfortable thoughts aside, Pete did something different.

He used a specific type of curiosity to ask himself a question that 99% of leaders are too afraid to face....a question that forces you to confront whether you’re actually on the path you’re meant to be on.

Answering it mea...

Your office is deciding results.

Anna Squires Levine, President of Industrious, leads a company that has spent more than a decade observing how office space impacts human behavior (across hundreds of locations and millions of workdays).

Many leaders assume the office is just a place where work happens.

But it's far more than that!

She explains that the office space is quietly influencing things leaders usually attribute to culture, motivation, or performance.

In their work, incredible patterns emerged at scale in:

• How people show up at work

This mistake taught leadership.

Marcus Perez, President of Altera Digital Health, shares a moment that unfolded in a helicopter at low altitude (where mistakes don’t get a second chance) and still shapes how he leads today.

A rule had been broken the day before.

The next day, his commander took the controls.

He didn't get lectured.

He got something far more...

Intense.

Deliberate.

Unforgettable.

Some lessons just don’t need words.

After Marcus shared this story with me on t...

Leadership tests you.

Jason Liu, CEO of Wood Mackenzie, felt that test immediately when he stepped into the role right after a major merger.

New team.

New culture.

Everyone watching how he’d show up.

Instead of trying to project confidence the traditional way, he made a choice that could’ve easily gone wrong.

It didn’t.

What surprised me wasn’t the move itself...

...it was what it revealed about fear, trust, and credibility at the highest levels of leadership.

Jason do...

Pressure felt like leadership (until it wasn’t)

Josh Epstein, President & Chief Business Officer at Coder, learned this the hard way.

I’ve seen urgency do two very different things to teams.

Sometimes it sharpens focus and everything moves faster.

Other times, it creates stress, confusion, and quiet burnout—while leaders think they’re “pushing for results.”

Josh shared how early in his career, pressure felt like the right move… until it started costing trust and momentum.

Increasing pressure wasn’t creating more effort...or the results he expected.

AI failure rates shock me.

Erin Gajdalo, CEO of Pluralsight, joined me and what she revealed about why AI projects collapse disturbed me even more..

I expected to talk about tools, frameworks, and roadmaps.

Instead, Erin asked me question I wasn’t ready for:

“Is your team actually ready for this? How can you even tell?"

Um...

Because most leaders — myself included — push for AI adoption without slowing down to ask if our teams can actually absorb the shift.

Erin has led major transformations at Avantax...

Winning gold didn’t end the pressure. It intensified it.

A truth Phil Andrews, CEO of USA Fencing, came to understand through experience.

That’s the incredible story behind Team USA’s recent historic gold…

…and the leadership turnaround that made it possible.

When I sat down with Phil, I wasn’t expecting what came next.

He walked into a sport in crisis.

Broken culture.


Divided membership.


Declining trust.


High visibility.


Zero margin for error.

And somehow, he rebuilt all of it...