This document provides advice on how to effectively manage one's boss. It emphasizes the importance of regular communication, keeping the boss informed on projects and timelines, and addressing any issues proactively before the boss finds out from others. Managing the boss well involves setting clear expectations, helping the boss advocate for the team, and looking for ways to lighten the boss's workload. Failing to manage the boss properly can lead to issues like the boss being surprised by bad news, appearing clueless, increased micromanagement, and the boss being unable to support the manager when needed. The document encourages establishing ongoing dialogue and transparency with the boss.

1. How$to$Manage$Your$Boss

2. Becoming)a)new)manager)is)an)experience)that)falls)somewhere)
between)ela5on)and)enduring)the)business)end)of)a)fire)hose.)In)
either)case,)those)comfortable)days)of)answering)for)the)quality)for)
your)work)and)your)work)alone)are)gone.

3. You$are$now$the$point$person$for$scheduling,$deadlines,$workflow,$
quality,$team$rela:onships,$and$a$whole$lot$more.$

4. I"don’t"want"to"add"one"more"ball"to"juggle"
in"your"workday,"but"I"would"be"le6ng"you"
down"if"I"didn’t"give"you"one"crucial"piece"
of"advice"that"will"make"your"management"
du<es"so"much"easier."

5. Make%sure%to%manage%your%boss.

6. Yes,%it’s%probably%uncomfortable%to%
consider%wielding%influence%over%the%
person%who’s%supposed%to%manage%you,%
but%the%fact%is%that%every%manager%should%
have%a%measure%of%control%with%the%person%
who%manages%them.

7. How$is$that$even$possible?$How$
does$that$work?

8. To#be#clear,#manipula0on#is#the#last#thing#we’re#talking#about#here.#
This#isn’t#about#forcing#your#boss#to#take#specific#ac0on#for#your#
benefit.

9. Instead,)you)need)to)be)fully)aware)that)you)have)a)great)degree)of)
control)in)how$your$boss$perceives$you.)Remember)this:)
• Managers)control)what)their)boss)thinks)of)their)team.
• Managers)control)what)their)boss)thinks)of)them.
While&this&influence&may&seem&awkward&at&first,&learn&how&to&use&it&
so&it&can&start&working&in&your&favor.

10. What%It%Means%to%Manage%Your%Boss

11. Let’s&keep&this&simple.&When&you’re&managing&your&boss,&you’re&
inten8onally&and&explicitly:
• Se$ng'his'expecta0ons'for'your'team
• Helping'him'go'to'bat'for'you'when'needed
• Giving'him'reason'to'brag'about'your'team'to'his'management

12. When%you%give%your%boss%regular,%specific%
input%on%on%your%team’s%performance,%
you’re%elimina9ng%most%of%his%worries%
about%project%performance%and%progress.%%
In#other#words,#you’re#feeding#him#regular#
status#updates.#This#is#a#concrete,#subtle#
way#of#lightening#your#boss’#workload.

13. Making'his'job'easier'makes'your'job'
easier.

14. This%principle%may%sound%complicated%and%servile,%like%I’m%asking%
you%to%read%your%boss’%mind%and%polish%his%shoes,%too.%But%in%reality,%
this%<p%gives%you%a%lot%of%clarity%around%the%specific%and%prac<cal%
reports%you%generate%for%your%boss.

15. When%you’re%crea-ng%updates%for%your%
boss,%don’t%spin%your%wheels%deciding%what%
to%include%or%what%to%judiciously%omit.
A"er%giving%and%receiving%hundreds%of%
these%reports%in%my%management%career,%I%
know%that%all%of%the%informa;on%you%could%
share%boils%down%to%these%four%issues:

16. What%your%boss%really%wants%to%know
• Exactly)what)projects)your)team)is)working)on
• An)educated)es:mate)on)how)long)it)will)take)your)team)to)
complete)the)work
• A)clear)deadline)for)the)en:re)project
• A)quality)benchmark)for)the)final)product
• The)projects)that)are)queued)up)next)to)work)on

17. As#you#keep#a#handle#on#all#of#the#micro5details#of#daily#produc6on#
coding,#make#sure#you#are#honestly#and#proac6vely#giving#him#
perspec6ve#on#your#team’s#weekly#ac6vity.

18. Keep$communica,on$open

19. When%you’re%new%to%managing%a%team,%it’s%
temp4ng%to%put%your%head%down,%keep%
plugging%away,%and%hope%that%the%teacher%
won’t%call%on%you.%Instead,%grab%your%
courage%and%be%willing%to%talk%to%your%boss%
frequently.

