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1. Reverse
Engineering Your
Manager
Shobhit Chugh
Will Eisner

2. Why bother reverse engineering your
manager?

3. Note
Any managers, situations, and examples used in this presentation are either the products of our
imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or
actual events is purely coincidental.
NOT :)

4. Let’s play a round of…
MISUNDERSTANDING OUR MANAGERS

5. Whatever kind of manager you have,
you have the ability to influence them
by understanding them
● Step 1: Understand what kind of manager
you have and what drives them
● Step 2: Use that understanding to
contextualize their actions and thinking and
their “good intent framework”
● Step 3: Create an influence plan based on
that understanding and context

6. MANAGER
PERSONAS

7. What kind of manager do you have?
High
Low
HighLow
Product
People

8. Photo by Marco Secchi on Unsplash

9. Photo by Hans-Peter Gauster on Unsplash

10. Photo by Joe Cox on Unsplash

11. Photo by Frankie Guarini on Unsplash

12. Where does your boss fit?
High
Low
HighLow
Product
People
High
Low
HighLow
Product
People
YOUR VIEW YOUR BOSS’ VIEW

13. SCENARIOS

14. Scenario 1: “The Reluctant Manager” is
letting your projects / career languish
Feels like
● Your manager is good at their main
job but not consistently focused
on you or your projects
● However, they may “swoop and
poop” when external pressures
arise
A good plan
● Be clear with what kind of
feedback you’re asking for and
getting
● Direct your manager’s product
brains to specific aspects of your
project
A bad plan
● Blame your lack of progress on
their lack of attention (will result in
defensiveness and reverse blame)
● Try to do it without their input (you
will end up accumulating debt that
is hard to payoff)

15. Scenario 2: “Lost in Translation” is
slowing down your roadmap
Feels like
● Short term discussions are
plentiful. Long term ones are
lacking
● Great feedback and development!
● No coherent strategy at a level
above you
A good plan
● Be excellent in areas they care
about
● Get feedback on longer term
strategy from other mentors within
the company
● Get wins across the organization
and bring your manager along
● Bring them along while flipping to
ego “You probably already thought
about this. What if we approached
it this way?”
A bad plan
● A direct mutiny or put down
● Treat their product feedback as an
annoyance

16. Scenario 3: “The Problem” is playing
politics and information control
Feels like
● You cannot trust your manager.
● They throw you under the bus, hold
back info, play you against your
peers, or complain about you
behind your back.
● Their product vision is not strong
A good plan
● If you don’t think you can be
successful, consider exit options -
internal and external
● State your concerns in the form of
how you could deliver more if you
had more visibility, alignment, etc
A bad plan
● Directly accuse or go over your
manager’s head (may result in
nasty retaliation)

17. Scenario 4: Hitting the accelerator with
“the Unicorn”
Feels like
● You are learning in every meeting
● You are meaningfully challenged
(sometime too much)
● “Impostor syndrome”
A good plan
● Clarifies your career aspirations
with your manager; tell them
exactly how you want them to
coach you
● Recognize their blind spots
A bad plan
● Tries to “win” at all costs
● Puts your ego against your
manager’s ego

18. WRAPUP

19. Bringing It All Together
● Assess your manager, and reverse engineer them
to understand their assessment of themself
● Use your manager’s mental model and “good
intent framework” as context for discussions and
requests with them
● When you have a big discussion scheduled with
your manager, invest the time in thinking it
through, and use this worksheet as a tool to
organize your thoughts

20. Exercise sheet available!
https://www.intentionalproductmanager.com/reverse-engineer

21. https://www.intentionalproductmanager.com/intentional-product-manager-group-coaching

22. careers.tripadvisor.com !!!

23. Reverse
Engineering Your
Manager
Shobhit Chugh https://www.linkedin.com/in/shobhitchugh/ @shobhitchugh
Will Eisner https://www.linkedin.com/in/weisner/