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

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
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
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)
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
5. Credit: Tanuki by Cloudtail the Snow Leopard, CC2.0 BY-NC-ND, https://www.flickr.com/photos/blacktigersdream/14523661040
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?
7. What is a Chief of Staff?
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
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)
10. Tailor the role to what you need.
11. Where have a Chief of Staff?
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
13. Functionally organized hierarchy CEO etc. Finance Engineering Product Chief of Staff
14. Engineering example CTO Support Quality Infrastructure Development Chief of Staff
15. Support example VP Support Analytics QA Operations Regional Chief of Staff • Americas (AMER) • Asia Pacific (APAC) • Europe, Middle East, Africa (EMEA)
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
17. Why have a Chief of Staff?
18. Benefits • Save time • Better internal communication • Better decision making • Increase leadership’s impact • Increase effectiveness and productivity
19. When to have a Chief of Staff?
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”
21. How to get a Chief of Staff
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
23. Alternate title examples • [VP/Director/etc.] Strategy and Operations • [VP/Director/etc.] Special Projects • [VP/Director/etc.] Global Readiness
24. Take away
25. 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
26. Hire someone to step in for you
27. Thank you
28. SD Slack: @arty-chan about.me/cynthiang cynthiang.ca Cynthia “Arty” Ng