At the urging of some colleagues, I've started working with a professional coach to help me work through some obstacles I encountered in this last year as a WordPress focus lead. I'm fortunate in that Automattic will pay for me to receive ten coaching sessions per year.

(Since I'm also taking a three month sabbatical this year, it works out pretty well for me to focus the bulk of my coaching sessions on the first half of the year, and then save one or two for reflection.)

I have a lot of issues with structure. I love it, but I'm terrible at creating it for myself. I thrive on external accountability. As I learned reading Better Than Before (which I've yet to finish), I'm an Obliger:

Obliger's respond readily to outer expectations but struggle to meet inner expectations.

Obligers may find it difficult to form a habit, because often we undertake habits for our own benefit, and Obligers do things more easily for others than for themselves. For them, the key is external accountability.

Better Than Before by Gretchen Rubin

Yeahhh, this is 100% me. 

Coaching, for me, is an attempt at external accountability. I have appointments, so I must keep them. I have homework, which my coach is expecting me to complete, so I have to complete it. I need to improve myself, because Automattic is paying this great coach to guide me through self improvement. 

For example, as part of my first coaching session, I filled out a "Year in Reflection" and "Self Discovery" form. The year in reflection felt like a natural extension of my previous post, but I found the Self Discovery form quite challenging. My self-reflections are usually unstructured (like my frenetic brain), so slowing down and focusing on specific questions was a nice exercise. For example, it took me a long time to answer question, which I think worth writing down publicly to keep myself accountable:

Look forward 20 years – you are attending a function where someone is giving a speech about you. What would you want them to say?

That I’m resilient and scrappy and get stuff done. That I never compromise my values for results. That I'm welcoming and never chased anyone with good intentions away. That I inspired a new generation of designers to contribute to open source.

After my first session, where we chatted about the forms I submitted, I was given some homework assignments:

  • Keep reading Taming Your Gremlin by Rick Carson, which I was assigned along with my discovery forms.
  • Clean my desk! I did that over the weekend, and it’s looking pretty nice now. (Maybe I’ll finally get around to putting up art.)
  • As part of my Self Discovery form, I had to write about the qualities I associate with a true leader. I’m now tasked with taking those qualities, turning them into the first-person, and making a poster I can print out (and hang up at my desk!). This is due by the end of today, so I’ll work on it after posting this ?

As I have more coaching sessions, I'll try to post more updates and insights. Here's to self-improvement in 2018!

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4 thoughts on “Coaching

  1. Love this. I’ve been thinking about participating in the coaching program too!!! Sounds great and I’ll look for more posts about it. Also, can’t wait to see your posters. ??

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