Cynthia "Arty" Ng Staff, Strategy & Operations (Chief of Staff to CEO Team) When Work Doesn't Fit the Mold, a Chief of Staff Steps In

Outline ● What a Chief of Staff is ● Where a Chief of Staff might fit ● Why/When you might want a Chief of Staff ● How to get a Chief of Staff

About me ● Experience wearing “multiple hats” ● At GitLab 5+ years ● CEO Shadow (2 weeks 2021-12/2022-01) ● Acting Chief of Staff to CTO (2022-11 to 2023-01) ● Internship for Learning (x2) with Chief of Staff to CEO Team (2023-03 to 2023-10) ● Staff, Strategy & Operations (Chief of Staff Team)

GitLab as of 2023-11-01 ● 2083 team members ● Fully remote in 65+ countries/regions ● 135 in Customer Support department ● 24x5 support and 24x7 emergency

Credit: Tanuki by Cloudtail the Snow Leopard, CC2.0 BY-NC-ND, https://www.flickr.com/photos/blacktigersdream/14523661040

Answer these questions ● Do you have a significant amount of work that doesn’t “fit” under existing teams? ● Do you find yourself trying to delegate that work without success? ● Do you think to yourself that you and your leadership team could be more effective and doing more “strategic” work if you simply had more time?

What is a Chief of Staff?

What is a Chief of Staff? “The chief of staff generally works behind the scenes to solve problems, mediate disputes, and deal with issues before they are brought to the chief executive. Often chiefs of staff act as a confidant and advisor to the chief executive, acting as a sounding board for ideas. Ultimately the actual duties depend on the position and the people involved.” - Wikipedia

Range of role 1. Project management and task prioritization. 2. Manage relationships and be a communication liaison. 3. Strategic thinking and problem analysis. 4. Anticipate and mitigate problems. 5. Grasp and add value to the leader’s vision. Adapted from: The Case for a Chief of Staff by Dan Ciampa, Harvard Business Review (May-June 2020)

Tailor the role to what you need.

Where have a Chief of Staff?

Where does a Chief of Staff fit? “It’s someone who runs the function for everything that doesn’t belong in a function.” - Sid Sijbrandij Chief of Staff partnership with the CEO, GitLab Unfiltered

Functionally organized hierarchy CEO etc. Finance Engineering Product Chief of Staff

Engineering example CTO Support Quality Infrastructure Development Chief of Staff

Support example VP Support Analytics QA Operations Regional Chief of Staff ● Americas (AMER) ● Asia Pacific (APAC) ● Europe, Middle East, Africa (EMEA)

Support work examples ● Training ● Internal documentation: organizing, auditing ● Preparing for non-product changes ● Process/workflow reviews and improvements ● Projects: evaluating vendors, migrations, other research

Why have a Chief of Staff?

Benefits ● Save time ● Better internal communication ● Better decision making ● Increase leadership’s impact ● Increase effectiveness and productivity

When to have a Chief of Staff?

When to consider a Chief of Staff ● Poor communication flow ● Inefficient or slow decision making ● Needing to increase productivity ● Inefficient workflows and processes ● Spending a large amount of time “putting out fires”

How to get a Chief of Staff

Communicate the role ● Clear list of responsibilities ○ If managing a team ● Level of skills and results ● Clearly delineate from other roles ● Experience in domain area ● Examples at GitLab ○ Chief of Staff to CEO / Team ○ Director of Global Readiness

Alternate title examples ● [VP/Director/etc.] Strategy and Operations ● [VP/Director/etc.] Special Projects ● [VP/Director/etc.] Global Readiness

Take away

What is a Chief of Staff for? “A [Chief of Staff] should handle several principal duties, all focused on making time, information, and decision processes more effective.” - Dan Ciampa The Case for a Chief of Staff, Harvard Business Review

Hire someone to step in for you

Thank you

SD Slack: @arty-chan about.me/cynthiang cynthiang.ca Cynthia “Arty” Ng