What happens when you’re standing at a pivot point — the kind where your next move could shift everything for your business, your team, or your career? In those high-stakes moments, success doesn’t come from spreadsheets alone. It requires empathy, emotional intelligence, and even self-compassion.
Kasey D’Amato knows this firsthand. A keynote speaker, executive coach, and strategic advisor, Kasey has guided founders and corporate leaders through major transitions with clarity and resilience. In our conversation, we dug into her four pillars of holistic leadership and how self-regulation shapes better decisions. We explored the “decision threshold,” why every choice has three outcomes, and how to balance head, heart, and gut when the numbers don’t tell the full story. Kasey also shared why grounding yourself is key to hearing other perspectives without defensiveness — and how empathy and self-compassion aren’t soft skills, but strategic advantages when the stakes are high.
To access the episode transcript, please scroll down below.
Listen in for…
- Finding the balance of the decision threshold – that point between gathering information and making the decision.
- Why does every choice have three outcomes?
- The Four Pillars of holistic leadership and how self-regulation shapes better decisions.
- How to balance head, heart, and gut when the numbers don’t tell the full story.
- Utilizing the Two-Minute rule to move out of indecision.
“I believe it is the critical moments of decision and how you handle your emotional intelligence in those critical moments and pivots that set you up for success, no matter how big your failures are along the way.” — Kasey D’Amato
Episode References:
- The Empathy Edge Podcast Episode: Ilana Ben-Ari: How the Empathy Toy is Changing the World
About Kasey D’Amato, Business Leader and Holistic Coach:
Kasey D’Amato is a keynote speaker, executive coach, and strategic business advisor who helps business founders and corporate leaders navigate high-stakes decisions and transitions with clarity, confidence, and resilience — without burning out in the process.
With over 20 years of experience across healthcare, entrepreneurship, and business consulting, Kasey brings a unique blend of business acumen, human behavior expertise, and emotional intelligence to her work. She is a former Dermatology PA who went on to launch multiple ventures — including a global skincare brand, a healthcare consulting agency, and an executive leadership advisory.
She’s consulted with Fortune-level companies, led workshops across the healthcare and financial industries, and spoken at major institutions like UCLA, USC, and the University of Miami.
Kasey is known for her dynamic, actionable, and emotionally intelligent approach to leadership — guiding ambitious entrepreneurs and executives to think bigger, lead better, and align their next move with both performance and personal fulfillment.
Connect with Kasey:
Website: https://www.kaseydamato.com/
LinkedIn: https://www.linkedin.com/in/kaseydamato/
Facebook: https://www.facebook.com/kasey.damato/
Instagram: https://www.instagram.com/kaseydamato/?hl=en
Connect with Maria:
Get Maria’s books: Red-Slice.com/books
Hire Maria to speak: Red-Slice.com/Speaker-Maria-Ross
Take the LinkedIn Learning Courses! Leading with Empathy and Balancing Empathy, Accountability, and Results as a Leader
LinkedIn: Maria Ross
Instagram: @redslicemaria
Facebook: Red Slice
FULL TRANSCRIPT:
Maria Ross 00:04
Welcome to the empathy edge podcast, the show that proves why cash flow, creativity and compassion are not mutually exclusive. I’m your host, Maria Ross, I’m a speaker, author, mom, facilitator and empathy advocate. And here you’ll meet trailblazing leaders and executives, authors and experts who embrace empathy to achieve radical success. We discuss all facets of empathy, from trends and research to the future of work to how to heal societal divisions and collaborate more effectively. Our goal is to redefine success and prove that empathy isn’t just good for society. It’s great for business. What happens when you’re standing at a pivot point, the kind where your next move could shift everything for your business, your team or your career in those high stakes moments? Success doesn’t come from spreadsheets alone. It requires empathy, emotional intelligence and even self compassion. Kasey D’Amato knows this firsthand, a keynote speaker, executive coach and strategic advisor. Kasey has guided founders and corporate leaders through major transitions with clarity and resilience. With 20 years of experience spanning healthcare, entrepreneurship and business consulting, she’s launched ventures from a global skincare brand to an executive leadership advisory and she’s brought her expertise to Fortune level companies and institutions like UCLA and USC. In our conversation, we dug into her four pillars of holistic leadership and how self regulation shapes better decisions. We explored the decision threshold, why every choice has three outcomes, and how to balance head, heart and gut when the numbers don’t tell the full story. Kasey also shared why grounding yourself is key to hearing other perspectives without defensiveness, and how empathy and self compassion aren’t soft skills, but strategic advantages. When the stakes are high, you’re going to love this one. Take a listen. Hello Kasey, and welcome to the empathy edge Podcast. I’m so excited to have you here to talk about making decisions in high stakes moments. That is going to be an excellent deep dive into pillar four of the five pillars of effective and empathetic leadership. So welcome to the show.
