Jaime Diglio

Most performance breakdowns don’t come from lack of talent, effort, or training.
They come from interactions.
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Leaders are capable.
Teams are smart.
Roles and expectations are shifting.

And communication hasn't caught up.

Feedback doesn’t translate into behavior.
Executive presence fades as the stakes rise.
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You know the moment.

You’re explaining something clearly, and a quiet thought crosses your mind:
Is this landing?

That’s where my work lives.
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Athletes and coaches practice for performance.
Professionals are expected to perform without reps.
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That gap is where leadership breaks down.
I call this The New ROI™: 
Return on Interactions.

In the age of AI, information is everywhere.
Performance is determined by how leaders communicate and show up in human-to-human moments that matter.
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I specialize in player -to-coach and coach-to-player communication, the interaction loop where executive presence is built and performance is either activated or unintentionally shut down.

As leaders move between roles such as player, coach, peer, and decision-maker, the language that once worked often doesn’t anymore.

This is especially true as organizations adopt AI and leaders take on broader scope, where expectations shift and how something is said matters as much as what is said.

______________

𝐎𝐫𝐠𝐚𝐧𝐢𝐳𝐚𝐭𝐢𝐨𝐧𝐬 𝐭𝐲𝐩𝐢𝐜𝐚𝐥𝐥𝐲 𝐞𝐧𝐠𝐚𝐠𝐞 𝐮𝐬 𝐰𝐡𝐞𝐧:

• Leaders need stronger executive presence
• A leader is promoted and needs to step up
• Teams are capable, but not communicating
• Leaders can't read the room
• Behavior isn’t changing
______________

The WIN Room™ was built to close a gap I experienced firsthand as a leader.

I knew what to do.
I learned firsthand that you don’t rise to the moment. You perform to the level of your practice. What’s rehearsed is what shows up under pressure.
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WIN stands for What I Need — the skills leaders need before the stakes are too high to improvise.

A leader at a global financial firm put it best:

“I’ve read all the leadership books. You showed me what they couldn’t.
How to actually put it into practice.”
______________

This approach is practice-based and results-driven.

To date, 98.4% of leaders who go through The WIN Room™ hit their performance targets, because the work is personalized and applied directly to real leadership interactions.
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If you’re looking to elevate how leaders show up, this is the work I do.

CEO | WIN Room Leadership & Sales Team Training | Keynote Speaker

Clients hire me to deliver my WIN Room programs for teams during times of transition, disruption and change. 

Focus on psychology of selling, neuroscience (brain based coaching), emotional wellness, soft skills, leadership and self-awareness coaching and training combines with Gen AI tools that is a proven secret weapon to help leaders and sales teams WIN.

▪️Facilitate Leadership Workshops
▪️Communication & Team Dynamic Strategies
▪️Leading & Selling through Transition
▪️Career Coaching
▪️Speaking Engagements

Focus Areas: Coaching leaders and their teams on EQ & self awareness, deal coaching, organizational & culture change, authentic & courageous leadership, self sabotage, diversity & building strong people focused teams.

Most people think confidence comes first.

That once you feel confident, you’ll speak up. Lead. Take the shot.

That’s not how it works.

I learned that lesson long before my career ever started…in a dirt driveway with a basketball hoop and a lot of missed shots.

Confidence didn’t come from believing harder.
It came from practice.
From proof.

I see the same pattern with many leaders. They wait to feel ready. They wait for certainty. Meanwhile, the WAR Room in their head gets louder, and clarity fades.

I wrote about this shift and what intentional practice actually builds in this article.

👉 Who helped you practice before you felt confident?

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Certified Partner

ICAgile Certified Professional - Agile Coaching

Talent Optimization Partner 

Speaker | Facilitator

Challenger Sales Training

Certified BASHO Sales Training

Value Selling

Consulting Theory & Practice

Cross Cultural Management

Performance Coaching

Welcome to The WIN Room™ where we train leaders, sellers & teams to perform like elite athletes.

Most leaders don’t fail because they lack skill. They fail because they lose impact in their interactions. In fact, 86 percent of workplace failures are caused by poor communication.

