It’s a fairly routine deployment, but this time, it’s not full of victories. Something goes wrong—seriously wrong—and when the dust settles, you discover the problem centers on a basic mistake from one of your programmers. To add to the pain, this particular programmer just happened to leave work early that day and miss all of the fun. Your stomach is churning, your head is pounding, and you’re about ready to rip loose a torrent of frustration on innocent bystanders. Welcome to management! Now is the perfect time to have a difficult conversation.

1. New$Manager’s$Playbook:$Having$
Difficult$Conversa<ons$With$
Employees

2. It’s%a%fairly%rou.ne%deployment,%but%this%.me,%it’s%not%full%of%
victories.%Something%goes%wrong—seriously%wrong—and%when%the%
dust%se>les,%you%discover%the%problem%centers%on%a%basic%mistake%
from%one%of%your%programmers.

3. To#add#to#the#pain,#this#par/cular#
programmer#just#happened#to#leave#work#
early#that#day#and#miss#all#of#the#fun.
Your%stomach%is%churning,%your%head%is%
pounding,%and%you’re%about%ready%to%rip%
loose%a%torrent%of%frustra8on%on%innocent%
bystanders.

4. Welcome'to'management!
Now$is$the$perfect$.me$to$have$a$difficult$conversa.on.

5. Difficult(Conversa1ons,(Defined

6. A"difficult"conversion"is"any"interac2on"you"have"with"your"team"
members"that"puts"you"in"posi2on"of"delivering"feedback"or"
correc2on.

7. As#a#programmer,#you#probably#weren’t#
forced#to#face#this#situa9on#because#you#
were#responsible#for#your#own#work,#
period.#As#a#manager,#you’ll#be#faced#with#
ini9a9ng#these#emo9onally<charged#
exchanges#on#a#regular#basis#in#a#
suppor9ve,#professional#manner.

8. Difficult(conversa0ons(can(range(from(poin0ng(out(a(flaw(in(a(
piece(of(work,(reinforcing(company(policy,(or(the(ul0mate—having(
to(tell(someone(to(clean(out(their(desk(and(pick(up(their(last(
paycheck(on(the(way(out(the(door.

9. We#all#love#giving#posi-ve#feedback,#like#breaking#the#news#about#a#
promo-on#or#heaping#praise#on#the#person#who#saved#the#project#
with#an#elegant#workaround.
But$when$someone$you$manage$screws$up$and$it’s$5me$for$some$
good$old8fashioned$accountability,$most$people$would$rather$pay$
out$of$pocket$to$endure$a$root$canal$than$have$to$tell$their$former$
peer$that$they$screwed$up.

10. Why$Difficult$Conversa4ons$Are…$
Difficult

11. Let$me$point$out$the$obvious.$No#one#
likes#conflict.$
In#today’s#work#environment,#where#we’ve#
been#steeped#in#poli7cally#correct#no7ons#
of#self:esteem#and#egalitarian#
rela7onships,#these#top:down#
conversa7ons#feel#soooo#1970s.##

12. Rather'than'playing'the'nice'guy,'you'have'to'act'like'an'authority'
figure,'asking'people'to'toe'the'line,'straighten'up,'and'start'doing'
be8er'work.'You’re'afraid'of'coming'off'like'your'junior'high'
principal'with'his'polyester'suits,'rigid'ideals,'and'wooden'paddle.

13. Warning:(Duck(and(Cover(is(a(Dead(End

14. Naturally,)most)people)avoid)that)uncomfortable)place.)
The$problem$is$that$most$managers$haven’t$found$a$more$
func7onal$system.$When$it$comes$to$team$issues,$they’d$rather$sit$
around$singing$“Kum$Ba$Yah”$than$give$nega7ve$feedback.$

15. In#fact,#most#well/inten1oned#new#managers#I#meet#tend#to#fall#
into#one#of#two#less/than/produc1ve#camps#when#it#comes#to#
conflict.

16. Those&in&the&first&camp!don’t!talk!about!
problems!at!all,!hoping!deep!in!their!hearts!
that!things!will!magically!improve!and!that!
everyone!will!just!do!everything!perfectly!
so!a!manager!won’t!have!to!step!in!at!all.

