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Art	
  of	
  the	
  W ingman	
  for	
  Business	
  is	
  dedicated	
  to	
  the	
  businesswomen	
  and	
  businessmen	
  who	
  seek	
  greatness	
  beyond	
  their	
  own	
  
and	
  find	
  their	
  successes	
  through	
  helping	
  others	
  succeed.	
  The	
  Business	
  Wingman	
  follows	
  the	
  path	
  of	
  the	
  selfless	
  person.	
  

	
  

Managing	
  Across	
  Generations	
  

	
  
Key	
  Points	
  
• Lead	
  by	
  example,	
  respect	
  everyone’s	
  diversity	
  
• Do	
  your	
  research,	
  every	
  generation	
  lives	
  by	
  a	
  different	
  code	
  
• Unify	
  the	
  team	
  with	
  common	
  goals	
  and	
  expectations	
  
	
  
	
  
We	
  are	
  in	
  a	
  unique	
  time	
  in	
  the	
  workplace,	
  where	
  there	
  can	
  exist	
  four	
  different	
  
generations	
  in	
  the	
  same	
  office	
  and	
  even	
  the	
  same	
  working	
  team.	
  If	
  this	
  resembles	
  
your	
  team,	
  then	
  I’m	
  sure	
  you	
  have	
  experienced	
  the	
  vast	
  differences	
  in	
  how	
  each	
  of	
  
those	
  team	
  members	
  both	
  approach	
  problems	
  and	
  work	
  together	
  with	
  others	
  in	
  the	
  
workplace.	
  	
  These	
  varying	
  differences	
  typically	
  can	
  cause	
  trust	
  issues	
  and	
  discipline	
  
problems	
  within	
  teams	
  especially	
  when	
  a	
  30-­‐year	
  veteran	
  of	
  the	
  workplace	
  learns	
  
one	
  day	
  that	
  his	
  new	
  manager	
  is	
  a	
  young	
  female	
  in	
  her	
  late	
  20’s	
  with	
  less	
  than	
  10	
  
years	
  of	
  experience	
  but	
  with	
  multiple	
  degrees.	
  This	
  situation	
  requires	
  the	
  morale	
  
and	
  leadership	
  of	
  a	
  Business	
  Wingman	
  to	
  help	
  minimize	
  any	
  issues	
  that	
  may	
  come	
  
up.	
  Managing	
  across	
  generations	
  is	
  essential	
  to	
  the	
  success	
  of	
  the	
  team.	
  
	
  

	
  
1) Lead	
  by	
  example,	
  respect	
  everyone’s	
  diversity	
  
In	
  every	
  office	
  and	
  in	
  every	
  team,	
  there	
  is	
  going	
  to	
  be	
  a	
  time	
  when	
  rumors	
  start	
  and	
  
someone	
  says	
  something	
  that	
  is	
  taken	
  out	
  context.	
  It’s	
  typically	
  a	
  he	
  said/she	
  said	
  
situation	
  where	
  someone	
  makes	
  a	
  big	
  assumption	
  based	
  on	
  stereotypes.	
  And	
  now	
  
you	
  have	
  a	
  situation	
  where	
  tempers	
  can	
  rise	
  and	
  productivity	
  can	
  fall.	
  
	
  
This	
  may	
  be	
  a	
  time	
  where	
  a	
  team	
  member	
  from	
  the	
  Baby	
  Boomer	
  generation	
  (Ted	
  
for	
  example)	
  sees	
  a	
  much	
  younger	
  team	
  member	
  from	
  the	
  Millennial	
  Generation	
  
(John	
  for	
  example)	
  watching	
  shows	
  on	
  Hulu.com	
  for	
  lunch	
  and	
  simply	
  assumes	
  that	
  
John	
  is	
  lazy	
  and	
  wasting	
  time	
  at	
  work.	
  John	
  is	
  a	
  proven	
  hard	
  worker	
  with	
  a	
  strong	
  
work	
  ethic	
  but	
  has	
  decided	
  that	
  since	
  he	
  is	
  on	
  lunch	
  and	
  in	
  not	
  required	
  to	
  work	
  
during	
  lunch,	
  that	
  he	
  can	
  spend	
  his	
  lunch	
  any	
  way	
  he	
  wants.	
  Ted	
  on	
  the	
  other	
  hand	
  
comes	
  from	
  generation	
  where	
  work	
  is	
  taken	
  seriously	
  throughout	
  the	
  day	
  and	
  there	
  
is	
  no	
  time	
  for	
  being	
  lazy.	
  