20. It’s%almost%impossible%to%communicate%too%much%with%someone%
who%is%accountable%to%someone%else%like%the%client,%another%
manager,%or%produc8on%for%the%results%of%your%work.
Put$him$at$ease$and$bring$keep$providing$informa5on$on$the$five$
issues$I$men5oned$above.

21. Prove&that&you’re&informed&and&in&
control

22. Regular(updates(show(your(boss(that(you(
are(keeping(tabs(on(the(essen5als(so(he(
doesn’t(have(to(peer(over(your(shoulder(all(
of(the(5me,(which(is(aggrava5ng(for(
everyone.

23. That%said,%realize%that%you’re%not%going%to%catch%everything,%
especially%when%you’re%in%a%new%role%or%you’ve%just%joined%a%new%
company.%Sooner%or%later,%you’ll%face%a%ques>on%and%have%to%have%to%
reply,%“I%don’t%know.”

24. Never,&ever&end&the&sentence&there,&however.&Always&add&in,&“I&
don’t&know…&and$I’ll$find$out.”
Chase&down&the&answer&within&15&minutes&or&by&the&end&of&the&day
—be&realis7c—but&make&sure&you’re&seen&as&the&person&with&the&
answers&instead&of&blank&stares.

25. See#things#from#your#boss’#point#of#
view

26. This%is%another%piece%of%advice%that%feels%like%a%hassle%but%is%really%a%
shortcut%in%disguise.%Try%asking%your%boss,%“How%can%I%make%you%
more%successful?”%Or,%“What%can%I%do%to%make%your%job%easier?”

27. These%ques(ons%require%a%small%risk%on%your%boss’%part,%because%
you’re%asking%him%to%pull%back%the%curtain%and%show%you%what’s%
really%going%on%in%his%world.%But%the%poten(al%reward%is%significant.

28. As#you’ve#probably#already#discovered,#most#people#come#to#
managers#because#they#need$something.#It’s#rare#to#have#someone#
offer#to#help.#In#fact,#no#one#has#ever#asked#me,#“Is#there#something#
I#can#do#to#make#your#job#easier?”

29. In#response#to#a#ques-on#like#this,#a#boss#
might#reveal#some#simple#adjustment#you#
can#make#that#will#create#a#huge#win#for#
them.#Even#if#you#don’t#get#a#specific#
answer#in#reply,#don’t#worry.#You’ve#s-ll#
made#a#great#aBempt#at#goodwill.#

30. How$Failing$to$Manage$Your$Boss$Hurts$You

31. Some%managers%avoid%this%topic%for%all%the%right%reasons.%They%want%
to%appear%respec8ul%and%compliant,%so%they%focus%completely%on%
their%team,%figuring%that%their%excep=onal%management%skills%will%be%
no=ced—magically!—by%upper%management.
Please&don’t&make&this&mistake.!

32. If#the#payoffs#for#managing#your#boss#are#
huge,#so#are#the#downfalls#when#you#
ignore#this#opportunity.#Here#is#the#
cascade#of#nega;ve,#unintended#effects#
you#can#expect#when#you#don’t#
communicate#and#shape#expecta;ons.

33. 1.#Bad#news#will#reach#your#boss#
before#you#do.

34. Missed&the&deadline?&Found&a&huge&bug&that&s2ll&needs&to&be&
squashed?
If#you#don’t#make#communica1on#a#priority,#one#fine#day,#your#boss#
is#going#to#get#blindsided#with#informa1on#you#didn’t#tell#him.#And#
he#won’t#be#happy.#

35. When%bad%news%needs%to%be%delivered,%
make%sure%you%tell%him%yourself—before%
other%people%do.
And$be'er$to$be$realis/c$about$exactly$
what$it’s$going$to$take$to$get$the$project$
back$on$track.$It’s$temp/ng$pick$a$deadline$
that$sounds$good$over$a$deadline$that$will$
actually$work$in$order$to$save$face.$
PleaseAAdon’t$do$it.

36. 2.#You’ll#appear#clueless.

37. Neglec&ng(regular(communica&on(creates(an(environment(where(
you(will(drop(the(ball(not(once,(but(repeatedly.(A;er(a(few(&mes,(
you(boss(will(assume(that(you’re(not(paying(a>en&on,(and(that(
trust?bus&ng(kind(of(damage(is(difficult((but(not(impossible)(to(
repair.(

38. If#you#have#a#choice#between#being#late#on#
a#project#or#appearing#clueless,#always#
choose#to#be#late,#and#present#a#solu9on.#
Being#late#might#be#someone#else’s#fault,#
but#you#have#no#one#but#yourself#to#blame#
for#being#clueless.