17. Those&in&the&second&camp!don’t!think!they!should!have!to!give!
correc4on!and!instruc4on—team!members!should!just!“get!it”.!
Usually,(a)er(months(of(watching(a(programmer(make(mistake(a)er(
mistake((without(interven:on),(their(internal(scorecard(gets(filled(
up,(and(they(decide(that(this(person(just(doesn’t(cut(it.(They(seethe(
with(frustra:on(and(decide(that(the(only(solu:on(is(to(fire(the(guy.

18. Clearly,(there’s(a(lot(of(room(between(those(two(posi5ons(for(clear,(
helpful(communica5on,(even(if(it’s(not(easy.(
So#what’s#the#answer?

19. Have%More%Difficult%Conversa3ons

20. Don’t&start&looking&for&a&magical&mantra&or&
a&perfect&script&to&make&these&
uncomfortable&situa6ons&vanish.&You&want&
to&learn&to&steer&the&ship,&not&look&for&an&
escape&hatch.&

21. A"willingness"to"look"this"problem"in"the"eye"and"prac6ce"having"
tough"conversa6ons"pays"huge"dividends."Believe"it"or"not,"these"
conversa6ons"can"be"handled"in"a"way"where"you"and"your"team"
can"see"them"as"a"normal—and"produc6ve—part"of"the"design"
process.

22. These%tricky%conversa0ons%can%actually%be%an%effec0ve%tool%to%
connect%with%team%members,%invest%in%their%skills,%and%help%the%
company%deliver%a%quality%product%that%keeps%them%economically%
viable.!

23. Before&you&call&someone&into&your&office&for&a&difficult&
conversa4on,&it&can&take&the&pressure&off&a&bit&when&you&know&your&
role&and&own&it&in&these&situa4ons.

24. Be#the#Conductor

25. Let’s&go&back&to&our&analogy&of&the&technology&manager&as&the&
conductor&of&an&orchestra.
Up#at#the#podium,#the#conductor#has#the#perspec2ve#to#see#and#
hear#everything.#They#know#when#the#bassoon#player#misses#her#
entrance.#They#hear#the#sloppy#fingering#of#the#third#violins#in#a#
difficult#passage.

26. What%does%the%conductor%do%in%response?
A"skilled"conductor"will"stop"the"rehearsal,"gently"and"clearly"point"
out"the"mistake,"and"have"the"musicians"run"the"sec8on"again,"
several"8mes"if"necessary.

27. Conductors*know*there*should*be*li2le*or*no*shame*in*these*
exchanges—it’s*just*part*of*preparing*an*en<re*group*for*a*
magnificent*performance.*Usually,*a*few*minutes*of*focus*can*
smooth*out*the*problem.

28. While&the&musicians&never&enjoy&ge4ng&singled&out&for&less7than7
stellar&playing,&they&also&understand&that&this&a:en;on&lands&on&
everyone&eventually.&It’s&part&of&being&in&an&ensemble.

29. For$more$persistent$problems,$conductors$
will$usually$call$the$musicians$aside$and$
suggest$something$like$extra$rehearsal$
9me$or$one:on:one$sessions$with$the$
sec9on$leader.$If$that$interven9on$doesn’t$
do$the$trick,$then$it$is$very$possible$that$
they’ll$be$looking$for$another$bassoon$
player$next$season.$

30. In#other#words,#clear#communica3on#concerning#individual#and#
team#performance#has#a#predictable#pa9ern,#and#the#world#doesn’t#
fall#apart#every#3me#the#conductor#points#out#a#need#for#
improvement.

31. Small%conversa-ons,%big%payoff

32. Likewise,(you(can(offer(ongoing(feedback(
in(small,(granular(ways(so(you(grow(
comfortable(giving(correc9on(and(your(
team(doesn’t(panic(when(they(receive(it.(

33. One$easy$way$to$do$this$is$by$offering$a$bit$
of$cri4cism$every$4me$you$review$a$piece$
of$work$from$a$team$member,$even$(and$
especially!)$if$it’s$minor.$Your$programmers$
will$soon$understand$that$you’re$paying$
aBen4on,$and$the$nudge$will$help$them$
level$up$their$game.

