Exited founder turned CEO-coach | Helping founders discover who they are as leaders and build high-performance, low-drama companies

Over 15 years I founded and served as CEO to three VC backed companies (one big exit and two learning experiences), all while presenting only the most polished, hyper-competent version of myself and my company, at all times. And then, in 2020 I left it all behind.When I signed the papers, officially removing myself as CEO of the company I’d started a decade prior, it felt like I’d been punched in the gut.Without my persona as the “CEO of VNN,” I realized that I had no idea who I was anymore, or what to do with my life.It was the opportunity of a lifetime.I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right.I was stuck.And then, I finally opened up.I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be “Ryan the CEO,” or “Ryan the entrepreneur,” or even “Ryan the guy who’s raised a ton of money and scaled a media company.”I was just, Ryan.And the most surprising things happened.1. The more I opened up, the more everyone else did around me. My network grew and developed into one of deep relationships spanning life and business.2. The more I let go, the more the universe seemed to place exactly what I needed on my doorstep. Things began to happen organically, in ways much better than I could have planned.3. The quieter my mind got, the more I was able to access an innate wellspring of creativity and inspiration that, frankly, made work feel easy and joyful.Me, the guy who’d worked so hard his whole life to be perfect, when I learned to let go and be me, great, meaningful work flowed out of me.And from that foundation, I started Inside-Out Leadership, a boutique executive coaching firm that helps founders transform their companies into their masterpieces and step fully into their lives.Today, in my work as a coach I see the tendency to present that veneer of polished competence in nearly every founder I meet. And while I recognize the need for presentation in some cases (fundraising, recruiting), I also see how that need to look good actually gets in the way of our learning and growth.If you're tired of doing your own impression of the "perfect leader," you're not alone.Shoot me a DM. There's another way. And it's fucking incredible.

Ryan H. Vaughn

Big news! I'm so excited to welcome Derek Haswell to the team as a Partner and Founder Coach! 

I met Derek early in my coaching journey, and have wanted to conspire together in some way for years. He's amazing. And now I'm eager to see what we get up to together at IO. 

In 2013, Derek accidentally co-founded a meditation company. He helped build an award-winning product, scaled to 8-figure ARR, and worked with some of the best meditation teachers in the world, including the Dalai Lama.

Today, Derek blends outer work (strategy, goals, accountability) with inner work (self-awareness, resilience, what's actually driving the stuckness).

In his own words:

“I've lived that trade-off as a founder and it sucked... for everyone. Then I discovered they could be part of the same path, and it changed everything. Now I help founders make the same shift.”

I’ve known Derek for years, as a coach, a builder, and a wonderful human being, and I’m so excited to co-create Inside-Out with him, and support our founders in scaling consciously.

Check out Derek's full story in the comments. It's worth the read.

Exited founder turned CEO-coach | Helped early/mid stage startup founders raise over $500m, and create equity value over $12bn (and counting...)

I have big news. But first, a story. 

I talk with founders every day who are in the middle of real inflection points.

Co-founder splits. Post-exit identity crises. Scaling without burning out. The weight of figuring out who they are as a leader.

But I only coach 15 people at a time, which means I can't work with most of the founders I speak with.

That's always bothered me, so we're doing something about it.

Introducing: Inside-Out Virtual Workshops.

Small (around 8 people). Led by me and the Inside-Out team using the same frameworks and modalities we use with our 1-1 clients, finally accessible to a broader group of founders.

The first workshop is Getting Unstuck. It's for the founder or exec who knows how to do hard things, but keeps hitting the same wall in one specific area.

Most approaches to this work outside-in: Better habits, tighter systems, more accountability. And if that's worked for you, great. But if you've tried all that and you're still stuck, the problem probably isn't discipline.

This workshop works from the inside-out, using IFS (Internal Family Systems), an evidence-based framework that has become one of the most powerful tools in serious executive coaching.

Give me 90 minutes. You'll leave with a new way of seeing the stuckness and a concrete experiment to take into your life.

WHEN: March 23rd. Noon to 1:30pm ET.
COST: Free

Space is very limited. Click the link in the comments if you'd like to apply.

A client told me: “The single most important thing for my company right now is the fundraise.”

Then he paused. “And it’s the thing I avoid every morning.”

