Delegation. You’ve heard the legends. You’ve maybe even seen this miracle management technique in action. You know that absolutely everyone sings its praises even as they struggle to implement it. But as a new technical manager, how do you make the magic of delegation work for you?

1. A"Real'Life"Handbook"for"Making"
Delega5on"Work"for"You

2. Delega&on
You’ve'heard'the'legends.'You’ve'maybe'even'seen'this'miracle'
management'technique'in'ac8on.'You'know'that'absolutely'
everyone'sings'its'praises'even'as'they'struggle'to'implement'it.

3. But$as$a$new$technical$manager,$how$do$
you$make$the$magic$of$delega7on$work$
for$you?

4. I’m$not$here$to$blow$sunshine$at$you.$Even$a6er$years$of$
experimen:ng$and$observing$un:l$I$got$it$right,$I$s:ll$have$
management$failures$when$it$comes$to$delega:on.
The$difference$now$is$that$when$I$hit$a$delega3on$snag,$I$can$
course$correct$on$a$dime$and$get$the$ship$headed$to$its$des3na3on.$
And$these$days,$I$have$to$do$that$less$and$less$because$I$know$how$
to$read$the$charts$and$steer$around$the$hazards.

5. Let’s&dive&into&one&of&these&typical&
problems&now.

6. Delega&on)Fail:)The)Best)Laid)
Plans…
Just%a%few%weeks%ago,%I%had%the%chance%to%
put%my%delega7on%skills%into%ac7on—from%
both%sides%of%the%management%table.

7. The$setup
I"manage"a"team"of"developers"for"Ryan."He"handed"my"team"a"new"
project"that"he"knew"inside"and"out,"but"needed"us"to"execute.
A"er%looking%at%the%project%requirements,%he%figured%that%he%could%
get%the%job%done%in%two%weeks,%so%he%handed%off%his%notes%and%
budgeted%one%developer%to%finish%the%job%in%three%weeks,%just%to%be%
on%the%safe%side.

8. Five%weeks%later,%we%s.ll%weren’t%finished,%even%with%three%coders%
hammering%away.

9. That%Painful%Moment

10. Quite&understandably,&Ryan&was&upset.&In&fact,&he&was&really&upset.&
Instead&of&ran9ng&and&raving&though,&he&simply&moved&the&other&
programmers&aside,&shuffled&his&own&workload&around,&and&he&
picked&up&the&tools.
Ryan%dropped%everything%and%spent%a%week%ge3ng%the%project%in%
shape%while%the%rest%of%us%stepped%back%and%carried%on%with%the%
rest%of%our%work%in%an%uncomfortable%silence.

11. Time%for%a%difficult%conversa3on

12. Back%to%the%team
Clearly,(we(needed(to(have(a(mee1ng(between(me,(Ryan,(and(the(
developers(so(we(wouldn’t(have(an(episode(like(this(again.

13. It#wasn’t#a#pre,y#scene.

14. As#painful#as#this#moment#was,#I#wanted#the#team#to#learn#as#much#
as#possible#from#this#ugly#situa9on#so#we#would#avoid#it#at#all#costs#
in#the#future.
In#a#private#mee,ng#beforehand,#I#asked#Ryan#to#call#a#team#
mee,ng#to#hold#my#toes#to#the#fire#over#this—in#front#of#everyone.#
Ryan’s#not#a#yelling#kind#of#guy,#so#I#had#to#encourage#him#to#raise#
his#voice#a#bit#to#get#the#team’s#a?en,on.

15. Why$the$drama?$The$team$needed$to$have$complete$awareness$of$
the$stakes$in$this$game.$We$needed$to$ask$the$painful,$necessary$
ques=ons$and$face$the$difficult$answers.

16. In#that#tense#environment,#it#came#out#that#even#though#Ryan#
thought#he#had#been#completely#clear#on#his#expecta9ons,#the#
team—including#me—misinterpreted#his#instruc9ons.#For#weeks,#we#
were#pushing#ahead#to#create#something#radically#different#than#
what#he#had#envisioned,#even#though#we#thought#we#knew#what#
he#wanted.
Ryan%thought%he%handed%off%a%carefully%labeled%road%map,%but%
when%we%looked%at%it,%we%saw%another%path%and%des:na:on%
en:rely.

17. Delega&on:*It’s*Always*About*Communica&on

18. Here’s&the&biggest&misunderstanding&I&see&with&delega4on.
Most%people%think%it’s%wonderful%because%they%get%to%pass%off%less%
rewarding%work%to%someone%else—and%it%s;ll%gets%done!%And%that%is%
magical.
But$there’s$a$deeper$beauty$of$delega3on.

