11 Unusual Requests From Bosses

Published: Sep 27, 2014
Updated: May 12, 2021
1 minute read

11 Unusual Requests From Bosses

Wardrobe Malfunction

Wardrobe Malfunction

A boss asked an administrator to cut off his tie, because it was caught in the paper shredder.

Go-Between

Go-Between

Another was asked to communicate between two execs who were not speaking to each other.

Earth Day

Earth Day

A boss told an admin to mail a box of dirt.

Plumbing Primer

Plumbing Primer

A supervisor told an admin to send an email to staff to explain how to properly flush the toilet.

Navigational Assistance

Navigational Assistance

A boss asked an admin to help land a helicopter on top of the office building.

MIA

MIA

An admin was told to call airport security to locate a missing shoe.

Sweet Dreams

Sweet Dreams

Another was directed to call a hotel in London to request soft pillows for the CEO.

Paper Chase

Paper Chase

A supervisor asked an admin to take samples of toilet paper from all the office bathrooms and compare them.

Bah Humbug!

Bah Humbug!

A boss told an admin to purchase—and assemble—Christmas trees in seven office locations.

Force of Habit

Force of Habit

A supervisor asked an admin to rent a nun costume for an event.

Some Job!

Some Job!

A boss told an admin to get a snake out of the women’s bathroom.

Dennis McCafferty

Dennis McCafferty

Content Writer

Dennis McCafferty, a writer for eWeek, Baseline and CIO Insight, has more than 20 years of experience as a writer. He has covered a variety of technology and business topics for a number of publications, including those of Ziff Davis. Dennis was also an editorial staffer for USA Weekend, the nation’s second-largest magazine, with more than 22 million readers.

CIO Insight Logo

CIO Insight offers thought leadership and best practices in the IT security and management industry while providing expert recommendations on software solutions for IT leaders. It is the trusted resource for security professionals who need to maintain regulatory compliance for their teams and organizations. CIO Insight is an ideal website for IT decision makers, systems integrators and administrators, and IT managers to stay informed about emerging technologies, software developments and trends in the IT security and management industry.

Property of TechnologyAdvice. © 2026 TechnologyAdvice. All Rights Reserved

Advertiser Disclosure: Some of the products that appear on this site are from companies from which TechnologyAdvice receives compensation. This compensation may impact how and where products appear on this site including, for example, the order in which they appear. TechnologyAdvice does not include all companies or all types of products available in the marketplace.