What was your first boss like?

Questions asked and answered for my daughters

Shaun Holloway
Lessons from Ordinary
3 min readNov 7, 2020

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My first boss… well, if you don’t count my mom (I’ve heard plenty of times growing up that “she’s the boss”), then the first person who employed me helped shape my view of how staff should be treated.

I was in the 8th grade (1993) and got the opportunity to work on a farm harvesting fall goodies… pumpkins, gourds, Indian and pop corn, corn shocks, etc. There were around 5–7 kids ranging in ages from my age through 12 grade, and each of us had varying levels of experiences and abilities.

Eyes in the Back of Your Head

My boss owned the farm and was one of those folks that showed little emotion, didn’t speak much, and was hard on you… but if you really paid attention, his execution was the exact opposite. He was caring, spoke when needed and with impact, and respected you based on how well you did your job… and rewarded you accordingly.

When I started out, I got the jobs you’d expect… here’s 10 acres of mini-pumpkins… pick as many bushels as you can for the next 3 hours. Yuck! A few of us were dropped off and left alone, while the older kids got to work the pumpkin rows or go off to machete corn shocks, which seemed like a much easier and rewarding task.

Being who I was, I always tried to do the best I could. We were not supervised in the field, and it was common to be put with kids who would goof off by throwing things or just doing nothing. I can tell you… goofing off didn’t win any points, and they weren’t asked to come back to work.

Eyes Looking Forward

I kept that work ethic up, and as my first season progressed, we were rewarded each weekend with the extra cash that came in. You did a great job… here’s an extra $20. My first boss demonstrated a quiet generosity that is still unparalleled to this day, and little did I know at the time, he knew who really did the work and who didn’t — who worked hard and who goofed off.

Not everyone got bonuses.

I worked there for 5 seasons… 8–12th grade. It was overall tough work on the weekends, but the rewards felt amazing — it wasn’t about the money either.

As I got older, I earned the ability to drive one of the tractors and have a small crew help harvest from the fields. I also got to be the crew I envied when I first started… harvesting corn shocks and spending time tying them up in the market area. There was no greater feeling at the time then driving the tractor up in the middle of a crowd with a full wagon load of produce… bringing in the harvest for other people.

Have Others Keep Watch with You

I have had a good balance of supervisor-types over my career, and I have been very fortunate to have more great ones than not-so-great ones. The great ones had key qualities I was able to integrate into my own philosophies and practices as a team leader.

The not-so-great ones also taught me valuable lessons of what not to do or how not to treat people, which helped me handle situations differently when I faced similar ones. Both valuable lessons, but the great bosses will teach you so much more.

To summarize, it boils down to these qualities my first boss demonstrated with me:

  • Trust is earned and is not to be taken for granted
  • Be overly generous with the fruits of your labor (pun intended!)
  • You don’t have to say as much as you think you do to have an impact. A strong presence is much more powerful.

It turns out I remember those seasons a lot more than I thought I did, and I definitely took more away from the work than I ever thought I would.

Thank you Mr. Jutte for these life lessons, the opportunity to be on your team, and for keeping Pigeon Roost Farm running season after season.

About the Juttes and their Farm:
https://www.pigeonroostfarm.com/Pigeon-Roost-Farm-About.htm

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Shaun Holloway
Lessons from Ordinary

Lessons from Ordinary. Business and life learning from everyday objects and common questions. http://www.srholloway.com