The Leadership Gap with Lolly Daskal

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Episode Summary

Today’s guest on The Successful Pitch is Lolly Daskal. She is the author of The Leadership Gap: What Gets Between You and Your Greatness, and she has amazing insights as to how you can be a better leader, and that everyone is a leader who influences somebody, impacts somebody, or makes a difference in some way. She has a formula for confidence, it’s one of the best I’ve ever heard. You’re going to want to be sure to listen to what that is, she said, “Leaders inspire people, but before they do that they have to inspire themselves.” And of course, you have to know yourself to do that. And she said, “Vulnerability is the new strong,” and, “Instead of looking at failure as something to avoid, look at it as a teacher, and not an undertaker.” I can’t wait for you to hear all of her tips on how to become a better leader.


Listen To The Episode Here


The Leadership Gap with Lolly Daskal

Hello and welcome to The Successful Pitch podcast. Today’s guest is Lolly Daskal. Lolly’s one of the most sought after executive leadership coaches in the world. She’s got cross cultural expertise that spans over 14 countries, 6 languages, and hundreds of companies. My goodness, that’s a lot of languages and travel. She’s the founder and CEO of Lead from Within, which is her proprietary leadership program that’s designed to be a catalyst for leaders who want to enhance performance and of course, make a meaningful difference. Not only in their companies but their lives and even the world. She’s got a really clever mix of modern philosophy, science, and nearly 30 years coaching top executives. One of her many awards is that she was designated a top 50 leadership and management expert by Inc Magazine, and Huffington Post honored her with the title of quote, are you ready for this, The Most Inspiring Woman in the World. So I am thrilled to have her on, she’s got a great book coming out that we’re going to be talking about called, The Leadership Gap: What Gets you Between You and Your Greatness. So Lolly, welcome.

I’m so happy to be here, thank you, John.

I am very impressed that you earned this title. So let’s start with that, The Most Inspiring Woman in the World. How did that come about?

Okay so nobody knows this, I’m blushing right now. I don’t know how it came about. It was something that was done, and something that I don’t really spend too much time reflecting on, and I’m very honored, but my whole purpose is to be of service to others. If I inspire others, then I can sleep at night, because that’s what I’m meant to do.

Yeah, that’s really what it’s all about, isn’t it? But that’s what’s inspiring I think, is I would like to just start with getting you to define, because you have such a global perspective, let’s have you define two words. The first one is, inspiring, and then the second one is, leader. So if you want to combine either one, say, “A good leader is someone who inspires, and inspiring is,” I’m going to let you free form with that.

Absolutely. First of all, I love that. I love this. Inspire, if you look at the word inspire, it’s about in, right? It comes from within. If you look at the best leaders that are out there, there are leaders that lead from within. I think that anything that we do, to leave a mark, to be admired, to make an impact, to make a difference, has to start with oneself. Leaders inspire, and we inspire leadership within ourselves. I think it’s almost like a full circle when you talk about inspire, and leaders.

What I hear you saying is, in order to inspire others, you have to first inspire yourself. Would that be accurate?

Well, you have to inspire yourself, and the thing is, is that you have to find something within yourself that inspires you, right. So inspire yourself about yourself, and then it’s almost like if you understand yourself, you can understand others. If you know what inspires you, you can understand what inspires others.

I like that a lot because it’s all about empathy, isn’t it? If you’re trying to get other people to take action, follow your lead, be part of your vision, you have to put yourself in their shoes and say, “Would this inspire me? Do I see the value in this, and am I as committed as I’m asking them to be.”

In my practice for over three decades, I found something to be very true; is that there’s a pattern in human behavior, is that when one person thinks they’re a certain way, they think nobody else is like that. What I have found is, there is a pattern. If one person is suffering from let’s say, self-doubt, then there are many others that are suffering from self-doubt. We have to realize that we’re not on an island. That as human beings we have a lot more in common than we think, and a lot more going on that is concise with another person. You don’t even have to put yourself in somebody else’s shoes as much as say, “What does it feel like for me, to be in this position? There are times when I felt insecure. There are times when I felt self-doubt. I’m sure that’s what it’s like for someone else.” So we really have to get to know ourselves and to understand ourselves, in order to understand others.

