Lolly is one of the world’s leading executive coaches, working directly with Fortune 50 CEOs and top political leaders. A pioneer of heart-based leadership, she is a regular columnist for Inc., Fast Company, Harvard Business Review, Huffington Post, and Psychology Today. She is one of the most prominent leadership voices of our time. She has been named one of the “The most inspirational woman” by the Huffington Post and featured in “100 Great Leadership Speakers for Your Next Conference” by Inc.
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- The Hero With A Thousand Faces by Joseph Campbell and Man’s Search for Meaning by Viktor Frankl – Lolly’s Top Business Book
- Lolly Daskal – Lolly’s website
- The Leadership Gap: What Gets Between You and Your Greatness – Lolly’s book
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3 Key Points:
- Leverage the impostor syndrome to be able to do what you need to do.
- Ask guiding questions in order to dig deeper and develop trust with others.
- Be the best you can be rather than aiming to be perfect.
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Time Stamped Show Notes
(click the time stamp to jump directly to that point in the episode.)
- [01:03] – Lolly is a single mom of three adult children. She loves being a leadership coach and has been for the last three decades – she’s always on the move
- [01:44] – One BIG and Unique Value Bomb: Lolly helps every single one of her clients realize the greatness that lies within them. Every entrepreneur and business person wants to do something significant but feels they are not enough. Lolly says this is the impostor syndrome wherein people believe that they cannot do it
- [02:41] – Lolly teaches people to leverage the impostor syndrome to be able to do what they set out to do
- [03:10] – Lolly says the impostor syndrome comes from envious feelings and from comparing yourself to others
- [05:02] – Worst Entrepreneurial Moment: Three decades ago, Lolly felt the impostor syndrome when someone approached her to ask for help with a business problem. Lolly felt she did not know enough and doubted herself
- [07:12] – JLD’s favorite question is – what is your biggest struggle right now? – he gets to know the person and is able to provide an answer because of that question
- [08:11] – Greatest AH-HA Moment: Lolly thought that she had to be perfect when she was just starting her business and this kept her from being who she needed to be
- [09:37] – JLD says it is important to ask questions
- [10:22] – Lolly learned there is a certain way you need to ask questions
- [12:36] – What is the one thing you are most FIRED up about today? Lolly has just finished her book – The Leadership Gap: What Gets Between You and Your Greatness
- [13:12] – Every person can relate to the book and it will help you get out of your gaps
- [13:57] – The Lightning Round
- What was holding you back from becoming an entrepreneur? –“Being perfect”
- What’s the best piece of advice you’ve ever received? – “Do what is right, not what is easy”
- What’s a personal habit that contributes to your success? – “Reading a book every single morning from 4 – [6:30] AM”
- Share an internet resource, like Evernote, with Fire Nation – HootSuite
- If you could recommend one book to our listeners, what would it be and why? – The Hero With A Thousand Faces by Joseph Campbell and Man’s Search for Meaning by Viktor Frankl
- [16:33] – Go to EOFirebook.com to get either of the books for free from Audible! (new members only)
- [16:55] – Connect with Lolly on her website
- [17:08] – Greatness lies within you, but you must make that choice in order for it to happen
Lolly: Yes, I am.
Lolly: Yes. Yes.
John: Lolly is one of the world’s leading executive coaches working directly with Fortune 50 CEOs and top political leaders, a pioneer of heart-based leadership. She is a regular columnist for INK, Fast Company, Harvard Business Review, The Huffington Post, and Psychology Today.
Lolly, take a minute. Fill in some gaps from that intro and give us a little glimpse of your personal life.
Lolly: So, who am I? Lolly Daskal is a single mom of three adult children. And I am a leadership coach and business consultant who has been doing it for over three decades. And I love what I do.
John: Wow. Love all of that. And you’re in New York City, am I right?
Lolly: Today I am. I’m usually on a plane, a train, or an automobile.
John: Well, that’s a good place to be based out of then. Because there’s a lot of all of those things in New York City. And Lolly, one thing that I’m curious about is what your specific area of expertise is. How would you break that down and then move on to what we should probably know as entrepreneurs about your area of expertise that we probably don’t?
Lolly: What’s unique about what I do is with every single one of my clients, I help them realize that greatness lies within them. Now, you might be saying to yourself, what does that mean?
