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It’s an introvert’s party too.

It’s an introvert’s party too.

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TableofContents

CONVERSATIONALLYSPEAKING:WHATTOSAY,WHENTOSAYIT,ANDHOWTONEVERRUNOUTOFTHINGS

TOSAY

TABLEOFCONTENTS

INTRODUCTION

1.MASTERCONVERSATION;RELATIONSHIPS.

2.EVERYONELIKESAVERBALMIRROR.

3.ICEBREAKING,MELTINGGLACIERS,ANDSTARTINGACONVERSATION.

4.COMMONQUESTIONSANDUNCOMMON,BETTERANSWERS.

5.EFFECTIVELISTENINGINTHREESTEPS.

6.BUILDINGABULLETPROOFFIRSTIMPRESSION.

7.TELLSTORIESLIKEHOMERANDAESOPCOMBINED.

8.MAKINGSAFETOPICSINTOFAILSAFECONVERSATIONS.

9.AVOIDAWKWARDANDUNCOMFORTABLESILENCES.

10.BODILYSPEAKING.

11.SOCIALCUESSAYMORETHANYOURWORDS.

12.EXITINGCONVERSATIONSWITHGRACE.

13.CONVERSATIONKILLERS.

14.IT’SANINTROVERT’SPARTYTOO.

15.CONFRONTINGWITHOUTCONFRONTATION.

16.LISTENTOOPENTHEMUP.

17.DIGITALLYSPEAKING.

18.A21-DAYCONVERSATIONBOOTCAMPPLAN.

19.HUMOR101.

CONCLUSION

CHEATSHEET







Introduction













I’vebeenfortunatetohavebeenexposedtoawiderangeofpeoplethatIwouldconsiderrolemodels.



Ihavemanyofthetypicalonesthatotherentrepreneursandauthorsdo,buthere’sanunconventionalone

thatmightthrowyouforacurve.



HenryKissinger.



First,somebackground.



HenryKissingerisprimarilyknownasanAmericandiplomatwhoservedunderPresidentsRichard

NixonandGeraldFord.HewenttoHarvard,andcurrentlyrunsKissingerAssociates,aconsultingfirm

thatbrokersinternationalnegotiationsanddealings.



SobesidestoanaspiringSenator,whyexactlyisherolemodel-worthy?



Well,hislistofaccomplishmentshasliterallychangedthecourseofhistory.Let’stakealook.



IntroduceapolicycalleddétentebetweentheUnitedStatesandtheformerSovietUnionattheheightof

theColdWar,whichmanyhistoriansconsiderthebeginningoftheendoftheColdWarandmutualrising

nuclearthreat?Check.



InstitutetalksbetweentheUnitedStatesandcommunistChinawhicheventuallyledtotherecognition

andformalizationofrelationsbetweentwonations,ending23yearsofpoorrelations?Check.



Oh,andnegotiatetheParisPeaceAccordstoestablishpeaceandenddirectUnitedStatesmilitary

involvementinVietnam?Check.



Hisbodyofworkspeaksforitself,butit’sreallythemannerandmethodthroughwhichheaccomplished

thesefeatsthatmakeshimahugerolemodelforme.



Athismostbasiclevel,HenryKissingerwasamastercommunicator,negotiator,andpeopleperson.

Thisishowhewasabletobringquarrelingcountriestogethernolessthanthreeseparatetimesinhistory,

andsaveliterallymillionsoflives.



Hewasabletotalkinwaysthatpeoplewouldlistenandseethebenefitofhiswords.Heknewjusthow

toappealtopeople’sdifferingmotivationsandintentionstoworkoutanunderstandingthatnevercould

havedevelopedotherwise.Hebrokepoliticalstandstillsandbridgedideologicalandphilosophical

differencesinwaysthatbothsparedandendedgreatconflicts.Hedeeplyunderstoodhowtobend

people’spositionstoembracerealityandcompromise.





Finally,hejustmadethingshappenthroughsheerskillandwill.



Canyouimaginehavingthatmuchsocialgracethatyoucanliterallybendthefateofnationswithyour

conversations?Meneither,butthatdoesn’tmeanit’snotaworthygoaltostrivefor.



