The Power of Empathetic Leadership
with Ashley Cox

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Discover the power of Empathetic Leadership with Story Engine’s guest, Ashley Cox. Curious about how to make a deeper connection with your team, clients and audience? Ashley talks about the role empathy can play in your business so that you can create a thriving work culture and lead from the heart.

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Kyle Gray: (00:37)

Hello and welcome to the story engine podcast. My name is Kyle Gray and today on the show we have Ashley Cox. Ashley Cox is a leadership coach who works with women and helps them develop their soft skills, like empathy, and turn them into strengths which are normally associated as weaknesses. And some people think if you have too much empathy, you’ll get walked all over, you won’t get respected, and so Ashley shows how to turn this supposedly weakness into a strength. We’re going to hear about how to use more empathy working with your team, working with your clients, and working with yourself. She’s got a lot of great ideas and great stories to share. So without further ado, let’s hand it over to Ashley.


Kyle Gray: (01:23)

Ashley Cox, welcome to the Story Engine podcast.


Ashley Cox: (01:27)

Hi Kyle, thanks so much for having me today. I’m really excited to be here.


Kyle Gray: (01:30)

Ashley, will you introduce yourself to my audience by telling us a story about a moment or a time that’s really defined who you are, how you show up in the world and what you’re doing today?


Ashley Cox: (01:44)

Absolutely. I spent the first 10 years of my professional career in the corporate world. And as a manager in the corporate world, I worked with huge teams of people, 250, 350 employees, and a lot of the people that I worked with, it was in a very male dominated industry, it was very entrenched in history and we’ve always done things the way that we’ve always done them. And so as a 22-year-old young woman coming into the workforce and coming into a leadership role, it was always the story of, “Well, you can’t be too compassionate, people will take advantage of you,” or “Don’t be such a softy, Ashley. People are going to treat you like a doormat.” And so I was told to essentially brush off these characteristics of compassion and empathy and being a nurturer, which are all very natural instincts for me. And just toughen up, you gotta put on your big bridges and just come to work and be tough.


Ashley Cox: (02:58)

And so for so many years in the beginning of my leadership journey I thought that that’s how I had to be. I worked in HR for many years in corporate and we were taking personality assessments, and I had scored the highest out of anybody in the room with empathy. And I remember one of my coworkers looking at me and saying, “Wow, you have a lot of empathy. How do you even make it?” And I was like, “I’m not empathetic.” And so in that moment I realized, “Oh my gosh, how have I been denying who I am as a human just because everybody else told me that I had to be this way?”


Ashley Cox: (03:46)

So at that point I thought, “What if I just embraced that side of my personality? What if I embraced empathy?” And I led from that place. And so when I did that, everything in my leadership journey and in my career changed 180 degrees. My employees respect me more, coworkers were able to come to me with bigger problems, I was able to get to the root cause of things that were going on that had maybe been going on for months or even years much more quickly because I tapped into that strength, that natural tendency that I had of empathy. And so my leadership journey really took off from there. And I spent a few more years working in the corporate world and then I decided I wanted to branch out on my own and start my own business. And so now I work specifically with female founders and I help them learn how to tap into and leverage those natural strengths of their own so they can lead their teams in a way that feels really good and gets amazing results.


Kyle Gray: (04:52)

I love that. And yeah, I think it’s a very undervalued skill, especially in corporate, but I still think in a lot of entrepreneurial worlds, we want to… There’s a very big focus on results, and bottom line, and creating things and having empathy, in some ways, doesn’t… Yeah, it doesn’t immediately seem like that.


Kyle Gray: (05:16)

Can you tell me the difference maybe between leading or what an advantage somebody leading with empathy and really tapping into that skillset, how can they uniquely lead their teams and how does that show up differently than the common understanding of what good leadership looks like?


Ashley Cox: (05:40)

Absolutely. I love this question, Kyle. And I also want to make a disclaimer before I answer that question, that not only women can lead with empathy, but so can our male counterparts. So if you are a guy who has a lot of empathy and a lot of compassion, I know that you also get a lot of the same comments that the women do about, “Oh, you need to toughen up,” but I want you to really embrace that and lean into it because we need more of that in leadership all across all industries.