19. There%is%nothing%like%the%experience%of%taking%an%idea%that%only%
existed%in%your%head—that%you%assumed%no%one%else%could%quite%
understand%the%way%you%do—and%see%it%completed%in%all%its%glory%
through%the%effort%of%many%people%working%together.

20. Doing&delega+on&well&creates&so&much&
value&that&I&want&you&to&have&a&really&
good&handle&on&how&delega+on&actually&
works.!

21. The$key$to$having$more$great$delega2on$moments$is$not$just$
providing$clear$communica2on$about$your$vision,$but$making$sure$
is$received$and$understood$by$the$very$people$who$will$be$
implemen2ng$it.
Fear%not.%I%am%not%about%to%start%rambling%on%about%touchy5feely%
communica7on%skills%that%will%take%you%years%to%perfect.%Instead,%
let’s%break%down%the%delega7on%problem%like%real%programmers.

22. Bugs%in%Your%Delega/on%Process
Basically,)glitches)in)the)delega0on)process)come)down)to)two)
types)of)errors:)compile0me)and)run90me)bugs.

23. Compile()me(bugs!crop!up!in!delega.on!when!when!you!haven’t!
been!careful!with!the!syntax.!In!other!words,!you!haven’t!verified!
understanding!when!you!communicated!expecta.ons!to!your!team!
and!made!sure!your!that!your!plan!was!understood.
The$result$is$that$you$get$a$completely$different$outcome$than$you$
needed—or$the$project$can’t$move$forward$at$all.

24. Run$%me$bugs!appear!in!delega+on!well!into!a!project!when!you!
haven’t!checked!on!progress!at!regular!intervals.!You!cross!your!
fingers!and!figure!that!a;er!another!24!hours!or!week,!things!will!
work!themselves!out.!I!mean,!your!team!is!competent,!right?
The$result$of$run$-me$errors$is$that$you$don’t$know$how$wrong$the$
project$is$un4l$the$last$minute,$causing$missed$deadlines$and$
contribu-ng$to$a$real$last6minute$disaster.

25. Let’s&take&another&look&at&this&issue.

26. Errors%in%ac*on

27. Think&of&delega.on&problems&this&way:"
Your"company"needs"to"produce"the"Mona"
Lisa,"and"your"team"gets"the"job."You"hold"
a"mee;ng"to"give"your"programmers"notes"
and"instruc;ons"about"this"amazing"
portrait"you"want"to"produce"in"three"
weeks."Then"you"turn"them"loose,"
expec;ng"great"things.
Three%weeks%later,%the%team,%eager%and%
proud,%hands%you%a%perfectly%executed%
drawing%of…

28. …"a"’69"Ferrari.

29. Oops.
The$compila,on$error$happened$when$you$didn’t$check$for$the$
team’s$understanding$of$your$instruc,ons$at$the$beginning$of$the$
process.
You$caused$the$run$.me$error$by$neglec.ng$to$ask$for$preliminary$
sketches$and$by$skipping$regular,$real9.me$progress$reports$to$see$
exactly$what$was$on$the$drawing$board.

30. So#it’s#all#the#manager’s#fault?

31. In#a#word,#yes.

32. And$while$that$seems$overwhelming$and$unfair,$remember$that$if$
this$much$responsibility$is$in$your$hands,$you$also$have$a$
tremendous$opportunity$to$iden9fy$and$head$off$the$problems$
before$they$cause$a$lot$of$drama$and$angst.

33. Debug&Your&Delega,on&Process

34. I’m$unapologe-cally$relentless$on$the$point$that$effec-ve$
management$depends$on$effec-ve$communica-on.$Here$is$my$best$
advice$on$strategically$and$smoothly$integra-ng$feedback$into$the$
normal$workflow.

35. Check&Understanding:&Best&strategies&to&
combat&compile&7me&bugs

36. •"Open%a%conversa,on."At"the"very"beginning"of"the"process,"check"
for"understanding."Insist"on"a"kickoff"or"design"mee<ng"where"all"of"
the"issues"can"get"on"the"table."

