Three Questions to Ask About Your First Job

At an event over the weekend, someone asked, “What was your first job?”  

It was a simple question, but I learned something new about one of my best friends. His first job was as a lifeguard. 

Can you guess my follow-up question? 

Yep. Did you ever have to save anyone? (He didn’t.)

My first job was working at a small engine repair shop. I was 12 or 13. I would ride my bike to the shop on summer afternoons to sweep the floors, do some inventory, and assemble new lawnmowers, weedeaters, and chainsaws.

It was awesome!

That first job provided breadcrumbs for my career journey. 

I learned three things in that first job, and there are three questions I wish someone had asked me at the time. 

1. I love putting things together.

I enjoyed taking the chainsaws out of the box, assembling the disparate parts, and handing them to my uncle to test. 

Through all my different jobs, assembling disparate parts into a well-organized, functioning operation has been consistent. I can complain about disorder, but love bringing order out of chaos.

2. I like working.

Work has gotten a bad reputation in a culture obsessed with pleasure and leisure. Work is not always fun, but humans are designed to contribute. That first job taught me the satisfaction of starting and completing a task.

I learned that work is not drudgery–especially when you are mindful of how it helps others. 

3. The people you work with are of utmost importance.

My first boss was my uncle. My grandfather also worked in the shop. They believed in me more than they should have. They praised me for taking fifteen minutes to do a task that would have taken them five. They were always happy to see me show up.

How would our workplaces be different if those in leadership positions acted happy to see their coworkers?

Now for the questions, I wish someone would have asked me at 13.

1. What pieces of this job do you enjoy? What makes them enjoyable?

2. What parts do you dislike? What makes you dislike them? 

Notice I suggest WHAT, not WHY. WHY is a bigger question than WHAT and often causes people to overthink and get defensive.

3. What do you specifically appreciate about your boss?

Which reminds me. In preparation for our Super Teams event, Julie Bauke shared this surprising insight, “94% of people would consider staying if their organization invested in their career.”

So, I should also get better at asking these questions RIGHT NOW if I want to keep my fantastic team together.


Brian Rutherford

Brian Rutherford is the Director of Operations for Leadercast. Brian has been telling stories professionally for twenty-five years. Stories that inspire people to see themselves and the world differently. Stories that challenge people to take meaningful action in the world.

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