It’sclearwhatthepowerofsimpleconversationcando–ifitcanshapehistory,justimaginehowmuch

moreenrichingitcanhelpourpersonallivesbe?



Conversationisthebedrockofanyrelationship,andit’sexactlyhowandwhyyouhavebondedwith

everypersoninyourclosestsocialcircles.Theremayhavebeensomecircumstantialluckinvolvedfrom

timetotime,butmyhopeisthatthroughtheprinciplesinthisbook,youwillbeabletostrikeupa

conversationwithanyoneatanytime,withnothingcircumstantialrequiredatall.



You’llunderstandhowandwhyaconversationplaysoutthewayitdoes,andseeitforthescienceof

patternrecognitionthatitreallyis.



Icoverallphasesofatypicalconversationfromicebreakingtoleavingonahighnote,andnearlyevery

partinbetween–notjustWHATtosay,WHENtosayit,andHOWtoneverrunoutofthingstosay…

butWHYeverythingworksthewayitdoes.



You’lluncoveradeepunderstandingofsocialmechanicsthatwillmakeyou,conversationallyspeaking,

preparedforanything.



WemightnotbeabletoreunitetheKoreas,butwecandefinitelymakeadifferenceinhowfulfilledwe

areonadailybasis.



1.Masterconversation;relationships.













Whatareyourgoalsinlife?Tooheavytostartwith?



Okay,sowhatareyourgoalsforthenextweek?Isitwork-related,hobby-related,orjustsocialin

nature?



Whateveryouendupansweringisnottheimportantpart–theimportantpartistherealizationthat

conversationandsmalltalkisgoingtobeintegraltoaccomplishingit.



Ourworldisnotruledbystrictrequirementsandobjectivity,despitewhatwemightliketobelieve.We

don’tliveinanythingremotelyresemblingameritocracy,andtherelationshipsyouareabletocultivate

arereallywhatpropelyouforwardinthislife.



Thus,there’salogicalthreadherethatIfeelobligatedtospellout.



Successrequiresasmanystrongrelationshipsasyoucancreate,andrelationshipsaremadestrong

byconversationthatdelvesdeepandallowstwopeopletoactuallyconnect.



Atitsbest,itallowspeopletodropallpretense,becomevulnerable,andrelatetoeachotherinwaysthey

neverthoughtpossible.Thisengenderslove,friends,business,andaccomplishments.



Beyondthebenefitsthatbecomingastrongconversationalistwillgiveyou,it’sjustanecessity.Youjust

can’tavoidsocialandinterpersonalinteractionunlessyoudecidetobecomeashut-in…buteventhen,

youhavetooccasionallyorderfoodoropenthedoorforthedeliveryman.



Unsurprisingly,mostpeoplearenotnaturalsatconversationandsocialskillsingeneral.Whenyouwalk

awayfromaninteractionthinkingsomeonewasawkwardormadeyouuncomfortable,that’stheexact

indicator.We’reneverexplicitlytrainedinthesethingsthewayweareingeometry,geography,andthe

capitalsofeverystateinthecountry.



Gee,Iwonderwhichoneisactuallymoreusefulintherealworld?



Peoplealsohavevariousinternalanxietiesandmentalblocksthatmightpreventthemfromsuccessfully

engagingpeopleinconversationonaregularbasis.



Regardlessofthepaththatledyoutothispointofwantinghelpandimprovement,restassuredand

comfortedthatitwillbeaneasierclimbthanyouthink.Likeanythingthatisnecessary,youmightinvolve

abitofkickingandscreamingasyouleaveyourcomfortzones,buttherearesomecompellingreasons

todoso.





First,conversationskillsopentrust.



Thefirstmeetingbetweentwopeoplecanbecautiousandtense.Ifyouhavenotbeenintroducedby

friendsandvalidatedbythenetworkeffect,yousimplydon’tknowsomeoneandwhetherornotyoucan

trustthem.Ifthey’llbetrayyouorbenicetoyou.Ifyou’llgetalongorhateeachother.