Kasey D’Amato 02:26
Thanks. Thanks for having me, Maria. I’m excited to chat with you, and as
Maria Ross 02:30
I do with all my guests, we want to know a little bit about your story. So tell us what your story is and how you came to this work. What’s the passion in this for you?
Kasey D’Amato 02:39
Yes, you know, that’s a great question. I love sharing my story, and I’ll keep it brief. I think, like so many leaders, we go through different iterations of our professional journey, and then we reflect and we feel compelled to pay it forward. So you know, my journey started in pharmaceutical sales right out of college wholesale startup company. That’s where I learned a lot of people skills and negotiation skills. From there, I actually went on to medical school pa training at USC, and became a dermatology PA. I practiced dermatology for 20 years in Santa, Monica, California, and in doing that, I started to get interested in the business side and leadership side of medicine. And so I started managing the practice, learning how to manage people, how to communicate better, how to improve systems and operations, how to understand cash flow, right? So I started my first consulting business for medical professionals. I still own that business today, and it’s still very much passion of mine. And then fast forward to I started a skincare company, and I raised capital, and over a 10 year period, went through different distribution channels eventually found a global distribution partner and made an exit in that process. Now, those of us that have gone through different pivots and iterations in our journey understand that each phase of our journey, we learn new skills about ourselves, new skills about how we operate. And in 2020, after I sold the company, and I essentially retired from clinical care at that time. I took a sabbatical. I took a step back, and I thought there were some very, very hard moments in the journey, in the pivots, in the shifts from, you know, I swung from big professions, right, from practicing clinical medicine to entrepreneurship, leadership, management and everything in between. When I reflected back about some of the dark times, the hard times, the significant burnout, the significant physical and mental challenges that were almost debilitating, those very dark times that people don’t talk about, where your mental health is suffering, finances might be suffering. The business might not be going as expected. Whether you’re the owner or a leader, your department might be underperforming or what have you and, you know, I really reflected on those times about, you know, how did I navigate that and how could I help other people? Because there are things the mistakes I made, certainly, and things that I did, that I navigated well to then come out now this point in life, you know, a certain stage of life where I have two homes. I have, you know, financial freedom and. Have built a life of what I consider fulfillment with a lot of contribution, and it’s really my mission to pay it forward. So I believe that it’s in the decisions that you make when you pivot, whether you’re a corporate leader, whether you are a business owner, whether you are leading a team, leading yourself. I believe it is the critical moments of decision and how you handle your emotional intelligence in those critical moments and pivots that set you up for success, no matter how big your failures are along the way. So that’s what I do now. I help people, both one on one, in group environments and teams, navigate these big pivots and understand your emotional intelligence around making big changes in your business, in your life that are impacted by extrinsic forces and intrinsic forces
Maria Ross 05:42
so good. I mean, there’s so many things in there, right, that we could talk about, but just this idea, you know, obviously, since 2020, and some of the seismic shifts, like people have been talking about pivot and pivoting so much, and then we’re also just living through cataclysmic transformation, whether it’s AI, whether it’s workforce and workplace culture, whether it’s the changing leadership paradigm, we are in this moment of change, and not that we never are, are not in those moments of change. But to your point, this is something actually I’m talking a lot about, in terms of empathy as a catalyst for thriving through change, yes, and understanding that it’s the people component, it’s the change management component, that actually gets us through those moments. It’s not, for example, AI is not just a technology issue or challenge. It’s a people challenge, right? And there’s so much there’s so much emotion, there’s so much fear, there’s so much excitement that is wrapped up in that that we can’t compartmentalize these changes. The commonality is that they all impact us as human beings. Number one, our capacity to absorb the change. Number two, our reactions to the change, our psychological and our emotional reactions to the change. So this is going to be such a rich conversation. I love it. So before we kind of go into the like, really drilling down into this decisiveness aspect and making those how and what we can think about in those moments where we have to make tough decisions, you have this model of the four pillars of holistic leadership that I think is relevant to kind of setting the table for that conversation. So talk to us a little bit about that.
