Ben Fanning

Ben Fanning Helping the employer and employee boost engagement, increase productivity, and reduce the catastrophic cost of quitting. Ben

In the corporate crucible, I’ve experimented to figure out what lights us all on fire. In my experience, I’ve noticed a common thread for making self discoveries and developed lots of strategies to help others (like you) do the same through coaching. Here are the ideas that drive most of my training:

1.) You don’t have to throw away your current career to have one that’s inspired (most are reliev

ed by this)
2.) Your path to reigniting your career starts by learning something new.
3.) You can have an inspired career, but you have to get around to understanding yourself first (not after the fact)
4.) You can do much, much more than you realize.
5.) There is almost always a better way

If you agree with anything above, you’ll enjoy being a part of this community. Big things are on the way, and I hope you’ll join me on the journey!

05/29/2026

Work hasn’t caught up...
Karthik Krishnamurthy, CEO of Ascendion, shared a powerful reminder on the show:

Most of us are already becoming AI-native in our personal lives.

We unlock our phones with our face.
We ask AI questions every day.
We expect technology to understand us instantly.
We don’t stop and think about it anymore.

So why should our experience at work be any different?

He makes a compelling argument that a leaders job isn’t just to adopt AI.

👉 It’s to help bridge the gap between how people live and how people work.

The companies that win won’t be the ones with the most AI tools.

They’ll be the ones whose leaders help their teams confidently cross that bridge.

How AI-native do you think your organization is today?

05/21/2026

AI Fraud is Winning

Matthew Thompson, President & CCO at Socure, shared that machine identities already outnumber humans online 80 to 1.

It’s a tidal wave of:

Fake job applicants.
Deepfake interviews.
AI-generated personas.

The sheer volume and complexity means leaders need to think very differently about how they defend their organizations.

After serving under General Stanley McChrystal in Army Special Ops, Matt now applies that same network-vs-network thinking to fighting fraud at scale.

Because the old approach — “protect the front door and call it a day” — is already too limited.

So leaders need to start asking:
How do you defend a business when you can’t tell what’s real anymore?

05/19/2026

Leading without all the answers is the job.

Keval Hutheesing, CEO at Cygnet.One, was 25 when he suddenly found himself responsible for 900 people during a crisis.

There wasn’t time to slow down and wait for perfect information.
People needed direction and customers needed confidence.
And the team was looking to leadership for answers.

Keval shares the mindset and strategy he relied upon to keep people aligned and moving forward even when the path wasn’t clear.

What’s helped you make tough decisions when you didn’t have all the information?

05/15/2026

The Wrong AI Bet

Arun Varadarajan, CCO at Ascendion, broke down why so many organizations are investing heavily in AI… but getting frustrated by little bottom impact.

“90% of projects fail because people don’t spend enough time defining the problem.”

It’s magnified when leaders rush into building before aligning on the real business challenge…
…and then get stuck in pilots, experiments, and “safe” AI initiatives that never transform how the organization actually operates.

AI without change.
Progress that isn’t progress.
That’s the wrong AI bet.

And it’s why ouor conversation became much bigger than technology.

It became a conversation about leadership conviction, organizational courage, and the willingness to rethink systems most companies never question.

Where do you think leaders are mistaking activity for results?

05/12/2026

Optimizing the Wrong Thing

Josh Kanagy, Hightouch CRO, said something in his interview that cuts against how a lot of companies are operating right now:

“When you optimize for the success of others… your own success gets taken care of.”

That sounds simple.
Until you realize how many organizations are optimizing almost everything else first:
• systems
• efficiency
• automation
• AI

And somewhere along the way, leadership becomes transactional.

Josh’s story — and where this philosophy comes from — completely reframed the way I think about scaling teams.

Because the companies growing fastest aren’t just building better infrastructure.

They’re building people capable of growing with it.

In this episode:
• The QBR that humbled him after Salesforce
• Why community builders often become elite leaders
• The hidden leadership risk inside the AI race

THE BEST SCALE PEOPLE.

05/08/2026

Rock concerts teach leadership.
Andy Freed, Chairman at Virtual Inc, has seen Bruce Springsteen nearly 100 times…

…and was so inspired by what he saw on stage that he wrote a leadership book about it.

Because Bruce can hold a stadium for 3+ hours…
while most leaders lose the room in 3 minutes.

Why?

Andy says Bruce understands something most leaders miss:
It’s not about the person upfront.

It’s about the audience.
The energy in the room.
The connection people feel.
The moments people remember after they leave.

That’s leadership!

I’ll be paying attention a lot differently at my next concert.
How about you?

05/05/2026

Life-Changing Advice
CRO Casey (Case) George shared the advice that shifted everything for him.

The best time for advice may be when things are going well (not poorly).
When you’re comfortable.
When you’re winning.
When there’s no reason to change.

And that’s exactly when a great mentor steps in.
Not to agree with you…
But to challenge you.

Casey shared a moment where a mentor told him:
“I’ll deny it if you tell anybody… but I think you should leave.”

I’ve stayed in a few roles too long myself.
And most of the time, I had to come to that realization on my own.
Looking back… a mentor probably could’ve helped me get there faster.

That moment pushed Casey to:
• Step outside what he knew
• Apply it in new environments
• Eventually lead global revenue at monday.com

In his interview
• Why growth usually starts before you feel ready
• How monday.com scaled into a $1.5B+ company
• What happens when response times go from 24 hours to two minutes

The best advice usually doesn’t feel good in the moment.

Question:
Have you ever stayed somewhere longer than you should have?

04/30/2026

Remember when we all turned to Zoom?

Zoom COO, Aparna Bawa, was in the room when it happened.

“Every hour… was like a curveball thrown at you.”

This was the moment that Zoom stopped being a tool
and became how people lived.

Then it became the fastest tech adoption in history.

And when something becomes that essential—
it stops being about company growth.
It becomes about how you lead.

04/28/2026

Systems Lag Change.
Hayden E. Stafford, President & CRO at Seismic, breaks down what happens when the pace of change outgrows the systems we build.

The danger is this:

The pace of change explodes.
The structure doesn’t evolve fast enough.
And when the signals said something wasn’t working…
the decision to adapt never happens.

That’s when things start to drift.
often in small ways that compound.

It’s not one big failure. It’s a series of decisions that never got updated.

Ever seen the system lag the change?

04/23/2026

Trust Can’t Be Automated.

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

But when it’s all on the line,
people don’t turn to the model.

They turn to the leader.

Systems can optimize all day.
But leaders are the ones building the relationships and trust behind it.

Eileen lives that.
She gives her personal cell phone to her entire organization.
And it goes back to something she learned early from legendary CEO Jack Welch—
you build trust through access and accountability.

We also talked about those moments where a deal looks right…
but something’s off.
And the decision isn’t about the data.
It’s about whether you’re willing to stand behind what happens next.

AI can help you get there.
But it can’t carry that weight.
👉 When it matters most… who do people actually trust?

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