May 6, 2025 at 11:55 pm

New Boss Needs His Email Set Up, But It’s Not Going To Happen Until He Approves A Travel Request

by Jayne Elliott

man's hand picking up a phone

Shutterstock/Reddit

New bosses often make rules without understanding the consequences, so when the rules come back to bite them, there’s a real sense of satisfaction for the employees involved.

In today’s story, one new CEO tries to cut costs by changing the rules about business travel.

What he didn’t know at the time, is that this would make it take a long time for his email account to get setup.

Let’s see how the story plays out.

What exactly is Travel?

In the late 1980s a company in New Jersey contracted me to set up a mainframe based eMail system.

They had dozens of sites, large and small all over the country.

Many of the small offices were staffed by people who had absolutely no experience with computers, so after the hardware was installed, we’d send two of our people out to train them.

The program was proceeding nicely when the company was acquired through a hostile takeover.

The new CEO made new rules.

The new owner was a tiny company that specialized in these takeovers.

Their model was to buy a company, sell off the valuable assets and liquidate the rest.

The guy they installed as the new CEO began by cutting expenses.

One of the new rules was that all interstate travel had to be approved in advance by two levels of management.

A lot of people quit or were fired.

People were leaving in droves, some voluntarily, but a lot were called in on a Friday, given their last paycheck and escorted to the door.

Among them were those people who did remote eMail setup. (They were in Chicago running a training seminar when they got the axe.)

One day I got a request from this new CEO’s admin requesting that I give him and his staff of hatchetmen access to our eMail.

We fast-tracked the installation of the hardware and I set up their userIds.

All that was left was for someone to show them how to use it.

There was only one person who could do the job.

The only one left qualified to do that was my office mate who I had trained to take over the system when my contract ended.

But our manager had resigned, and her manager had been let go in one of the purges.

According to the org chart we now reported to the CIO, the only C level left from the old company.

He knew his days were numbered so he wasn’t particularly motivated.

My office mate filled out the travel request form and sent it to the CIO for approval.

He spent about a week carefully considering it, weighed the alternatives and finally decided that this trip was necessary.

He approved it and sent it across the river to his boss, the new CEO.

He finally got a call from the CEO’s admin.

Another week went by and the CEO’s admin called me wanting to know when someone would set up their eMail.

Hmm, I’ll have to check with the guy who does that. Let me put him on the speaker phone.

Yes Ma’am. I have the request. I will come to your office as soon as your boss approves the travel request.

What travel request?

Per his orders all interstate travel must be approved by two levels of management. I report to the CIO and he reports to your boss.

You don’t need a travel request to come into the city.

He explained the situation.

Sorry Ma’am I live and work in New Jersey. Your office is in New York.

Those are two different states. The rules issued by your boss specifically say that without prior approval, travel expenses will not be reimbursed.

From where I live I will have to park my car at the train station, take the train into the city then a subway uptown to your office.

There is no way I am going to shell out that money until I know I will be reimbursed.

As soon as I get approval I will call you to schedule the trip. Have a nice day.

It was almost 3 weeks until the CEO finally got around to approving the $20 travel request.

That CEO’s new rule was really stupid, but it’s great that it backfired on him.

Let’s see how Reddit reacted to this story.

This is true.

Screenshot 2025 05 03 at 7.40.49 PM New Boss Needs His Email Set Up, But Its Not Going To Happen Until He Approves A Travel Request

This person expected a different ending.

Screenshot 2025 05 03 at 7.40.59 PM New Boss Needs His Email Set Up, But Its Not Going To Happen Until He Approves A Travel Request

Another person loves how the story played out.

Screenshot 2025 05 03 at 7.41.24 PM New Boss Needs His Email Set Up, But Its Not Going To Happen Until He Approves A Travel Request

Seriously, this travel expense should be approved!

Screenshot 2025 05 03 at 7.41.50 PM New Boss Needs His Email Set Up, But Its Not Going To Happen Until He Approves A Travel Request

Bosses sometimes make really stupid rules.

And the rest of us have to make them see it.

If you liked that post, check out this one about an employee that got revenge on HR when they refused to reimburse his travel.