Kasey D’Amato 07:22
Yes. So I’m to me, the four pillars of becoming a holistic leader is looking at yourself and then understanding your industry, your team. So basically, the four pillars are understanding business as a whole. You’re the industry that you’re in. How does it work? It’s a living, breathing thing, right? There is something going on with your industry. There is changes with the industry. What’s happening in the marketplace? Are you paying attention to everything from the financial side of things, if you’re in a public company or whatnot, or just industry changes? Do you understand the business acumen of what you’re doing? That is pillar number one. Pillar number two is your self leadership. Are you developing that mindset, muscle, that resiliency, that you can overcome the challenges, whether they are extrinsic coming from outside forces, which is regulatory, economy and industry. Those three things are your external in a professional setting. How are you navigating those from a self leadership standpoint? So that’s pillar number two. Pillar number three is your team leadership. How is your communication developing? How is your systems and processes? How are you elevating others around you, whether it is in the workplace or at home? How are you leading the people that are in your ecosystem, in your stratosphere, day to day? How are you leading them in a way that is impactful and is empowering for them. And the fourth one is industry leadership. How are you establishing yourself as a thought leader? How are you making yourself irreplaceable? How are you finding your place in your professional journey, in your industry and becoming known? And so you don’t need to become famous by any means, and this could be something very much internal. But how are you finding your place in your industry, that you are uniquely different, special, and you have this unique skill set of being you as part of your leadership, your core leadership, and understanding your true identity as it relates to your industry well?
Maria Ross 09:16
And this is so important, right? It’s really, it always seems to come back to this idea that I talk about, which is getting your own house in order before you can effectively lead and impact change. Yes, in other people, in your organization, in the world, in your community, right? It’s making sure that we have this awareness and that we’re taking stock of what we bring to the table, what our strengths are, where we might need some upskilling, all of those areas. And I imagine the reason I wanted you to talk about that first was because I imagine that that’s creating the foundation as well for decisions. Don’t live in a vacuum. That’s it so. And if you’re making decisions and you are scattered, you are on. Moored. I guess you could say yes, you’re not going to make the most effective decisions. So talk to us about your approach to making those pivots. Do you classify pivots in different ways? Do you classify decisions in different ways?
Kasey D’Amato 10:15
Yes, definitely. So the first thing when it comes to assessing Is it time for a change. Right Decisions come because we all have to change and adapt. Whether it’s a season of life for ourselves, whether it’s a season in our industry, change is happening around us. We can’t stop it. And so we navigate the change exactly we navigate the change. And to your point, how do we be empathetic and understand human emotions related to change? And so the first step I look at is an assessment between the extrinsic change and the intrinsic change. So extra meaning those big three, industry economy and like regulatory things like that. If we’re thinking about professional what’s happening outside of our control that we don’t have a whole lot of control over, then intrinsic what’s happening within us or in our very nuclear, small setting. So what about us as a person, or maybe our intimate relationships in the home, you know, environment, things like that. Because if we are disrupted, or we’re disrupted with our life partner, or something like that, that’s going to carry over into what we’re doing. So the first thing I look at is what’s changing, and I would create like a matrix in the external world, what’s happening that we don’t have too much control over, a little bit, but not a lot, in regulatory and economy and industry and then internally? What is changing about us? Are we going through a season of life? Are we becoming, you know, something new happening? Kids are going to college, or, you know, we have some impact on our finances? Is there something happening internally or within our personal, very intimate, personal relationships. Can then from
Maria Ross 11:44
can you look at internally, also from a team perspective? Yes, not just yourself, but yeah, what’s going on within your company, within the with correct? What’s going on for each of your team members?
