Member since September 2026
Teresa L. Gregory is an Executive Leadership Strategist, keynote speaker, and bestselling author who helps leaders see what they may be missing: the hidden patterns, assumptions, and habits influencing how they make decisions, communicate, and lead.
With more than 20 years of experience in leadership development, organizational learning, and business strategy, Teresa brings real-world experience, practical insight, and engaging storytelling to the stage. Her work has included organizations such as Microsoft, Boeing, Kaiser Permanente, and Cisco, helping leaders and teams navigate change, strengthen accountability, communicate more effectively, and turn complex workplace challenges into clear action.
Teresa spent more than eight years at Microsoft, where she designed and delivered leadership and professional development programs for global audiences and helped create the company's award-winning Standards of Business Conduct training. Her speaking and facilitation experience has taken her from executive meeting rooms to international conferences and programs across the United States, Europe, Asia, and Australia.
At the heart of Teresa's work is a simple belief: many leadership challenges aren't caused by a lack of talent, motivation, or another leadership tool. Sometimes the real obstacle is something we don't see.
That's where Teresa starts.
Through relatable stories, candid conversations, and practical frameworks, she challenges audiences to slow down, question their assumptions, and recognize the patterns that may be shaping their choices. She then helps them turn that awareness into intentional action.
Her signature topics include intentional leadership, hidden mindsets and bias, decision-making, active listening and communication, accountability, navigating change, and women in leadership.
Teresa is the founder of Squared Success and co-author of the Amazon #1 bestselling book *Wired to Win*. Whether she's delivering a keynote, facilitating an executive session, or leading an interactive workshop, Teresa wants audiences to leave with more than inspiration. She wants them to see something differently and know what they're going to do differently because of it.
I light up when I see that “aha” moment happen, when someone suddenly recognizes something that has been hiding in plain sight.
I love talking about leadership, hidden mindsets, decision-making, communication, confidence, and the assumptions we make without even realizing we're making them. I'm fascinated by how those small, often invisible patterns can influence the way we lead, the opportunities we pursue, and even how we see ourselves.
I don't believe growth always means reinventing who we are. Sometimes it's about getting quiet enough to recognize what's getting in our way, questioning what we've always believed, and giving ourselves permission to make a different choice.
That's also why I love conversations about career pivots, women in leadership, navigating change, building stronger teams, and leading with intention. I've experienced my own pivots and changes, and I've learned that having the courage to question the plan can sometimes open doors you never knew were there.
I'm especially passionate about helping leaders recognize the assumptions and biases that can quietly affect their decisions and relationships. I want people to leave my sessions thinking differently, but I also want them asking themselves, “What am I going to do differently now that I see it?”
Give me a room full of curious people who are willing to challenge “the way we've always done it,” have a few laughs, get a little uncomfortable, and walk away seeing something differently, and I'm in my happy place.
One of my favorite stories to tell starts in a coffee shop.
Within seconds of seeing someone, I had already created an entire story about who they were. I hadn't spoken to them or heard their story, but my brain had already filled in the blanks.
Seven seconds. That's how quickly we can form an impression without even realizing it.
I use that moment to open a bigger conversation about the assumptions and hidden patterns influencing how we lead, communicate, hire, promote, and make decisions.
At first, people smile because they recognize themselves in the story. Then the room gets quiet when I ask, “What story are you creating before you have all the information?”
That's the moment I love. We're no longer talking about someone else's bias or leadership problem. We're looking at ourselves.
For me, that's what a great story should do: make you laugh, make you think, and help you see something you can't unsee.
For years, I had a five-year plan.
I knew where I was going, what the next step should be, and what success was supposed to look like.
My career didn't start in an executive meeting room or on a global stage. It started at Target, pushing carts. I worked my way into leadership and learning roles, and eventually landed at Microsoft, where I spent more than eight years developing programs, facilitating global events, and working with leaders across the organization.
On paper, the plan was working.
And I got really good at planning what came next. The next role. The next milestone. The next accomplishment.
But somewhere along the way, I realized the very plan that gave me direction could also keep me from seeing opportunities I never thought to put on it.
So I threw out the five-year plan.
I didn't throw out goals. I stopped believing I needed to know every step before taking the next one.
I started asking different questions:
What am I curious about? Where can I make the greatest impact? What feeds my soul? And what would I try if I wasn't worried about whether it fit the plan?
Those questions changed everything.
They also made me pay closer attention to the invisible things that shape our choices: the assumptions we make, the stories we tell ourselves, the biases we don't recognize, and the expectations we've inherited about what success is supposed to look like.
That's ultimately what led me to create Squared Success.
Today, I've gone from pushing carts to Microsoft, from corporate leadership development to entrepreneurship, and from facilitating meetings to speaking on international stages. None of that would have appeared on my original five-year plan.
And that's the lesson I carry into my work with leaders today.
Clarity doesn't mean knowing exactly where you'll be five years from now. It means knowing who you are, what matters to you, and what you're willing to do next.
