Lolly Daskal's Headshot

209: Lolly Daskal on How Curiosity & Self-Reflection Can Set You Free

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Lolly Daskal's HeadshotLolly Daskal is one of the most sought-after executive leadership coaches in the world.

As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world. Based on a mix of modern philosophy, science, and nearly thirty years coaching top executives, Lolly’s perspective on leadership continues to break new ground and produce exceptional results.

Of her many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of  The Most Inspiring Woman in the World.

Her writing has appeared in Harvard Business Review,, Fast Company (Ask The Expert), Huffington Post, Psychology Today, and others.

Click to tweet: .@lollydaskal is sharing her story on Women Taking the Lead #inspiration

Playing Small Moment

Early in a difficult childhood, Lolly made a conscious decision to not play small or undervalue herself as she journeyed through self-discovery. Lolly was a curious child and an avid reader who became enamored with her life, finding out who she was and what life was all about. While reading Viktor Frankl’s Man’s Search for Meaning, Lolly really identified with the challenges and finding meaning behind them and rereads the book each year to keep the message fresh in her mind. Lolly knows that in her darkest moments she will find treasure, and knows it will always be an amazing learning experience.

Each night before bed, Lolly asks herself a two-part question that allows her to revel in daily triumphs and set goals for the following day. Lolly knows now that life is in stages, and the decisions you make at a certain level must be the right choice for that point in your life.

The Wake Up Call

Lolly has a history with perfectionism and had to learn the difference between perfection and excellence. She thought she had to be perfect and on top of everything and ended up exhausting herself. Lolly started asking herself if she was trying to achieve perfection or excellence. Being perfect is not achievable, but Lolly knew she had to bring quality and excellence to what she does and let the ideal of perfection go.

Style of Leadership

Lolly leads from within and by example. She does everything with heart, compassion, empathy and without judgements or assumptions. Lolly truly tries to be present in the moment with each person or group that she is with, either virtually or in person. Lolly feels that if she can be present in the moment, it allows her to have a robust future of all the great little moments that add up.

What Are You Excited About?

Lolly’s lifelong dream of being an author is coming true with her first book, The Leadership Gap: What Gets Between You and Your Greatness. Lolly is extremely excited and passionate about this book, as she has written about the methods she uses with clients so people can coach themselves, and have awareness about themselves, in a way that they normally wouldn’t. This book is different than other leadership or business books, as it’s not about what you should do, but about who you should be.

Biggest Leadership Challenge

With Lolly’s dream in full force, her perfectionist self has come back in full storm. Many years ago, Lolly made a promise to herself that she was going to live each day with a purpose of serving others. It’s hard keeping that promise, being of service every day. So, Lolly’s goal of reaching the New York Times Bestsellers List, would enable the book to become its own entity and allow her to help others she normally wouldn’t be able to.

Leadership Practice

Lolly has a couple of practices that allow her to be a better leader. Being disciplined and coming up with rituals on a daily basis, gives her the freedom to be who she wants to be. Every night she asks that two-part question, and in the morning between 4:30 and 6:30, she reads an entire book. These practices make her a better leader because she is always learning, growing and changing.

Advice For Younger Self

Have more compassion. Lolly says her compassion came from not having compassion, and suffering about it, when she was younger. Lolly would also advise her younger self to not be as harsh on herself and learn that it’s okay if things aren’t working out the way she wants. Everything will be ok.

Inspirational Quote

“Greatness is a destiny that is available to anyone. We just have to choose it.”



BOOK WEBSITE: Lolly’s proprietary insights are the subject of her new book, The Leadership Gap: What Gets Between You and Your Greatness, and is available for pre order now.




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