4 Must-Ask Questions to Avoid a Horror Story on Your First Day of Work

4 Must-Ask Questions to Avoid a Horror Story on Your First Day of Work

Whether it’s your first job or your fifteenth, your first day on the job can be scary if you’re not prepared.

In honor of Halloween, I’m going to share a real-life horror story. Imagine, if you will, a balmy summer day in 1998

I showed up at the office for my first day of work promptly at 8:30 a.m. in my brand-new lavender Laura Ashley skirt suit. (No, the outfit isn’t the horrifying part! Well, okay, maybe a little.)

I introduced myself to the receptionist and proudly announced, “I’m here to see Bill Allen.”*

“Welcome,” the receptionist said, “I’ll call him and let him know you’re here.”

Half an hour passed, then an hour. The receptionist called and left Bill a message again. And again.

As I was beginning to despair (and maybe panic), I spied an acquaintance from my high-school swim team walking past. “What brings you here?” he asked, and I told him.

“Oh,” he said, “Bill’s on vacation this week.”


If it wasn’t for that chance encounter, who knows how long I would have waited? I might have even figured that I didn’t have a job after all and just gone home!

Amazingly, the first-day bloopers didn’t stop there. Over the years, I’ve witnessed a surprising number of logistical missteps on the first day of work, even when everyone involved (including me!) should have known better.

Don’t let this happen to you…whether you’re fresh out of school or a career veteran, read on for 4 questions you should always ask to avoid a horror story on your first day at a new job.

*Not his real name.

SCARE #1: The Site Switcheroo

After grad school, I landed an awesome job at Bloomberg in Washington, DC. Which is why it made perfect sense that on my first day, I was expected to report to… the company headquarters in NYC??

Companies love to host new hires for orientation sessions on a different floor, in a different building, or even a different city from where you had your interview – or where you’ll actually be working.

SCARE #2: Time Traveling

You don’t need me to tell you to show up for your new job on time. In fact, you’ll be there a few minutes early, right? Great! Unless you get there before the office opens, like I did – and then was stuck hanging around the locked front door until someone showed up and was willing to let in a random stranger.

After that, I swore to arrange to show up at least half an hour after the work day starts on my first day, to avoid that awkwardness. In fact, some hiring managers (including me) prefer it when a new hire doesn’t show up first thing. Who wants to be showing someone around the office before you’ve even had a chance to boot up your computer?

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SCARE #3: One-Hit Wonder

Here’s the real wild card. Sometimes there’s something unusual happening at your new workplace on your first day. Believe it or not, my missed connection with Bill Allen wasn’t the only time this has happened to me! At another job, they told me, “Our work day starts at 9:00 a.m.”

What they forgot to add was that, once a month, they had a department-wide all-hands meeting starting at 8:30 a.m. And guess which day was my first day?

I can still feel my face burning from the embarrassment of marching into the meeting late in front of the entire group. Whether it’s “Jeans Day,” the annual company karaoke competition, or a boss on vacation, a one-off occurrence on your first day can really throw you off.


What can you do to avoid these simple but surprisingly common first-day scares? Use the 4 questions below.

  1. Should I come straight to the office, or go somewhere else?
  2. What time does the office usually open?
  3. Would it be all right if I plan to arrive at [usual opening time plus at least half an hour]? I like to give everyone a chance to settle in before I get there.
  4. Is there anything special scheduled for my first day?

Be sure to ask both your manager and your HR contact – if their responses don’t match up, get to the bottom of it fast. That’s a sign you were about to walk into your very own horror story!

Have you lived through a terrifying first day of work? Let me know in the comments!

More Career Hacks:
Use This Mantra to Ask Smarter Questions at Work
37 Bento Box Lunches You Won’t Be Embarrassed to Take to Work
How to Dress Like a Boss in 5 Minutes or Less

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  1. Alexandria Gunn says:

    Oh my! I’ve been lucky that my first days have all been quite smooth. One of my interviews involved absolutely no traffic on the road when I was used to miles of tailbacks, so I ended up half an hour early. I thought I’d have chance to do a pre-interview toilet break but the hiring manager saw me and was more than happy to interview me early. I’m not sure if she thought I was just uber excited about it or had got the wrong time and was happy to go along with it…Luckily, she knew the area I was driving in and what the traffic is usually like so was equally surprised when I said that there was nothing at all.

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