Everyday Leadership In Your Startup and Lollipop Moments

Drew Dudley presented at TEDxToronto and gave a speech that completely resonates with me. Drew spoke about “Everyday Leadership“. When I think about today’s leaders, I think about President Obama, Richard Branson, my ex-boss Stuart Mckee and the list goes on and on. Drew believes leadership is not a characteristic reserved for the extraordinary. He believes that each of us can discover the leader within ourselves.

“We’ve taken this title of leader and we treat it as if it was something that one day we’re going to deserve, but to give it to ourselves right now means a level of arrogance or cockiness that we’re not comfortable with. And I worry sometimes that we spend so much time celebrating amazing things that hardly anybody can do that we’ve convinced ourselves that those are the only things worth celebrating, and we start to devalue the things that we can do everyday. – Drew Dudley”

Last week I wrote about “Transparency: Too Much Or Not Enough In Your Startup Culture?“. I mentioned that we have a daily huddle and we share one thing that we appreciate about someone on the team. For me, I see leadership every single day in every single one of my employees when they are able to share what they appreciate about someone. Each of my employees has the ability to be extraordinarily powerful in each others lives.

In Drew’s speech he talks about how he was giving out lollipops. I’m not going to even try to paraphrase the story that he shares so I would highly encourage you to just go watch the entire TED talk. I will quote Drew one more time:

We need to redefine leadership as being about lollipop moments, how many of them we create, how many of them we acknowledge, how many of them we pay forward, and how many of them we say thank you for.

In our thinkspace culture we have three core values, one of them is:

  • Wow Customer Service, Every Engagement, No Exception.


When I think about this core value, I also think about how my team is creating “lollipop moments” every single day for each of our thinkspace members and their customers. There’s something really special in that. Every single day we can be leaders.

One of my favorite quotes comes from Tom Peters:

“Leaders don’t create followers, they create more leaders.”

What are some of your “lollipop moments” in your startup company?

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