Kasey D’Amato 11:57
Right? Correct. So usually when I’m doing a workshop, I draw like a bull’s eye, so it’s the self in the middle, and then it goes out right from each layer of people that we’re in contact with. So definitely, team in the environment, 100% can be sort of that, like intrinsic. That’s the people that we’re around all the time, because we have a lot more control over our intrinsic, our self, our team, our relationships at home, right? The people that we’re contact, in contact with all the time, we have control over how we want to show up, which then will influence how others perform in that space. And so the extrinsic world is out here, and it’s changing, and it’s doing all the things that it’s that’s going to do. And then we have to take control over adapting, and we have more control than we realize. And so when we’re facing these, you know, the way I look at it is there’s three outcomes to every decision. You are either feeling torn or you’re feeling stressed, or there’s some emotion, there’s some negative emotion that you’re feeling, and if that is happening, that means that it’s time to face a decision. And there’s only three outcomes of every decision. One is you choose. You intentionally choose to accept status quo, and you choose. I’m going to accept it. I’m going to stop allowing myself to feel negatively about this, because I chose this, this path, and I prefer it over any other path, and so I’m not going to be annoyed, frustrated, stressed, whatever. I’m going to choose to reframe the narrative and look at this in a different way, and accept status quo by changing my mindset and things like that. Then there’s all sorts of tools, I’m sure you have as well to do those sort of things. The step two is I’m going to find a solution that’s a win win for the other people that are in my intrinsic world. So there is a solution to this current situation, this current challenge, that is a that will have a positive outcome on my team, on the business, and on myself simultaneously. The challenge is to find that solution, to not be stuck in the problem and the negative emotion, to switch that to being solution focused in a way that is going to benefit everybody. And when you can solve that, that’s when businesses take off, and that’s when you know fulfillment. That’s when you get ready to top places to work, like all those things. And then the third door is You’re done. You’re burning it down, like Game Over. Peace out. I’m shutting this thing down. I’m exiting this I’m quitting, I’m out. That’s it. There’s the door and, you know, there’s dust on my heels, and I’m running for it, and I’m not looking back. And so when people are feeling the negative emotional state, whether it is, you know, stress, burnout, frustration, you fill in the blank, right? You know, I would say there’s three options here. We’re either going to use the tools to accept it. We’re going to use tools to find the Win, win outcome, or we’re going to choose, like I am emotionally done. There is no tool in the world. I’m out and that’s it. There’s three outcomes, right?
Maria Ross 14:53
So on those first two, when you say you accept it, but then you’re parsing out the second one is actually to. Adapt to it.
Kasey D’Amato 15:01
Yeah. The second one is different, yeah. The second nothing changes except your mindset around it, status quo. The second one is, there’s actual real changes, the whether it’s your operations, whether it’s your communication, whether it is, you know, other elements of the team, whether it’s products or services you’re offering. Like, there’s actually tangible change like the we’re going to sit down, we’re going to restrategize this, we’re going to shake up the snow globe, and things are going to look different.
Maria Ross 15:27
We’re going to embrace it better. We’re going to embrace it.
Kasey D’Amato 15:30
The first one is nothing changes except your mind.
Maria Ross 15:33
Can you give us an anecdote, even if it’s anonymous, with a client that you’ve worked with, and what their specific scenario was, and how kind of approaching it from this perspective, what that resulted in?
Kasey D’Amato 15:45
Yes, I’ll give a couple examples, one from sort of a employee leadership standpoint. And this comes up a lot with, like, compensation negotiations, things like that, people that feel like they’ve hit a glass ceiling. And so this is a very common tool. We use this in the medical consulting business quite often, and there’s a negotiation happening here, and this person is, you know, at the top, and they feel like there isn’t any more room for compensation. So they either a accept that, and they accept that they’re probably not going to grow that way. They’re going to have to think about investing in things outside of their current w2 role, right? And do some other things outside, because it’s not going to be here. Or they get innovative with the facility they’re working at. And they think about, Okay, what if we launched a new division? What if we started doing research studies? What if we expanded in this certain way, or did a satellite location, or something like that? And the third option, when it’s the exit, would be, you know, what the personalities here? Maybe it’s the owner or what have you like that the environment is a bit toxic that I’m not sure it is worth the conversation on the expansion, even though there could be a lucrative outcome here. There’s other elements where, you know what I’m done with this situation, yeah, and so that’s a common one that could come up with, with someone who’s negotiating on more like leadership and growth side. A lot of times, I work with people who are serial entrepreneurs. They have multiple businesses, or they may be working in a very high powered w2 and they have a business they’re growing on the side. This is another common one. And so we have this decision about, okay, what are we going to do here? Because at some point we’re going to have to make a hard decision on, you know, are we going to keep growing this business on the side, and you’re going to hire a CEO, and you’re going to hire a leadership team, and you’re going to keep working as a w2 or you’re going to make a change and shift what you’re doing and take that risk. And so again, we’re looking at the doors we’re looking at, are we going to accept status quo? If there’s too much pressure on your time, you’re going to have to, you know, hire some people, right? That would be door two, find a solution. That’s a win, win. And door three would be like, I’m going to exit one of them. One of them