I see founders in inner conflicts like this every day. This type of dynamic can take years to unwind, and kill companies and relationships along the way. 

After nearly a decade of coaching founders, I've found one reliable method for resolving inner conflicts like these: 

Internal Family Systems, or IFS. 

IFS is a leading toolset at the bleeding edge of exec coaching, and is built on the only scientifically proven method to change emotional learnings, Memory Reconsolidation.

It's a core tool in our practice at Inside-Out, and we're teaching founders how to use it themselves live on March 23. 

When we looked inside at this particular issue, we found two competing parts.

One part wanted the company to grow. The other part said, “If this fails, you’ll look like an idiot in front of your investors.” So we work on the problematic part. Once you do that, the system stops conflicting.

This doesn't take weeks of months. The best coaches help clients get unstuck in an hour or less. 

Want to learn how it works? Apply for our first intimate workshop on March 23. Application in comments.

"The moment you doubt whether you can fly, you cease forever to be able to do it."
–J.M. Barrie, Peter Pan

I've played basketball my entire life, and here’s what I’ve noticed. If I step on the court
believing I'm the best player there, I hoop. If I'm uncertain, I play poorly.
Leadership works the same way. If you believe you'll win, you'll win. If you believe you'll lose, you'l lose.
Confidence is king.

But real confidence isn't peacocking. It's not pretending you have all the answers. It's not even earned through success. You can build a great company and still be one bad outcome away from doubting yourself.

Real confidence comes from alignment between who you are inside and how you show up in the world.
The ball’s in your court.

For most of my career, creativity came from pressure. From big problems I had to solve. From outcomes I needed to hit. 

But there's a different kind of creativity that lives underneath all of that. It comes from joy. From play. From love. I call this place presence. And it's where the most interesting work happens.

I see this all the time working with post-exit founders. During the scale-up, every identity shift serves the company. But after the exit? When that crutch is gone and you're staring at a blank page, wondering what's next?

That's when the real work begins.

Because now you're not choosing who to be based on what needs to get built. 
It's terrifying. And it's also the most creative place I've ever been.

There’s a hidden force behind many “productivity problems.”

It’s not laziness. It’s not discipline. It’s not even time management.
It’s fear.

When pressure, uncertainty, or self-doubt creep in, the brain doesn’t lean into bold work.

It looks for safety. Suddenly emails feel urgent. Slack feels necessary. Small,
controllable tasks replace the ambiguous, high-stakes ones that move things forward.
From the outside, it looks like busyness.
From the inside, it’s avoidance, rooted in fear.
And the insane part? It feels rational.

Understanding how fear quietly reshapes attention, decision-making, and execution is
one of the biggest unlocks for founders and high performers.

Because you’re not always fighting a workload problem.

Sometimes you’re fighting a fear problem.

The most defining part of leadership isn’t certainty. It’s the unknown.
Especially now, when AI and systems increasingly handle the predictable, repeatable, “figured-out” work, what remains for founders and CEOs is ambiguity.

Leadership becomes a cycle:
Enter the unfamiliar.
Navigate the discomfort.
Create clarity.
Hand it off.
Repeat.

The lesson is simple, and I’m trying to follow it myself.
Stop treating discomfort as a warning sign.
It’s usually evidence you’re exactly where you need to be.
Learn to recognize it.

Normalize it.
Build the internal capacity to move forward anyway.

Most people have picked a side on AI.
Either it's the greatest tool ever built, or it's an existential threat we're sleepwalking into.

The binary is comfortable. But the leaders I work with who are navigating this most
effectively have learned to hold something harder: Both.

The fear is real. It lives in the gut. It wakes you up at 3am thinking about the world your kids will inherit. The excitement is equally real. As it should be.

The mistake isn't feeling one or the other. The mistake is collapsing into one becausethe other is too uncomfortable to carry. 

The most important things in life are paradoxical. They resist resolution. And AI may be the defining paradox of our time.

As F. Scott Fitzgerald said, "The test of a first-rate intelligence is the ability to hold two opposing ideas in mind at the same time and still retain the ability to function."

Angry seagulls are going to make you a better leader. Stick with me and I’ll
explain.

You"re in a board meeting. An investor cuts you off. "I don't think you know what you're doing. Your strategy is completely wrong."
Do you fight back or shut down?
When this happened to me once, I made two mistakes.