A lot of people are sometimes afraid to show their vulnerability, “I’m the leader, I’m supposed to be perfect all the time. I can’t let my team see that I’ve ever had doubts or worries.” What are your thoughts on that?

I think it was over 20 years ago, I coined this phrase in an organization and I said to the leader, “Vulnerability is the new strong.”

And he was like, “What do you mean? What do you mean?” I said, “The more vulnerable that you are, the more you show your true colors. The more you tell them that things aren’t going right, you’ll have an organization that feels, A, connected to you, B, they’ll want to help you, and three, they’ll be part of the solution.”

So that’s where the strength comes from. I said, “Try it, try it for one month. Try to be more transparent than you are,” because his way of leadership was, “It’s my way or the highway.” I said, “Nobody feels that you’re human, and you have to bring some humanness to who you are, and he goes, “How do I do that?” And I said, “Well, vulnerability is the new strong. That’s your motto.” And it really worked. It took him a little bit more than a month to catch on to what it meant, but people kept saying, “Hey, did you drink Lolly’s Kool-Aid?” Because they were like, “What did you do to him? What’d you do to him?” And I just said, “Well, we tapped into his humanness.”

Source: Pexels

Nice. Well, I can’t tell you how many investors I’ve interviewed that say, “You know, when people pitch me for money, be a human. Don’t pretend like you have all the answers,” and the same thing is true when you’re pitching someone to buy your product. You need to show some vulnerability in the pitch, I think. Can you expand on how someone could be vulnerable and strong at the same time that they’re pitching, let’s say to get a new client.

Absolutely. I believe anything that you do in your business, comes to pitching, comes to having a conversation. I think you have to bring your best self forward, and that means, everything that you have to offer, has to be put on the table. Usually, people think I’m only going to talk about all the great things about who I am. And I find it very exciting actually, and very enticing when someone says, “You know, I have these skills. But I notice that I have these other skills that might not always work, but I’m mindful of them, and I’m learning to leverage them, but I’m aware of them.” That to me makes someone vulnerable, makes them strong because they realize they’re a whole person. They’re not only one side of only doing great things, but they’ve made some mistakes and they’re learning about it, and they’re leveraging it. I’d rather be aligned with someone like that than someone’s always like, “Everything is great, and everything is wonderful,” because it doesn’t really work that way.

One of the things that I’ve noticed when I’m coaching people on how to pitch to get new clients is, if you tell a story of a time when there was a problem, because let’s face it, there’s usually some bump in the road during a long experience with a client, but how you handled it. You didn’t keep it a secret from them, you collaborated with them. That’s a much more compelling pitch, “That person is going to have my back,” and you tell the story of when it wasn’t always perfect. That really separates you from just one hit after another.

Absolutely. You know, I always tell my clients that failure should be a teacher and not an undertaker. Some people think it’s like the death of them, and I always say, “Failure is a delay. It’s not a defeat. It’s temporary,” I always tell them it’s a detour and it’s funny because most people want to not talk about it, but I think failure is something that we cannot avoid. It’s something that actually is part of our learning lessons. So I think it’s very important to talk about failure. I fail all the time, and it just means that I have to try a new way, to A, try it in a new way, or do something different. Think in a different way.

Source: Pexels

I love that, well I’m all about inspiring people to be confident when they pitch. Let’s talk about The Leadership Gap, your wonderful book that really, you’re defining the difference between what people should be focused on, versus what they actually do when they’re managing people. Can you tell us what the big gap is?

Yeah, so the big great thing about this book is that if you learn this system, it’s situational. That means that every time you have a meeting, every time you meet someone, you can ask yourself this inner question, “Should I stand in my greatness? Or will I reveal my gaps?” And just by asking that question, you will know how the meeting goes. So I’ll give you an example.


