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CoS Pods Mastermind Sessions


Chief of Staff Network



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CoS Pods Mastermind Sessions

Mastermind Sessions

Mastermind sessions are designed to enable one or more Pod members to leverage the shared brainpower of their fellow CoS in a private conversation. The format of these meetings can take various shapes, but we've put together a few suggestions to help you make the most of your time together.


1.) Choose a Pod Leader(s)

Before each session, you should select 1-2 Pod Leader(s). The Pod Leader has a few responsibilities:

  • Choose a central theme or specific topic for the conversation. This can be as broad as "making the most out of the role" to more specific challenges like "dealing with a difficult employee".
  • Share any pre-reads or context as a starting point for the discussion. Get everyone thinking on Slack before you meet! Use the Knowledge Hub for curate resources.
  • Lead the discussion - help ask questions, make sure everyone has a chance to contribute, keep the conversation organized.‚Äć

‚Äć2.)¬†Designate a Note Taker

  • Select one or more volunteer note takers for the meeting. You'll appreciate having these notes to revisit later on!
  • We suggest using the shared google doc you used in your first session.

3.) Set guidelines for the meeting

  • Should this conversation be kept confidential?
  • Does it make sense to bring in an external speaker or expert to participate?
  • What are the goals for the conversation?

During the Meeting

1.) Let the Pod Leader(s) open up with their questions or insights on the topic

2.) Naturally, the conversation will veer into other areas, take guidance from the Pod Leader to bring the discussion back to the main topic

3.) No one has all the answers! Write down your questions to share with others in the community.



1.) Share the notes back on your Pod's Slack channel

2.) Share insights or pose additional questions privately or in one of the public channels

3.) Choose a new Pod Leader for your next meeting!


Topics & Starter Questions

CoS Role & Leadership

  • How do you help your CEO say no?
  • What are the most challenging parts of your CoS experience?
  • The art of delegation: assigning work to team members (influence vs. direct management)
  • Setting professional boundaries between yourself and Principal, SLT, and organization
  • How to tell if you're succeeding as a CoS?
  • Opportunities post-CoS role - how to leverage the role into other senior leadership positions?

Team & Culture

  • Best practices for Talent Management & Retainment Programs
  • Culture building exercises (exec team + company)
  • Leading executive offsites - best practices / advice
  • Working with executive assistants or hiring associate Chiefs of Staff

Strategy & Execution

  • Operationalizing OKRs
  • Best practices to running quarterly Board Meetings/Decks
  • Best practices - Managing projects and general task lists - tools, tips and practical support
  • Quarterly or annual strategic planning lessons
  • Internal comms frameworks
  • Best practices for keeping a productive day


  • What does it take to be successful?
  • Work-Life Balance
  • Being a Chief of Staff and a Parent
  • How to become more self-aware?
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