First, I said "okay" while quietly resenting the investor. That didn't work.
Then I pushed back and defended myself. Also a mistake. It took me years to find the third option. Get curious.

Not the kind of curious where you ask questions to trap them. The kind where you stay grounded in yourself while opening up to what you might be missing.

You're going to run into "angry seagull" investors. It's not if, it's when.
You can fight back. You might win the moment, but you won't grow.

You can blindly agree. You'll lead your company somewhere you don't believe in. Or you can ask questions. Really listen. Stay confident while staying open.

How you react when you're uncomfortable dictates the trajectory of your company and
career.

So…

What angry seagulls are in your life right now?
The investor who keeps pushing back?
The co-founder who questions every decision?

The board member who never seems satisfied?

What would it look like to stop resisting them—or blindly accepting them—and start
getting curious about what they're here to teach you?

https://lnkd.in/gHUzHVcZ

The most comforting and terrifying thing I’ve learned in business is the same truth. Here's the story.

My real education happened inside a startup accelerator. 12 intense weeks, surrounded
by founders, mentors, and Thursday night “fireside chats.”

One moment stuck.
A wildly successful executive paused when asked for his single biggest lesson for entrepreneurs. “Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies is that, with the successful ones, you can’t tell.”
That perspective has followed me through every stage of my career.

Do they teach that in school? I wouldn’t know.

https://lnkd.in/g_P32hAy

One late night, I got a call from a board member.

It was around 11pm my time, which means it was probably 3am his time.

What he said stuck with me forever.

Most leaders don’t have a strategy problem.
They have a validation problem.

The most dangerous addiction in business isn’t money or power.
It’s being liked.

Applause feels like progress.
Agreement feels like safety.

Slowly, decisions stop being about what’s right and start being about what won’t upset anyone.

That’s not leadership.
That’s people-pleasing with a title.

Control is the most expensive illusion in your company.

My Zen teacher used to tell me, “Sit down, hold everything still, and watch what moves.”
What moves is everything you don't control. Your thoughts arrive uninvited. Your
emotions surface without permission. The narrative you've built about agency begins to
quietly unravel.

AI is doing something similar at civilizational scale. It moves too fast, builds too
suddenly, disrupts too completely to let you maintain the fiction. But I've come to believe that confrontation is a gift.

The founders who thrive aren't the ones who reassert control in the face of uncertainty.

They're the ones who find a different relationship to power, one that doesn't require control as its foundation.

That's not passivity. It’s a more sophisticated form of strength.

"You have power over your mind, not outside events. Realize this, and you will find strength." — Marcus Aurelius

This video has been making its way around the Internet. You should stop and watch before you keep reading.

Most people think reading 900 words per minute is impossible. Until they do it.
What changed?

Not their brain. Not their intelligence.
Their belief about what was possible.

We’ve seen this before.

Same with running the four-minute mile.
And having smart machines.

Entrepreneurs do this constantly.

We build invisible ceilings and convince ourselves they’re real.
Then a crisis hits. Or something else forces your hand.
And you discover the ceiling was never real.

When people read 900 words per minute for the first time, there’s genuine shock. Like they discovered some supernatural ability.
But they always had it. They just never gave themselves permission to use it.

Most limitations are just untested assumptions.

Question the ceilings. Test the assumptions.
You’ll probably discover you’ve had the ability all along.

An interesting question to sit with:
What limitation are you currently living with that is, in fact, just a belief?

The best CEOs I know have shorter to-do lists than you.

A perk of my work is getting an intimate look into the habits and systems of leaders across the world.

And something I've noticed about the best CEOs isn't what they do. It's what they decide NOT to do.

Most people let their to-do list become infinite. They pack in as much as possible, check off what they can, and roll everything else forward. The list never ends. And they wear it like a badge of honor.

But here's what they're avoiding: The confrontation of choice.

Saying "I'm not going to do this thing" feels permanent and final. Like you're actively choosing failure in that area.

And that's uncomfortable.

So instead, people keep everything on the list. They tell themselves, "I'll get to it eventually" and avoid the psychological weight of consciously letting something die.

The best CEOs do the opposite.

