The First 90 Days as Chief of Staff

The pre-built operating system that turns a new CoS's first 90 days from chaos and overwhelm into ..

Sessions
12
Steps
39
Last edited
Jul 9, 2026
Created by
Nova

About this process

A multi-session Nova process that walks a new Chief of Staff, COO or Head operations through the first 90 days of the role, phase by phase. It starts with a structured 30-conversation listening tour, opens the company decision log on day one, then sequences the install of a working leadership meeting, the four-layer rhythm of business, the first cross-functional decision, OKRs, and the first quarterly planning cycle. Every meeting template, every question script, every cadence is pre-built — so the CoS isn't reinventing the work, they're running it. Benefits A real, sequenced 90-day plan instead of 47 unfinished tasks Decision log live from day one — decisions stop getting re-litigated Leadership meeting that produces decisions instead of status updates Rhythm of business visible to anyone who joins First quarterly planning cycle delivered with structure that carries forward A clear answer to the question every new CoS dreads: "What did you actually do this quarter?"

Sessions at a glance
#SessionSteps
01The three-pillar structure402Deliverables & Priorities203First conversation with the CEO504Leadership team conversations605Second CEO conversation106Third CEO conversation307To-do list308To-do list - P2309To-do list - P3310To-do list - P4311To-do list - P5312To-do list - P63

The process in detail

12 sessions · 39 steps
01

The three-pillar structure

4 steps
  1. 1

    The pre-read rule: Share  any items that need a decision this week.

  2. 2

    Decisions (40 minutes) 

  3. 3

    Blockers (15 minutes) 

  4. 4

    Signal (10 minutes) 

Read the full text
1. The pre-read rule: Share  any items that need a decision this week.

The pre-read rule: Nothing is decided without a pre-read. This is non-negotiable in both models, but it's especially important here because the decision surface is smaller. The pre-read format is simple: here is the decision we need to make, here is the context, here is what we recommend, here is what we need from the group. One page (or use video)

⏲Circulated 24 hours in advance (or sooner)

If the pre-read doesn't arrive on time, the item is pulled from the agenda.

That rule - pull the item if the pre-read is late - will feel aggressive the first time you enforce it. It will be respected by week four.

It teaches the organization that the meeting's time is not available for underprepared thinking.👈

2. Decisions (40 minutes) 

Decisions (40 minutes) - items that need a decision this week, with the decision owner identified before the meeting. Pre-read circulated 24 hours in advance.

The meeting makes the decision - it does not "discuss it further."

3. Blockers (15 minutes) 

Qhat is one team blocked on that another team can unblock. Specific. Named.

4. Signal (10 minutes) 

One metric or qualitative read from each leader. Not status. Signal. "What changed in your part of the world this week that the rest of us should know."

02

Deliverables & Priorities

2 steps
  1. 1

    Before the meeting

  2. 2

    The Monthly Ritual: Deliverables & Priorities

Read the full text
1. Before the meeting

Before the meeting, the manager fills in their section of a shared document - one per team member. No templates. Just this:

•What I believe your top deliverables are this month
•The one thing that, if delivered, would be a significant achievement
•What I think you need to start now that you may not have started
2. The Monthly Ritual: Deliverables & Priorities

The team member opens the session at the start of the meeting. They read in silence - no speaking. Then they add their own deliverables:

•Additional deliverables I have on my plate that aren't captured above
•On my radar: things I'm tracking that I haven't flagged yet

Then the conversation begins. Not about tasks. About deliverables.

The distinction is load-bearing: a task is something you do; a deliverable is something that exists when you're done.

The four elements in the document

•Top Deliverables (your top priorities) - the primary outputs expected this month. Written by the manager first, reviewed and amended by the team member. These become the single source of truth. If priorities change mid-month, this space is updated. Not the manager's memory. Not Slack. This.
•Plant the Seed - things that must be initiated this month even if they won't be completed this month. Long-lead work, relationship-building, early research. The trap for most teams is that they only count things that finish. Plant the Seed makes starting count.
•Ambition of the Month - one deliverable that, if achieved, would be considered a real win. Not a stretch goal in the OKR sense - this isn't a target. It's a flag in the ground. It says: this month, I'm aiming at something that matters, and I want you to know it. It changes how the team member makes tradeoffs during the month.
•On My Radar - a free field. Things the team member is watching, thinking about, or quietly worried about or even working on. Not commitments. Not yet. But surfacing them in a structured context allows the manager to either elevate them, deprioritize them, or simply acknowledge that the team member is thinking ahead. This field, more than any other, reveals how your best people think.
New Board
  • Name
  • 🎯 Priorities Top deliverables
  • 🚀 Ambition of the month
  • 📡 On my radar
  • Name
  • 🎯 Priorities Top deliverables
  • 🚀 Ambition of the month
  • 📡 On my radar
  • Start typing...
  • Start typing...
  • 🌱 Plant a seed Get started
  • 🌱 Plant a seed Get started
  • Name
  • 🎯 Priorities Top deliverables
  • 🚀 Ambition of the month
  • 📡 On my radar
  • Name
  • 🎯 Priorities Top deliverables
  • 🚀 Ambition of the month
  • 📡 On my radar
  • 🌱 Plant a seed Get started
  • 🌱 Plant a seed Get started
03

First conversation with the CEO

5 steps
  1. 1

    What do you want me to do?