There are seven archetypes within the re-think system. I’ll give you the first one so you’ll understand how it means to stand in your greatness, or stand in your gap. Let’s say you have a business, right? And you want to make an impact in the world and you’re very passionate about this business and this new venture. You need to be a rebel, who is confident, in order to be able to pitch that in a way that it comes across, that it’s a magnificent idea. So you need to be a rebel who is confident.

But guess what? For every single rebel that is confident about what they want to do in the world, and what business they want to create, there is a gap that we feel like an imposter, who has self-doubt. If we are not mindful of that, that means when we get up to pitch, when we get up to tell our story, if we’re not feeling good about ourselves, if we have self-doubt, if we feel like an imposter, that will come across. So we have to ask ourselves, “Will I stand in greatness as the rebel who is confident, or will I allow my gap to lead and show that I feel like an imposter who has self-doubt?” That in itself will be a game changer when you’re pitching.

It’s situational. You can ask yourself that question, and you could pivot and leverage the imposter. In my book, I talk about seven different ways that you can leverage the imposter, that you don’t have to show up with self-doubt. That you can stand, and pitch, and be the rebel who’s confident.

Well, I think almost all of us have experienced that feeling of, someone’s going to tap me on the shoulder and say, “I’m sorry, there’s been a horrible mistake, you don’t know what you’re doing, get out of here.”

Exactly. Exactly.

Can you share with us one of the tips of how to deal with this imposter syndrome that you mentioned, your seven of them?

Yeah. I want to share two because I want to bring as much value as I can, and my research shows that there is 99.9% of us that feel this way. So, if we can help the 99.9%, let’s do that, right?


Interestingly enough I do coach the 1% because he feels he has no imposter, and that he’s filled with confidence, so much confidence, and he hired me because he wanted to learn empathy. He goes, “Teach me how to have empathy, I don’t have empathy for someone else because I have no self-doubt.” Let’s go back to all the rest of us who do suffer from the imposter syndrome, and who has self-doubt sometime or another.

The first thing I think I’d like to share a ritual that I do, that I think can help people. Every night, I do a two part ritual. At the end of the evening before I go to sleep, I ask myself, “Lolly, what did you do well today? What did you do that was really great today? And what did you do,” either it’s a skill, or having a conversation, or making an impact with someone. When I think about that, and I go, “Wow, that was really great.” Then I say to myself, part two, “What can you do tomorrow to be even better?” So I’m doing two things in this exercise, which we’ll learn to leverage the self-doubt and the imposter that maybe I sometimes feel.

The first thing is, confidence doesn’t come from looking in a mirror and saying, “I am great, I am wonderful.” Confidence comes from competence plus capabilities. Confidence is believing you’re able, but competence is knowing you’re able. That’s the difference.

So what I do at night is, I think about all my competencies, and I think about my capabilities and I anchor them, “You did that well,” so I confirm it in my head, “Lolly, you did it. You made it. You’re making a difference. You’re doing it. You’re doing a great job.”

The second part of that exercise, why it works so well is, I’m not comparing myself to anybody else. I’m only comparing myself to myself. I am measuring my capabilities and my competence against myself. Most people out there that feel like an imposter, who have self-doubt, is because they’re so busy comparing themselves to others.

You know I’ve never heard anybody else say that, and I love it. The source of why we feel like an imposter is not because we’re looking at our own progress or lack of, but because we’re comparing ourselves to other people who might have achieved more than we have at the moment, and that’s where it comes from. That’s so great, Lolly.

Yeah, well you know the truth is John, there’s always going to be somebody out there that is better, faster, prettier, smarter, wiser, more handsome, than we are. Trust me, I know that for a fact; but if we take that out of the equation and we only bring it inward, right, where we have that inspire, we inspire ourselves.

So those are two things that really, really work. I’ve been doing their practice for a long time. Guess what? Every single day, I do better than I did the day before. Can you imagine, after 30 days of doing that, where you’re going to be at in your mind, and where you’re going to be at in your business?