Ashley Cox: (06:11)

So my answer to your question would be that when we can lead with empathy, we approach a situation from, “If I were in this situation, how would I want someone to treat me?” And so we start to look at this situation by saying things like, “I’m coming into this with a positive intent. I’m assuming that this person had positive intent. They didn’t maybe set out to make this mistake or say this thing that has gotten them into trouble or not do the tasks that they were supposed to do. I want to come into this situation with an open mind and an open heart to say, maybe this person really didn’t understand the instructions. Maybe there was some other situation or issue that came up that was outside of their control that they needed my help as the leader or the manager to clear out of their way in order for them to really be able to move forward. Maybe I’ve created an environment where they don’t feel like they’re comfortable enough to come to me, but when I can tap into that empathy side, then people feel more comfortable coming to me and sharing things that they might not otherwise have shared.” So there’s a lot of benefits to being empathetic and it doesn’t mean that you’re going to become a doormat or get run over if you employ some other leadership skills to balance that out.


Kyle Gray: (07:43)

It makes a lot of sense, especially when building teams. And it’s a certain value you can create because I remember being a young new person in a startup trying to learn a lot of the ropes and just desperately trying to figure everything out, and I wasn’t receiving a lot of empathy back then amongst all the challenges and things. I felt a need for at least a little bit of like, “Yeah, you’re doing awesome. I like this, not that.” And so I try to do that with my own team these days. Even if they make a mistake, but again, just letting them know, “Hey, I’m grateful that you’re working for me. I’m grateful for these contributions,” and just giving them an ability, or again, I think just simple reminders like that and acknowledging the value that people are adding can really inspire a lot of loyalty and creativity.


Ashley Cox: (08:43)

Yeah, absolutely. Absolutely. And I always like to remind my clients and my audience in general that none of us are exempt from making mistakes. And a perfect example is there was a several month period of time where I had actually spelled my own name wrong in my Instagram bio, that’s really embarrassing to admit, I don’t know how many thousands of people might listen to this podcast eventually, but I had transposed two letters because I got in a hurry when I set my account and I just went about my business. It can happen to anybody. And at the end of the day, it’s not something that’s going to make or break the business. And so when we get all uptight or righteous over mistakes being made, it would do a lot of good to just step back and say, you know what, at the end of the day, is this really going to make or break my business? And let some of those things go.


Ashley Cox: (09:41)

Give constructive feedback, give the correction, “Hey, we need to be a little more careful. Pay attention to detail, but it’s not that big of a deal. I don’t want you to stress over it. Let’s just fix it and move on.” But so many people don’t address the issue and then they just let it boil and become this monster that’s hiding in the room with the team. And so then the team feels it and the leader feels it, and everybody feels like they’re stuck in this awkward stage or moment. And it’s the leader’s responsibility to pull the team out of that and to keep things moving forward.


Kyle Gray: (10:23)

That makes a lot of sense. And, yeah, having this core communication and foundation is essential. Can you tell me about, since we’re talking about everybody makes mistakes, I’m certain that there are ways that people can misuse this talent and this gift as well, what are some of the pitfalls that people who are empathetic and using that in their leadership should be aware of and avoid?


Ashley Cox: (10:51)

That is such a great question. Any strength can become a weakness if it is not used properly and any weakness can become a strength if you learn how to leverage the complementary strengths from the other side. What I mean when I say that is yes, we can go way too far with empathy when we don’t expect that anyone in our team is doing anything wrong, that everybody really is trying their best and that they would let you know if they had a problem. You’re just giving too much rope.


Ashley Cox: (11:39)

You hear the saying, “You give too much rope and you hang yourself with it.” When we give too much rope and we don’t set those boundaries and we don’t set expectations, we don’t create a structure for our team, then it’s super easy for them to just do exactly what we’re expecting of them and that is do whatever they want.


Ashley Cox: (12:04)

If our team is running around doing whatever they want, that’s an indication of you as a leader, not setting strong boundaries, not having solid expectations in place, not creating the guidelines, the rules, and the structure for your team. Yeah, you can absolutely be overly empathetic and become a doormat and be run over and sit back and wonder what happened. Why did my team run amok?


Kyle Gray: (12:30)

That makes a lot of sense. I think a lot of people, and I think particularly a lot of the women you’re working with this may be the case too, it’s easy to be empathetic with your team, but it’s not always easy to be empathetic with yourself if you make those same mistakes or yeah, are doing things.


Kyle Gray: (12:53)

How can you, I think it’s a big challenge as a leader to hold yourself at a very high standard and any kind of mistakes that you make or whatever drawbacks or weaknesses that you have, you deserve to be in the same way that you would understand with one of your employees or team members, cultivate that same understanding with yourself. Is that something you work with and what does that look like in practice?


Ashley Cox: (13:21)

Absolutely. It is something that most of my clients struggle with at some point or another in their leadership journey. Whether it’s on the front end thinking, “Ah, I just don’t know if I’m cut out to be a leader. I don’t know if people are going to listen to what I say. Who am I to tell other people what to do?”