  2. 2

    What's the company actually trying to do this year, in plain language?

  3. 3

    What are the three things blocking it?

  4. 4

    What's the one piece of structure that, if installed, would unlock the most?

  5. 5

    Other notes:

Read the full text
1. What do you want me to do?
Add notes
2. What's the company actually trying to do this year, in plain language?
Add notes
3. What are the three things blocking it?
Add notes
4. What's the one piece of structure that, if installed, would unlock the most?
Add notes
5. Other notes:
Add notes
04

Leadership team conversations

6 steps
  1. 1

    What is working really well right now that we should not break?

  2. 2

    What's the one thing that, if it were fixed, would make the biggest difference?

  3. 3

    Where do decisions get re-made or re-litigated? What's an example?

  4. 4

    Where do you spend time you wish you didn't?

  5. 5

    What's a thing nobody is naming that you wish someone would?

  6. 6

    Other notes.

Read the full text
1. What is working really well right now that we should not break?
Add notes
2. What's the one thing that, if it were fixed, would make the biggest difference?
Add notes
3. Where do decisions get re-made or re-litigated? What's an example?
Add notes
4. Where do you spend time you wish you didn't?
Add notes
5. What's a thing nobody is naming that you wish someone would?
Add notes
6. Other notes.
Add notes
05

Second CEO conversation

1 step
  1. 1

    Here's what I'm hearing.

Read the full text
1. Here's what I'm hearing.
"I’ve finished my initial listening rounds, and I’m starting to see how our current reality aligns with our goals. My goal today isn't to suggest changes yet—I want to finish my full assessment first—but I wanted to share what I’m hearing to get your perspective. I’ve identified what we need to protect, what we might need to evaluate, and where our biggest levers for speed might be. Before I go further, I’d love to know: Does any of this surprise you, or does it confirm what you already suspected?"

Group your findings into themes (e.g., "People feel the vision is clear, but the processes are slowing them down"). Advice: Use the phrase: "The consistent pattern I’m hearing is..." This shows you are looking at the system, not just gossiping.

Before suggesting new things, evaluate what is already there. Advice: Categorize existing initiatives. Tell the CEO: "We have great momentum on X (Keep), but Y is causing friction (Kill/Revisit), and Z needs more resources to succeed (Tweak)."

Ask "Perspective-Sifting" Questions 🔍 Based on what the team is saying about [Issue X], how does that align with the original intent when you set up this process?" or "What historical context am I missing that explains why we do it this way?"

Frame Opportunities as "Levers" 🏗️ Don’t present a "To-Do" list; present a "Growth" list.

The "Gap Analysis" 🕳️ Highlight the distance between what the CEO thinks is happening and what the employees say is actually happening. Advice: Soften the blow by saying: "There is a high-level alignment on the 'What,' but a breakdown in the 'How' at the individual level." "Is there anything I’ve shared that feels completely disconnected from what you see at your level?"

Propose the "Next Ritual" 🔄 Advice: Suggest one "Quick Win" and one "Systemic Change." This proves you are building those train rails we talked about, rather than just being a "save boat."

✍As you listen to the CEO's reaction, try to categorize their responses and take notes.

Add notes
06

Third CEO conversation

3 steps
  1. 1

    Proposal.

  2. 2

    Approve/Decline

  3. 3

    Meeting notes.

Read the full text
1. Proposal.

Here's what I'd recommend. Take time going over the proposal before our meeting.

Upload files or add links
2. Approve/Decline
Choose one
  • Approve
  • Request changes
  • Decline
3. Meeting notes.
Add notes
07

To-do list

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
08

To-do list - P2

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
09

To-do list - P3

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
10

To-do list - P4

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
11

To-do list - P5

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List

What "good" looks like now?

A new senior IC joins the company during this phase. By the end of their first week, they can answer three questions without asking anyone:

•What are we trying to do this quarter?
•How does my team's work connect to that?
•How will we know if we won?
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
12

To-do list - P6

3 steps
  1. 1

    🎯 To do List

  2. 2

    🗂 List of Links & Resources

  3. 3

    📋 Change Log, Notes & Decisions.

Read the full text
1. 🎯 To do List
Add tasks
2. 🗂 List of Links & Resources
Upload files or add links
3. 📋 Change Log, Notes & Decisions.

📋🗂 This is a change log where you can take notes and record any changes, delays, or improvements that have occurred while working on this milestone or goal. It ensures transparency among all stakeholders and serves as a record of these changes.

Add notes
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Created byNova·Official process
Last edited Jul 9, 2026·12 sessions · 39 steps