They stack rank their tasks by importance, look at their calendar, and slot only what will fit. Then they consciously move everything else to next week's list, or kill it entirely.

The result? They finish their work most days. And they get exceptionally good at one of the most important skills in leadership, which is saying no to important things.

Because here's the truth…

Your workload never decreases as you grow. You just get better at leading. And having less time forces you to delegate, empower your people, and build your organization instead of just working harder.

Your to-do list is a daily training ground for this.

Every day, you're forced to confront what dies so something more important can live.

That confrontation is the work.

Not the hustle of doing more, not the performance of appearing busy.

The discipline of doing what counts. And ruthlessly eliminating what doesn't.

https://lnkd.in/gbCGxgNW

Open article: Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care by leadinsideout.io

Inside Out Leadership — CEO's Personal Management System: Prioritize Deep Work & Self-Care

Scaling a company means giving away the work you used to take pride in.

Watch and listen to why that moment is harder than most founders expect.

I once heard a story that stayed with me.

A little girl walks through a garden for the first time. It was overwhelmingly beautiful, and
she runs inside to tell her mother.

Her mother smiles. “Those are pretty flowers, aren’t they?”
The next day, the girl returns to the garden… and sees “pretty flowers.”

The label stripped the magic. It flattens wonder into familiarity.

I catch myself doing this in business.
A group of complex, brilliant, unpredictable humans becomes “the sales team.”
Or “engineering.”

And without realizing it, I narrow how I see them.

Abstraction isn’t wrong. It’s essential.
But every so often, a moment of awe — in nature, in conversation, in work — reminds
me:

Reality is always richer than the words we use to contain it.

I’m doing my best to remember that.

https://lnkd.in/gxyzemuH

Have had the pleasure and privilege of getting to know Ryan, and +1 to all this

Founder/CEO at HealthBar | Healthcare Delivery & Payor Model Innovator/Entrepreneur/RN

If you don't know Ryan Cummins, you absolutely need to make it a priority!


Having Ryan close our 'Health'care 2026 conference with a keynote address is going to be engaging and empowering

The work he's doing is absolutely incredible 

His curiosity to learn is unmatched

And his focus on future generations is inspiring.....


Don't miss an opportunity to hear from, and meet Ryan at 'Health'care 2026!

healthcare2026.com

#health #healthcare #business #ceo #entrepreneurship #events

I’m the founder and co-CEO of Pragmatico, an AI cultural transformation company. 

I serve as a Fractional Chief AI Officer for organizations like Prime Hospitality Group and Audiochuck (creator of Crime Junkie),  where we grew AI adoption from 12% intermittent use to 95% skilled, active usage.

Building world-class teams that solve real business problems is what gets me out of bed in the morning. 

I'm also a 3x-exited founder and executive coach. I’ve spent the last decade helping hundreds of leaders transform their cultures through data-driven insights and coaching. I co-founded Emplify, an employee engagement measurement company, which was acquired by 15Five in 2021. I started my executive coaching practice shortly thereafter. 

On the personal side, I’m a proud Colombian immigrant, drummer, hot yoga enthusiast, and world traveler (40 countries and counting). 

Here on LinkedIn, I write about:

- The human aspects of AI transformation
- How to lead well without losing yourself
- Lessons learned from my own entrepreneurial and leadership journey

Other awards and accomplishments include:

- Amazon best-selling author of “Agile Engagement”
- Indiana Latino Businessman of the Year 
- Indianapolis Business Journal 40 Under 40 
- Inc. Magazine's 30 Under 30 
Whitehouse.gov "Champion of Change"

Santiago Jaramillo

Anthropic just analyzed 2 million AI conversations, and I want every executive in my network to hear what they found:

There’s a strong correlation between input sophistication and output quality.

Translation: The people getting strong results aren't necessarily better at prompting.

They have domain fluency.
They spot weak outputs fast.
They already know what “good” looks like before they type a query.

This is the part most companies get backwards:

They invest in prompt engineering workshops. 
They build template libraries. 
They hire AI trainers to teach people how to talk to machines.

But the real multiplier was never the prompt. 

It's the human with strong critical-thinking skills and deep subject-matter expertise.

Founder, Co-CEO & AI Transformation Lead (3X Exited CEO & Founder)

Five years ago, I sat down for a Forbes interview about “ikigai,” the Japanese concept of “reason for being.” I sounded like a guy who had it figured out.