Maria Ross 17:53
is done. Yeah, well, and we talk a lot on the show and in my work around the fact that we’re looking at decision making and a little bit of a different lens in terms of making decisions as a company or as a leader for your that impact your team, right? It could be, it could be a positive decision, like we’re rolling out this new strategy, it’s great. It could be layoffs, right? It could be lots of different decisions, and we talk a lot about the role of empathy in synthesizing multiple points of view, yes, and being able to do that swiftly, yes, so that you can actually make the decision and not kick the can down the road. Yes. So for you, what’s your approach to helping leaders who might struggle with that? Right? It’s because sometimes it’s easy, quote, unquote, easier. Yeah, if I am decisive, I just want to make the decision myself, and I want to be able to communicate that to other people and have them accept it, right? But that’s not always reality, like we talked about. There’s there’s emotions that happen. So how do you help leaders understand that other points of view can be additive to the decision making process, and also how to balance it without like there’s so many, so much input coming at me now, I’m paralyzed to make a decision because I’m trying to chase an elusive decision that makes everybody happy. Yeah, no such decision exists, right? So what are some of the tools or strategies you use to help leaders do that dance between synthesizing and being open to other ideas, but then knowing when they’ve collected enough to
Kasey D’Amato 19:28
make a call. Yep, I call that the decision threshold. And so the decision threshold, in my perspective, is the balance of your head, your heart and your gut. So you’re collecting information that’s your head. You’re collecting the data around this decision this decision, getting ready to launch something, or you’re getting ready for layoffs, right? So you’re collecting the data. What do we know, from a numbers perspective, business, cash flow? What do we know? Like, let’s get all the objects, just the facts from everybody, just the facts. Let’s get it all on a whiteboard, on a spreadsheet. Let’s get all the objectives. Of facts. Okay, so that’s process number one. Process number two is the heart is the emotional piece of this, which is, what are we holding on to that might not be serving us anymore in this decision? So what are we holding on to? Because there’s an emotional connection, whether it’s loyalty to the team, if you’re thinking about layoffs, things like that, there’s human emotions there, or is there something else about a product or service that we’re particularly emotionally connected to, because a lot of work went in to build it, but it’s maybe not the right piece we, you know, so that the heart part of it is, what are we holding on to that may not be serving us when we’re looking at the head part, right? And so. And then, you know, it’s not always the answer is not always in the numbers. So that’s the tricky part, because the human emotion, the emotion does have some influence over the numbers as well. So these are sort of independent quadrants. And then that gut reaction is, you know, the numbers say this, the emotions say this. But my gut reaction is the opposite, and I can’t explain why, right? And so then we, you know, kind of put all these things together, and we’re looking at the numbers, the heart, the emotions, what are we holding on to that it’s time to let go of and that gut feeling. And then really do some process where you sit down and you really think, okay, if I’m making decision based on one of these things, that’s not good. We need to be making a decision based on at least two out of the three. Need to be in an alignment if we’re leaning on only numbers, but the emotions and the gut check are saying something else. We might have some regret. We might have some recourse at the end of this, some damage control on the other side of this, right? So two of those three must be in alignment, and the third one has to be, you know, able to adapt and see the other way. So you know, to your point where you have to get the information somehow, some way at the beginning, but then at some point, you have to make that final call, and you have to be able to balance the head, the heart and the gut, and be able to understand, okay, how do we align these in a way that’s going to allow us to feel ready and confident in this final decision?
Maria Ross 22:09
Oh, I love this well, and it’s also the way you’ve laid this out, makes it very apparent why you need to have multiple voices at the table. Yes, because you might not see everything correct. You might not. There might be things you don’t know, because maybe you’re the Senior VP, but you don’t know what’s actually going on on the ground or with customers. So you have to be open to getting from your people. Like, look, I know I don’t have, I only have one angle on all of this. It might be the highest angle, yes, but I don’t see the details. So I need to be open, and I need to create an environment where my team can come to me and say, I don’t think you’ve thought about this. Yeah, I don’t think you know about that, and that helps them not only avoid risks, but uncover opportunities, right? Definitely. So if you’re going at it thinking that the decision is x, but you actually get input from people, and you realize, no, the decision is not that. It’s actually why that’s right, that’s right, right? So how do you help leaders make that leap of feeling like they’re the ones that have to have all the answers to being open to saying, of course, there’s things I don’t know, because I only have one vantage point,
Kasey D’Amato 23:18
1,000% and I think that’s why I mean, I love the fact that more and more people are doing workshops, the ones that you host, the ones that I host, right? And they’re being more open minded to seeing this. Because you need the collective leadership team to come together to workshop this out. Essentially, you have to have multiple voices looking at the data. You have to have multiple voices talking about, what’s the emotional Why do we feel so connected to the thing? Yeah, what is the emotion around it? You have to have multiple it cannot be you in a vacuum making this decision. You know, I suppose in a perfect world are not a perfect world. In the alternate world, it could be only you making that decision, but there will be negative outcomes to that, right, right?
