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Chief of Staff Roadmap

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This is a must have resource for Chiefs of Staff starting a new role. This template allows you to plan out a roadmap of new work, prioritize what's important, and help make your exec feel like a superhuman.

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Chief of Staff Roadmap

Welcome!  This template was created to help you manage your many projects and priorities as a Chief of Staff.

My recommendation is to fill it out on your own first, adding in what the task is, what kind of work it is, and your proposed solution.  For example, for the Admin Backlog example I gave below, I proposed delegating this to an EA to free up your and your Exec's time from doing mundane tasks.

Once you have filled out this table, share your Roadmap with your Exec.  Work together during your 1:1 to prioritize projects.  Not only will this give your Exec visibility in how much you're juggling, but it will also help you understand what the most urgent priorities are.  Finally, when new projects arise, you can ask your Exec where on the priority list the new project falls.  I also recommend tracking it in your shared Action Tracker (whether it's on Notion, or Asana, or something else.  Just be sure to mark these as deliverables or milestones so it's explicitly clear that you're on track.)

Be sure to establish with your Exec: what does success as a CoS look like to them?  Make sure you reach a mutual agreement on this definition of success.  For example, Matt and I agreed that my primary goal as his Chief of Staff is to enable him to feel like a Superhuman.  This means that everything I do has to enable that: from delegating mundane tasks to someone else so he doesn't get bogged down, to focusing him on important things that tap into his Zone of Genius like Strategy and Coaching.  Therefore, all my projects either clear off his plate of tedious work, or they enable him to double down on things he really enjoys doing.  I delegate out things I don't enjoy or aren't in my Zone of Genius where possible, and take care of the things that are (this includes most Operational work that I love doing, but Matt dislikes doing.)  It's a win-win!

Lastly, regarding the tracker: you can toggle the different views.  Anything marked "currently on plate" are active projects.  You can also see all projects (including Delegated and Completed tasks.)  Feel free to play around with the different Tags, and sort the priority according to 0 being most urgent and 1000 being the least.

Happy planning!

-Regina

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Who’s Regina Gerbeaux?

Founder and operator, turned executive coach.

I was the first Chief of Staff and COO to Matt Mochary, coach to the CEOs at OpenAI, Scale AI, Flexport, Coinbase, Reddit, and more. My operational write-ups are featured in the Mochary Method Curriculum as key resources for every founder ready to scale their company, and used by hundreds of fast-scaling companies.

I work with the Top 1% of Leaders. When we work together, you stop flying blind. Every problem you bring to the table, I pattern-match against decisions I’ve seen decacorn companies make behind closed doors—so you avoid the mistakes they’ve already made. If you’ve ever wished there was a Stack Overflow for scaling company challenges, it exists. It lives in my brain.

Not only will you have the information to make smart decisions, but I’ll also help you understand the psychology behind everyone you work with. Whether it's your leadership team, customers, or board, you’ll become a master communicator, able to bring people into your corner and win.

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