I didn't.

I was exhausted from a decade of 70-to-80-hour weeks.

Had a combover I hid behind. 

All with the silent promise I'd made as an immigrant kid: succeed no matter what.

Last week, I sat down again with Nell 3D [Derick Debevoise Dewey] to tell the parts of my story I couldn't before:

Why the Emplify exit left me feeling more lost, not less. 

What a ten-month sabbatical taught me about my worth.

How that reckoning is shaping the way we built Pragmatico.  

Why we insist AI transformation serves the people inside it.

What’s something you had to unlearn after hitting a goal you'd been chasing for years?

Link to the full article in comments.

Tomorrow, I'm speaking on stage for the first time in 6 years. It feels different this time.

Last time I did this, I was building Emplify and talking about employee engagement. 

A lot of what I shared came from research. Good research. But still research.

Now I run an AI transformation firm. I sit in rooms every week with leadership teams trying to get people to actually use AI. 

Not buy it. Not talk about it. Use it.

One organization went from scattered adoption to 90%+ daily AI usage in under 90 days. 

Tomorrow, I get to walk through exactly how that happened with the CHRO of Indiana Farmers Insurance.

Six years ago I had frameworks. Now I have scar tissue and receipts.

If you're at RESOLVE tomorrow, come find me. I'd love to hear what you're seeing with your own teams.

I just sat in on a discovery call where a leadership team wanted to jump straight to agentic AI.

One problem: nobody on the team is using AI daily yet.

Their last AI project actually killed internal trust. 

And now leadership wants to leap to the most complex implementation possible.

But here's what we keep seeing across companies:

The organizations that actually get to agentic AI are the ones that first built daily AI habits across their teams. 

Here's the truth that needs to be said out loud: 

Daily adoption has to come before automation. 

Culture has to come before tools.

And leaders have to go first.

Yes, the future will belong to humans orchestrating AI at scale. 

But that only works after you've built the muscle memory, trust, and shared vision across your entire organization.

Most leaders will skip this step because it's slower and less sexy than launching an AI agent.

But it's the only path that actually builds real momentum.

What's a situation you've experienced where the best way to speed up was actually to slow down?

I'll be honest: I initially made the same mistake as everyone else with AI adoption.

Called Pragmatico an AI training and education firm. Led with training. Tool tutorials. Prompt libraries.

Execs loved our workshops.  

But when I'd check in 60 days later, their teams' usage was flat. Every time.

The leaders got it, but the organization didn't move.

Turns out we'd been solving for the wrong layer entirely.

That realization led to a framework that's driven 90%+ active AI usage at Audiochuck, Prime Hospitality Group, and Indiana Farmers Insurance.

On March 12 at 2pm ET, I'm walking through that framework live + the diagnostic that shows exactly where your organization is stuck.

You'll walk away with a 30-60-90 day plan you can actually act on.

Link to register in comments.

What's the biggest barrier you've hit trying to get your team to actually use AI consistently and skillfully?

Spotify's CEO just said its top engineers "haven't written a single line of code" in 2026.

But the real headline was what came next:

"We're in the middle of the change, so you also have to be very agile. The things you build now may be useless in a month."

That's the CEO of a company worth $95B telling Wall Street he's navigating this in real time. Just like the rest of us.

I sit across from leaders every day who are feeling that pain. 

They're making decisions about technology they're still learning. Meanwhile, the entire landscape seems to shift almost weekly.

One executive told me recently: "I feel like the blueprint keeps changing before we finish building."

 I've heard some version of that sentence a dozen times.

Here's what I've noticed separating the companies that are adapting from the ones that are stuck:

They stay loose enough to scrap Tuesday's plan when Monday night reveals a better one. 

They give teams real permission to experiment, fail, and restart without shame. 

They treat uncertainty as the operating environment, not as a problem to solve first.

Nobody has this figured out. Not Spotify. Not your competitor. Not the vendor promising you a roadmap.

The companies making progress just got honest about that sooner; and started moving anyway.

What's the best piece of advice you've ever heard about agile leadership in times of change?

People talk about the "loneliness of leadership" like it's about being alone.

It's not.

It's about carrying information you can't share.

