Lolly Daskal on Leading from Within

When Lolly Daskal was 18 years old, she looked in her mirror and asked herself a single question:

“Lolly. Who do you want to be in this world?”

She arrived at a simple answer:

“Every time I encounter someone, I want them to feel better because they were in my presence.”

At the time, Lolly didn’t know she would go on to be a world-renowned leadership executive coach, best-selling author, be named Most Inspiring Woman in the World by the Huffington Post, or give a Ted Talk with over 2 million views. Today, she’s here to share the leadership insights she’s learned from the decades in the industry that got her to where she is today. 

Watch this conversation with Lolly on my Youtube channel here.

The True Leader

Lolly said that for years, we’ve been stuck in a rut of valuing the wrong type of leader, and that we need to fundamentally shift these priorities to create more effective leaders in our society. 

“True leadership comes from not those in power, but from those who empower others,” she said. 

Instead of looking to the loudest person in the room, Lolly said we should look to those who have a strong inner architecture and lead from within. 

Overcoming Imposter Syndrome

Studies show that the overwhelming majority of us suffer from imposter syndrome. So how do you climb past that massive barrier? 

First, know you’re not alone. “We’re in good company,” Lolly laughed. 

Second, remember that knowledge comes through power. If you’re feeling self-doubt, Lolly said it’s imperative to “become a student of your own business.” Additionally, there’s power in recognizing your strengths and weaknesses. 

“I’m a big believer that we have to leverage our skills and our strengths, but if we don’t know our weaknesses I believe they end up owning us,” Lolly said. 

At the core of a successful leader is a strong sense of character, Lolly explained. And in order to develop that character, you must constantly reflect on how you can improve, not get distracted by others. 

“We’re so busy comparing ourselves to others that we don’t get to learn about ourselves,” she said. 

Finding Courage In a Time of Perceived Helplessness

Few lives have remained unscathed by the coronavirus pandemic, and as people reel from the impact, Lolly said it is the most essential time to think about being a leader. 

“When we think we have no control, I think it’s most important to go inward, find out who we are, and do the things to motivate us to get us out of our little bubble of thinking we have no control,” she said. 

This challenge may be profound and novel, but like any obstacle we may face in our lives, it’s one that offers an opportunity: will you live in your greatness or your gap?

“We have tremendous opportunity. Because most people are feeling overwhelmed, challenged. So the person who steps up is the person who is going to stand out.”

For all of our listeners leading teams during this uncertain time, Lolly has a story from centuries ago, which she also shared in her wildly popular Ted Talk. When Alexander the Great led his men through the Bactrian desert, he refused to drink any water they offered him, not wanting to take any from his thirsting troops. 

Similarly, during this time, Lolly said you have to meet people where they are at. 

“Get into the foxhole with your people. Find out what they’re suffering from. What their challenges are. Let them feel supported. Let them feel that you care.”


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