Think about it this way. If you’re pitching someone, how can you pitch better tomorrow? What can you do better tomorrow? What else can you add? What else you can delete so it’s much better? So I think that’s a game changer.

That’s a huge game changer. First of all, you’ve given us the real secret formula to confidence as it replaced to competence and capabilities, and then the real secret to why some of us, or most of us, feel like imposters. The fast cure is ask yourself these questions at night, and secondly, stop comparing yourself to other people. Even if you start to catch yourself doing it, going, “Oh, whoa, what am I doing here? No wonder I feel like an imposter,” that combination is a huge win.

I just want to tell you a little secret. Most people that are in the room feel exactly the way you do. Just know that. I sit with very high-level individuals, and non-achieving individuals and they say, “Lolly, I feel like an imposter, they’re going to find out I’m not as smart as I am. I didn’t go to the best schools. I’m sitting on this board and I have thousands of people listening to me. I can’t believe it.” So just realize that we all suffer from it.

Nice, the empathy factor really helps there. One of the things you talk about is why training fails to solve the problem. I’m really fascinated by, okay, you give somebody some information, they teach their team, “Okay this is what we want to do now,” but this whole concept of soft skills is really where I want to take a little deep dive. I’ve worked with architecture firms, and they’re always shocked when they hear from their clients that, we’re going to pick the designer to redesign our offices or build a skyscraper; not on your designs, but on who we like the most. And the soft skills of likability, and empathy, and confidence, and storytelling, are just not taught and they don’t know how to keep using them. They keep going back to, “Oh here’s my design, do you want to hire us.” How do you get people to first see it, and then train their team to do it?

Interesting that you’re talking about that because you might not know this, but I read a book a day. What I noticed was, in the books that I was reading about business and leadership, most books will tell you how to be. They’ll tell you what to do, they’ll tell you even why to do it, and I think that they were missing the core foundational as we talked about earlier, that humanness. What brings you to greatness, is that who we are. I think most people align themselves with the person that knows the most about themselves, and who knows what I call, their greatness. Who stands from their best potential, who brings out their humanness, who has loyalty and trust, and confidence, and integrity.

All those delicious things that people feel connected to. And so, when I work with leaders, I always say, “It has to start with you. You have to lead by example. You have to show others what it means to be a true leader. It means about leading from within. You have to find out who you are and what’s important to you. Then you have to let people know what’s important to you, and how their story, who they are, is important to you. So not only you have to know about yourself, but you have to show interest in others, and it’s the celebration of who we are as a collective, is what makes a company so successful.”

It’s funny I was having a conversation earlier today and they said, “You know, why do you get hired, Lolly?” And I said, “Well most people hire me because they want the results that I was able to give another organization. They were able to reach their targets, their employee engagement has gone up, they’re making more money, all the wonderful things that people hire coaches for,” correct? Then I come in and I say, “Well, we’re going to talk about who you are,” and they go, “No, no, no, no, no, we don’t want that. We want what you did for the other company, we want to know how to reach our metrics, we want to know how we can make more money. We want to know how we can have more employee engagement, that everybody feels connected, here.” And I said, “Yeah, it starts with who you are.” And they’re like, “No,” I go, “Yes, it does. Just give me the six months and you will see the revenue will go up. The results will be met, the targets will be met.”

So most people are like, “We don’t really want to do the work,” I said, “I know, it’s hard work. It’s usually the soft things, right, that are the hardest things to do. They’re not easy at all. Taking a little bit longer when you see someone and asking them how they are and connecting with them, takes a little bit more than, “Okay, do your job. You have to stop, you have to listen, you have to learn about others.” And I think that’s very effective when it comes to training and connecting with people.

I love it. Well, you gave us a little snapshot of one of the seven different archetypes of the rebel, do you have another favorite one that you want to share? I’m really intrigued to learn about the navigator because I think you’re always pivoting when you’re leading and things are changing all the time, but if there’s another one you want to talk about, I think that would be great.