Thefirstfewmomentsareaquickhazeofattemptingtocollectbasicinformationwithwhichtomakean

informeddecisionabouttrust,openingup,whotobuildrelationshipswith,andwhotoignore.



Initialconversationisaneffectivewayofdetectingeachother'sinterestandmostimportantly,figuringout

whetherwecouldbecomfortablewitheachother.Smalltalkmayseemverysuperficialandrather

innocentbutintermsofinterpersonalrelationships,it'sactuallyaveryimportantfilteringmechanism.It

cangivepeopletheinformationtheyneedwhethertheyplantoletthispersonindeeperintotheirlivesor

holdthematacertaindistance.



Smalltalkandconversationisreallykindofasociallyacceptedgatewayforyoutoletotherpeopleknow

whatyou'reinterestedin,what'simportanttoyou,whatyourpersonalityislike,andyourpersonaltwist

orspinoncommonknowledgeorcurrentevents.



Withrustyornon-existentconversationskills,youruntheriskofbeingperceivedassomeonethatis

untrustworthy,notworthspendingtimewith,orjustawkward.



Second,conversationskillsmakepeoplefeelsafe.



Conversationcanbeasshallowasyouwant.Butdonecorrectly,itmakespeoplefeelcomfortableand

safewithyou,andultimatelytrustyou.



Initialsmalltalkandconversationistypicallyneutralinnature,andaboutharmlesstopicsthatmost

peoplecanagreeon.Anythingelseandit’snotreallysmalltalk,it’sjustabrasiveandoff-puttingin

nature.



Yetstill,thereistheopportunitytoprovidecontextandinformationaboutwhoyouare,whatyourvalues

are,andhowyouconductyourselfsopeoplecanbecomecomfortableandtrustyou.Thissmalltalkisthe

gatewaytofriendships,opportunities,andrelationships.



Whenpeoplefeelsafe,theyreciprocateandattempttodrawyouintotheirsphereofpersonalspace.

They’llsharewithyou,andwhenyouhavetwopeoplesharinginformation,thatisthefoundationoftrust

andintimacy.



Ourtruefriendsarewhowefeellikewillbethereforusthickandthin.Youdon’tgettothatpositionjust

bystandingnexttoeachothersilently,nomatterhowlongyouhavestood.Friendshipsandrelationships

areaseriesofsharedmomentsandconnections,drivenbyconversation.



Ergo,upgradeyourconversationquotientandcapacity,andfindyourselfatthecuspofmanymoredeep

relationshipsandfriendships.







2.Everyonelikesaverbalmirror.















There’sasayingthatessentiallystatesthatthebestwaytoengagepeopleistoletthemtalkabout

themselves.Givethemthespacetoexplaintheirmotivationsandintents,andnoonecanresistthe

temptationoftalkingabouttheirowncleverness.



Comingfromadatecoachingbackground,Icantellyouthatthesameadviceholdstruebecauseithas

thesamegoal.Onadate,it’snotabadruleofthumbtodotheminorityofthetalking,andallowyourdate

totalkaboutthemselvesandtheirthoughts.



Weinnatelyknowthatthishastheeffectofdrivingaconversationbecausepeopleliketotalkabout

themselves.Italsogivestheappearanceofasmooth,flowingconversationbecausebothpeopleare

drivingtheconversationalongandworkingtogetherforasinglepurpose–totalkabouttheother

person.Theendresultisthattheotherpersonwilljustlikeyoumore,becausetheyhaveperceiveda

greatconversationtohavetakenplace.



So…doyoufindyourselfclammingupwhenyoumeetnewpeople?Nervousandanxiouswithothers?



Thenbecomeaverbalmirror.Shinetheconversationbackontotheotherpersonandseeyour

interactionsblossom.



Mostpeoplehaveacertainamountofmentalblocksindealingwithpeoplethattheydon’tknoworhave

justmet.



Buttheywilllovetoengageontopicsthattheyarecomfortableonorexpertson…andwhoisn’tan

expertonthemselves?



