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What Stands Between You and Your Greatness? with Lolly Daskal [Episode 443]

Lolly Daskal, a leadership executive coach who works with many Fortune 500 CEOs, speaker, and author of the great new book, The Leadership Gap: What Gets Between You and Your Greatness, joins me on this episode to talk about the personal exceptionalism of every individual, and how sellers can dig deep to find it.


  • Lolly talks about the greatness within each person. At certain moments it is felt, when the body is energetic, the mind is in flow, and life is in synch.
  • Daniel Pink says, everybody leads. Lolly says, own your leadership — how you impact others, regardless of your title or position — and take responsibility for it.
  • Lolly gives her definition of greatness. It’s about being confident of abilities, loyal, and trustworthy. It has the characteristics of what it means to be successful. She discusses a code of conduct based on core principles.
  • Lolly noticed that her clients complained of seven issues, or human weaknesses. Lolly calls them gaps, that come out when we are stressed. She identifies archetypes, as taught by Carl Jung, pairing them against opposing gaps.
  • If we’re no longer able to change a situation, we have to change ourselves. Lolly uses the acronym RETHINK for the seven archetypes and personas in her book. Rebel, Explorer, Truth Teller, Hero, Inventor, Navigator, and Knight.
  • Lolly asks clients to consider themselves a work in progress. Without progress there is no growth. True leadership means transformation. What did you learn today, so you can be better tomorrow? Nothing stands still.
  • Surround yourself with people smarter than you, so you can learn. Lolly has read a book a day for 27 years, so she can always learn something new. (She skims and retains it.)
  • All of us have all the archetypes within us, and they show up in different kinds of ways, as needed by the situation. Clients ask how they can be at the top of their game. Lolly redirects them toward knowing who they are, rather than how they should do things. People tap into who you are, and that’s how they align with you. People buy from who you are.
  • Lolly explains the gap. The Rebel, driven by confidence, has a gap, the Impostor, driven by doubt. Do you want to stand in greatness, which is finding confidence, or do you want to lead with self-doubt? She explains luck is being prepared.
  • Perfection is not real. Lolly substitutes excellence for perfection, by bringing excellence to everything she does. Bringing the best you have, is good enough.
  • Two final thoughts from Lolly: read The Leadership Gap, and get a coach who will ask you questions, to go deeper.

Episode Transcript

Andy Paul  0:53  

This is Andy. Welcome to Episode 443 of the Sales Enablement Podcast, where I hold in-depth conversations with today’s leading experts in sales, marketing and leadership six days a week. Joining me on the show today is Lolly Daskal. Lolly is a leadership executive coach and works with many fortune 500 CEOs. She’s a speaker, and author of the great new book, the leadership gap between you and your greatness. So Lolly, does everyone have greatness within them?


Lolly Daskal  2:51  

I truly believe that every single person does have greatness within them. 


Andy Paul  2:58  

So how do people become convinced of the fact that they do have this greatness potential for greatness within them?


Lolly Daskal  3:06  

So, actually I’ll give you a little hint. There are times in our lives when within our body, we feel energetic, we feel good in our mind. It feels like we’re in flow. In our lives, it feels like everything’s adding up and everything is in sync. I’m not saying this happens all the time. But I’m sure everybody that’s listening to your podcast has one time or another has had these three things happen. Your body feels energetic, your mind feels in flow, and everything seems to be working out. It’s almost like the dots are all connected. Those are the moments that we are standing in our greatness.


Andy Paul  3:50  

Interesting. So you have to be able to recognize that and you talk about this concept flow in the book.


Lolly Daskal  3:55  

I talk about it in a book because I want people to realize it. Most of us are so busy being distracted and running from one thing to the next. But sometimes we don’t slow down long enough to realize that we have something within us that we might not be tapping into. Some people think success is just like doing. And I find that in order to tap into greatness, we almost have to stop. Listen to ourselves, find ourselves, reflect about ourselves, in order to unleash it.


Andy Paul  4:30  

Hmm. Wow, that’s interesting. I’ve used the word running from thing to thing but it’s actually in some cases, I think people actually run from greatness and their potential to succeed.


