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Executive Onboarding: Shishir's Tips & Best Practices
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Designing your 8-week plan
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Area
Description
I'll know I am ready for this when....
1
Team
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)
2
Business
How the business works
I've learned how our business / go-to-market model works and set a path for our next bets
3
Product
How the product works
I've learned how our product works and set a path for our next product bets
4
Technology
How our tech stack works
I've learned how our tech stack is built and can draw a picture for a new employee
5
Cadence
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.
6
Strategy
What our strategy is
I've written a strategy memo and sent it out to the team.
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Area
Goal
Week
Milestone
Team
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)
1
1-1s with all reports
2
1-1s with all next level reports
2
1-1s with all peers
3
1-1s with key culture carriers (ask around for who they are!)
3
1-1s with key cross-functional leads
3
Reviewed interview feedback for the last N hires
4
Draft of new org plan ready for soft socialization
5
(fill in)
6
New job descriptions written
6
New interview kits in place
7
(fill in)
8
New org rolled out
Business
I've learned how our business / go-to-market model works and set a path for our next bets
1
1-1s with key sales and marketing leaders (including BD, ops, comms, legal, etc as appropriate)
1
Get finance team run-down of past performance
2
Shadow 5 sales pitches
2
Shadow 5 support calls
2
Go through active marketing campaigns
3
Do side-by-side training of sales tools (Salesforce, etc)
4
Pitch a client as primary
4
Handle 5 support calls as primary
5
Draft of “My observations of our business” and recommended changes
6
(fill in)
7
(fill in)
8
Publish revised business plan / strategy
Product
I've learned how our product works and set a path for our next product bets
1
Go through unaided new user onboarding for each of the key personas of the product (persona 1, persona 2, admins, etc)
1
1-1s with key Product, Eng, Ux leaders
2
Have each product area leader walk through how their area of the product works
3
Review last N product reviews for each product area
4
Eigenquestions
5
(fill in)
6
Draft of “Proposal for new product bets”
7
Meet with key product leads to socialize revised plan
8
Publish review product bets
Technology
I've learned how our tech stack is built and can draw a picture for a new employee
1
Have each eng area lead draw me a picture of how their part of the stack works
2
Redraw all the pictures and present back for feedback (”did I get this right?”)
3
Have engineer help setup a dev environment for me
4
Fix a bug
5
Draft list of key tech choices that we’ve made - circulate for feedback
6
(fill in)
7
(fill in)
8
Successfully describe the tech stack to a new incoming engineer
Cadence
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.
1
Attend all meetings my predecessor went to
2
Attend/ observe most of the skip-level meetings that my reports go to
3
Attend/observe most of the meetings that my peers go to
4
key rituals
5
Draft a new Meeting Operating System for the team
6
(fill in)
7
Construct new templates for new meetings
8
Roll out new Meeting Operating system (update calendar invites, publish meeting docs)
Strategy
I've written a strategy memo and sent it out to the team.
1
Read last N board decks and make notes / questions
1
Read last N post-planning strategy memos and make notes / questions
1
CEO briefing: What’s on their mind?
2
Get current strategy pitch from key functional leaders and random employees
2
CEO check-in: Early questions and impressions
3
Interview board of directors on their views on strategy
3
Meet with trusted 3rd parties (analysts, other investors, etc) and ask for competitive strategy breakdown
3
CEO check-in: Early questions and impressions
4
Eigenquestions
5
CEO report: Your early proposal on the strategy ー including eigenquestions
6
(fill in)
7
Strategy offsite with key leads to align on key questions
8
Publish revised strategy
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