The Onboarding Playbook Every New Chief of Staff Should Have

Hi {{first_name|there}},

This week is about the first 90 days in a Chief of Staff seat, and how much of the job gets decided inside them. The role takes its shape in that window whether you direct it or not, and most people only find that out looking backward.

Our new onboarding playbook breaks that window into three thirty day moves. Then Launchpad, which is one week of doing that work with a cohort and a faculty around you. Enrollment closes tomorrow.

Most Chiefs of Staff inherit a job description that was written generically, or never written at all. You show up on day one, your principal says some version of "I need leverage," then disappears into back to back meetings. What you do over the next three months decides how much of this job you get to design, and how much of it just fills up with whatever nobody else wanted.

We have watched hundreds of members go through this transition, and the ones who land well do roughly the same things in roughly the same order.

Days 1 to 30 go to learning the principal rather than the business: how they take in information, what kind of work drains them, where their calendar contradicts their stated priorities, and whose opinion actually moves them.

Days 31 to 60 go to one visible win, picked because it is genuinely painful, fixable in a month without budget or headcount, and impossible to miss once it is done.

Days 61 to 90 are where the role either converts or stalls, and this is the part most people skip. Define the seat in writing now that you know what the company needs from it. Take over a recurring mechanism rather than a project, because projects end and mechanisms compound. And the first time you genuinely disagree with your principal on something that matters, say so. Principals do not keep Chiefs of Staff who only reflect their own views back at them.

👉 Read the full playbook

The playbook above is what those 90 days look like when you run them alone. Launchpad is one week of running them with help. Two live workshop days on September 16 and 17, office hours on the 18th, and a faculty who have all sat in or alongside the seat.

Four modules cover the operating system of the role, strategic execution, influence and communication, and getting real leverage out of AI. What matters more is what you carry out of the week. You build a 90 day mandate plan, a project charter, a decision memo, an executive update, and a full Chief of Staff operating plan as the capstone, each one drafted for your actual seat rather than a case study. That first document is exactly what the playbook above spends its closing section arguing for.

It is built for operators stepping up from EA or ops roles, sitting Chiefs of Staff leveling up, and first timers who want the frameworks before day one. You finish with a certification badge, the private cohort, and access to the full learning modules, templates and frameworks to carry through your role.

September 16 and 17, office hours on the 18th. Enrollment closes September 10.

If you are inside your first 90 days right now, read the days 61 to 90 section twice. And if Launchpad has been sitting on your list, tomorrow is the deadline for the September cohort!

Scott