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When Work Doesn't Fit the Mold, a Chief of Staff Steps In

When Work Doesn't Fit the Mold, a Chief of Staff Steps In

This was presented at Support Driven Leadership Summit: https://www.supportdriven.com/leadership-summit-oakland

When you have a lot of work that doesn’t clearly fit into the organization chart reporting lines, a Chief of Staff may be the right person to help better execute on cross-team collaboration and your strategic vision.

In any department, team and individual responsibilities are typically defined and scoped. What happens when work doesn’t fit that scope or crosses lines in messy ways? It often falls to the head of a department, but a single person only has so much time and already has a stack of other problems. While a “Chief of Staff” is often used to describe someone reporting to an executive, whatever the title you choose for your cross-team collaboration leader, having an individual in such a role can improve efficiency, and strategic planning and execution. We’ll briefly talk about what a Chief of Staff is, how we’ve used Chief of Staff at GitLab, and how it can apply to your support organization.

Full script available at: https://cynthiang.ca/2023/11/14/presentation-when-work-doesnt-fit-the-mold-a-chief-of-staff-steps-in

Cynthia "Arty" Ng

November 14, 2023
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Transcript

  1. 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

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  2. 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

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  3. 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)

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  4. 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

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

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  6. 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?

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  7. What is a Chief of Staff?

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  8. 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

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  9. 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)

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  10. Tailor the role to what you need.

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  11. Where have a Chief of Staff?

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  12. 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

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

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  14. Engineering example
    CTO
    Support
    Quality
    Infrastructure
    Development Chief of Staff

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

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

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  17. Why have a Chief of Staff?

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

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  19. When to have a Chief of Staff?

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  20. 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”

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  21. How to get a Chief of Staff

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  22. 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

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

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  24. 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

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  25. Hire someone to step in
    for you

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

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