Every entrepreneur, every CEO, every businessman and woman that I’ve ever encountered, and this is if I’m coaching them, facilitating them in workshops, talking to them at events and conferences, every single person comes over and says to me the same thing, “I wanna do something significant in the world. I wanna do something impactful in the world, but something inside me feels like a fraud. Something inside me doesn’t believe that I can do it.”
And so, the first thing that I always say to every single person that I meet, “Greatness lies within you. Because what you’re suffering from might be the imposter syndrome. And the imposter syndrome strikes 99.1 percent of very high-achieving individuals.” And then I teach people what does it mean to leverage the imposter so they can do what they need to do in the world.
John: So, let’s kind of get a little granular right here. What’s something that we, entrepreneurs can really take out of what your area of expertise is and maybe apply to our business, to our life, even to our day-to-day?
Lolly: Absolutely. So, let’s go back to the imposter syndrome because I think every single person listening to your pod suffers from it from one – in one way or another. And so, the first thing we have to understand, where does it come from?
The imposter syndrome comes from the driver and we get triggered by when we’re busy comparing ourselves to others. When you’re constantly looking over your shoulder and saying, “Oh, my God. Look what John Lee’s doing. Look what Joel’s doing. Look what Richard’s doing. Look what Susan’s doing. Look what Sarah’s doing.”
Then what you’re doing constantly is looking outside instead of looking inward. If you’re constantly comparing yourself to others, then you don’t have time to work on your business. You don’t have time to be the entrepreneur that you really are. You can’t ignite the way – I love John Lee says, “How do you ignite? Are you ready to ignite?”
So, if you wanna ignite the driver to compare yourselves to others has to be leveraged. And the thing that we can do to help each other or to help right now in this moment is to say, “I’m gonna stop comparing myself to anybody else. But I’m going to measure my success from within.” Meaning we go inward and we decide what is our capabilities? What is our competence? That will give us the confidence to do what we need to do.
People think that in order not to be an imposter is to “fake it until you make it.” I don’t believe in that. I believe it becomes from knowing what you’ve mastered, knowing what you’re good at. That will give you the confidence to show up and ignite the way you need to ignite.
John: Well, you have wisdom, you have experience, you have successes. But like all entrepreneurs, you also have failures. And I wanna dive into not just one of those failures, but the worst entrepreneurial moment that you’ve experienced to date. So, Lolly, rip off that Band-aid, take us to that moment in time that you consider your worst entrepreneurial moments and tell us that story.
Lolly: So, the reason why I can talk about the imposter syndrome so well is because it happened to me. Over three decades ago, I was teaching a workshop and someone came over to me and said, “I really need you to help me with a business problem that I’m having.” And John, for the first three seconds, I’m like, “Why the hell is he talking to me? I don’t know what to do.”
And I started to doubt myself. I started to think, “I’m not good enough. I’ll send him off to someone else. I’ll recommend him to someone else. I’ll refer him to someone else.” And it was in that moment that I was falling apart. I was feeling self-doubt. But I said to myself, “Okay, Lolly. What are you gonna do? You have a choice now in this moment. You have a choice to choose to get into the self-doubt, what I call “gaps,” or you can stand in your greatness and do what you know best.”
But it took me a couple of minutes before that choice was and I was like, “Start talking, Lolly, before he leaves. Start answering him before he walks away.” And what I did was what I think great coaches usually should do and could do is I was silent. I said, “I’m ready to listen. What’s your problem?”
And then I just kept asking him open-ended questions without fixing his problem. All I did was ask question up question, the way you do, John. You ask great questions, right? And you get people to reveal everything about themselves. And that’s what I did for two-and-a-half hours; all I did was ask questions. And before you knew it, he said, “Oh, I really like the way you make me feel about myself. I feel so empowered.”
And it went from being the worst moment, the worst entrepreneurial moment, because it almost didn’t start my business, to then being one of the best moments because I learned to be myself and to do what I do best.
John: Ask questions, Fire Nation. To me, this is just a simple and brilliant technique because how are you going to “fix somebody’s problem” or help somebody if you don’t even really know that much about them? Everybody has a unique situation, business, life, fill in the blank. Ask questions and one of my favorite questions by the way is, “What is your biggest struggle right now?”
Just let them open up about something that they’re struggling with day to day, an obstacle, a challenge, a pain point. But then you can start to learn more about them, so that down the road, after multiple more questions, after you’ve learned more about them, maybe then you can start to form what that actual solution will be in the form of, maybe it’s gonna be coaching. Or maybe it’s a product, or a book, or a service, or a community, fill in the blank then.
