Chief of Staff Spotlight: Christine Lai

What is a Chief of Staff and what do they do? There are none better to ask than the Chiefs themselves. In this series, we talk with current and former Chiefs of Staff about their role as well as their personal motivations and secrets to performing it well.

Christine Lai

Christine Lai

  • Title:                    Chief of Staff

  • Company:           Delivering Happiness

  • Years:                   2013-present

  • Industry:             Culture & People


Tell us a little bit about Delivering Happiness and what your primary responsibilities are as Chief of Staff.

Delivering Happiness is a "coachsulting" [hybrid coaching + consulting] company that seeks to inspire passion and purpose in workplaces for a happier world. The company was born out of Zappos’ CEO Tony Hsieh's 2010 book Delivering Happiness: A Path to Profits, Passion, and Purpose. The book is part biography of Tony’s career/part business guide, and also introduces the idea of creating a culture of happiness to be used as a model in both business and life. The book segued into a couple of businesses, which eventually merged into the company it is today. We work with companies on defining their culture and co-creating a plan to ensure their culture and values are aligned and support their business, customers, and team.

My role as Chief of Staff varies day-to-day and leans more on the operations side of things. I joke sometimes that on any given day I may serve as an advisor, coach, mentor, parent, or therapist. On the operations side of things, I support the organization and team to align and focus on priorities and projects. I also work on collaborations and cultivating opportunities with current and prospective clients. With the team, I help ensure they have the needed information and resources to deliver their work.  

How did you find this opportunity, and how did your background prepare you for the role of Chief of Staff?

I was first introduced to Delivering Happiness via a good friend of the CEO’s, who then subsequently connected me to learn more. As with previous roles, I was initially drawn to the organization by its mission [to inspire passion and purpose for a happier world], and was intrigued to see how I could support in delivering on that mission. When it comes to meeting new organizations and opportunities, as in relationships, I think it’s important to “date” and get to know one another before committing. So I dated Delivering Happiness for about nine months to get to know the team, partners, clients, and explore where synergies existed between what the organization needed to grow and where that aligned with my skills and talents. After identifying the opportunity, I proposed the role of Chief of Staff.

My inspiration for creating the role as COS came mainly from the White House, along with my previous role as executive strategy director with a start-up hospitality company. Overall, I consider myself a generalist, and can often serve as a pinch-hitter on the team…filling in where gaps may exist until there is a more clearly defined opportunity/role where we can bring someone on to the team with more direction and guidance. My experience in building and cultivating teams and co-creating and executing on strategy aligned with where Delivering Happiness was at the time, so the Chief of Staff role was a good fit for me and the organization and team.

What is the overall mission of your role as Chief of Staff?

The overall mission for my role as Chief of Staff is to support the team and ensure we are “drinking our own champagne” [because who wants to eat their own dog food!?] — that we are doing the work ourselves [around culture] because that’s the work we are supporting others to do. I also foster alignment for the team, so that each team member is evolving personally as well as supporting the growth of the organization. To execute on this, I describe the COS role as a sounding board and translator to the CEO. Where the CEO is often operating from a more visionary perspective [at 30,000 feet] and the COS is more tactical, providing air cover and guidance [at 10,000 feet] and the team is executing on all fronts [in the trenches].

What skills do you believe are most critical to your success in this role?

The Chief of Staff role is first and foremost about connecting and building rapport with people, both inside and outside of an organization. The ability to put yourself in others' shoes to understand how it is they can best serve the organization for the most generative outcome is also an important part of the role. As COS, although the role serves as a trusted advisor to the CEO, the role isn't about making the CEO happy; it's to do what's best for the company, as that will ultimately [hopefully] make the entire organization and team successful. This means you must also think about things in a holistic way and keep clear priorities. As a sounding board for the CEO and executive team, you need to be able to hear challenges and ideas, understand how those information points fit into the big picture, and how you can ultimately serve to move the company forward.

What motivates you in your work?

I get so much energy from being able to help actualize and maximize potential. When I first started with Delivering Happiness, I could see there was so much potential and wanted to help the organization and team deliver on that potential. I was given the opportunity to help figure that out, to co-create a strong, big-picture vision and collaborate with the team to align towards that vision. I continue to feel so grateful for the opportunity.

How long did it take you to feel comfortable with your CEO, and, as a COS, what is the key to a great fit with an executive?

The fact that I was introduced to the CEO by a good friend of hers helped instill a transfer of trust, and also taking the time to "date" and really get to know the organization and the team was important. Trust is a huge component in finding a great fit with an executive, and that takes both self-awareness and patience. You want to be able to complement a CEO's strengths and identify opportunities to support them. Aligning your values, communicating, and determining how things can best operate in the organization is also important.

Do you feel like you have ownership in your work? If so, how do you establish that?

Yes, I feel like I have an immense amount of ownership. This is the first time Delivering Happiness has had a Chief of Staff and once I got to know the CEO and others around her, it was almost as if they had been looking for what I was offering for a while. Creating the role and having the good fortune to be introduced to the CEO at just the right time really allowed that transfer of trust to take place. That helped me move nimbly through the company and establish ownership in my work.

How do you define success as a Chief of Staff?

One way I define success as a Chief of Staff is having a strong pulse on the company and team’s overall health and happiness and ensuring it’s at optimal levels. I'm successful if I know how individual team members are doing, contributing to their overall growth and learning, and aligning their growth with the company's growth.

What advice would you give your successor/another COS?

Get clarity on how to best serve the mission of the organization and the CEO. Understand where the opportunities exist between the CEO and the company, and figure out how to align your strengths to optimize the organization.

If you were to hire a COS, what qualities would you look for?

Such a great question! I keep going back to alignment. I'd want to find someone with shared values who is creating positive impact in the world. Someone who has an abundance mindset (versus a scarcity mindset), who approaches things with curiosity. An individual who is open and continues to invest in the work around self-awareness and development so they, in turn, can support the growth of others on the team. Someone who is considerate and caring, and can connect with others on a deep level. On a more operational level, hiring someone who is focused on details and execution are important qualities. Someone who can identify collaboration opportunities and understand the need and value of cross-functional, dynamic teams. At the end of the day, bringing on board a true partner in both thought leadership and tactical execution.

What's next for you?

I am currently on sabbatical, experimenting and exploring around collective impact and communities. A through line in a lot of my work is in identifying opportunities and mapping and matching those opportunities with talented individuals. I'm thinking about how this relates to community and the idea of bringing people together to do things that are bigger than themselves. It's very much like the work I've done as Chief of Staff, just in a different arena.