Ifthereisanyonethingabouthumannatureyouneedtolearn,peoplelovetotalkaboutthemselves.The

averagepersonnavigatestheworldwiththemselvesasthecenter.Theyprocesstheinformationthe

worldgivesthemfromtheirownpersonalperspective.



Piggybackonthiscommontendencysothattheybasicallydoalltheworkwhenyou'retalkingtothem.

Yourjobistoreadthesignalscarefullysothatyoucanchangethedirectionoftheconversationsothat

theycankeeptalking.Andthefunnythingaboutallofthisisthatthebetteryouareatlisteningtopeople,

themoretheywouldthinkyouareagreatconversationalist.Prettyparadoxical,right?



Conversationstendtosufferasaresultofpeoplefeelingthattheyareinthespotlight.Liketheyare

performing,andwaitingtobejudgedforwhattheysay.Thattheyareinthecenteroftheroomand

everyone’seyesareonthemandmakingthemincrediblyself-conscious.Peopleclamupandthisisthe

exactphenomenonwhenyoujustcan’tthinkofanythingtosaytosomeone.





Thetruthisyou'reagoodconversationalist.Youjustletthepressureofhavingtoperformgetthebestof

you.Thisiswhenanxietyaboutperformingkicksinbecauseyouhaveaveryhumanandcommonplace

fear.Whatfearisthis?Thefearofrejection.Nobodylikestoberejected.Nobodylikestobemadeto

looklikeafool.Buttherealityisthatyoualreadyhavethosegreatsocialskills.



Oneofthebestwaystotrainyourselftodothisistomastertheartofmakingtheotherpersontalk.



Sowhenyoumeetanewpersonandstructureanddirecttheconversationbasedonwhat'simportantto

them,youhaveyourselfaninstantconversation–thebestpartofitisthatthere'snoheavyworkonyour

part.Thereisnoneedforyoutofeelthatyouareperformingbecausetheconversationisallaboutthem,

andtheyfeelthesamewayintalkingaboutsomethingsocomfortabletothemasthemselves.



It'sveryimportantthentofocusonwhatyourjobis.Asimplemindsetshiftcanhelpyouhere.



Yourjobduringconversationsisnottograbthespotlightandcomeupwithsomethingprofound,witty,

intelligent,orfunny.You’renotintheconversationtoteachorpreach.



Dumbitdown!Instead,yourjobistoguidetheconversation.Throwyourselfintherefromtimeto

timetolurethepersondeeperintotheconversation.Theactualcontent,theactualmeatofthe

conversationcanbeprovidedbytheotherperson.



Thebetteryouareatguiding,thesaferyoufeelandthelessanxiousyougetabouttalkingtopeople.

Eventually,asenseofmomentumkicksin,andyoucanprettymuchtalkwithanybodybecausethereality

isregardlessofwhethertheyliveontheothersideoftheplanetorasmallcorneroftheUnitedStates,

everybodyisthesame.Everybodylovestotalkaboutthemselves.



Themorepracticeyouhaveofluringpeopleintalkingaboutacommontopic,toluretheminandhave

thembasicallytakeovertheconversationwithyouguidingthematcertainstages,themoreconfidentand

ateaseyouwouldfeelaroundstrangersandwithanytopic.



Thiscanmeanthedifferencebetweenahigh-performingsalesperson,andsomebodywhocan'tsell

anythingevenifhisorherlifedependedonit.Thiscanalsomeanthedifferencebetweenmeetingthe

personthatyou'redestinedtolivetherestofyourlifewithanddyingalone.Thestakesareprettyhigh.



Greatconversationsreallyareallaboutcallandresponse–peoplecannotresistthecalloftalkingabout

themselves.Firstfocusonthesetopicsandtransferthefeelingandpracticeyougetfromthem.



Keyphrases:



1. Tellmemoreabout____.

2. Oh?Howdidthataffectyou?

3. Howdidyoucomeupwiththat?

4. [Repeatthelastfewwordsofwhattheyjustsaidandtrailoff…]

5. Whydidyouthinkofthat?

6. Whatwasthebestorworstpartofthat?

7. Whydoyouthinkthathappened?







3.Icebreaking,meltingglaciers,andstartingaconversation.

