Inside The WIN Room™, we focus on mastering the New ROI: Return on Interactions™. Because every conversation with yourself, your team, or your clients is either making money or losing it

We teach you to move from the WAR Room to the WIN Room™:
- WAR Room: Doubt, disconnection, transactional conversations, missed targets
- WIN Room: Confidence, clarity, trust, consultative conversations, aligned performance

We offer corporate programs, executive coaching, and high-impact keynotes to help you shift how you lead, sell, and communicate under pressure.

This is the training ground for performance that sticks.
The New ROI starts here. Step into The WIN Room™.

Contact us at jaime@thewinroom.com

In The WIN Room™ we deliver personalized performance coaching programs for leaders, sellers and teams so they can perform their best, when it matters most.

Performance isn’t luck, it’s practiced. We give people a competitive edge with practical, unconventional skills rooted in sports psychology, behavioral science, and social intelligence.

Our clients lead to master the new ROI in the age of AI.

Return on Interactions™

How to go from losing money to making money in every conversation.

What We Deliver:

▪️Sales and influence coaching 
▪️Executive presence training
▪️Modern Leadership skills 
▪️Team dynamics 
▪️Communication effectiveness
▪️Mindset & resilience training
▪️Next-in-line leader development

Our workshops, keynotes & coaching programs are designed as immersive experiences where you put what you learn into practice immediately because information without action is just noise.

Founder | Performance Coach

Coaching MBA students at Harvard Business School on entrepreneurial sales.

Sales Coach

I deliver keynote presentations & immersive workshops focused on change, resilience, mindset, leadership and next level communication what I call The New ROI: Return on Interactions.

Check out my TEDx here…

TEDx | Keynote Speaker | Author

Delivered WIN Room sales, leadership & employee engagement programs to 600+ employees. 
▪️+16% in employee engagement 
▪️+22% in pipeline over 12 weeks
▪️- 12% in attrition numbers

Future of Work Lab | Sales Director

National Sales Leader: Banking, Capital Markets, FinTech & Insurance

▪️Eagle Award top 1%
▪️10X Winner’s Circle 2006 - 2016
▪️Top 1% Sales Team in North America consistently getting 90% of my team to Winners Circle. Sales Leader | Financial Services, Capital Markets & Insurance

Sales Leader | Financial Services, Capital Markets & Insurance

Event Marketing Manager

Masters in Industrial Organizational Psychology

Marketing Communication Coordinator

On Air Promotions

Women’s World Cup

Marketing/Sales

I get teams in The WIN Room by mastering the New ROI: Return on Interactions™ | Author, Moneyball Leadership | TEDx + Keynote Speaker | Harvard Sales Coach | Former Gartner, Microsoft

The New ROI™ | Training Leaders in Transition to WIN | Author, Moneyball Leadership | TEDx & Keynote Speaker | Harvard Sales Coach

My son broke his wrist blocking a shot last week.

He’s the big man in the middle. The anchor.  This was supposed to be their final season together before high school splits them up.

Now he’s in a cast. Watching from the sideline. Convinced he’s letting his team down when they need him most.

⸻

That same week, I was facilitating workshops with leaders stepping into new roles. New expectations. New pressures. That “now what?” moment when everything shifts.

Different circumstances.
Same struggle.

How do you lead yourself through transitions when nothing feels the way you expected?

Driving my son to his game to cheer on his teammates, I told him what I’d been telling those leaders all week.

Your worth didn’t break with your wrist. 

You’re still the anchor. The team still needs you. Just not the way you planned.

Being a leader isn’t about executing the perfect play.  It’s about remembering what you’re building, even when you can’t do it the way you expected.

⸻

Whether you’re a kid in a cast or a leader navigating a restructured team, the challenge is the same.

When the script changes, can you remember your value?

Your role might shift. The path might look different. But what you’re working toward - building something bigger than yourself, doesn’t change.

The setback is real. The disappointment is valid. But your value? That doesn’t change. 

👉 What keeps you anchored when everything changes?

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