Overcoming Leadership Insecurity: Kylie's Journal

October 3, 2016

This journal is an opportunity to share my voice with the Chic Geek community, let you know what’s happening inside the organization, and publish my musings as a founder, entrepreneur and leader.


<3 Kylie





In the past year, the Chic Geek team has grown 120%! Today, I’m humbled to count 20 dedicated women who share my passion for technology and entrepreneurship.


I’m excited to welcome our most recent team members:


Lena Shulyakovskaya, Mentorship lead

Denise Duncan, Events Coordinator

Rayne Grein, Meetngeek Organizer



I’m a young leader and I have moments of insecurity, where I think, “What am I doing?” Often, I have more questions than answers when it comes to leading this fast-growing team.


I’ve made mistakes - plenty of them - learned, grown, and then made some more. I’m imperfect and it’s a never-ending cycle, but Chic Geek is a learning ground. Not just for me, but for our volunteers and community members too.


One of our core values is STAY CURIOUS - we never stop learning (AKA making mistakes).



I want to be a leader that creates a safe environment for team members to make mistakes and learn. I want to open dialogue for honest, two-way conversations about where things could be better.


But how do I achieve that? I’m on a journey to become a good leader and a good manager. Some of my learnings have been inspired by books I’ve read and podcasts I’ve listened to (see note at the end for a list of my resources). They also come from conversations with individuals I look up to and admire.


Most recently, I spoke to Trent Johnsen, CEO of Hookflash who had the following advice:



1. Communicate the BIG PICTURE


Practice sharing the vision of where you’re going. Get your team excited about the destination and ask them to help you along the journey. At Chic Geek, I share our vision and mission at every team meeting and incorporate it, as often as possible, in emails and Slack messages to our team.



2. Come from a PLACE OF SUPPORT


Leadership is built on personal credibility and trust. SUPPORT EACH OTHER Other is another Chic Geek value and that means we foster a “help me, help you,” mentality. Servant leadership means caring about the people you work with.



3. Don’t eat other people’s FROGS!


Mark Twain captured it best. He said, “if the first thing you do each morning is to eat a live frog, you can go through the day with the satisfaction of knowing that is probably the worst thing that can happen to you all day.” In this case, frogs are those tough tasks that we want to avoid. We all have them, but as a leader, it is not your job to eat everyone else’s frog.


In other words, focus on your own frogs. While I support others with theirs, I merely encourage them to work through their own frogs rather than taking it on myself. Leadership is about EMPOWERING OTHERS to find their individual resourcefulness for worst case scenarios, not solving all the problems by yourself.



My next leadership learning focus is around setting and managing expectations.


If you have any advice or are struggling with this too, leave a comment or tweet us at @chicgeekyyc.


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