39. 3.#Welcome#to#micromanagement.

40. If#your#boss#is#convinced#that#you#don’t#have#a#grasp#on#the#
process,#sooner#or#later#he’s#going#to#step#in#and#start#managing#
your#team#for#you.

41. As#you#can#guess,#this#leads#to#a#huge#erosion#in#your#team’s#
confidence#in#you.#It’s#painful#for#your#boss,#who#has#to#pull#himself#
away#from#his#own#work#to#take#over#yours.#And#it’s#demoralizing#
for#you,#because#it’s#an#ongoing#reminder#of#what#you#should#have#
done#to#keep#the#ship#afloat.

42. Keep$in$mind$that$in$stressful$situa1ons,$your$manager$might$resort$
to$micromanaging$as$his$way$of$picking$up$the$tools,$just$as$most$
new$managers$are$tempted$to$start$coding$when$things$become$
stressful.$$$

43. Your%boss%may%resort%to%micromanagement%if%he%has%recently%been%
promoted%and%is%more%comfortable%managing%programmers%than%
managing%managers.

44. 4.#Your#boss#doesn’t#have#your#back#
when#it’s#7me#for#answers.

45. If#a#rela(onship#based#on#communica(on#
and#trust#(and#regular#updates)#isn’t#in#
place,#your#boss#can’t#go#to#bat#for#you#
when#customers,#other#departments,#or#
his#own#boss#wants#to#know#what’s#going#
on.
Don’t&take&that&chance.

46. It’s%Never%Too%Late:%Start%managing%your%boss%
today

47. If#you’re#hearing#about#this#concept#for#the#first#5me,#don’t#worry.#
Chances#are#that#you#intui5vely#understand#some#of#this#
informa5on,#which#is#just#common?sense#communica5on.
There’s'no'reason'to'cross'your'fingers'and'hope'you’re'doing'it'
well'when'you'can'have'a'solid'plan'instead.'

48. • Invite(your(boss(to(give(you(
construc1ve(feedback(so(you(can(
clearly(see(his(priori1es(and(
perspec1ve.(This(also(helps(frame(the(
rela1onship(as(one(of(collaborators,(not(
adversaries.

49. • Ask%your%boss%for%a%weekly%mee1ng%where%you%can%keep%him%in%
the%loop%on%progress,%hangups%and%changes%that%crop%up%along%
the%way.%Establishing%a%regular%dialogue%removes%anxiety%from%
boss?employee%interac1ons.%

50. • If$your$boss$has$a$standard$format$for$
status$reports,$go$with$it,$even$if$it$
seems$frustra8ng$or$a$waste$of$8me$
ini8ally.$Part$of$your$job$is$to$make$his$
job$go$smoothly,$so$be$willing$to$offer$
this$support.

51. • Establish*a*“No*Surprises”*policy*with*
your*boss.*Promise*each*other*that*
you’ll*go*to*each*other*first*when*big*
issues*need*to*be*sorted*out.

52. • Create'a'clear,'mutual'methodology'for'measuring'and'
communica6ng'progress.'Avoid'vague'responses'like'“almost'
done”'or'“we’re'making'good'headway”'that'can'convey'false'
expecta6ons.

53. • Build'alliances'with'people'who'aggravate'your'boss—with'his'
blessing,'of'course.'If'there’s'a'client'who'is'always'complaining'
about'nothing'or'a'produc>on'manager'who'needs'a'process'
explained'six'>mes'before'he'moves'ahead,'offer'to'take'on'the'
issue.'Some>mes,'the'tension'comes'down'to'a'personality'
conflict'that'sends'him'around'the'bend'but'doesn’t'really'bother'
you.'Be'willing'to'give'him'a'break.

54. If#you’re#s+ll#feeling#a#li1le#hesitant#about#managing#your#boss#a6er#
all#of#this#advice,#take#a#step#back#and#remember#your#essen+al#role#
as#a#manager:#You’re'a'communica-on'hub.#Keep#that#one#concept#
front#of#mind#every#day,#whether#the#project#status#is#on#track#or#
off#the#rails,#and#you’ll#steer#yourself#clear#of#many#basic#
management#problems.#

55. Become&a&Be(er&Technical&Manager
I"get"paid"to"coach"newly"minted"technical"managers."My"clients"
quickly"feel"drama:cally"more"confident"and"capable"and"start"
seeing"be=er"performance"from"themselves"and"their"team"within"
weeks.
I"am"taking"the"same"insigh-ul,"ac2onable"lessons"I"teach"in"my"
coaching"and"pu8ng"them"out"as"a"free"newsle<er."Sign"up"to"
become"a"be<er"manager"here.