	
  
As	
  a	
  Business	
  Wingman,	
  it	
  is	
  your	
  responsibility	
  to	
  help	
  diminish	
  the	
  situation	
  and	
  
set	
  a	
  new	
  tone	
  for	
  the	
  team	
  and	
  squash	
  the	
  problem.	
  Lead	
  by	
  example	
  and	
  show	
  
how	
  the	
  team	
  should	
  respect	
  everyone’s	
  diversity.	
  Help	
  explain	
  to	
  Ted	
  that	
  this	
  is	
  
not	
  a	
  problem	
  and	
  reinforce	
  to	
  Ted	
  that	
  you	
  also	
  think	
  it’s	
  ok	
  and	
  that	
  John	
  is	
  still	
  a	
  
valued	
  hard-­‐working	
  member	
  of	
  the	
  team.	
  It’s	
  the	
  little	
  things	
  that	
  matter.	
  
	
  
2) Do	
  your	
  research,	
  every	
  generation	
  lives	
  by	
  a	
  different	
  code	
  
Although	
  we	
  are	
  referring	
  to	
  4	
  different	
  working	
  generations,	
  I	
  am	
  going	
  to	
  remove	
  
the	
  Traditional	
  Generation	
  (also	
  known	
  as	
  the	
  Greatest	
  Generation)	
  from	
  the	
  
example	
  and	
  focus	
  on	
  Baby	
  Boomers,	
  Generation	
  X	
  and	
  Millennials.	
  There	
  is	
  a	
  great	
  
article	
  from	
  Workforce	
  Central	
  Florida	
  that	
  explains	
  the	
  working	
  characteristics	
  of	
  
the	
  generations	
  of	
  working	
  Americans,	
  and	
  we	
  will	
  be	
  taking	
  some	
  references	
  from	
  
them.	
  
	
  
Working	
  Characteristics	
  of	
  Baby	
  Boomers	
  
Since	
  Baby	
  Boomers	
  grew	
  up	
  during	
  a	
  time	
  of	
  war	
  and	
  constantly	
  battled	
  authority	
  
and	
  lived	
  to	
  fight	
  for	
  their	
  rights,	
  they	
  tend	
  to	
  disagree	
  with	
  strong	
  authoritative	
  
management	
  and	
  are	
  the	
  first	
  to	
  speak	
  out	
  in	
  disagreement.	
  
	
  
Boomers	
  don’t	
  quickly	
  take	
  to	
  technology	
  when	
  it	
  comes	
  to	
  having	
  meetings.	
  They	
  
prefer	
  to	
  communicate	
  one-­‐on-­‐one	
  and	
  like	
  to	
  look	
  someone	
  in	
  the	
  eyes	
  when	
  
asking	
  questions.	
  Boomers	
  are	
  not	
  found	
  of	
  flexible	
  or	
  relaxed	
  work	
  schedules.	
  
	
  
Boomers	
  are	
  proud	
  of	
  their	
  professional	
  career	
  and	
  accomplishments	
  (rewards	
  and	
  
recognitions).	
  They	
  prefer	
  a	
  competitive	
  working	
  environment,	
  quality	
  of	
  work	
  and	
  
being	
  personally	
  involved.	
  When	
  rewarding	
  Boomers,	
  do	
  it	
  in	
  the	
  form	
  of	
  money	
  or	
  
title	
  recognition.	
  
	
  
	
  
	
  
	
  
Working	
  Characteristics	
  of	
  Generation	
  X	
  
Generation	
  X	
  (also	
  known	
  as	
  Gen	
  X)	
  grew	
  up	
  in	
  the	
  shadows	
  of	
  Baby	
  Boomers	
  and	
  
recognized	
  their	
  extreme	
  work	
  ethic.	
  Because	
  of	
  this,	
  Gen	
  Xers	
  work	
  hard	
  but	
  prefer	
  
to	
  work	
  in	
  companies	
  that	
  offer	
  a	
  strong	
  work/life	
  balance.	
  	
