Ask a Chief of Staff

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Weekly

Latest

2026-10-27

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12 recent issues

• Covers: Operational frameworks, executive communication, onboarding strategies, user manuals, and career growth tactics for Chiefs of Staff.
• For: Current and aspiring Chiefs of Staff and strategic executive operators.
• Best for: Chiefs of Staff looking to improve executive support, alignment, and operations.
• Skip if: Professionals outside executive support or operational leadership roles.

Start with

• Issue 107: Automate Your Friday Update, Not Your Judgment: Explains how to streamline weekly executive updates without sacrificing critical strategic judgment.
• Member Exclusive: The 360° User Manual System: Details how to map communication and decision styles across executive leadership teams.
• Issue 103: The First 9️⃣ 0️⃣ Days as a New Chief of Staff: Provides tactical guidance on navigating the first ninety days in a new role.

Sponsors seen

• WisprSponsor

  Give Wispr Flow a try and stop self-editing before your ideas even make it out. Try Wispr Flow Free *If you’re interested in sponsoring a future issue

  Issue 103: The First 9️⃣ 0️⃣ Days as a New Chief of Staff · 2026-09-01
• Oceans TalentSponsor

  Oceans Talent connects you with AI-fluent, rigorously vetted remote operators — EAs, marketing specialists, finance support — matched to your business in 24 hours

  Issue 102: The First 6️⃣ 0️⃣ Days as a New Chief of Staff · 2026-08-18
• BrevSponsor

  This is where Brev comes in. Brev is an AI system of action that works across your existing tools to track goals

  Issue 105: The User Manual Every Chief of Staff Needs (But Probably Doesn't Have) · 2026-09-29
• MicrosoftPartner

  Bringing a Chief of Staff Mindset to AI Transformation | Mon, Oct 5 · 3–5pm PT · SF Tech Week A panel with leaders from LatchBio, Atlas Computing, and Standard Cybernetics on what it actually takes to drive AI adoption inside an organization. Hosted in partnership with Microsoft.

  Issue 104: The Trap of Being Too Competent to Quit · 2026-09-15
• goodrPartner

  How Chiefs of Staff Make the Invisible Visible | Tue, Oct 13 · 5–7pm PT · LA Tech Week A panel with Chiefs of Staff from Venmo, goodr, Hiyo, and Rhaeos on how to measure and communicate the impact of work that mostly happens behind the scenes. Hosted in partnership with goodr.

  Issue 104: The Trap of Being Too Competent to Quit · 2026-09-15

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