CAD Management: Shock Your Boss

Shocking your boss in a negative way can get you into hot water.  No boss likes to be caught looking bad, uninformed, or unprepared.  You would do well to keep him or her in the loop and up to date on every aspect of your duties and the areas your boss oversees.

I want to discuss shocking your boss in a positive way by doing things that will please and surprise them.  Bosses want and expect performance, but they may define it differently.  If you want to shock your boss with something unexpected, make sure it is within the areas they look for to be impressed.

Generational Shift
With the introduction of third or fourth generations in the modern workplace, you may find yourself working with and/or for a generation that is one or even two steps away from your demographic.  I have always been interested in generational changes and how they impact the perspectives, desires, motivations, rewards, and success drivers of the individual employee.  Having done a good amount of specific research for a presentation at the leadership event at Autodesk University, I have been seeing traits that impact the way people get along.  While the broad-brush definitions of a generation and its perspectives are not specific to individuals, there are patterns and generalities that seem to be displayed as the worker and boss interact.
Here are the general definitions of the five generations that might be in your workplace:

Traditionalists (WW2 Generation) - born before 1946. (65 and older)

Baby Boomers - born between 1946 and 1964. (46-64)

Generation X - born between 1965 and 1976. (34-46)

Millennials (Gen Y) - born between 1977 and 1994. (18-34)

HomeLanders (a new designation) - born after 1994. (18 and younger)

Generational blend works with those that are near the beginning or end of a generation. Employees at these intersection points may exhibit perspectives and hold values from a prior or later generation.  So with this framework, let’s take a look at what might “shock your boss” in a positive way.  And keep in mind: the bigger the generational gap between you and your boss, the more dynamic the shock might be.
Shocking your boss is when you do something that he or she thinks is out of character and brings positive results.  Their definition of the character traits that they are looking for and the results they seek.  It is not your understanding of what your boss might want, it is his reality.  You do not shock someone by doing what they expect.  Rather, it is the unexpected that shocks.  Your boss has a well-defined framework for what they expect from you (if they are paying attention).  They know what you do and how you do it.  They know what you embrace and what you reject.  They know what excites you and what can be dull and boring for you.  They expect you to continue along the same path.  Doing something that is outside your normal pattern has shock value, and when it is a positive thing that they appreciate, it can move them toward seeing more value in you. 

With this in mind, let’s take a look at what each generation might see as something that other generations “just don’t get”.  If you do these things, you are more likely to impress your boss.  Each of these reflects what a boss may value, and when you exhibit or at least respect these concepts, your boss may be encouraged.

If you work for a Traditionalist:

Play by the rules.  Even when you are tempted to go around the rules and guidelines that might be in place, do not do it if you report to a person that is deeply entrenched in following the rules.  It might ‘cramp your style’ and make things take a little longer, but defying the rules when you work for someone that has followed the rules for more than 40 years can hurt you.  When you follow the rules, make sure that you mention how you complied. Then sit back and watch the boss grin and appreciate you.

Communicate in a formal manner.  Send a memo outlining your targets and plans.  Set up a regular written reporting process, even if it is just emails, and then follow it up and stay on schedule with the reports and check-ins.  Your boss may be used to seeing things in print and verifying things in writing.  Give them that and keep it going.

Put duty before fun, even when you need to just take a break and blow off some stress.  Keep focusing on getting things done prior to indulging in any diversions.  Traditionalists are tied to duty and consistency.  Keep it all about business and stay the course to win points with the boss.

If you work for a Boomer:

Stay loyal to company.  Put the company first or at least very near the top of the list.  Take one for the team, even if it means that you may appear to have failed.  Like the Traditionalist but not quite as far, Boomers are generally loyal to the firms they work with. 

Work well in teams.  Boomers generally approach projects and decision-making as a team sport.  When you work hard at staying a part of a team and keep them in the loop, they love it. 

Don’t let them become uninformed.  Unlike Traditionalists, who want written reports, Boomers may want it written and may not.  But what they do want is to be informed.  Do no let them be unaware of issues affecting their areas, teams, or projects.

If you work for a Gen X:

Do something outside the box.  They are not bound by the rules.  When you creatively go around them, they like it – unless, of course, it is a rule that they created. 

Don’t always ask them to make the decisions.  Make some yourself.  They may bristle, but they actually appreciate initiative and command decisions.  They are use to making calls on their own.  Teams are nice, but not needed for everything.

Focus on end results.  Like I mentioned they want to get to the goal line.  How they get there is up for discussion.  Maintain ethical behaviors, but get the job done.  Be a tireless worker like they are.  Don’t rest on your laurels, they never do.

If you work for a Millennial:

Think technology.  Answer all questions with at least one tech tool.  They are use to it and expect technology to address issues and tasks. 

Get involved in their cause.  They may have some participation in service or support community outside the firm or inside the firm.  They may donate time or talent to these causes.  See if you can team up with them on this effort.

Communicate informally and often via email, text, chat, or whatever.  Include them in your thought and decision flow.  They are adept at multitasking and expect others to be also.

Get involved with them outside of work.  They blend work and social activities all the time.  If you get a chance, ask them to dinner or just to meet after work in a casual environment.  They will appreciate interacting with you in another environment.

Not too many are working for HomeLanders just yet.  They are too young to be the boss, but we will see them move into supervisory roles sooner than others and at a younger age.  Keep your eyes open.


Adjusting your interaction based on the generational differences between you and your boss will work if they are older or younger than you.  Avoid typecasting yourself by the generation you live in and try to adapt to a more flexible way of working.


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