34. For$the$naysayers$who$think$that$their$
team$should$just$“get$it”$without$even$this$
simple$level$of$interven:on,$let$me$give$
you$a$wake<up$call.
Yes,%we’ve%all%had%employees%who%walked%
on%the%scene%somehow%knowing%exactly%
what%needed%to%be%done%and%did%it%
without%a%whisper%of%direc<on.%It%is%a%
beau<ful%thing%to%behold.%

35. A"er%dealing%with%both%interns%and%seasoned%programmers%for%
years,%I%can%tell%you%that%these%rock%stars%who%seem%to%automa;cally%
“get%it”%had%someone%invest%in%them%and%train%them%in%the%basics%of%
team%culture.%

36. Now$it’s$your$turn.$Here’s$how$to$use$that$power$wisely.

37. Be#a#Surgeon,#Not#a#Barbarian

38. In#every#manager’s#office#there#hangs#an#imaginary#sword.#
It’s%a%sword%of%decision%and%power%that%was%handed%to%you%with%the%
posi4on,%making%it%possible%for%you%to%respond%to%your%team’s%needs%
without%having%to%run%to%your%manager%every%4me%there’s%an%issue.

39. Most%new%managers%eye%it%nervously,%
hoping%and%praying%that%they’ll%never%have%
to%touch%it.%Others%are%more%passive:
aggressive,%eyeing%it%in%front%of%team%
members%and%saying,%“Don’t%make%me%
reach%for%this.”

40. In#either#case,#the#sword#rarely#gets#used,#which#just#makes#the#
manager#look#really#clumsy#every#8me#he#tries#to#pick#it#up.

41. Prac%ce'creates'ease'and'finesse

42. Watch&li)le&kids&playing&with&swords.&The&
first&8me&they&have&one&in&their&hands,&
they&either&make&feeble&jabs&or&they&run&
around&screaming&and&hacking&the&air…&
and&their&siblings.&&

43. New$managers,$unfortunately,$do$the$same.$Some$are$so$6mid$with$
their$power$that$their$team$has$zero$confidence$in$their$skills$or$
leadership$abili6es.$Others$use$it$only$when$they’re$boiling$over$
with$frustra6on,$leaving$their$team$to$hit$the$decks$to$avoid$their$
wrath.

44. When%managers%make%a%conscious%choice%
to%prac2ce%using%this%power%on%a%
consistent%basis%with%an%average%
workflow,%they’re%reducing%their%learning%
curve%and%increasing%their%effec2veness.%
With%a%li(le%prac-ce,%you%can%turn%your%
sword%into%a%scalpel,%making%small,%
pinpoint%cuts%that%leave%li(le%mess%and%
quick%healing,%just%as%a%surgeon%does.

45. The$keys$to$this$approach$are$a$commitment$to$improving$a$bit$
each$week$and$having$a$simple,$reliable$plan$to$follow.$A;er$years$
of$trial$and$error$and$watching$some$truly$remarkable$managers,$
here’s$the$playbook$I’ve$created.

46. Six$Steps$to$Naviga.ng$Difficult$
Conversa.ons

47. Whether&your&first&difficult&conversa4on&is&
in&the&future&or&you’ve&been&handling&
them&badly&for&months,&have&the&courage&
to&go&through&the&process&whenever&it&
presents&itself.&I&guarantee&you,&in&most&
cases,&the&outcome&won’t&be&as&bad&as&you&
think&it&will&be.

48. Step%One:%No+ce%the%signals%that%say,%“Time%
for%a%difficult%conversa+on!”

49. When%you’re%having%conflict%with%someone,%you%can%feel%the%
frustra8on%all%over%in%your%body.%%Pay%a=en8on%to%the%pit%in%your%
stomach,%clenched%fists,%or%tension%headache.%They’re%a%signal%that%
it’s%8me%to%clear%the%air.

50. Some%mes,(the(signal(isn’t(a(feeling.(You(
might(hear(yourself(say(things(like:
This%always%happens…
He%never%gets%this%right…
Not%again…

51. Whatever(your(par-cular(trigger,(know(it(well(and(use(it(as(a(flag(to(
take(ac-on(instead(of(bury(your(head(in(the(sand.

