Drew Dudley on Day One Leadership and “Lollipop Moments”

Drew Dudley is an internationally acclaimed leadership coach, best-selling author, and renowned TED speaker. 

He is on a mission to help people unlearn some dangerous lessons about leadership. As the founder and chief catalyst of Day One Leadership, he has helped top organizations around the world increase their leadership capacity. His clients have included McDonald’s, American Express, JP Morgan Chase, the United Way, and more than 100 colleges and universities. 

Today, he’s going to share insights regarding his “Day One” process of leadership, acknowledging failure, and the importance of the “lollipop moment.”

Lollipop Moment

Drew started telling the story about his “lollipop moment” to young fundraisers to demonstrate that how they go about raising money is the most important part of building their legacy, not necessarily the amount of money they raise.

The story goes something like this. 

Drew was working on a fundraising effort at a university, and was talking to students on registration day. 

There was a young woman very nervous about starting her first day, and she told her parents she didn’t think she could do it. Then, Drew approached the group she was standing in, gave a lollipop to the boy standing near her, and said “give this to the beautiful girl next to you!”

She didn’t tell Drew this until four years later, but that was a major moment that convinced her to stay at university. And that guy who handed her the lollipop? Now, he’s her husband.

But the woman didn’t tell Drew this until four years later, when he was about to leave that university. That’s the key to his lollipop theory.

“Maybe the most powerful moment of leadership in my life and the biggest impact I had on another person is a moment I don’t remember.”

The takeaway for the fundraisers he coaches? You’re going to be having experiences like that that are so good for you and for your organization along your journey. So don’t just look at the money. Think of all those lollipop moments. And on a broader scale, Drew said this showed him that most of the impact you’ll have on the world will not be in the ways you plan, but in the unplanned consequences of your actions. By recognizing and harnessing the power we have to positively influence others, we can create more of those moments. 

It’s a philosophy that applies to the most well-known CEOs and those who might not even think they’re a stereotypical “leader,” which is the most powerful takeaway of Drew’s message: we all have it in us to be a leader, we just have to reshape what leadership means. 

“Most of the leadership on earth comes from people who don’t consider themselves leaders. That to me is something we could shift.”

Why do you matter?

Why is it important that people see themselves as leaders? Drew said it gets to the core of how people value themselves.

In his workshops and talks, Drew often asks participants why they think they matter. And most respondents can’t come up with an answer. This, to him, is unacceptable. 

“Unless we have evidence that we matter, we deny that we do.”

If we embrace this lollipop theory, this idea that we have the capacity to change others’ lives for the better, we do matter. 

The Day One Process

Drew’s “Day One” process has a simple goal: closing the gap between who you are and the person you want to be, so you can create more of those lollipop moments. 

Drew says there should always be a gap between those things, because you should also be striving for self-improvement. But his work focused on narrowing that gap as much as possible. 

When building this process, Drew called upon some experiences in his own life: his diagnosis with bipolar disorder, struggles with alcoholism and weight loss journey. When he struggled through these things, he realized the importance of recommitting to a goal on a daily basis. 

“You have to treat every day of the voyage as if it’s the first day. Because that means you can’t rest on your laurels from the past, and you can’t be intimidated by how many more days there are to stay committed to this.” 

A key part of this process is prioritizing your “to be” list over your “to do” list. To stick to the former list, Drew encourages his followers to ask themselves six questions every morning, developed through the following steps:

  1. Pick your values
  2. Define what they mean
  3. Turn them into questions
  4. Look at those questions every single day to “pass” your own test

It’s a system rooted in behavioral psychology, which showed him that questions are a more powerful driver of human behavior than goals. When building it, he called upon:

Zeigarnik Effect: The items on your to do list take up more mental space than completed items

Question Behavior Effect: Asking questions about a behavior makes one more likely to engage in that behavior. 

Forgiving Yourself

When Drew was struggling with the incredible obstacles he faced: his partner dying by suicide, battling addiction, weight and mental illness, he realized he needed to rethink the role tragedies and failures played in his philosophies. 

“Build failure into the plan,” he said. 

For the participants in the day one process, that means they’re allotted 65 days in a year where they can not answer those questions they’ve set for themselves. 

In Drew’s life, those days might look like eating a large pizza instead of sticking to his diet. But those dozens of days don’t negate the hundreds where he remained committed, and the 100 lbs he lost in the year he stuck to this plan.

Special Offering:

Drew’s full, interactive online leadership development program Day One Direct is available for only $10 USD (Regular $199 USD). The proceeds support front line healthcare workers. Details can be found here.

Drew recommends you read:

Good to Great – Jim Collins 

The Five Dysfunctions of a Team: A Leadership Fable – Patrick Lencioni 

Linchpin : Are you Indispensable? – Seth Godin 

Everything is Wonderful and Horrible – Stephanie Wittels Wachs

Connect with Drew:

Drew’s website: https://www.drewdudley.com/

Drew’s Book: 

This Is Day One: A Practical Guide to Leadership That Matters: https://amzn.to/2zZvMZw 

Follow Drew on Instagram: https://www.instagram.com/dayonedrew/

Follow Drew on Facebook: https://www.facebook.com/DayOneDrew/

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