Sometimes the biggest breakthrough isn't creating a better five-year plan.
It's having the courage to throw out the old one and make room for what's possible.
What if some of your most important decisions are being influenced by assumptions you don't even realize you're making?
In this thought-provoking and practical keynote, Teresa L. Gregory introduces her PAUSE Framework to help leaders slow down the split-second judgments, assumptions, and hidden mindsets that influence how they communicate, make decisions, and lead others.
Through relatable stories, reflection, and actionable strategies, Teresa helps audiences recognize where their thinking comes from, examine the gap between intention and impact, and make more deliberate choices.
Audiences leave with a practical framework they can use immediately to interrupt autopilot thinking, challenge assumptions, and lead with greater clarity, intention, and impact.
High performers are great at taking action, but more action isn't always the answer.
In this engaging talk, Teresa L. Gregory challenges audiences to look beneath the surface and uncover the hidden mindsets, assumptions, and patterns influencing their decisions, relationships, and careers. Through personal stories, reflection, and practical strategies, she shows how greater awareness creates the clarity needed to make more intentional choices.
Audiences leave prepared to question old assumptions, recognize what may be keeping them stuck, and take their next step with greater clarity and confidence.
Most people think they're listening. Teresa says they're reloading — nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right.
Most people think they're listening. Teresa says they're reloading, nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right.
One of my favorite stories to tell starts in a coffee shop.
Within seconds of seeing someone, I had already created an entire story about who they were. I hadn't spoken to them or heard their story, but my brain had already filled in the blanks.
Seven seconds. That's how quickly we can form an impression without even realizing it.
I use that moment to open a bigger conversation about the assumptions and hidden patterns influencing how we lead, communicate, hire, promote, and make decisions.
At first, people smile because they recognize themselves in the story. Then the room gets quiet when I ask, “What story are you creating before you have all the information?”
That's the moment I love. We're no longer talking about someone else's bias or leadership problem. We're looking at ourselves.
For me, that's what a great story should do: make you laugh, make you think, and help you see something you can't unsee.
For years, I had a five-year plan.
I knew where I was going, what the next step should be, and what success was supposed to look like.
My career didn't start in an executive meeting room or on a global stage. It started at Target, pushing carts. I worked my way into leadership and learning roles, and eventually landed at Microsoft, where I spent more than eight years developing programs, facilitating global events, and working with leaders across the organization.
On paper, the plan was working.
And I got really good at planning what came next. The next role. The next milestone. The next accomplishment.
But somewhere along the way, I realized the very plan that gave me direction could also keep me from seeing opportunities I never thought to put on it.
So I threw out the five-year plan.
I didn't throw out goals. I stopped believing I needed to know every step before taking the next one.
I started asking different questions:
What am I curious about? Where can I make the greatest impact? What feeds my soul? And what would I try if I wasn't worried about whether it fit the plan?
Those questions changed everything.
They also made me pay closer attention to the invisible things that shape our choices: the assumptions we make, the stories we tell ourselves, the biases we don't recognize, and the expectations we've inherited about what success is supposed to look like.
That's ultimately what led me to create Squared Success.
Today, I've gone from pushing carts to Microsoft, from corporate leadership development to entrepreneurship, and from facilitating meetings to speaking on international stages. None of that would have appeared on my original five-year plan.
And that's the lesson I carry into my work with leaders today.
Clarity doesn't mean knowing exactly where you'll be five years from now. It means knowing who you are, what matters to you, and what you're willing to do next.
Sometimes the biggest breakthrough isn't creating a better five-year plan.
It's having the courage to throw out the old one and make room for what's possible.
What if some of your most important decisions are being influenced by assumptions you don't even realize you're making?
In this thought-provoking and practical keynote, Teresa L. Gregory introduces her PAUSE Framework to help leaders slow down the split-second judgments, assumptions, and hidden mindsets that influence how they communicate, make decisions, and lead others.
Through relatable stories, reflection, and actionable strategies, Teresa helps audiences recognize where their thinking comes from, examine the gap between intention and impact, and make more deliberate choices.
Audiences leave with a practical framework they can use immediately to interrupt autopilot thinking, challenge assumptions, and lead with greater clarity, intention, and impact.
High performers are great at taking action, but more action isn't always the answer.
In this engaging talk, Teresa L. Gregory challenges audiences to look beneath the surface and uncover the hidden mindsets, assumptions, and patterns influencing their decisions, relationships, and careers. Through personal stories, reflection, and practical strategies, she shows how greater awareness creates the clarity needed to make more intentional choices.
Audiences leave prepared to question old assumptions, recognize what may be keeping them stuck, and take their next step with greater clarity and confidence.
Most people think they're listening. Teresa says they're reloading — nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right.
Most people think they're listening. Teresa says they're reloading, nodding, making eye contact, and waiting for their turn to talk. Active listening looks different: you take in what the client actually said, reframe it back in your own words, and confirm you got it right.