52. Step%Two:%Don’t%fume.%Commit%to%take%
construc8ve%ac8on.

53. Avoiding(ac+on(will(only(create(resentment.(Choose(a(+me(in(the(
immediate(future(where(you(can(discuss(the(problem(with(this(
person(so(you(can(both(move(forward.

54. Step%Three:%Make%a%plan.

55. If#you’re#on#the#verge#of#losing#your#temper,#go#for#a#walk#or#take#
some#deep#breaths.#This#is#not#a#<me#to#prepare#an#exact#script#or#
build#a#bullet?point#litany#against#this#person,#it’s#just#<me#to#zero#in#
on#the#core#of#the#problem#and#possible#solu<ons.

56. Let$off$a$li*le$steam,$talk$out$loud$to$
yourself$(in$private!)$or$sketch$out$your$
opening$line$(see$below),$but$don’t$burn$a$
lot$of$@me$on$this$point.$Move$forward.

57. Step%Four:%Have%the%mee0ng%in%private—soon.

58. Yes,%this%is%uncomfortable%for%the%team%member,%but%talking%to%them%
one%on%one%will%provide%a%calm%environment,%remove%the%possibility%
of%distrac:ons,%and%keep%eavesdroppers%out%of%earshot.%

59. And$if$they$do$have$that$sinking$feeling$as$
they$follow$you$to$your$office$for$a$private$
conference,$that’s$okay.$It’s$an$honest,$
nearly$unavoidable$reac=on.$This$is$a$
ma@er$that$needs$a@en=on,$and$they$will$
know$that$immediately.

60. Step%5:%Be%steady%and%on%point.

61. This%is%not%the%*me%to%pull%out%every%infrac*on%from%the%past%six%
months%or%be%so%vague%about%the%problem%that%your%team%member%
has%no%idea%what%problem%you’re%actually%discussing.%

62. Don’t&yell.&Don’t&repeat&yourself.&Don’t&
bombard&them&with&informa7on&in&the&
hopes&of&making&your&cri7cism&more&valid.

63. Ven$ng&your&anger&isn’t&produc$ve,&so&stay&focused&on&the&
outcome&you&really&want&from&the&discussion.&Using&a&single&
framing&sentence&usually&makes&things&crystal&clear.

64. I"like"to"use"the"word"“disappointed”"in"these"discussions."It’s"a"
subtle"way"of"telling"this"person"that"I"do"hold"them"in"high"esteem,"
and"this"incident"doesn’t"match"that"overall"impression.

65. Here’s&one&of&my&favorite&go1to&scripts&in&these&tense&situa6ons:
"John,'I'was'really'disappointed'when'X'happened.'I'want'to'
understand'why'and'find'out'what'we'can'do'to'make'sure'it'
doesn’t'happen'again."

66. Step%6:%Shut%up.%Listen.%Then%listen%some%
more.

67. Silence'can'be'a'very'powerful'tool'in'these'situa5ons.'While'it'can'
be'excrucia5ng'to'let'empty'space'hang'out'there,'do'it.
Drink&some&coffee&or&count&to&10,&but&let&the&other&person&have&
some&8me&to&collect&their&thoughts&or&get&past&an&emo8onal&
moment.

68. When%your%team%member%does%respond,%resist%the%tempta3on%to%
refute%what%they’re%saying%or%meet%their%defensiveness%(which%is%
completely%understandable)%with%defensiveness%of%your%own.%Be%
willing%to%take%the%blame%for%any%mistakes%on%your%part%and%circle%
around%to%the%solu3on.

69. Always'focus'on'the'solu0on.

70. While&an)cipa)ng&these&difficult&conversa)ons&is&never&a&picnic,&
each&)me&you&move&past&the&fear&and&choose&to&get&through&them,&
you&develop&more&experience,&more&perspec)ve,&and&more&
confidence.

71. Even%be'er,%you%are%able%to%improve%communica4on%within%your%
team,%making%your%job%even%easier.

72. One$day,$you$may$even$find$a$team$
member$knocking$on$your$door$saying,$
"Can%we%talk?%I%screwed%up%and%I%want%to%
make%sure%it%doesn’t%happen%again."

73. 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.