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don't try
this at home
self-improvement as a
senior leader
Phil Calçado


@pcalcado | philcalcado.com
phil gets


into


management
@pcalcado | philcalcado.com
just like being a
consultant, but now


I get to
fi
re people
@pcalcado | philcalcado.com
phil gets


into


senior management
@pcalcado | philcalcado.com
• hyper growth


• everything is broken all
the time


• we have no idea how to
monetize this


• we are one DMCA away
from becoming
Grooveshark
@pcalcado | philcalcado.com
performance review
fl
at structure
20% time
freedom & responsibility
job levels
hiring strategy
sponsoring projects R&D
okrs
sta
ffi
ng strategy
remote work
multiple o
ffi
ces
acquisitions
acquihires
@pcalcado | philcalcado.com
HARD TO
SWALLOW
PILLS
the higher in the orgchart you are the
less time/patience/experience your
own manager will have to coach you
@pcalcado | philcalcado.com
@pcalcado | philcalcado.com
but how do you


know what to


apply and when?
@pcalcado | philcalcado.com
write a
failing test
make it
pass
refactor
@pcalcado | philcalcado.com
it turns out people
hate being jerked
around as leadership


“learns more”
@pcalcado | philcalcado.com
The expensive
education of


Phil Calçado
Phil Calçado


@pcalcado | philcalcado.com
i think I am


ready for my


next gig
@pcalcado | philcalcado.com
• we don’t have a lot of
users, but they are
passionate


• high revenue but low
margin


• btw our competition is
Amazon, Google, and
Microsoft—no biggie
@pcalcado | philcalcado.com
“you are great at
delivering product, but
you have no idea how to
handle budgets”
@pcalcado | philcalcado.com
phil gets


the hell out of


senior management
@pcalcado | philcalcado.com
@pcalcado | philcalcado.com
instagram.com/snarky_the_pup
phil gets


dragged back into


senior management
@pcalcado | philcalcado.com
• we got acquired, but we
don’t know why


• it turns out they don’t
know why either
• merge these completely
different platforms


• oh, and win enterprise
deals while at it
@pcalcado | philcalcado.com
4 completely
different jobs
• ~10 years


• same-ish title


• 4 companies
@pcalcado | philcalcado.com
so, what do I tell


senior managers?
@pcalcado | philcalcado.com
managers make sure
the team’s delivery
machine works to
expectation
@pcalcado | philcalcado.com
senior managers do
whatever is needed


in the current stage
@pcalcado | philcalcado.com
but there are


some principles…
@pcalcado | philcalcado.com
fi
gure out what


your boss thinks


you should be doing
@pcalcado | philcalcado.com
think of your role as
discrete parts
@pcalcado | philcalcado.com
think of management
books the same as
design pattern books
@pcalcado | philcalcado.com
thought leadership


is just another word


for marketing
@pcalcado | philcalcado.com
+
@pcalcado | philcalcado.com
favor internal peers


for networking
@pcalcado | philcalcado.com
the best kept


secret in senior
management…
@pcalcado | philcalcado.com
technical skill is
relevant again
@pcalcado | philcalcado.com
?
@pcalcado | philcalcado.com
@pcalcado | philcalcado.com

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don't try this at home: self-improvement as a senior leader