Master the New ROI: Make Money in Every Conversation
- Jaime Diglio
- Oct 13
- 3 min read
People often ask me what a day in the life of an entrepreneur looks like.
The truth? No two days are the same. But the one constant?
Interactions.
Take a morning I had last week. By 11 a.m., I had:
Prepped a keynote
Advised a CRO on a leadership challenge
Coached a client through a high-stakes presentation
Spoken to a class of students about self-leadership
On paper, it was a packed schedule. In practice, it was something deeper: a real-time reminder that every single interaction was either making money or losing it.
Welcome to the New ROI: Return on Interactions™.
Why the New ROI Matters More Than Ever
For decades, leaders measured ROI in spreadsheets and performance dashboards. But in today’s landscape, performance is driven by communication.
In today’s world, every conversation is a rep and every rep counts.
Here’s What Adds ROI:
A client call that builds trust
A team meeting that brings clarity
A check-in that boosts confidence
And What Drains It:
An unclear email
A confusing meeting
A tone that triggers doubt
The New ROI isn’t just a mindset, it’s a metric that every leader should be measuring.
Why Most Leaders Are Losing Money Without Realizing It
Let’s go back to my busy morning last week. At face value, I was doing all the things: client work, strategy, thought leadership, mentoring. But what really mattered wasn’t the quantity of meetings.
It was the quality of those interactions.
Here’s what I see all the time: leaders who are sharp, ambitious, and busy but they’re unintentionally losing money in the way they communicate.
They're stuck in reactive mode of responding, updating, and rushing but not connecting.
They’ve defaulted to communication that’s fast instead of focused.
That’s where performance starts slipping through the cracks because money is lost in the nuance of tone, timing, and trust.
Self-Leadership Is the First ROI Decision You Make
In one of those morning calls, I was coaching a client through a high-stakes board presentation. She had all the right data but none of the presence. Why? Because she hadn’t connected to what she needed before walking into the room.
That’s where ROI is born: in your ability to lead yourself first.
Every interaction begins with you.
When you step into a conversation unclear, distracted, or out of alignment you’ll show up in a way that loses impact, influence, and income
Ask This After Every Conversation
If your days feel packed, pressured, and pulled in every direction, try this:
Pause and ask: “What return do I want to create in this conversation?”
That single question reveals more about your performance than any spreadsheet ever could.
Final Takeaway: Your Day Isn’t Measured in Time It’s Measured in Impact
So, back to that day in my life as an entrepreneur.
What looked like a jam-packed schedule was actually a string of ROI decisions. Each interaction either created value or lost it.
This is the game-changer: success today isn’t about cramming more into your calendar. It’s about how intentionally you show up in the moments that fill it.
In leadership, your conversations are the currency and the return you get will always match the intention you bring.
Ready to master the New ROI that actually moves you forward?