Maria Ross 24:00
Yeah, right. Well, research shows us that diversity of thought makes for better business decisions, right? And it’s, it’s reminding me, and I’m going to put a link for my listeners to a past episode I did a few years ago with a entrepreneur named Alana Ben Ari, and she has a product called the empathy toy. I think I can’t remember what the name of her company is, but it’ll be in the link to the episode, and it’s this toy that they use in workshops where one everyone in the group knows they see a picture of what this is supposed to look like when it’s constructed, and then one person or group is given the pieces, okay, and they have to rely on the other people to figure out we did this virtually, because it was during the pandemic, but she also does them live. And we had to someone, had to get instructions from everybody else on what, how to put it together. Okay, what we didn’t know is that we were all looking at a different side of it. Okay, so you might see a purple square and a green. Triangle in your view. But the other person is, like, there’s no purple square, right? What? I don’t even that’s an extra piece. I don’t even know why you have that, right? Yeah. So it just brought the point home. And then we had to figure out how to communicate that, yeah. So where we landed was we basically, you know, after trying to say, Well, I see this. I see this. That was just confusing her more, right? So what we did was we said, Okay, pick a piece and tell us what it is. And she would pick up a piece, and someone would go, I see that piece in my picture. It is connected to this yellow thing. And someone would go, I have the yellow I can see the yellow thing, right? It’s now connected to this purple thing. It was just so fascinating and so simple. Yes, to understand the power of perspective of lived experience, in that it doesn’t matter what level you are in the organization, it doesn’t matter how much education you’ve had, it just depends on your unique vantage point. That’s it in making those decisions, and I think it probably still holds true, you know, I know you help individuals with pivot points and decisions, not just teams, you know, get that perspective from other people that might have a vantage point about that person. Yes, that’s maybe a perception gap for that person. So how do you encourage them to be okay with gathering feedback and be in a place, from an emotional intelligence standpoint, where they don’t take that feedback defensively
Kasey D’Amato 26:30
as as criticism? That takes a lot of work with leaders. So I work a lot with the core leader, either founder or CEO and their executive team, which is great because most of the people I work with, the founder or the CEO, is open to the feedback. Now, it’s not always easy, and a lot of times, you know, they’ll receive some feedback, and you know, it sits a little harder than is comfortable for them, but at the end of the day, you know, even if they resist, they hear it, and we’ll start to make changes. And so I think communication is probably the biggest roadblock, is that the feedback oftentimes from the team is that they won’t always feel like that founder or the CEO is hearing them, yes, hearing what the executive team or the leadership team is sharing and sharing with ideas, or sharing what’s going on, or sharing feedback, right, you know, from the numbers or from the emotions. And so I think it’s really the communication of that top leader, yeah, being open to receiving in not just criticism, just ideas in general, and being 100% with that. And I think as soon as they open up and they see, oh, wait a minute, if I open up to the brainstorm idea, I can also be open to the criticism on your suggestions. I should say, Yeah. On the way that they operate, yeah. And as soon as they see that, and they see the small shift and the pivot and the morale improve in their team, and now next thing you know, the bottom line improves, right? Well, now they’ve been positively rewarded. Now it’s Pavlov’s dog. We’ve given them the treat Exactly. Now they want more. And now they’re like, let’s do this again.
Maria Ross 28:05
Let’s so do you have any strategies that you’ve used with leaders to help them get over that hump?
