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?

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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?

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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?

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Connect with the Host, #1 bestselling author Ben Fanning

Speaking and Training inquires

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