Ashley Cox: (13:45)

There’s a lot of that self hesitancy in the beginning and then as they start to get into their leadership role, when things start to go sideways, as they generally do when you’re leading a team of people, something is to go awry at some point or another. Immediately the response is, “Oh, I must be an awful leader. I don’t really know what I’m doing, so I must be the problem.”


Ashley Cox: (14:10)

Yes, your team is a reflection of your leadership abilities but it doesn’t mean that you’re a bad person. It doesn’t mean that you’re an awful leader. It means there’s an opportunity for you to develop a skill that you don’t currently have.


Ashley Cox: (14:24)

If you can look at it more objectively to say, “You know what, I could really sharpen my communication skills. I think that would help our team work better together,” or, “I really need to work on my delegation skills. I have a tendency to keep all of the tasks to myself or give them to employees and then take them back when I feel like they’re not getting done quick enough, they’re not getting done correctly.”


Ashley Cox: (14:50)

When we can learn to assess our skill development and identify those gaps where we need some additional training and improvement, then that takes the personal side out of it and it makes it more of an objective look at really, just like anything else we would in life.


Ashley Cox: (15:09)

I can’t go out tomorrow and build a rocket ship. I don’t have the skills to do that. If you’ve never led a team before, you probably don’t have the skills to do that, and it’s the same exact concept. You have to develop those skills to become a really effective leader.


Kyle Gray: (15:24)

I love that. I think it’s something that really everybody encounters on their journey to really growing. I think it’s part of the process of becoming an entrepreneur, I think it is becoming a better person which requires making these attempts and uncomfortable things and really a lot of growth.


Ashley Cox: (15:45)

Oh yeah, absolutely.


Kyle Gray: (15:46)

One of the things that could be particularly uncomfortable sometimes is having this same empathy not only inward and not only on your team, but maybe towards the clients you’re working with. Can you tell me about some of the applications and advantages of being an empathetic leader while working with clients or maybe even spreading your message before they become clients?


Ashley Cox: (16:13)

Yeah, I think that empathy goes a long way when we’re working with clients because especially if you’re in a field where people don’t really understand maybe what it is you do or how you help or maybe they’re at the very beginning.


Ashley Cox: (16:30)

I work with a lot of wedding professionals, and so their clients are brides. Brides generally are getting married for the first time and they’ve never been through this process before. In a wedding consultant type of business, maybe a wedding planner, a florist, a photographer, whatever you might be in the wedding industry, you have to have a lot of empathy that your bride literally has no what she’s doing. She’s never planned a wedding. She doesn’t have your experience or background. She doesn’t know what questions to even ask, let alone probably what answers she would even have for those questions.


Ashley Cox: (17:12)

Having a lot of empathy toward your client can help to build a stronger bond with them and make them not feel stupid. I think a lot of times we hear things out there like, “Oh, customers are stupid,” or, “They don’t really know.” Yeah, they don’t know. They’re ignorant in the true definition of the word. They just don’t have the knowledge that you do.


Ashley Cox: (17:36)

Sometimes we get so far ahead in our professions or industries that we forget what it’s like to be new. We forget what it’s like to not know the basics and that can really damage your relationship with your customers. If they’re feeling small or belittled or that they’re frustrating you or that they’re always wasting your time. It’s a really fine line to walk to be empathetic but also not overly empathetic to where then they start taking advantage of you and you’ve got scope creep and all of these other negative side effects of being overextending in your empathy.


Kyle Gray: (18:17)

Talk about scope creep for a little bit because as an agency, as somebody skillful, this is something that we are inevitably going to face. Whether we’re empathetic, whether we’re not empathetic, I think there are some clients out there who will always try to push the boundaries, and God bless them, we have empathy for them too. But tell me what that situation looks like and how can people tactfully navigate that?


Ashley Cox: (18:48)

Oh, I love this. I love this conversation because leading a team of employees and working with clients has a lot of parallels and a lot of similarities. I think if you are a small business owner and you’re a one man team or a one woman team, you are essentially leading your clients through this process every single step of the way.


Ashley Cox: (19:12)

There are always going to be people who, if you don’t ask you don’t know. If they’re having some scope creep then they’re probably just trying to push the boundaries to see how much you’re going to give in. It comes back to having clear boundaries and clear expectations.


