2019-2020 Chief of Staff Mastermind Cohort 1

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Various: Virtual and In-Person (see details below)

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Refund Policy

Refunds up to 30 days before event

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Join the 2019-2020 Chief of Staff Mastermind Group: a year-long learning cohort that combines the power of chief of staff-specific training, group and 1:1 coaching, and peer advisory to take your performance and career to the next level. Just a few benefits:

  • Community: It's easy to feel isolated, and a cohort becomes friends, creating a depth of relationships beyond online forums. 70% of past workshop attendees say they keep in touch more than a year later.

  • Connection: Whether you need connections to tools, resources, or experts for help or advice, a cohort helps cut through the BS and connect to what you really need. One CoS saw ways for his organization to partner with a fierce rival organization to stave off a common threat from a disruptive technology. The CoS reached out the CoS of the other company's CEO at our event, "greased the skids," and the two organizations went from enemies to “frenemies” and survived the threat.

  • Continuous Learning: Our learning model creates space to apply the frameworks, models, tools, and resources that will help you excel. Extended by personalized coaching that enables you to craft experiments, learn, and iterate when you're back at your desk.

Key elements of the Mastermind Group include:

  • 12 months, starting in March 2019.

  • Up to 15 participants (space is limited to 15 to enable depth of relationships and sufficient coaching time).

  • Bi-weekly, 1/2hr-1hr virtual group meetings.

  • 3 in-person 1-day workshops (tentatively slated for Seattle, NYC, Austin - actual locations may change based on geographic dispersion of participants).

  • Monthly 1:1 coaching call with Tyler.

  • Workshop, learn best practices, and tackle challenges in real-time as they unfold, with peers in CoS roles.

  • The curriculum includes The Art of Leading from Behind, Managing Meetings Before They Manage Your Leadership Team, Managing Conflict Before It Manages Your Leadership Team, Systems & Strategic Thinking for Chiefs of Staff, Mastering the CoS-Executive/Staff Partnership, and more.

  • Other topics will be determined by the group (unfolding realities, your challenges in the moment that the group can help with).

  • Private membership site for 24/7 access to all meeting video/audio and materials.

Notes: If there is demand, we will form more than one cohort, by geography or other factors. We will actively avoid having direct competitors in the same cohort.

Need help making the business case/getting budget approval to participate? Here's a draft letter to your executive sponsor, with some suggested talking points and ROI suggestions, for you to edit and make your own!

Questions? Call me at 206-660-5738 or email me at

What past coaching and workshop participants say:

"Chief of Staff as Leader helped me reboot and find space for dealing with my specific challenge and response with peers." - CoS at a midsize technology investment company

"After Managing Conflict Before It Manages Your Leadership Team, I led our leadership team in a discussion that resulted in our executive's realization that he needs to spend less time with them. It wasn’t easy, but I got good marks for the way I moved through the difficult portions of that meeting, and they thanked me." - Chief of Staff at a well-known Journalism/Media outlet.

"Tyler was a fantastic sounding board, offering suggestions and direction based on both his personal experience as a CoS; as well trends, themes, and best practices he'd gleaned based on conversations with the hundreds of Chiefs of Staff he has in his network. He was a valuable resource for me and I look forward to working with him again." - Tamara Rezler, Strategic Initiatives, Chief of Staff, Growth Companies

Tentative Schedule:

March 7, 2019 – KICKOFF, In-Person Workshop 1 (NYC) September 4 - Virtual group meeting

March 20, 2019 -- Virtual group meeting September 18 - Virtual group meeting

April 3 - Virtual group meeting October 2 - Virtual group meeting

April 17 - Virtual group meeting October 16 - In-Person Workshop 2 (Seattle)

May 1 - Virtual group meeting November 6 - Virtual group meeting

May 15 - Virtual group meeting November 20 - Virtual group meeting

June 5 - Virtual group meeting December 4 - Virtual group meeting

June 19 - Virtual group meeting January 8, 2020 - Virtual group meeting

July 10 - Virtual group meeting January 22 - Virtual group meeting

July 24 - Virtual group meeting February 5 - Virtual group meeting

August 7 - Virtual group meeting February 19 - Virtual group meeting

August 21 - Virtual group meeting March 11 - FINAL Workshop (Austin)

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Date and Time


Various: Virtual and In-Person (see details below)

Refund Policy

Refunds up to 30 days before event

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