Reboot Podcast Episode Extras #24 – Building High-Performing Teams Through Coaching – with Steph Yiu

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Steph Yiu

Steph Yiu

Chief Customer Officer at WordPress VIP

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Episode Description

In this Podcast Extra, Andy Crissinger delves into the world of coaching and its transformative impact on corporate culture with guest Steph Yiu, Chief Customer Officer at WordPress VIP and leader at Automattic.

They explore the extensive Reboot program at Automattic, which focuses on trust, open feedback, and building a supportive environment for personal and professional growth. Steph shares her journey of incorporating coaching tools into her leadership role, and they discuss how these tools have empowered her to lead through complex organizational reorganizations and facilitate tough conversations.

Helpful links to topics addressed in this episode:

Understanding a Team’s Natural Development Process: The Tuckman Team Development Model | The Brightest Bulb Challenge: From Individual Contributor to Team Leader | Leading Through Transitions

Show Highlights

Memorable Quotes: 

“Every professional athlete works with coaches. So it’s so funny to me that within businesses and organizations, we don’t consider coaching as an absolutely essential tool because I think it is.” – Steph Liu

“Prior to Reboot and all of this coaching investment, we didn’t really have many tools for our leaders. Now, I feel like our leaders are really well supported.” – Steph Liu

“We’re not an organization where you only get access to coaching if you’re doing something bad. And we’re also not only an organization where you only get access to coaching if you’re a team lead or you’re an executive. It’s available to everyone.” – Steph Liu

“I’ve gotten better at moderating conversations and moderating tough conversations, both internally and externally, because I’ve seen our Reboot coaches and other coaches in our program, deploy moderation skills.” – Steph Liu

“I would say for me personally, one-on-one coaching has been absolutely transformative. I do not think I would be Automattic today if I did not have coaching, truly. I do not think that I would have been able to grow my career without one-on-one coaching.” – Steph Liu

“Having somebody who can consistently help me see where I need to grow and the skills that I need to form has helped me accelerate my career development because otherwise, I would have been feeling in the dark. And so that’s been incredibly helpful.” – Steph Liu

“I would say you need to be prepared to invest in coaching. You don’t just show up and the coach gives you a bunch of stuff and you’re suddenly you’re a better leader. It’s really that true investment in that conversation, being open and vulnerable and willing to explore what’s working, and what’s not, challenging your own assumptions. Those types of conversations are how you get a ton out of the like leadership benefit and acceleration and growth and all of that.” – Steph Liu