Ashley Cox: (19:28)

I think one of the most important things that I do in my business and that I also teach other new business owners is having a boundaries or expectation conversations with your client upfront and then put it in writing and give them some instructions. What are your office hours? When are you going to be responding to emails? So that way they know that if they send you an email at 8:00 at night, not to expect us reply right away. You’ll reply in business hours the next morning. Or if you work in the evening, you can always set up Boomerang, which is a Gmail extension to send that email out first thing in the morning, so you can still be working, but they don’t know it.


Kyle Gray: (20:21)

Even still just setting the expectation of, “Hey, I do remote work. I work different hours than most people and I may send you an email at 8:00 but that doesn’t mean that if you send something back that you’re going to have my immediate attention.” Just still having your office hours or when to expect communication from you even if you step outside of it a little bit, gives you that freedom to do it without making it into a slippery slope.


Ashley Cox: (20:48)

Absolutely. If the client starts to get outside of the scope, it’s just a gentle reminder. “This is outside of the scope of our project. If you’d like to talk about the opportunity to work on this project, let’s just hop on a quick 10 minute call, we’ll figure out what it is that you need, and we can take care of you right away.” Don’t make it a big deal. Don’t fret and worry over it.


Ashley Cox: (21:11)

They probably have forgotten what the boundaries and the expectations are. It’s your job as the business owner to remind them gently and then to give them an alternative solution. “Hey, we can talk about that. Absolutely, let’s hop on a quick phone call and figure out what you need.” If you make it awkward, it’s going to be awkward. But if you don’t make it awkward and you’re just handling it as a conversation, then that’s all it’s going to be.


Kyle Gray: (21:38)

I like that a lot. Can you tell us now, you’ve given us hundreds of little moments and hundreds of little opportunities to use empathy to improve our situation with ourselves, with our teams, with our clients, but this seems like, and as most things do, it’s a practice, it’s a muscle that you build every day.


Kyle Gray: (22:00)

Either somebody that doesn’t have it, or maybe they’ve been denying it, or it doesn’t exactly come naturally to them, what does it look like to start practicing empathy? What’s something simple we can do every day to start building that skill?


Ashley Cox: (22:16)

I love that question. I think the most important place to start could be with yourself. We talked a little bit about that. If you can’t have empathy for yourself, it’s really hard to have empathy for other people.


Ashley Cox: (22:28)

A really super easy practice that you can start every day for yourself is to maybe set a reminder on your phone, just for a random time, 2:30, 1:22, 8:13 PM, it doesn’t matter. Whatever time, but just put a reminder on your phone. “How have you practiced compassion for yourself today?” You can stop and think, “Okay, did I talked to myself kindly today?” “Have I given myself grace when I didn’t know the answer right off?” “Have I taken a minute to really reflect back on all of the incredible things that I’ve done?”


Ashley Cox: (23:09)

I struggle with this, still. I think it’s just human nature. We all have a tendency to be our own worst critic. Yesterday I was in my mastermind group, and everybody was going around the table giving an update on what they had done the previous month. I was sitting there going, “You guys are killing it. You are just making some boss moves. That’s amazing.”


Ashley Cox: (23:29)

When it got to me, I was like, “I don’t know how I’m going to follow that.” Then I said, “Within the last month I did a complete rebrand. I had new brand photos taken and got those posted. Had a new website developed, and I wrote and published a book.” It wasn’t a shabby month, but immediately because all these other people were doing amazing things, it was easy for me to slip into that mindset and say, “I wasn’t enough this month.”


Ashley Cox: (23:59)

I immediately caught it and said, “Wait a second, I killed it this month. I did some really amazing things, and I really freaking proud of that.” I think, just, it becomes not maybe always the first thing that slips out of your mouth, but you catch it a lot quicker when you’re practicing it on a daily basis.


Kyle Gray: (24:22)

I like that. Acknowledging your wins is a really big thing, because I think, again, as entrepreneurs and high achievers, we do these things, and as we’re doing these things, we’re like, “It’s just what I did every day. It’s not really that big of a deal.” Often, yeah, these great things are happening and if you don’t give yourself the opportunity to acknowledge and enjoy what you’ve been creating and doing, then you end up burning yourself out.


Ashley Cox: (24:47)



Kyle Gray: (24:48)

Can you tell me about a time where you really didn’t want to use empathy, but you were like, “I’m going to trust it and do it,” and then it turned out to be a really good choice?


Ashley Cox: (25:01)

Gosh. I feel like there’s probably a hundred examples I could give you about that particular situation. I feel like I mentioned earlier, I worked in human resources for most of the time that I was in corporate America, about eight of the years that I was in corporate.


