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 MomentDrew 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 ProcessDrew’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-improveme...