But not until you’ve asked the questions. The questions that make them feel like you’re getting to know that individual, that person in a real way, so you can actually provide them with a custom answer. Nobody wants just that blanket, that vanilla answer. We want an answer customized for us.
Now, on that note, Lolly, I wanna kinda shift to another story that you’ve had. Now, that was obviously an “ah-ha” moment of like, “Wow. I can just ask questions and get to know people.” But you’ve had a lot of these great ideas. What’s one of the greatest ideas you’ve had to date. Take us there. Tell us that story.
Lolly: So, when I first started my business, I thought that I had to be perfect. And I thought that I had to be the smartest in the room. And I thought that I had to know it all. And I’ll never forget, I wasn’t doing a great job because I was so concerned about being the smartest and being perfect, that it was keeping me from being who I needed to be.
And I’ll never forget, we were sitting in a room, I was the only woman in the board room. And it was a bunch of guys sitting around the room. And everybody was asking questions and I was thinking, “Say the perfect thing, Lolly. Say the smartest thing.” And then they called on me and I missed my mark. I was like, “Huh?” And I was like, “There you go. Looking stupid.”
And after that, I promised myself, “Stop looking for perfect, Lolly. Stop trying to be the smartest. Just try to bring your best. Try to bring excellence to everything that you do.” Even if it means that they ask you a question and you don’t know the answer. Rephrase the question and say, “Are you talking about this? Do you mean this? Can I have clarity on this?” And that buys me time to start thinking of an answer that will make me smart. Or will allow me to have the answer to the questions that they’re asking.
But let go of being the smartest. Let go of being perfect. And just bring the best to every moment.
John: I love the theme that’s really developing within this interview, which is Fire Nation, ask questions. Always be a person of curiosity. Always be wanting to learn more and to know more. And to say, “Hey. I may know a lot about X, but I don’t know that much about A thru Z, minus X. And there’s definitely people that know more about X than I know as well.”
So, why can’t I just continue to have this mindset of learning? And continue to add value through this further learning that I’m going forward with.
So, Lolly, would that story kind of like now, in your back pocket, what do you wanna make sure that our listeners get or are really walking away so that we can apply this to our business?
Lolly: So, I really like the theme of where we’re going. It’s not where I thought we were gonna go, but it’s great about this. So, I would like to share something with your listeners that will give them an “ah-ha” moment. So, in the very beginning, even though I was asking questions, I learned that there’s a difference of how you can ask questions.
So, and this is a system that I teach. I might as well – this is a little secret that I’ll give to everybody listening today. So, in my system that I teach, there are two kinds of individuals. There’s two kinds of archetypes, and personas, and behaviors.
No. 1 will get you to greatness. The other one will lead you down a gap. A gap is where you’re most likely failing and not succeeding. The first way of greatness is, is for us to be a navigator. If someone comes to you with a problem as a customer, as a client, as a business, and they start asking you questions, the way to stand in your greatness is to guide them and steer them through a problem. It’s not to tell them what to do. But to be open-ended questions, to be inquisitive, to be the kind of person that gets involved and says, “How, what, when, and where?”
The opposite of that is when we’re standing in our gap, when we’re leading from our gap, when our business isn’t where it needs to be, when the person who we are is not at our best, is that we end up leading from the gap of the fixer. The fixer is when someone comes to you with a problem and all of a sudden, you start barking answer at them. You say, “This is what you should do. I’ve done it before. I know how to do it. This is the only way to do it.”
When you do that, people think you’re arrogant. When you lead as a navigator, people trust you. When you lead as a fixer, people think you’re arrogant.
So, the choice is yours. Do you wanna stand in greatness as a navigator and be successful? Or do you wanna lead from your gap as a fixer and most likely people will think you’re arrogant and it will cost you in your partnership, and your business, and your leadership, and in anything you wanna create.
John: Wow. I think that’s a pretty clear choice Fire Nation. Lolly, thanks for sharing that little secret with us there. What are you most fired up about today? I mean you just have kind of shared how you’ve gotten to where you are now by asking questions, by being curious, by always learning. Where has that gotten you to in the spectrum of where we are today? Like what are you really excited about right now?
