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Executive Onboarding: Shishir's Tips & Best Practices
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Designing your 8-week plan


1. Pick your onboarding areas.
Treat these as placeholders, but pick a set of topic areas and try to write a clear description of the goal. Feel free to drag to prioritize (perhaps based on what you are most to least comfortable with), and it will reorder the view in the next step.
Search
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.
There are no rows in this table

2. For each area, outline the key milestones.
Now outline a plan. For each area, go week by week and add a goal for where you want to be on that goal by that week.

Add rows for each {areaweek #}
0
Search
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
Draft of “Product observations and
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
Ask key employees for a list of the that distinguish the team
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
Draft of key strategic ready for review
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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