I love them all because they’re within all of us, so let’s talk about the navigator. And it’s everybody on this podcast. It’s everybody who is smart, everybody who is good at solving problems, and the way they solve problems is being very practical and very pragmatic. They can look at something and they can solve it. What makes them really great, is then when people come to them with a problem, they navigate them, they steer them, they guide them, and because they do that people trust them. You recognize a navigator very easily, but, there’s a gap. For ever navigator that is very good at navigating and staring, and having people trust them, the gap is a fixer who becomes arrogant. The fixer sounds like this, “This is what you need to do. This is how you should do. This is when you should do it, and this is why you should do it, now go do it.”

So that fixer, and I’m sure we’ve seen this, A, in our marriages, we have seen this in our partnerships. Somebody comes to you with a problem, and instead of just stopping and listening, we all of a sudden want to solve the problem for them so it goes away. Guess what we’re doing? We’re disempowering them. A true leader, a successful person, will empower people by listening and then starting, but not fixing it. Not saying, “This is what you need to do.” Most people know what they need to do, they just need to be able to talk about it, talk through it and say, “You know what, that’s what I’m going to do. That makes sense.” That’s how we empower people. The best coaches are navigators, the best leaders are navigators, the best entrepreneurs can navigate through things and empower the customers, their clients, their joint venture, anything. They know how to navigate and that’s what we have to remember. At any given moment, we can ask ourselves, “Greatness, or gap. Navigator, or fixer.”

Well, you know men, in particular, have this reputation of trying to fix everything as opposed to just listening. But certainly in a leadership role, when someone comes to you with a problem, you get them addicted if you’re always fixing their problems, right? They don’t even start to think for themselves, they’re like, “I don’t even want to think for myself, I just want my boss to tell me what to do,” and that never develops them into a leader, does it?

Absolutely not, and if you own your company or let’s say you’re a coach, let’s go to that for a second. Let’s say you’re coaching someone, and you’re always fixing their problem. That person’s going to end up blaming you, “You couldn’t fix my problems,” and they’re either going to fire you, or they’re not going to want to work with you. If you’re a boss, and you’re always telling people what to do, and they are not allowed to showcase who they are, they’re going to leave. They’re not going to stay because they don’t want to do it your way, they’re there because they have capabilities and competence, right? And they want to showcase them.

You’re really an expert, Lolly, in giving us contrast and distinctions, and the one I really am curious about is the gap that happens between having an intuition and using that for manipulation or for good. Can you tell us a little bit about that?

Yeah, I love that archetype. That archetype is the explorer. The explorer is someone that wants to go into unchartered waters. It’s starting a new business, it’s starting a new venture; something that hasn’t been done before. What I have found is, the best explorers use their intuition. They use their intuition to go to new places, new thoughts, new ideas. Why? Because intuition, the concept of intuition, is letting go of what you know, in order to let something new come in. When you do that, guess what you have to do? You have to let go of control. You have to let go of, this is how it has to be. And when you can’t let go of control, you find yourself in a gap. And you find yourself being an exploiter who manipulates. An exploiter is someone who wants so much control over what is going to happen, that they end up using people, and they end up manipulating people in a way that they don’t even realize it.

It’s someone who comes in and says, “Get it done now, do it my way or else you’ll pay the price for it.” That’s not the way to create something, that’s manipulation. That’s exploiting people. When we go into new places, when we find ourselves at the edge of our discomfort, the thing is that we have to allow to become the explorer and to let things come to us because, the truth is, is that we only know what we know. Intuition allows us to go to a place we might not have thought of. So somebody might say that, “What is intuition? I want to understand what intuition is.” The science of intuition tells us that our brain is almost like a memory chip. We see things and it goes into our brain and there’s a chip, and there’s another chip, and another chip, and another chip, and so what happens is over time there’s all these chips in our brain of information and knowledge that we’ve accumulated. Intuition is that all of a sudden those chips get connected and we say, “Ah, I know what to do.” That’s intuition.

I love that definition.

It’s connecting the dots from all our previous experiences, as opposed to just, “Oh, well, it’s a gut feeling,” I love that there’s some science behind it.

