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Executive Onboarding: Shishir's Tips & Best Practices
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Calendar View of 8 week plan

Pick a start date:
10/4/20

Calendar View of Area Milestones
10
Search
Today
May 2022
MonthWeekDay
Sunday
Monday
Tuesday
Wednesday
Thursday
Friday
Saturday

Gantt View of 8 week plan
10
Search
Business
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
Cadence
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
Ask key employees for a list of the that distinguish the team
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)
Product
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
Draft of “Product observations and
(fill in)
Draft of “Proposal for new product bets”
Meet with key product leads to socialize revised plan
Publish review product bets
Strategy
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
Draft of key strategic ready for review
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
Team
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
Technology
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
Sep 28
Oct 12
Oct 26
Nov 9
Nov 23
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
Ask key employees for a list of the that distinguish the team
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
Draft of “Product observations and
(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
Draft of key strategic ready for review
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
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