Lolly Daskal  4:43  

I really think people are running fast almost in their external life so they have to evade or they avoid self reflection and self examination. That’s what I find with most people like, what can I be busy with? So I don’t have to think about myself.


Andy Paul  5:00  

So do you find that true? And because you have longer clients now fortune 500 CEOs and global 500 CEOs and so on, is it true among them as well? Or have they gotten to that position because they have done the self reflection they have assessed themselves?


Lolly Daskal  5:17  

Absolutely not. They have not assessed themselves when I start to work with them, they’re the ones that are running, running, running, they’re not running from their greatness in as much as they’re running towards what they think is greatness. And when they miss the mark, sometimes it costs them in a way that, maybe they’re not connected to their team or maybe their organization isn’t thriving the way they want it. Or maybe the board feels that they could be a better leader, whatever the reason is, usually a CEO is not very reflective. I’m the one that comes in and teaches them what it means to slow down to go faster. What it means is to work smarter, not harder. I think that’s what a coach usually does. And that is my job to begin with, to enlighten my clients about what true leadership is and how we can get them to greatness.


Andy Paul  6:12  

Well, let’s unpack this idea of true leadership because you’ve written the book, The Leadership Gap, but I mean, it’s more like Dan Pink talked about the cells human as is, you know, everybody’s basically in sales these days is some degree or another.


Lolly Daskal  6:29  

This is what I always say to everybody that I meet in an organization. If someone is listening to someone pays attention to what you say, someone follows what you say, You’re influencing, you’re impacting someone, you are a leader, and you have to own that you have to take responsibility for that. The truth is that you don’t have to have the title or the goal or the position. It’s about how you influence and how you impact someone. 


Andy Paul  7:03  

Yeah. And so we have an audience here that listens to this podcast. That’s the thousands of people that are basically in the sales profession that influence a central part of what they do. I’ve always thought that just the act of selling something to somebody is a leadership act. Now you have to inspire somebody to take action with you.


Lolly Daskal  7:26  

And you know, what’s interesting about that in sales, people don’t really buy about what you’re selling, people buy who you are, buy from who you are. So that’s even more important that you know, how you have greatness within you. And you know, when we talk about greatness, I want to just define that. This is not a concept that I’m talking about. This is a concept of knowing your capabilities, it’s knowing about your confidence, it’s tapping into your integrity. It’s about being someone who people can trust. It’s about being someone who is loyal. That’s what I’m talking about when I talk about greatness. 


Andy Paul  8:14  

Hopefully it is that greatness is really like having the ingredients for success as greatness is not success itself. It’s having the ingredients that enable you to succeed.


Lolly Daskal  8:30  

Perfect. It’s exactly what I always say it’s having the characteristics of what it means to be successful. You need to always say to my clients, you need a code of conduct, what is your code of conduct? What are your values? What are your principles, because that will lead you to greatness. If you know what your code of conduct is, if you know your principles, any fast decision that you have to make will come easy to you because you can always say, Oh, I’m a man or I’m a woman of integrity. Oh, I have confidence and I’ll do this or I am loyal. So I’ll do this. The reason You have those principles so that you can live your effervescent life. And we’re always doing a lot of things at one time. So how do we make our decisions clearly and definitively? We have to do it from our code of conduct from these, what I call core principles of who we are.


Andy Paul  9:21  

So the leadership gap. So what is this gap you’ve identified?


Lolly Daskal  9:30  

What I have identified, and it’s interesting, because this came to be true for me, and I’m in my business for over three decades. When I first started out working with individuals, I would hear things over and over and over again, and it started to create a pattern in my coaching and my consulting people were talking about seven things over and over and over again. And then I said to myself, wow, these are weaknesses within human beings. Not only the people that I work with, but it seems like everybody’s talking about it. I found them to be because I’m a year younger. And he talks about the fact that we all have shadows within us. And I found that we have within us these gaps that sometimes lead us down a road, we don’t want to go and usually they come out when we’re stressed. Usually they come out when we’re not thinking clearly, usually it comes out when we’re challenged. What I have found is, and I know we want to talk about the gaps, but I really want to stress this is that within us, there is a polarity within us that we can be standing in our greatness or we can be leading from our gaps. And we have to be aware of the polarity within us because then we can choose who we want to be. But within us there’s just as much weakness as there is greatness and strength.