Whenfacedwitharoomfulofpeoplewedon’tknow,it’sathreateningsituationforalmostallofus.How

dowepickonepersonout,engagethem,andbreaktheicewiththem?



It’saninherentlyuncomfortablesituationthatmakesusafishoutofwater.Wedon’twanttodisrupt

peoplethatmightbehavinganicetalkwithsomeoneelse,becauseweknowthatwe’vebeenannoyed

whenrandompeoplehavebutted-in.Wedon’twanttosaythewrongorawkwardthingthatwillstartan

interactionoffonthewrongfoot.



Mostofallwejustdon’twanttoberejected!However,aswithallthingsthathingearoundthefearof

rejection,realizingthatjudgmentisfarlessprevalentthanyouthinkcandowonders.Inotherwords,

onceyoucangetoverthementalblocksofgettingrejectedfromaconversation(which,honestly,doesn’t

happenmuchatall),you’llrealizethatit’sjustamatterofopeningyourmouthanddoingit.



Ofcourse,thereareoptimalwaystodoitsothatyoucanstartoffaninteractionaseasilyaspossible,and

that’swhatI’lltalkabouthere.Almostall(appropriate)icebreakersarewelcome,butnotallicebreakers

arecreatedequally.



Talkaboutwhatyouhaveincommonatthatmoment.



Evenifyou’resomewherethatyou’veneverbeenbeforewithagroupofstrangers,thereareboundtobe

commonalities.Forstarters,you’reallatthesamelocation,aren’tyou?



Socialeventsalwayshavethemesandcommonalitiesthatyoucandrawontoicebreakconversations.If

it’snotabirthdaypartyorcollegereunion,whatistheonereasonthatbroughtthisseeminglyrandom

groupofstrangerstogether?Isitakickballparty?



Itcanbeasbasicasanetworkoffriendsinvitingtheirfriendsandfriendsoffriendstohangoutat

somebody'shouse.Youcantalkaboutthefriendsyouhaveincommon.Youcantalkaboutthefactthatyou

areinthisinterestingnewhouse,andthatyougotinvitedacertainway.



What'simportantisforyoutoclearlyidentifywhatmostpeopleinthatparticularsocialspacehavein

common.Searchdeepandyou’llfindit.Fromthere,youcanbranchintoactualconversationandlearn

aboutwhatmakespeopledifferent.



Tosumitup,startwithabroadcommonality,thennarrowintotheopposite.Focusintopeople’s

specifictraitsafterbreakingtheicewithasharedreality.





Keyphrases:



1. Howdoyouallknowthehost?

2. It’smyfirsttimeatthisbar…isitalwaysthisrowdy?

3. Checkoutthatwalldécor,it’ssofunny.

4. Soeveryonehereplayskickball?Whohasthemostpowerfulleg?

5. Host’shouseissonew,isn’tit?I’msojealous.

6. Wheredoyouthinktheygotthenameforthisbar?

7. Whydoyouthinkthatguyoverthereisn’twearingshoes?



Leadtheconversationtothemafterbreakingtheice.



Recallinthepreciouschapterthateveryonelikesaverbalmirror.Theremaybenogreaterpleasurethan

talkingaboutourselvesandexplainingindetailourmotivationsinourdailylives.



Alsorecallthatthisopenspeopleup,andmakesthemperceiveyouasafriendevenifyoujustmet.Ifyou

canprobepeopleaboutthemselvesandfindatopicrelatingtothemselves,youcanencouragethemto

strayontothattangent.



Onceyouidentifythat,keepdwellingonitsothattheycanbasicallytalkmoreandmoreaboutthat

particulartopic.Thegoalhereisasmoothtransitionfromyouricebreakerintoaconversationwithactual

substanceandconnection.



Aruleofthumbhereisthatyouwillprobablyberequiredtodo75%oftheleadingandtalkingatthe

beginningofaninteraction.Youwillneedtofillthesilencesyourself.



