All Areas and Milestones

Who the team is and how it is structured

I've recommended my go-forward org structure (after meeting everyone on my team and my peers) and reset the hiring plan (including job descriptions and interview kits)

How the business works

I've learned how our business / go-to-market model works and set a path for our next bets

How the product works

I've learned how our product works and set a path for our next product bets

How our tech stack works

I've learned how our tech stack is built and can draw a picture for a new employee

How the team works

I've published a doc on my go-forward meeting cadence, changed all the relevant meetings, and published new templates showing how I want each one to run.

What our strategy is

I've written a strategy memo and sent it out to the team.

1-1s with key sales and marketing leaders (including BD, ops, comms, legal, etc as appropriate)

Get finance team run-down of past performance

Shadow 5 sales pitches

Shadow 5 support calls

Go through active marketing campaigns

Do side-by-side training of sales tools (Salesforce, etc)

Pitch a client as primary

Handle 5 support calls as primary

Draft of “My observations of our business” and recommended changes

(fill in)

(fill in)

Publish revised business plan / strategy

Attend all meetings my predecessor went to

Attend/ observe most of the skip-level meetings that my reports go to

Attend/observe most of the meetings that my peers go to

Draft a new Meeting Operating System for the team

(fill in)

Construct new templates for new meetings

Roll out new Meeting Operating system (update calendar invites, publish meeting docs)

Go through unaided new user onboarding for each of the key personas of the product (persona 1, persona 2, admins, etc)

1-1s with key Product, Eng, Ux leaders

Have each product area leader walk through how their area of the product works

Review last N product reviews for each product area

(fill in)

Draft of “Proposal for new product bets”

Meet with key product leads to socialize revised plan

Publish review product bets

Read last N board decks and make notes / questions

Read last N post-planning strategy memos and make notes / questions

CEO briefing: What’s on their mind?

Get current strategy pitch from key functional leaders and random employees

CEO check-in: Early questions and impressions

Interview board of directors on their views on strategy

Meet with trusted 3rd parties (analysts, other investors, etc) and ask for competitive strategy breakdown

CEO check-in: Early questions and impressions

CEO report: Your early proposal on the strategy ー including eigenquestions

(fill in)

Strategy offsite with key leads to align on key questions

Publish revised strategy

1-1s with all reports

1-1s with all next level reports

1-1s with all peers

1-1s with key culture carriers (ask around for who they are!)

1-1s with key cross-functional leads

Reviewed interview feedback for the last N hires

Draft of new org plan ready for soft socialization

(fill in)

New job descriptions written

New interview kits in place

(fill in)

New org rolled out

Have each eng area lead draw me a picture of how their part of the stack works

Redraw all the pictures and present back for feedback (”did I get this right?”)

Have engineer help setup a dev environment for me

Fix a bug

Draft list of key tech choices that we’ve made - circulate for feedback

(fill in)

(fill in)

Successfully describe the tech stack to a new incoming engineer