Andy Paul  10:44  

Yeah, and you identify these seven archetypes based on union construct power young and yeah, each one is yeah, you identify it by its name, I’ll say rebel. But on the other hand, you know, at the other end of the spectrum, he said the other pole is the imposter, right?


Lolly Daskal  11:11  

We both have the polarity within us, because most people will talk about finding your strengths. Most people will do all these discs, assessment and Strengthsfinder, and they’ll do Myers Briggs and all of that. But what that does is it only talks about your strengths and how you can move forward. And so people need to realize that the same strength that you have sometimes can stop working against you. And they do end up costing you a gap. And you have to be mindful of this


Andy Paul  12:04  

And they stop changing and evolving because they don’t look inward. They don’t think about who they are and these elements for greatness they need to have.


Lolly Daskal  12:28  

Absolutely, and so many, many stories in the book from across the world, you know, you step into the offices, the intimate offices of Fortune 500 CEOs and into the boardrooms. And you get to understand that each one of these leaders, even though they’ve reached some great heights, they have gaps. And it’s only through awareness. Some people get it through coaching. Some will get it by reading this book, and they’ll recognize it within themselves, but it sometimes takes an outside force to ask the question You are great at what you do. But are you really where you need to be? And sometimes the answer is actually a lot of times it’s no and then the question is, Are you doing the same thing and expecting you now to grow to the next level? And if that is true, they won’t get you there. You need to pivot. You need to transform, you need to look at your gaps and see if it’s keeping you from who you want to be.


Andy Paul  13:24  

Yeah, this favorite saying from this Italian playwright, Giuseppe Lampedusa wrote this play called the leopard back in the 50s. And the quote is, if we want things to stay as they are, things will have to change. 


Lolly Daskal  13:38  

And I always say, if we’re no longer able to change a situation, guess what, we have to change ourselves.


Andy Paul  13:48  

And you make that point in the book. 


Lolly Daskal  14:05  

Right in the book, I use the word rethink as because it’s the rethink for the seven archetypes. And when I work with organizations, it’s called the rethink system. Because the rethink stands for an acronym for the seven archetypes and personas that I talked about throughout the book.


Andy Paul  14:23  

We talked about leaders and leadership and people are successful. But really what you’re identifying is a certain complacency, which sort of seems at odds right with people that have achieved a certain level of success or for any of those of you listening or those of us who are listening is saying, Yeah, we were not really complacent. We’re still struggling that there is if we refuse to change, we are being complacent.


Lolly Daskal  14:57  

You know, the idea is, I try to take it out of struggle. And I always have my clients reframe that and say we’re a work in progress. And if you stopped progressing, you stopped thriving and growing, and you stopped learning. So for me, I think true leadership is always when you’re evolving, growing, changing, transforming, that equals success that equals greatness.


Andy Paul  15:20  

Well, and for those listening to sales audiences this is the key to succeeding because our customers aren’t standing still, our markets aren’t standing so the products aren’t standing still. We certainly can’t stand still, as soon as we think we know and you identify this in the book, as soon as you think you know, everything there is to know then you start stagnating.


Lolly Daskal  15:39  

Yeah, you know, I love thinking about Steve Jobs. Right. Steve Jobs was a pretty smart man. He surrounded himself with plus players and people that were much smarter than he was. Why because he wanted to evolve. He wanted to grow, he wanted to learn. It’s the same thing with sales. You have to ask yourself, what can I do today to be better? Tomorrow, what did I learn about today that tomorrow I could be different. It’s a ritual that most salespeople can say to themselves because they can always be growing and always be evolving and always be learning.


Andy Paul  16:11  

Yeah, well, I mean, that’s new. And I’ve had this conversation before. That’s why I do this podcast, right? Every day I surround myself with someone smarter than me. We have a great conversation, and it helps me continue to learn and evolve. 


Lolly Daskal  16:30  

And you get to have a podcast and you get to learn from others and I learned from others but through reading.


Andy Paul  17:40  

All right, so let’s let’s dig into these archetypes. So we’ve described the seven that we all fit into one of these seven, the rebel, the explorer, truth teller, hero, inventor, navigator, knight. So are any of these more prevalent than any of the others?