  
	
  
Gen	
  Xers	
  are	
  naturally	
  independent	
  and	
  entrepreneurs	
  at	
  heart.	
  They	
  are	
  constantly	
  
looking	
  to	
  re-­‐evaluate	
  their	
  career	
  path	
  and	
  because	
  of	
  that,	
  they	
  focus	
  on	
  the	
  skills	
  
and	
  experience	
  of	
  the	
  job	
  rather	
  than	
  the	
  relationships	
  that	
  can	
  be	
  built.	
  Changing	
  
jobs	
  every	
  3	
  to	
  4	
  years	
  is	
  not	
  uncommon.	
  Gen	
  Xers	
  are	
  tech	
  friendly	
  and	
  would	
  
rather	
  communicate	
  through	
  IM	
  or	
  email	
  than	
  have	
  in-­‐person	
  meetings	
  so	
  that	
  they	
  
can	
  multi-­‐task.	
  	
  
	
  
Working	
  Characteristics	
  of	
  Millennial	
  Generation	
  
The	
  Millennials	
  (Generation	
  Y)	
  are	
  also	
  known	
  as	
  the	
  Internet	
  Generation	
  and	
  the	
  
Echo	
  Boomers,	
  are	
  the	
  youngest	
  in	
  the	
  workforce.	
  This	
  generation	
  grew	
  up	
  in	
  a	
  
world	
  already	
  inundated	
  with	
  technology	
  and	
  multitasking,	
  which	
  translates	
  to	
  
being	
  flighty,	
  non-­‐committal,	
  and	
  with	
  low	
  attention	
  spans.	
  	
  
	
  
Millennials	
  have	
  also	
  been	
  known	
  to	
  be	
  the	
  entitled	
  working	
  generation	
  where	
  they	
  
feel	
  that	
  because	
  they	
  choose	
  to	
  work,	
  they	
  are	
  entitled	
  to	
  flexible	
  work	
  schedules,	
  
instant	
  feedback,	
  recognition,	
  and	
  high	
  expectations	
  from	
  their	
  employer.	
  
	
  
Millennials	
  are	
  extremely	
  comfortable	
  with	
  technology	
  and	
  prefer	
  to	
  use	
  it	
  to	
  
communicate	
  rather	
  than	
  meet	
  in	
  person.	
  Millennials	
  also	
  seek	
  work-­‐life	
  balance	
  
and	
  lack	
  loyalty	
  to	
  a	
  workplace	
  and	
  it’s	
  employees;	
  it’s	
  all	
  about	
  the	
  experience	
  of	
  
the	
  position.	
  They	
  tend	
  to	
  be	
  entrepreneurial	
  and	
  goal	
  oriented,	
  but	
  work	
  is	
  a	
  means	
  
to	
  an	
  end.	
  	
  
	
  
3) Unify	
  the	
  team	
  with	
  common	
  goals	
  and	
  expectations	
  
After	
  reading	
  about	
  the	
  vast	
  differences	
  among	
  the	
  generations	
  in	
  the	
  workplace,	
  it’s	
  
easy	
  to	
  see	
  that	
  there	
  can	
  clearly	
  arise	
  differences	
  and	
  arguments	
  among	
  the	
  team.	
  
Your	
  role	
  as	
  the	
  Business	
  Wingman	
  is	
  to	
  identify	
  these	
  misunderstanding	
  and	
  
mitigate	
  the	
  risk	
  before	
  anything	
  happens.	
  I’m	
  not	
  saying	
  that	
  you	
  should	
  become	
  
the	
  team	
  babysitter	
  and	
  listen	
  to	
  gossip	
  all	
  day.	
  I	
  am	
  saying	
  that	
  this	
  effort	
  is	
  a	
  part	
  
of	
  your	
  everyday	
  management	
  and	
  leadership	
  among	
  the	
  team.	
  