You might be the only one who knows the company has six months of runway. 
Or the big customer or key employee is at risk. 
Or the org design isn't working. 
Or a decision is coming that may hurt people you care about.

And now there's a new weight on top of all of that:

You're expected to drive AI adoption while you're still figuring it out yourself.

Nobody sees that part. 

You're supposed to learn fast enough to lead credibly while keeping your team steady enough to actually adopt the change.

That's two full-time jobs stacked on each other.

Leadership is hard because the job is heavy.

Finish this sentence: The hardest part of leadership nobody talks about enough is _______.

I'm not an AI expert.

I just happen to be less afraid of the learning curve than most. And I know why.

My first investor pitch. Walking in with a new deck and sweaty palms. They asked the one question I didn't have an answer to. (They always do.)

The first time I had to let someone go. Sitting across from another person, knowing their mortgage depends on this conversation.

The first time I had to tell 50+ employees about a pivot that would change everything about their jobs.

I survived all of that. Grew through all of it.

Learning AI isn't harder than any of those moments. It's just newer.

Most executives have been in "expert mode" for so long that the discomfort of being a beginner feels foreign. 

But the muscle memory is still there. You've done hard things your entire career.

This is just the next one.

What was the hardest "beginner moment" of your career?

I hear so many CEOs whisper about AI as if it were an affair.

But behind closed doors, many are using it for everything. Board decks. Investor updates. Strategy docs. 

But publicly? They frame AI as something they’re "looking into."

That gap is creating a dangerous culture problem.

When the CEO uses AI privately but doesn't talk about it openly, the rest of the org gets a clear message:

This isn't safe to admit.

So employees hide their AI use, too. Or worse: they don't use it at all.

Meanwhile, competitors where the CEO openly talks about their AI use are lapping them.

The unlock is permission. 

And that starts with the CEO saying "I built this board presentation with Claude in 45 minutes” with their chest.

I watched a CEO who built a $200M company freeze in front of ChatGPT last month.

Like a kid on the first day of school.

He hasn't been a beginner at anything professionally in 17 years.

Think about that.

Seventeen years since this man was bad at something in front of other people. 

Nearly two decades of being the one with answers. 

The expert in the room. The person everyone looks to.

And now I'm asking him to fumble through prompts that a 22-year-old intern would probably nail on the first try.

Here's what nobody tells senior leaders about AI adoption:

The hardest part of learning AI is psychological, not technical.

Most executives haven't practiced being publicly, visibly bad at something in years. 

And the higher you've climbed, the more terrifying that feels.

Daily AI users: What advice would you give a senior leader sitting down in front of ChatGPT for the first time?

Most knowledge workers can be 50-75% more productive with AI. Today.

But where's the starting line?

Patrick Rodgers just asked me this on the Build Boldly podcast.

Here's what I told him:

The starting point is a leadership decision:

"Are we going to get serious about AI adoption or not?"

That has to come first.

Then crawl, walk, run.

Pick one Gen AI tool as a company. 

Get good at it. Don't try to master five platforms on day one. 

80% of what people need can be accomplished by learning a single tool with real depth and consistency.

Then create the conditions for that first real win: when someone does in 15 minutes what used to take 10 hours.

Once someone hits that moment, they don't go back.

It's like being handed a computer after years using a typewriter.

Really enjoyed this conversation, where we also cover:
- Simple use cases that create immediate impact (meetings, email, documents) 
- The real risks of employees using personal AI accounts at work 
- Why leaders have to go first, and what happens when they don't 

Link to the full episode in comments.

I've been watching AI vendors discover what every founder learns the hard way.

The easy money eventually dries up.

Last year, enterprise deals were closing in 60 days. 

Companies spent $1.249 trillion on AI software. Board mandates were flying. FOMO was everywhere.

Now? Six months to close. 

Legal shows up.

Finance shows up. 

Everyone is asking the same question: "What's the actual return?"

A Gartner survey hit hard: Only 11% of customer service leaders said generative AI met their primary business objective. 

And that’s customer service: one of the most mature AI use cases we have.

The threshold for a pilot has gone up across the board, says Oisin Hanrahan at Keychain. 

Kyle Chu at PopSockets put it plainly: "We've gotten a lot more disciplined in making sure we understand what the outcome of a specific purchase is, not just following the hype."