Ashley Cox: (25:26)

There was an employee who just wanted to fight us on every single thing that we were asking him to do. He was a front end bagger. I worked in the grocery industry. We’d ask him, “Could you go out and get some carts?” “Isn’t it so-and-so’s turn? I just don’t want to go get them.” “Okay, no, we need you to go get the carts.”


Ashley Cox: (25:54)

It was just a thing, after thing after thing after thing, from little things like, “Go get the carts, which is your job,” to, “I need you to clean the restrooms. They’re a disaster,” which nobody wants to do. That’s the worst job, to refilling bags on the front end, to taking a product back. Everything single thing.


Ashley Cox: (26:14)

I just was done. I was at the end of my rope. I thought, “Oh, my gosh, if he complained one more time, I’m just going to fire him. I just can’t deal with this guy anymore.” I had a supervisor who was like, “Okay, maybe just sit and talk with him. Find out what’s going on. Why is he so combative? What’s going on?”


Ashley Cox: (26:34)

I did, very reluctantly, mind you, sat down with him and I talked to him. We’ll just call him Fred. Was like, “Fred, what’s going on? You’ve been fighting us tooth and nail every step of the way for the last couple of weeks. I don’t get it.” Come to find out, Fred’s wife had gotten cancer, and they were dealing with this diagnosis. He was having a really hard time and he just felt angry at the world.


Ashley Cox: (27:02)

Through that conversation, obviously you can probably assume I felt like a big turd at that point. Was like, “I’ve really thought that Fred was being combative and he didn’t care, and he didn’t want to work here. What was his issue?” I was ready to let him go, but just by sitting down and extending empathy, and talking to him, and finding out what was going on, Fred opened up. He told us that this very real situation was happening.


Ashley Cox: (27:29)

We were able to give him a leave of absence. He was able to take care of his wife. When he was able to return to work, he was a much happier employee. It was just taking that five, ten minutes to sit down and talk to him.


Kyle Gray: (27:42)

I love it. That shows a lot, a lot of value in there. Something that, again, is really counterintuitive sometimes to do.


Ashley Cox: (27:50)



Kyle Gray: (27:51)

Ashley, you’ve taken us on quite a journey of exploring many different useful, valuable, profitable ways to create more empathy in our business, on our team, with our clients, with ourselves. There’s been a lot of value in this. I want to invite you to share any closing thoughts with us, and then let us know where we can go and contact you, and maybe dig deeper into our own empathy practices.


Ashley Cox: (28:19)

Thank you so much. I really appreciate those kind of words, Kyle. I would encourage everybody to look at your journey with empathy, whether it’s with yourself, your clients, or your team members as a very profitable venture. Because when we can be kinder to ourselves, we have the courage and the confidence to do more, to step into bigger roles, to take bigger risks, bigger chances. When we have more empathy with our clients, we have the opportunity to create loyal clients for life who trust us infinitely, who refer their friends and families because they know that we have their best interests at heart.


Ashley Cox: (29:05)

When we have empathy with our team members, we might just have the opportunity to save an employee who might be on the verge of maybe being fired. But when we have empathy for our employees, they will give it back to us tenfold. Creating loyal and engaged teams that are super passionate about you as a leader are going to take your business to heights that you’ve never even experienced.


Ashley Cox: (29:34)

I’ll just leave you with those few little comments. You can find me on my website, at, that is dot C-O, and you can also find me on Facebook and Instagram, I tried to keep it pretty simple. If you type that in anywhere, you should be able to find me.


Kyle Gray: (29:51)

I love those .cos. I rep the .co these days, as well. You want to make sure, because it’s an easy one to mistake, but it’s only two letters instead of three. Way better, everybody.


Ashley Cox: (30:05)

Right? It’s already shorter.


Kyle Gray: (30:06)

Yeah. Ashley, thank you so much for joining us on the Story Engine Podcast today.


Ashley Cox: (30:12)

Thanks so much, Kyle. This has been such a blast. I hope that you all have gotten so much value out of this conversation, and I look forward to connecting with you guys wherever you might find me online.


Kyle Gray:

Thanks for listening to the Story Engine Podcast. Be sure to check out the show notes and resources mentioned on this episode and every other episode at


If you’re looking to learn more about how to use storytelling to grow your business, then check out my new book, Selling With Story: How to Use Storytelling to Become an Authority, Boost Sales, and Win the Hearts and Minds of Your Audience. This book will equip you with actionable strategies and templates to help you share your unique value and build trust in presentations, sales, and conversations, both online and offline. Learn more at 


Thanks for listening, and I’ll see you next time.