Lolly Daskal  17:59  

So I want to rephrase what you said. And what I believe is that all of us have all of these archetypes within us. Do we tend to lean into something more than others? Yes, depending on what business you’re in and what actual challenges that you’re being faced with. But the truth is, we have all of them. And because I believe we hold people, and I believe that they show up in different kinds of ways. So you might be saying, oh, but I’m more like the rebel. I’m really not about the knight. But the knight is about loyalty and how many times in your life in your business in your relationship and partnerships did loyalty come up? I think it comes up a lot. So we have to rethink this again, we have to learn and reassess what we really think about these archetypes because they tend to show up more than we know.


Andy Paul  18:51  

So as someone who’s thinking about leadership gaps and how we address these, they have to go through each seven or harder. They say, okay, I’m primarily this, and I’m primarily a rebel, let’s say. 


Lolly Daskal  19:11  

So if you’re a salesperson, you have to make a phone call. And let’s say you have some really bad news to tell your clients and your customer. You need to be the truth teller, you need to tell the truth. Instead of the deceiver who comes across and creates suspicion. These archetypes are situational. Whatever is going on in the moment, we can choose which archetype to be so we can stand in our greatness instead of leading from our gaps. Maybe you’ll need to be the hero, the one who’s courageous with a client instead of the bystander who’s a coward because they’re fearful. So it’s really important to assess the situation because that’s what these archetypes are. It is depending on our circumstances and our challenges. 


Andy Paul  20:10  

Okay, right. I love that. That provides some great context. And so I just want to spend time talking about the rebel because I sort of lead with that. I think that aligns with a lot of what people do in sales in terms of sort of focusing on changing the status quo or helping buyers make decisions to change status quo. And you talk a lot about confidence in there but saying confidence is enough because salespeople least stereotypically are perceived to be hey, I’m so confident, they could sell anything.


Lolly Daskal  20:46  

So, the interesting thing is, I had a conversation with Bob Berg and I distinguished for him what confidence is, and he’s like, I love that. And so I will say with confidence that it’s not about ego and it’s not about standing in the mirror in the morning saying I’m the greatest and doing power poses are the best at what I do. I don’t believe that’s what confidence is. I believe confidence is your capabilities plus your competence equals your confidence meaning what you’re really good at and what you can master brings your confidence. And this is what I told Bob Berg, I said, damn confidence is believing you’re able and competent is knowing you’re able. So by knowing that you get your confidence from your competence.


Andy Paul  21:47  

That was a good point. I just want to make sure I remembered because otherwise, I have to go back and listen to the recording to try to find this particular note so you make the statement, which is that the most successful people are the most competent. You said the truth is the most successful people are the most competent. Is that really true?


Lolly Daskal  22:07  

Because what happens is that they have these competencies, right? They’re masters at something. And because they are the master at what they do, they can go out and change the status quo code. They can go in and change the status quo. They can go out and do something different. They could make something impactful. They can turn the world upside down. They can do whatever they want to do, because they do have that. I don’t think competence is isolation of confidence. 


Andy Paul  22:41  

Interesting. Well, I think that in the sales context it is as you know, I think I see times sometimes that people are really confused about what they would need to be competent in. And what we’re seeing in many cases is sort of a diminishment. 


Lolly Daskal  23:19  

So I want to stress this, and I think you’ve hit on something that’s really an aha moment and very insightful. Most people will ask me, you know, I need to be really great at my job, right? So if I say, let’s talk about sales, right? So they’ll say, what apps do I need to know? What technology do I need to know? How do I know? How can I be on top of my game? And I say, I don’t think that’s important right now. I say who you are is more important of how you do things. Because people will tap into who you are. And that’s what will make them align with you. That’s what will make them trust you. That’s what will make them have confidence in you. And if you’re a person of integrity, if you’re a person that has competence and you come across as someone they can trust, then whatever you’re selling them will be okay. And people don’t get that they’re buying from who you are as a person. And that’s what this book is about. It talks about who you’re going to be. That rebel means to step forward in your confidence and competence. Let people know what you’re really good at. And let them find that they can find alignment with you. You don’t have to sell anything to anyone but present yourself in the best light of who you are.