	
  
For	
  example,	
  rather	
  than	
  encouraging	
  others	
  to	
  hold	
  their	
  opinions	
  to	
  themselves	
  
and	
  letting	
  pent	
  up	
  anger	
  and	
  frustration	
  build,	
  it’s	
  imperative	
  that	
  you	
  notate	
  that	
  
there	
  are	
  differences	
  in	
  how	
  we	
  approach	
  each	
  situation.	
  Reinforce	
  to	
  the	
  team	
  that	
  
everyone	
  is	
  diverse,	
  unique	
  in	
  their	
  experience	
  and	
  wisdom,	
  but	
  each	
  person	
  is	
  here	
  
because	
  they	
  bring	
  a	
  certain	
  element	
  to	
  the	
  table	
  and	
  together	
  they	
  can	
  make	
  
something	
  great.	
  Then	
  by	
  identifying	
  a	
  common	
  goal	
  to	
  reach	
  for	
  and	
  an	
  understood	
  
set	
  of	
  expectations,	
  you	
  can	
  start	
  to	
  see	
  the	
  team	
  unite	
  to	
  help	
  each	
  other	
  solve	
  
problems	
  and	
  approach	
  the	
  situation	
  differently.	
  
	
  
Visit	
  our	
  blog	
  at	
  http://www.artofthewingman.com.	
  

