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 meant walking away from the very finish line everyone expected him to cross.

That moment of clarity unlocked a version of himself he hadn't met yet...

...one capable of:

- Finishing full-distance Ironmans.

- Leading a global engine for 100,000+ businesses.

Most leaders are too afraid the deeper question because they’re terrified of the answer.

Pete leaned in and shows us this conversation how we all can too.

When has asking the right question helped you?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

Your office is deciding results.

Anna Squires Levine, President of Industrious, leads a company that has spent more than a decade observing how people behave at work (across hundreds of locations and millions of workdays).

Many leaders just 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

• How they interact

• What actions and behaviors are encouraged or avoided

• And how energy moves through the day

Leaders rarely talk about this...even though they’re already accountable for the office space and the very outcomes it shapes.

Do you ever think about how your office space can impact your results?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

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 the show, it became clear why that personal experience carried more weight than any traditional feedback session ever could.

Our conversation raises questions around:

✅ When the most dangerous leadership decision is when you choose not to step in.

✅ What really happens when you delay accountability under real risk.

✅ How you know when stepping in helps… and when it backfires.

👉 What mistake taught you the most?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

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 doesn’t talk about fear like something to eliminate.

He talks about how leaders carry it, manage it, and still move forward anyway.

You hear it in how he leads teams across 30+ countries.

You see it in why he choose to put himself out front as the face of a 100-year-old brand.

And you feel it in the moments where control would’ve been easier, but courage mattered more.

This conversation stuck with me.

When has leadership tested you the most?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

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.

It was one uncomfortable shift (that felt slower at first)...

...that ended up making everything faster.

We unpack the full story in this week’s episode.

So:

👉 When things slow down, how effective has pressure been for you?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

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, LPL, and now Pluralsight... and she’s seen the same silent pattern across industries:

Leaders blame the tech.

Teams blame the workload.

But the real problem is almost always hidden deeper.

Readiness....and getting their quickly....is everything.

In our conversation, she breaks down:

👉 The blind spot most CEOs overlook.

👉 Why 50% of AI projects fail.

👉 What separates teams that finish from those that stall.

👉 The first move every CEO should take when they realize their team can’t keep up.

👉 And how her transformation background gives her a unique advantage in the AI era.

This conversation changed the way I think about leading through AI.

What’s the biggest AI readiness challenge you’re seeing in your teams right now?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

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…before making Olympic & Paralympic history.

But not long after the gold, the pressure shifted….


Public controversy.


Intense scrutiny.


And—death threats no leader should ever face.

Leaders talk about “high stakes.”

BUT this is what high stakes actually looks like.

Phil shares:

• The day-one move that stabilized a fractured team


• The bold Olympic decision that changed everything


• The backlash that hit not long after the gold


• How he led through threats, scrutiny, and congressional attention


• The leadership tools he relied on when everything was on the line

This is a powerful story of crisis leadership, culture repair, and resilience.

If you’ve ever led under pressure, you’ll never forget this lesson.

What’s one leadership lesson pressure taught you?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter

Dan Michelson, CEO of RLDatix North America, shared the feedback that reshaped how he leads.

When things go well, it can actually blind you to areas where he needed to improve.

...and this is why so many successful leaders often fail.

Most top performers don’t realize they’re slipping until someone has the courage to tell them something they didn’t want to hear.

Dan shared that his initial reaction to feedback early in his career was to blame the person giving him the feedback...and years later, he’s more grateful for it than almost anything else.

And when he stepped into leading a 2,300-person organization, the stakes around feedback got even higher. Any past success wasn’t going to carry him anymore. Clear, direct communication had to.

That’s when he embraced the mantra that now guides his leadership:

“Coaching is caring.”

He even had a 3.5-hour feedback conversation with a leader on his team — not because something was broken, but because growth mattered that much.

Here’s the truth:

Feedback is rarely comfortable.

But avoiding it costs far more.

Great leaders choose the kind of discomfort that makes them better.

Agreed?

-----

Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

Subscribe to my Youtube channel

LinkedIn

Instagram

Twitter