Lolly: So, I have given birth to a new book. It’s called The Leadership Gap: What Gets Between You and Your Greatness. I’ve taken all the systems and all the knowledge and all the wisdom that I have worked with my clients, and you get to read about that in these pages, in my new book. But this is what has happened. Every single person that has read this book says, “Lolly, this is about me. How do you know me so well? I’m on every single page of this book. This story might be about a CEO, but you know what? I have the same problems.”
And that’s what’s so great. Every single person can find themselves in the book, so they can learn to stand in their greatness. But if you find yourself in your gaps, this book will teach you how to leverage those gaps so that you are successful. And you have the kind of business that you wanna have.
John: And Fire Nation, no matter where we are on our journey, we’re always either about to be falling in the gaps, getting out of the gaps, looking into the gaps. In the gaps though, this is gonna be a very valuable read for all of those things. And I mean Lolly’s only given you a little taste of what this is about. And I’m sure we’ll get into a little bit more of this later, but first, we have to thank our sponsors, then we’re coming back with our lightening round. So, don’t you go anywhere.
Lolly, are you ready to rock the lightening rounds?
John: What was holding you back from becoming an entrepreneur?
Lolly: So, the biggest thing for me is what I mentioned before about this thing about perfection. Being perfect. And I learned that perfect isn’t real. And if I can just switch the words from going for perfect and striving for excellence, I know that I can reach it. So, that has been the biggest shift for me. Learn to go for excellence and not perfect.
John: What’s the best advice you’ve ever received?
Lolly: Do what is right, not what is easy.
John: What’s a personal habit that contributes to your success?
Lolly: I read a book every single morning.
John: How long usually?
Lolly: I read between the hours of 4:30 and 6:30 in order for me to always be expanding, evolving, to be the best version of myself.
John: What are the best ways that you go about actually finding the books that you’re going to consume?
Lolly: So, I have certain subjects that I’m very passionate about and it falls under leadership, business, I love quantum physics. I like philosophy and psychology.
John: Have you read Extreme Ownership by Jocko?
Lolly: I have not. And guess what I’m doing right now everybody? I am writing that down.
John: Can you share an Internet resource like an Evernotes with Fire Nation?
Lolly: I use Hootsuite. And I’ve been using it for a while. I like it because it allows me to tweet – be over a weekend, I can put everything in there. But then it allows me to be present during the week and show up, and I don’t have to worry about what kinda tweets I’ve posted. I can be more present once I don’t have to worry about, “What did I say today?” Everything I wanna say is logged in. Now I can be present to whoever is speaking to me.
John: Now, you’ve read a lot of books due to your habits. Now, what would you say your No. 1 recommended book would be for Fire Nation, knowing that, of course, we already have Leadership Gap on our bookshelves, because we take action?
Lolly: Great. The Leadership Gap is a definite read. So, I have a tossup between two books. The first one is The Hero with a Thousand Faces. It’s written by Joseph Campbell. And anybody that has watched Star Wars knows it’s based on this book because it talks about the hero’s journey. And I think every entrepreneurial goes through their own hero’s journey. And if you wanna ignite, it’s a must-read.
And then as a life book, to be the best entrepreneur that you can be, I think everyone must read, The Man’s Search for Meaning by Viktor Frankl.
John: Fire Nation, you can head over to eofirebook.com to get either one of these on audible for free if you haven’t already. That’s eofirebook.com.
Now, Lolly, let’s end it today on a fire with you giving us a parting piece of guidance. The best way that we can connect with you, and then we’ll say good-bye.
Lolly: So, the best way to connect with me is if you’re interested in getting the book, theleadershipgapbook.com. And if you get it today, you get bonuses and gifts. And usually you can find me at lollydaskal.com. And what I’d like to leave everybody with is that greatness lies within you. But you must make that choice in order for it to happen.
John: Love it. Fire Nation, you’re the average of the five people you spend the most time with, you’ve been hanging out with LD and JLD today. So, keep up the heat and head over to eofire.com. Just type “Lolly” in the search bar. Her show notes page will pop up with everything that we’ve been talking about today. These are the best show notes in the biz. Time stamps, links galore. Of course, make sure you’re checking out, The Leadership Gap, her wonderful book. And her website’s lollydaskal.com.
Lolly, thank you for sharing your journey with Fire Nation today. For that, we salute you and we’ll catch you on the flip side.
Lolly: Thank you so much.
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