Yeah, the science talks about that it’s the chips in our brains that get connected, that’s why if you ever listen to someone speak who’s very intuitive, they say things that have five words or less. That’s how you know they’re intuition. They go, “Get it. Done it. Know it. Feel it.” They speak in very short words because all of a sudden they got so connected, it’s almost like an energy that comes out that says, “Get it done.” The minute you use the word because then it is not intuition. So be careful.

Oh, that’s interesting. Because you’re justifying something as opposed to just stating it.


This whole concept of needing to be in control versus trusting your intuition, especially when you’re pitching. If you feel like you have to try to control the potential buyer, and, “You should do this, and you should do it by this time, and here’s why, because the price is going up,” or blah, blah, blah, blah, blah, and creating all this scarcity, is really manipulation more than intuition, don’t you think?

Brilliant John. I couldn’t have said it better. That’s exactly what it means to stand in your gap. That exactly what’s going to cost you and anybody saying, “I want to work with you, I want to do business with you,” so I couldn’t have said it better.

Oh, thank you. Well, I love what you’re talking about, I think it’s very valuable, I think we’re in the gap and we’re not even aware of the gap. First of all, whether you just want to lead yourself, if you have your own business or you just want to become a better leader, this book, The Leadership Gap: What Gets Between You and Your Greatness, is so important for everyone. Whether you perceive yourself to be a leader or not, because until we become aware of these different archetypes, and figure out what the contrasts are, we can’t even begin to change our behavior or improve, and then go back to the questions that you ask yourself at night. So I am going to, not only say, “What did I do great today,” but then put it in the context of, “What did I do great today as the explorer, and what could I do better tomorrow as the explorer.” That gives me a whole nother frame of reference.

I love that. I just want to say one thing about what you just said, can I add something?


For anybody that believes that they’re not a leader, then I say that’s not the truth; because the definition of a leader means, are you influencing someone? Are you impacting someone? Are you making a difference in someone’s lives? And I think every single person can say yes. That to me is a leader. You don’t have to have a title or a position – it could be a mom, it could be a dad, it could be a coach, it could be anybody in your life that is when they talk to you – they make a difference in your life. They’re having an impact. So I believe everybody’s a leader to someone.

Source: Pexels

That’s so great and so valuable. That motivates everybody’s self-esteem, to start thinking of yourself a leader even if you don’t have the title of manager, VP, or what have you, in or out of a company. I love that, because as a parent clearly, you lead your children. And you know, I think it keeps going back to what you said. You look inside, you gotta lead yourself, you gotta parent yourself-

Since you read a book a day, I guess I want to ask you, in addition to your own book, is there a book you want to recommend that has inspired you or give you some really great insights that you want to share?

Absolutely. So there’s a book that I read every day, excuse me, there’s a book that I read every year on my birthday, so I re-read it and I’ve been doing it for 27 years.


The book is called, Man’s Search for Meaning by Viktor Frankl. I don’t care what business you’re in, I don’t care how old you are, this book is a book that will give you a code of conduct for the rest of your life. The reason I read it is that it reminds me of, number one is, there are so many wonderful things. It teaches me that whatever I’m going through, whatever challenges I’m going through if I could find meaning in it I’ll be able to survive it.


It teaches me when I could no longer change a situation, then I have to change myself. It teaches me that I can’t take anything for granted and that if I need to, as I call in my words, “Move myself to greatness,” maybe I need to change my attitude. It just teaches me these wonderful things and reminds me year after year to just keep grounded in the aspects of how I want to live my life. So A Man’s Search for Meaning is a book that I buy them in droves and I give them out as gifts. It’s just an amazing book.

Well, speaking of amazing books. Yours is certainly up there in my mind, The Leadership Gap: What gets Between You and Your Greatness. And your twitter handle is @lollydaskal and obviously, we’re going to put it in the show notes, you can get the book online. I can’t thank you enough for sharing your wisdom. You really have great insights into how we can all be leaders and make a difference and an impact.

Thank you so much for having me, it was a pleasure and a privilege.

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