Andy Paul  24:45  

Why don’t you make the point in the book that people too often attribute success to the overwhelming amounts of confidence right when they look back and portray a successful businessperson Steve Jobs for instance, they downplay the competence that downplay the hard work component of it.


Lolly Daskal  25:02  

I think he’s the epitome of what I would say. I know people have all kinds of opinions of how he was as a leader. But in some aspects, he really showed us that a true leader is about creating this surrounding where they’re constantly learning from others, you could have confidence, you could be a smart person, but you could always learn from someone.


Andy Paul  25:33  

So I want to bring up one other facet in there, because it starts playing and sort of leads into the whole issue of the polarity of the rebel, which is sort of the imposter syndrome is the role of luck. So, you know, luck, what plays a role in everybody’s success to some degree or another? How do you see it?


Lolly Daskal  25:54  

I don’t think luck is mystical or anything like that. It just means you’ve done a lot of hard work. And then you had an opportunity and you recognize the opportunity as something you should take hold of. And so I think that’s how people create luck. You know, many years ago, there was this book called law of attraction, and it was like you think it and it will become it? And the truth is, that’s great and good and fantastic. But I really believe that you have to create the opportunities and that means doing the hard work and doing what you need to do in order to recognize those opportunities and circumstances where you can show up and call it luck.


Andy Paul  28:04  

Yeah, I mean, like, my father always said, the harder you work, the luckier you get.


Lolly Daskal  28:09  

Very smart father.


Andy Paul  28:10  

Yeah. Those opportunities present themselves in those usages. Being in a position to take advantage of them and recognize them and take advantage?


Lolly Daskal  29:07  

But in the very beginning when I first started out doing what I’m doing right now, being a coach and a consultant, I wanted to be perfect. I thought perfection was a metric that I should reach in order to be great. But then I found out very early on the perfect doesn’t exist. It’s not real. There’s no such thing as perfection because the truth is, we’re human beings made out of our imperfections, right? We have these gaps, right? They do exist. And then I have this distinction very early on. We need both of us to be a whole person. But I found something interesting with the word perfection. And I felt that if I was going to grow out of a bad habit of trying to be perfect, what did I need to become because I would have this void, right? I can’t say stop being perfect. So I found that if I told myself that Lolly, you need to bring excellence to everything that you do. It would allow me to be myself more than having to be perfect. So these days and it’s been a practice for a long time, I asked myself, if you’re striving for perfection, you won’t get it. But if you’re striving for excellence, and you bring the best of what you have to offer, that should be good enough. And that’s what I meant by the book, it’s like, the best parts of who you are, should be good enough.


Andy Paul  30:33  

How do you cultivate your self awareness and assess your skills, you know, for understanding where you are in the gap.I mean, what are some practical steps people can take to say, okay, I need to really think deeply about who I am.


Lolly Daskal  31:06  

I believe that we do very well when we have a coach, when we have outside feedback, because we only know what we know. And even though we’re inquisitive, we only can ask the questions of what we know about. So I think having someone look in with us, they can ask us in the book, I call them navigators. They’re very good at staring through a situation. They’re very good at guiding us in open ended questions. If you have somebody in your life that can not fix you, but ask you questions to go deeper. That would be great. So get a coach, read a great book, and do workshops. listen to podcasts. This is a great podcast, listen to this wonderful podcast.


Andy Paul  32:00  

Excellent advice. So I’m sorry, an interesting question to end on is, do you want to get lots of great quotes in your book? I mean, do you have specific words of wisdom that you live by?


Lolly Daskal  32:13  

Absolutely. First of all, I don’t compare myself to anybody else. And if I’m going to be measuring myself about who I need to be, it has to come from within. I find that if I’m busy comparing myself to others, I won’t get anywhere. And if I find that if I’m only measuring who I am and where I want to go, I can get further. And I think that most people don’t realize this, but greatness lies within everyone. We just have to choose it. It’s a destiny. That is our choice and we have to tap into it.


Andy Paul  33:25  

Thank you very much for being on the show. And friends, thank you for spending this time with us today. Please come back and join us again tomorrow. Until then, really appreciate taking a minute to go to iTunes, wherever you listen, then leave a review. We really want to know what we can do to make this a better experience for you. So again, thanks for joining me. Until next time, this is Andy Paul. Good selling everyone.