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The Enneagram & Work: Why Self-Awareness Matters

When I took over as the Director of Marketing for Breakout seven months ago, I immediately sought out knowledge in all forms regarding leadership and management. Leading a healthy, happy, effective team was new territory for me. But leadership concepts are about a dime a dozen these days. There are endless books, podcasts, lectures, TED talks, etc. available in the market to learn from. The volume can be overwhelming. Where do you start? Which principle is most important? Is there something I’m missing that’s going to screw my team up?

These were all honest questions and the information out there is (mostly) all helpful. But I believe that beyond textbook knowledge on leadership & management, one thing has stood out to be the most important and impactful thus far — truly knowing yourself & knowing those that work around you.

The Importance of Self-Awareness

Earlier this year Forbes online published an article stating that self-awareness is both essential for great leadership & significantly lacking in today’s workforce. If at this point you haven’t entirely bought-in on personality typing or are annoyed with everyone comparing “numbers” lately, here’s where I challenge you to set down pre-conceived notions and lean in.

Let’s take the Breakout Marketing Team for an example. As director, I’m driving a ship with two helpmates churning out a lot of content and managing many accounts. I am a textbook 1w2 on the Enneagram.

What This Means for Me

Details matter – a lot. Quality & making sure we catch and/or quickly fix any and all hiccups matters deeply. A clear plan of action with all necessary details outlined is essential for a functioning workplace, in my mind. The fear of something not being perfect can make me hesitant to ship quickly. I feel a big pull to keep projects on my own plate or jump in to help others along, thanks to my 2 wing. I’m hardest on myself rather than seeking fault in others.

What This Means for Our Team 

We’ve built a team around what we have & what we need. Details are important, both to me and the bottom line. While I handle the details and pacing of project management, Ryan (who is also a 1w2) handles the nitty-gritty numbers, digital posting, regulating & updating ads. He handles those details so that I don’t have to stay in the weeds, allowing me to have more margin to manage and Ryan to be the resident expert on all those things. His strong helper wing also means that before I can jump in to “help” on new projects or unforeseen fixes, Ryan is already one step ahead of me getting it done.

Marketing doesn’t happen without creativity and content. Also, operating a company with many integral people spread out across the country means relationships are key. Colin as an Enneagram 9 is a true treasure. 9s are known for an uncanny ability to pull characteristics from all other numbers on the Enneagram most effectively. The consistent creativity & inspiration of a 4, mixed with the 3’s willingness to perform in front of the crowd, plus the spontaneity and fun of the 7, with the helpfulness and customer-service inclined mind of a 2, Colin not only creates & stars in our Breakout content, but he also coordinates the communication for all our wonderful managers.

Colin & Ryan’s abilities to do what they do really well in their roles allows me to do what I’ve been called to do in my role — lead & manage. Because I know that who they are in their core is well-fit for the tasks at hand, I can trust them without micro-managing. Because I know myself, I also know where to press in, and where to back off. I can articulate my weaknesses to my leadership & my team, surround myself with those strong in areas that I am not, and know when to hold on to the tasks that are a solid fit for where I shine (hello, Basecamp).

Successful leaders know where their natural inclinations lie and use this knowledge to boost those inclinations or compensate for them.” – Forbes

This matters. Knowing you — the real, deep-down, when push comes to shove you — matters. To know how to lead and manage others well, you have to know who you are as a person and how you uniquely interact with others. If you haven’t already done so, I highly encourage you to dive into your Enneagram number and those of your team. Knowing the core personalities, strengths, and weaknesses of each person on the team not only makes everyone more self-aware, but it also creates a common language and channel for open communication.


4 Responses

  1. This is a really fundamental concept to grasp before you can grow as a person, friend, employee, leader, or anything else. You just have to know yourself well in order to get better.

  2. Basher says:

    Thanks for the in-depth post Cassie!

    • Cassie Dilly says:

      Thanks for reading, Brian! I’d be interested to know the types of each of the managers in your region. It was really eye-opening to have our leadership team at HQ discover their types and see how many similarities existed. Lots of 3s back here in the Warehouse!

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