Kasey D’Amato 28:10
You know, everybody’s different because everybody’s personality, style is different, and I think it’s very the situation is different from a founder and someone who started the business from the infancy to a corporate leader, right? Who’s hired into a role. So there’s different emotions around from the founder standpoint versus a CEO standpoint, or executive leader that comes in and it’s one of their jobs in their career, and they take it very serious, but it’s different than the founder. So I think it’s a person by person approach, and the first steps that I look at is I look at them as a human and I look at what are they doing with their personal relationships outside of work. I look at what they’re doing with their hobbies. The very first thing I ask my clients is how they’re feeling, not that they’re happy or sad, but from an energy state. I want to know if they’re energized today or if they’re feeling heavy. And then I you know, I wanted to see how well rounded their life is. The more well rounded they are outside of business, the more the faster they will be open minded to their team, the more the workaholic they are, the harder shell crack that they have to to crack.
Maria Ross 29:14
Well, they’re putting everything in that identity, in that situation, and that’s why, you know, pillar number two is self care, because you’ve got to build up that capacity. You’ve got to replenish that tank, yeah, so that it’s in a place where I can take this in, I can absorb it without defensiveness. I can I can understand that it’s just information. It doesn’t impact my identity, it doesn’t impact my self worth. It’s not a criticism. It’s just information.
Kasey D’Amato 29:41
That’s it. That’s it. There’s a question I ask. I call it the three who theory. So if you have three who’s surrounding you, I know that that person will move fast and will get significant. The change will happen quickly and relatively easily for the three who’s is, is this particular leader? Do they. Have a collection of mentors and advisors, people with different skill sets that they lean on for different things. Do they have a collection of kind of peers and colleagues that are different than advisors? Advisors are people that have significantly more experience in a certain area of business or life, and it could be anywhere from faith advisors to business to life coaches, do therapy, any of those things, right? And the the middle tier of who’s is really their peers and colleagues. Are they in networking groups? Are they surrounded? And so they’re hearing other ideas from colleagues. They’re hearing, oh, I met, you know, Sally, and she’s in a similar role in a different business, doing this, and Joe’s doing this, and they’re hearing other peers, and they’re being a little more open minded to what others are doing. Yeah. Do they have the right support team underneath them? Do have they brought on the right people in the right places? And are they utilizing those team members in the right way, right people that build the right three levels of who’s become unstoppable, really?
Maria Ross 30:59
Yeah, yeah. And that’s what, you know, it’s so, I mean, I love doing my workshops for teams, but you know my two hour workshop is not going to solve all your leadership issues, because what happens in those moments where the scenarios come up and you need the reinforcement and you need the practice and you need the sanity check and the role playing ability, right? So building those coaching circles in for my clients, or even for like senior executives outside of their organization, the power of that community. I have studied hundreds of successful, empathetic and effective leaders through my research, through my podcast. That’s how the empathy dilemma book was built one of the pillars of self care was about, do you have a peer group, an advisory group, whether it’s ad hoc, do you have because to a T, all of those leaders that I interviewed, that I was deconstructing the recipe from had something like that. They were part of a mastermind. They were part of a coaching circle. They had a growth mindset. Yep. And it was like you said, I love the way you said that you’re able to accelerate faster,
Kasey D’Amato 32:06
so much faster, so much faster. You You know, when you have those three you’ve got your peer circle, just like, you know, your programs, you’ve got the right mentors and coaches. You really, truly, there is no problem that’s going to come up, because, let’s face it, all the problems that come up, all the challenges. It’s a mindset issue. So when you can get your mind to overcome the challenge, then the actions you know follow, yeah, and so yeah, when you have those groups surrounding you, the right people, right? You overcome those. You barely stay in that, that point, yeah, time you know, more than a few moments or a day, but it’s quick. You move past that very, very fast,
Maria Ross 32:45
yeah, well, and those moments don’t all come up within the nice confines of a two hour workshop, correct? You know? And that’s the challenge with a lot of learning and development curriculums, or professional development curriculums, is that they’re one hit wonders, right? Like I’m checking the box, and we did all this for our people, and then we never revisit with them again. That’s all right on these particular topics, to help them. I mean, that would be like, just like this. The example I love to give is my son, when he was like, seven or eight, took like, two taekwondo classes, yeah. And yet, when people would ask him, like, even a year or two later, he would say, Oh, I know taekwondo. I took a class, right? But I was like, No, you’re not practicing it exactly like I love the confidence, babe. But you know, it’s you’ve got to continually be in an environment and provide that environment for your employees where it’s constant growth, it’s constant it’s and giving them the support for when they try it and they stumble. That’s right, right? Critical piece, that is the critical like, maybe they’re not facing the major decision when you come in and do the workshop, but if they’re working with you as an ongoing coach, that’s right, maybe the major decisions are down the road, and that’s where they’re really going to need to lean on you and lean on a support team
Kasey D’Amato 33:57
to come together. That’s right. I meet with sometimes after a workshop. It will be either monthly meeting or will be quarterly, depending on who I’m meeting with. Yeah, going through that head, heart, gut, every time we’re looking at data, we’re looking at their project. We’re working on, what are we celebrating for KPIs and all the nerdy number stuff? Yeah. And then the next question is, how we’re feeling about this, how are we feeling about the team? Are we feeling about the project? How are we feeling at the program? How are we feeling about what’s the emotional like? First, when we look at the objective data, we celebrate the highs. We’re going to troubleshoot, you know what it was challenging from objective then we’re going to talk about, are we feeling energized about this, or is there something that’s feeling heavy, in which case let’s address that. Yeah, by the way, right, yeah.
