🚀 Chief of Staff Spotlight: Meet Adrian Lai

Chief of Staff and Head of Operations at Wonderschool

Internal communications partners with many colleagues across departments. This is a part of a series spotlighting our critical partners — including the Chief of Staff.

About Adrian

Adrian Lai is Chief of Staff and Head of Operations at Wonderschool, a child care software startup backed by a16z. He is responsible for building cross-functional alignment between teams, preparing executive communications and also manages the People Operations and Business Operations teams. Previously, Adrian led Growth & SEO at Houzz, was a Product Manager at Spin, a strategy consultant at McKinsey, and a lead data analyst at Meta.

What led to your professional path as Chief of Staff?

For half my career, I worked as a Product Manager and I saw that you can have an amazing team of engineers, designers and analysts aligned on a common goal, execute phenomenally yet run into hurdles when having to get help from other teams.

I wanted to be in a role where I can help teams succeed from the outside — get them the resources they didn't have, identify collaboration opportunities across teams and celebrate successes across the org. That is what I want to do as Chief of Staff.

How do you support internal communications in your role?

My biggest contribution to internal comms is managing the company's weekly All Hands. In any organization, there's a lot of miscommunication as a message is passed from one person to another, getting lost in translation. I believe it's really important that there's an avenue for direct communication between employees all the executives.

Every week, I open up the All Hands deck for every employee to edit and then make sure that the content is clear and coherent before it goes live. Having All Hands every week sounds like a lot, and in ways it is — as I wrap up one All Hands, I'm already planning the next one, but we believe the effort is worth it and it's personally very gratifying to see coworkers learn things they didn't know about every week.

What is the unique value that you see internal communications providing to an organization? 

We all suffer from the Curse of Knowledge. Once we learn something, we don't know what it's like to not know it — we take it for granted. Therefore, it's immensely important that we force ourselves to help everyone else learn what's going on, and that's what internal communications needs to do — remind us to knowledge share because we inevitably forget to do so.

What advice do you have for other disciplines to collaborate with Internal Communications?

Suggest to internal comms what you want to share with the rest of the org, maybe what you know is more valuable than you think it is.

How do you describe internal communications to others?

Getting coworkers to understand each other's perspectives. 

What is one Internal Comms project you are particularly proud to have accomplished in your role? 

One of the recurring sections in the weekly company All Hands is the employee Q&A, and we make a conscious effort to not answer these questions the moment they are asked. When employees submit All Hands questions, they are usually meaningful and difficult.

These questions deserve time to discuss and solve for. In past companies, I have seen executives rush to answer these tough questions and frankly the answers come off out-of-touch and dismissive. We give ourselves roughly a week to assess, brainstorm and align on a solution for each issue before sharing it with the company, and have as a result deployed meaningful new HR policies that we would not have been able to enact otherwise.