Samplequestionchain:



1. Didyouseethatcowheadmountedonthewall?Thisplaceiscrazy!

2. I’veonlyseensomethinglikethatinTexasbefore,haveyoubeen?

3. Oh,wherewereyouborn?

4. NewYorkdefinitelydoesn’thavecowslikethat.Whydidyoumovehere?

5. I’veheardthattheagriculturejobmarketisstronghere,butIneverknewexactlywhatthatmeant.

Whatexactlydoyoudowithinit?

6. Soitsoundslikeajobthatprovidesanicelevelofwork-lifebalance.Isthatwhatyouwere

lookingfor?

7. Great!Where’syournextvacation?IjustwenttoThailandandhighlyrecommendit.



Fromageneralobservationofthedécor,toaskingaboutwheresomeoneoriginatedfrom,todeeper

motivationsanddesiresinashortseriesofquestions.



Avoidcontroversy.



WhileIdon’tgenerallytellpeopletospoutgeneralitiesliketheweather,thereisatimeandplacefor

conveyingyouropinionandstandingoutabovethefold.



Icebreakerswithpeoplethatyoudonotknowarehardlytheplaceforthat.Youropinionscanoftenbe



polarizing,whichisnotanegativething.Butgiventhatyourgoalhereissimplytobeginaninteraction

andmakethemcomfortablewithtalkingtoyou,beingtheslightestbitabrasivewon’thelpthatgoal.



Mosttopicscanbetalkedaboutfreely,butwhatmakesthemcontroversialishavingtoostrongofan

opiniononthem,andimmediatelyconveyingthattoothers.



Keepingthegoalinmindofbeginninganinteraction–whathappenswhenyourunacrosssomeonewhose

viewsdon’tlineupwithyours?Youwillbeseenasanenemyoratleastunpleasantperson,asmost

peopleareunabletoseparateacivildisagreementwithpersonalvendetta.



Itdoesn’treallymatterhowyouhandlethesituationofconflictingviews.Whenthishappenswith

someoneyoujustmeet,it’sinstincttowritethemoffbecauseyoudon’tknowaboutthemotherthanthe

factthatyoubuttheadsphilosophically.Ifyoufindyourselfhere,theconversationmightnotbe

salvageable.



Sostayawayfrompotentiallydangeroustopicslikereligion,politics,race,genderpolitics,orother

divisiveissues.Youcanbringthemup,butdon’tofferyouropiniononthemuntilyougaugehowtheother

personreacts,ifatall.



Ifitappearsthatyoumightagreephilosophically,thenfeelfreetoofferyourunfilteredopinion.Butthat

wouldbetheexceptionratherthantherule.



Notedetailsandprovideyourown.



Youmightbedetectingathemethatconversationsrequiresomeeffortandthinkingonyourfeet.Youcan’t

justcoastinaconversationandexpectthatyourautopilotresponseswillproducetheconnectionsthatyou

want.



Takingnoteofdetailsthattheotherpersonprovidesyouwithisaninstanceofwhereyoucan’tcoast,and

youmustactivelybelisteningtotheotherperson.



Mentallycatalogsomeimportantdetailsoraspectsofastorythatappeartoexciteyourconversation

partner,andreturntothoseintimesofdoubtorimpendingsilence.



Bydetails,Imeanliketheirhometown,occupation,hobbies,andotherpersonalinformationtheyhave

divulgedtoyou–thingsthattheycanrelatetoorthatmadetheirfaceslightupwhentheywerebrought

up.



Thisway,youwillalwayshavesomethingtotalkaboutandinstantlyinjectenergybackintothe

conversation…aswellasavoidawkwardlullsandsilences.Youmaynotknowthatmuchaboutthem,but

youshouldbeabletodetectwhatapersonmightbeinterestedinandexcitedaboutwithinafew

minutes.Maintaininterestandfocusbyfocusingonthem.



Onyourside,youshouldreciprocatewithpersonaldetailsandstorieswhenappropriate.Ifyouhavea

personalstorythatrelatestoaperson’sinterestorcontext,itwilldrawthemtoyouandmakethemview

youasapersonwithmoreinherentvalue.





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