This signals a necessary course correction. 

The companies that built for hype are scrambling. 

The ones that built for driving outcomes are getting conversations.

How are you currently measuring AI outcomes?

Accenture is now tracking executive AI logins and tying usage to promotions.

I get the impulse.

You invest $100,000+ in AI infrastructure. Nobody uses it. The ROI vanishes. 

So you measure logins, make it mandatory, and connect it to advancement.

Here’s the problem: when you make the metric the goal, people game it.

They log in. Generate a useless prompt. Log out. 

The number goes up. The work doesn't change.

There’s a better way:

Tying promotion criteria to AI fluency instead. 

Not "did you log in" but "can you show me how AI changed your work?"

The difference matters:

Login tracking asks: "Did you use the tool?" 
AI fluency asks: "Can you solve problems with AI that you couldn't before?"

One creates performance. The other creates capability.

The companies that are ahead with AI right now are building cultures where AI is just as valued as any other core competency.

The best feedback you can get: When someone walks away from your session and captures the core idea better than you did.

Grateful for the chance to share with such an engaged audience at RESOLVE. The energy was incredible!

Blurring the lines between Career, Church and Community

Oh joy - Another "AI" Session...😵‍💫
but this one hit like a sermon 👏🏾

🗣AI adoption isn’t a technology issue.
It’s a culture issue disguised as technology.

Right now many folks and orgs are moving fast...deploying tools, launching pilots, writing policies. But the biggest barrier isn’t the technology. It’s that many people still don’t have clarity on how AI affects their role or how to actually start using it.

So the real work isn’t just implementation.

It’s a mindset shift in how people approach their roles and how work gets done.

The organizations that succeed won’t just introduce AI. They’ll lead the cultural shift that makes adoption possible.

Thanks Santiago Jaramillo! Well done. Talk soon!

Overall, Great 2026 Resolve Conference! Enjoyed all the sessions on employee comp, benefits and healthcare trends. And even teamwork presented by two time Olympic Soccer Champ, Lindsay Tarpley - OLY .

NFP, an Aon company 
Andrew Everhart Bryan Brenner Paul Ashley, CEBS Megan Nail, CCP, SHRM-SCP, CEBS

The AI industry has a massive blind spot.

We measure AI progress as if we're building human replacements.

Every major benchmark isolates AI on tasks humans currently do:

"Can it write this report?" 
"Can it analyze this data?" 
"Can it make this decision?"

But the "jagged frontier" tells a different story.

AI capabilities are wildly uneven:

Superhuman at synthesis, still mediocre at memory and branded slide decks. 

Brilliant at pattern recognition, useless at navigating a room full of stakeholders with competing agendas.

That means the right question was never "can AI do this job?" 

It was always "what happens when a skilled human and AI tackle this together?"

Those are COMPLETELY different performance curves. And almost nobody is measuring the second one.

The benchmarks that actually matter:
👉🏽 Time to insight/outcome when human + AI collaborate vs. either working alone
👉🏽 Quality improvement when AI handles what it's great at while humans manage the edges
👉🏽 Bottleneck reduction across entire workflows, not just isolated tasks
👉🏽 Creative range expansion when people use AI to explore territory they couldn't access before

The companies pulling ahead right now aren't asking "which jobs can AI replace?"

They're asking "what becomes possible when our people and AI work together?"

That second question is harder to answer. It's also where all the value is.

Where have you seen human + AI outperform either working alone?

(Image credit: Tomas Pueyo)

Most executives are still using AI like a glorified search engine.

That's kinda like using an iPhone 17 for nothing but phone calls.

The game has changed: AI can now DO things, not just respond to questions. 

Claude Code can build and test an entire website while you sleep. 

Claude Cowork can reorganize your files, pull data from PDFs, and draft summaries autonomously. 

NotebookLM can turn 50 research papers into a podcast.

The people and companies pulling ahead right now are giving AI tasks and setting deliverables.

Managing output as if Claude was a brilliant new hire who needs clear direction.

That's the shift we're helping clients make: from querying AI to delegating to it. 

From spell-checking an email to offloading entire workflows.

That's a completely different muscle.

What's a task you've successfully delegated to AI, not just asked it about?

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The Battle

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