Maria Ross 34:36
I love it. I love it. So kind of, as we wrap up, what’s your final piece of advice for people that are in transition, in a pivot and feeling paralyzed by that strategic decision making process.
Kasey D’Amato 34:50
Yes, the first is to accept it. The first is to accept I am in a decision making process, and then to say, How long do I want to stay? In this place. I call it the two minute rule. So you know, when I was a young, young child, apparently had a small tantrum. I barely remember this, and went to my parents and my cousins and all my family were kids were playing in the other room, and instead of my parents saying to me, you’re going to have a timeout, you’re misbehaving all the things they said, everybody else is having a good time, and you are in this state of mind where you’re cranky. How long do you want to be cranky having a tantrum before you want to have fun? And I said two minutes. So now I use the two minute rule as an adult. I use it over time. We joke about it in my family, yeah, because how long do you want to stay in the indecision? How long do you want to torture yourself? And so to me, it’s the first to say I’m in a state of indecision. How long do I want to be here? Is it two minutes? Is it one week? Is it one quarter? Put it on your calendar and say I am choosing to decide or get people, resources, help, support from mentors and coaches to make this decision, because the first is to accept you’re in the state, and the second is to acknowledge, how long do you want to be in the state of indecision, because nothing is moving forward while you’re staying in this moment of indecision. So you put it on the calendar. Is it one more day for you? Is it one week? Is it two minutes? What is it? Put on your calendar, and then if you feel still stuck that you commit to getting coaches and mentors and community to get you through it.
Maria Ross 36:26
I love that I talked to my teams, my attendees, about putting a deadline on your thoughts, exactly, which is similar. It’s the whole like, No, literally, put it in your calendar. Yeah, that’s right, and communicate that openly to wherever you need to get the input from, like, Hey, I’ve put on my calendar that Friday. I’m making this decision, so if you’ve got any input for me, yep, come see me, email me, call me. Let’s make a meeting. But I’m making the decision on Friday, so speak now and for or forever. Hold your peace. Kind of a situation, right?
Kasey D’Amato 36:58
That’s it. That’s it. Put the timeline on it. Yep. Two Minute Rule.
Maria Ross 37:01
I love it. Kasey, thank you so much for all these great insights and nuggets today. Such a rich conversation. I will have all your links in the show notes. But for anyone that might be exercising while we’re talking, can you give them one place on the air that they can contact you?
Kasey D’Amato 37:17
Yes. Kasey D’Amato, which is k, A, S, E, y, D, A, M, A, T, o, so it’s Kasey D’Amato dot com, same on LinkedIn or Instagram. So shoot me a DM anywhere I’m in the process of writing a book. Probably when this comes out, my book will be out. So awesome. Share it at that time. So yeah, connect with me. Would love to share and bounce around ideas.
Maria Ross 37:39
I love it. Thank you so much for being here. Thanks Maria and thank you everyone for coming to another episode of the empathy edge. If you like what you heard, you know what to do. Please rate and review or share it with a friend or a colleague, and until next time, please remember that cash flow, creativity and compassion are not mutually exclusive. Take care and be kind For more on how to achieve radical success through empathy, visit the empathy edge calm. There. You can listen to past episodes, access show notes and free resources. Book me for a Keynote or workshop and sign up for our email list to get new episodes, insights, news and events. Please follow me on Instagram at Red slice Maria, never forget, empathy is your superpower. Use it to make your work and the world a better place.