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Managing Across Generations

  • 1.               Art  of  the  W ingman  for  Business  is  dedicated  to  the  businesswomen  and  businessmen  who  seek  greatness  beyond  their  own   and  find  their  successes  through  helping  others  succeed.  The  Business  Wingman  follows  the  path  of  the  selfless  person.     Managing  Across  Generations     Key  Points   • Lead  by  example,  respect  everyone’s  diversity   • Do  your  research,  every  generation  lives  by  a  different  code   • Unify  the  team  with  common  goals  and  expectations       We  are  in  a  unique  time  in  the  workplace,  where  there  can  exist  four  different   generations  in  the  same  office  and  even  the  same  working  team.  If  this  resembles   your  team,  then  I’m  sure  you  have  experienced  the  vast  differences  in  how  each  of   those  team  members  both  approach  problems  and  work  together  with  others  in  the   workplace.    These  varying  differences  typically  can  cause  trust  issues  and  discipline   problems  within  teams  especially  when  a  30-­‐year  veteran  of  the  workplace  learns   one  day  that  his  new  manager  is  a  young  female  in  her  late  20’s  with  less  than  10   years  of  experience  but  with  multiple  degrees.  This  situation  requires  the  morale   and  leadership  of  a  Business  Wingman  to  help  minimize  any  issues  that  may  come   up.  Managing  across  generations  is  essential  to  the  success  of  the  team.      
  • 2. 1) Lead  by  example,  respect  everyone’s  diversity   In  every  office  and  in  every  team,  there  is  going  to  be  a  time  when  rumors  start  and   someone  says  something  that  is  taken  out  context.  It’s  typically  a  he  said/she  said   situation  where  someone  makes  a  big  assumption  based  on  stereotypes.  And  now   you  have  a  situation  where  tempers  can  rise  and  productivity  can  fall.     This  may  be  a  time  where  a  team  member  from  the  Baby  Boomer  generation  (Ted   for  example)  sees  a  much  younger  team  member  from  the  Millennial  Generation   (John  for  example)  watching  shows  on  Hulu.com  for  lunch  and  simply  assumes  that   John  is  lazy  and  wasting  time  at  work.  John  is  a  proven  hard  worker  with  a  strong   work  ethic  but  has  decided  that  since  he  is  on  lunch  and  in  not  required  to  work   during  lunch,  that  he  can  spend  his  lunch  any  way  he  wants.  Ted  on  the  other  hand   comes  from  generation  where  work  is  taken  seriously  throughout  the  day  and  there   is  no  time  for  being  lazy.     As  a  Business  Wingman,  it  is  your  responsibility  to  help  diminish  the  situation  and   set  a  new  tone  for  the  team  and  squash  the  problem.  Lead  by  example  and  show   how  the  team  should  respect  everyone’s  diversity.  Help  explain  to  Ted  that  this  is   not  a  problem  and  reinforce  to  Ted  that  you  also  think  it’s  ok  and  that  John  is  still  a   valued  hard-­‐working  member  of  the  team.  It’s  the  little  things  that  matter.     2) Do  your  research,  every  generation  lives  by  a  different  code   Although  we  are  referring  to  4  different  working  generations,  I  am  going  to  remove   the  Traditional  Generation  (also  known  as  the  Greatest  Generation)  from  the   example  and  focus  on  Baby  Boomers,  Generation  X  and  Millennials.  There  is  a  great   article  from  Workforce  Central  Florida  that  explains  the  working  characteristics  of   the  generations  of  working  Americans,  and  we  will  be  taking  some  references  from   them.     Working  Characteristics  of  Baby  Boomers   Since  Baby  Boomers  grew  up  during  a  time  of  war  and  constantly  battled  authority   and  lived  to  fight  for  their  rights,  they  tend  to  disagree  with  strong  authoritative   management  and  are  the  first  to  speak  out  in  disagreement.     Boomers  don’t  quickly  take  to  technology  when  it  comes  to  having  meetings.  They   prefer  to  communicate  one-­‐on-­‐one  and  like  to  look  someone  in  the  eyes  when   asking  questions.  Boomers  are  not  found  of  flexible  or  relaxed  work  schedules.     Boomers  are  proud  of  their  professional  career  and  accomplishments  (rewards  and   recognitions).  They  prefer  a  competitive  working  environment,  quality  of  work  and   being  personally  involved.  When  rewarding  Boomers,  do  it  in  the  form  of  money  or   title  recognition.          
  • 3. Working  Characteristics  of  Generation  X   Generation  X  (also  known  as  Gen  X)  grew  up  in  the  shadows  of  Baby  Boomers  and   recognized  their  extreme  work  ethic.  Because  of  this,  Gen  Xers  work  hard  but  prefer   to  work  in  companies  that  offer  a  strong  work/life  balance.       Gen  Xers  are  naturally  independent  and  entrepreneurs  at  heart.  They  are  constantly   looking  to  re-­‐evaluate  their  career  path  and  because  of  that,  they  focus  on  the  skills   and  experience  of  the  job  rather  than  the  relationships  that  can  be  built.  Changing   jobs  every  3  to  4  years  is  not  uncommon.  Gen  Xers  are  tech  friendly  and  would   rather  communicate  through  IM  or  email  than  have  in-­‐person  meetings  so  that  they   can  multi-­‐task.       Working  Characteristics  of  Millennial  Generation   The  Millennials  (Generation  Y)  are  also  known  as  the  Internet  Generation  and  the   Echo  Boomers,  are  the  youngest  in  the  workforce.  This  generation  grew  up  in  a   world  already  inundated  with  technology  and  multitasking,  which  translates  to   being  flighty,  non-­‐committal,  and  with  low  attention  spans.       Millennials  have  also  been  known  to  be  the  entitled  working  generation  where  they   feel  that  because  they  choose  to  work,  they  are  entitled  to  flexible  work  schedules,   instant  feedback,  recognition,  and  high  expectations  from  their  employer.     Millennials  are  extremely  comfortable  with  technology  and  prefer  to  use  it  to   communicate  rather  than  meet  in  person.  Millennials  also  seek  work-­‐life  balance   and  lack  loyalty  to  a  workplace  and  it’s  employees;  it’s  all  about  the  experience  of   the  position.  They  tend  to  be  entrepreneurial  and  goal  oriented,  but  work  is  a  means   to  an  end.       3) Unify  the  team  with  common  goals  and  expectations   After  reading  about  the  vast  differences  among  the  generations  in  the  workplace,  it’s   easy  to  see  that  there  can  clearly  arise  differences  and  arguments  among  the  team.   Your  role  as  the  Business  Wingman  is  to  identify  these  misunderstanding  and   mitigate  the  risk  before  anything  happens.  I’m  not  saying  that  you  should  become   the  team  babysitter  and  listen  to  gossip  all  day.  I  am  saying  that  this  effort  is  a  part   of  your  everyday  management  and  leadership  among  the  team.     For  example,  rather  than  encouraging  others  to  hold  their  opinions  to  themselves   and  letting  pent  up  anger  and  frustration  build,  it’s  imperative  that  you  notate  that   there  are  differences  in  how  we  approach  each  situation.  Reinforce  to  the  team  that   everyone  is  diverse,  unique  in  their  experience  and  wisdom,  but  each  person  is  here   because  they  bring  a  certain  element  to  the  table  and  together  they  can  make   something  great.  Then  by  identifying  a  common  goal  to  reach  for  and  an  understood   set  of  expectations,  you  can  start  to  see  the  team  unite  to  help  each  other  solve   problems  and  approach  the  situation  differently.     Visit  our  blog  at  http://www.artofthewingman.com.