37. •"Plan,&plan,&plan."Put"some"muscle"into"project"prep"through"
wri4en"instruc5ons,"sketches,"and"concept"descrip5on"for"this"
opening"mee5ng"to"eliminate"confusion"and"loose"ends."Don’t"
leave"essen5al"issues"to"chance."Unfortunately,"people"may"not"
take"the"5me"to"read"all"of"your"notes,"so"walk"through"the"details"
with"the"essen5al"players"and"verify"that"they"understand"
expecta5ons.""Realize"that"many"people"are"“visual"thinkers”,"so"
don’t"skimp"in"the"diagrams"and"wireflows.""You’re"not"crea5ng"
“bureaucracy”,"you’re"communica5ng"an"idea,"and"it"takes"work."""

38. •"Expect'and'encourage'ques1ons."Be"humble"enough"to"ask,”"
What"am"I"missing?"I"know"I’m"overlooking"something."What"issues"
could"use"some"clarity"before"you"dig"in?”""Don’t"assume"people"
“get"it”"the"first"Dme,"and"work"to"know"the"communicaDon"styles"
of"your"team,"so"you"can"communicate"effecDvely."

39. •"Cul$vate)a)safe)environment)for)
ques$ons,)always."Every"project"has"
ques2ons"that"only"appear"as"the"project"
moves"along,"especially"if"you’re"using"an"
agile"development"approach."Reward"
those"who"have"the"courage"to"ask"and/or"
give"you"bad"news"early"in"the"process,"
when"there’s"s2ll"2me"to"fix"it."

40. •"Realize'the'complexity'of'what'you’re'doing."Effec'vely"
communica'ng"technical"tasks"is"an"intricate"job,"so"don’t"get"
ra<led"by"layers"of"unan'cipated"ques'ons"that"emerge."

41. Check&Progress:&Best&strategies&to&combat&run&
5me&bugs

42. •"Don’t&become&an&infinite&loop&error."Check"in"with"programmers"
early"and"o6en"rather"than"giving"them"the"benefit"of"the"doubt"(or"
unreasonable"op=mism)"and"leaving"them"to"do"their"own"thing."

43. •"Follow%your%gut."When"you"get"that"internal"sense"telling"you"to"
kick"back"and"“give"things"a"li7le"more"9me,”"that’s"the"signal"to"
check"in"with"your"team."Most"likely,"something"needs"a7en9on—
now."

44. •"Schedule(well*+med(check*ins."If"a"
project"is"due"Friday"at"noon,"don’t"wait"
un7l"Thursday"at"qui<ng"7me"to"get"a"
progress"update."If"there"are"new"people"
on"your"team,"touch"base"more"frequently"
so"they"get"comfortable"with"a"higher"level"
of"contact."

45. •"Make%your%interac.on%quick%and%painless."Stop"by"cubicles"for"
short"stand5up"mee7ngs"to"hear"what’s"happening."If"you’re"using"
agile"development,"these"touch"points"are"as"essen7al"as"breathing."

46. •"Do#an#actual#test#drive#of#the#progress."If"you’re"making"
furniture,"it’s"easy"to"see"progress."Just"count"the"number"of"
finished"tables"or"cabinets!"With"programming,"accomplishments"
are"harder"to"see"at"a"glance,"so"(politely)"ask"for"a"liAle"proof"so"
you"can"catch"problems"early."

47. What%if%You%Get%a%Ferrari%Anyway?

48. Sure,&a&Ferrari&is&a&beau,ful&thing,&but&not&if&you&were&expec,ng&a&
Mona&Lisa.
Even%when%you%think%you've%done%everything%right%(as%Ryan%and%I%
thought%we%did),%bugs%can%s;ll%creep%in.

49. What%can%you%do%when%it%feels%like%it’s%too%late?

50. • Start&by&taking&responsibility&for&the&miscommunica7ons.&
Blaming&team&members&and&insis7ng&“they&just&don’t&get&it”&
doesn’t&move&the&project&or&the&team&forward.&In&fact,&it’s&very&
harmful&to&morale&and&loyalty.

51. • Iden&fy)the)root)of)the)problem.)Where)did)the)project)start)
heading)off)the)rails?)Did)you)ignore)your)intui&on)when)it)was)
nudging)you)to)check)in?)Were)team)updates)too)vague)and)
untested?

52. I’m$really$a$big$fan$of$delega1on.$Though$it$can$be$bumpy$and$
unpredictable,$but$the$rewards$for$you$and$your$team$are$huge.
Take%a%breath,%set%aside%misconcep3ons%and%fears,%and%commit%to%a%
more%hands5on%approach%with%communica3on.%Once%you%and%your%
team%learns%to%trust%the%process,%it’s%a%gi>%that%keeps%on%giving.

53. 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%>>