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Mistakes We Made in People Management

January 06, 20263 min read

Handwritten Ledgers, Messy Payroll, and the Lost Art of “Winging It”

If you think you’ve got it tough juggling work apps and invoices today, let me paint you a picture: Every grocery order written down, by hand. White bread, gallon of milk, pork and beans, one by one. Every cent added up on a physical tape (and don’t forget to subtract your tax by looking it up on a paper card).

Tom and Shirley both cracked me up telling stories about stacks of handwritten bills, five-page-long orders, and handing literal, physical time cards to the payroll person. If you wanted to know your bank balance, forget online banking, Kim talked about praying the numbers were right at the end of the month after penciling everything into the checkbook. Basically, if you made a mistake, it was hours of hunting for that ten bucks.

Looking back, I appreciate how EASY the automation is now. No more mysteries about when the credit card money lands, or “uh-oh, the time card fell behind the register again.” (Yes, that happened more than once.)

Our People Mistakes: Too Many Promotions, and a Couple “Bums” Who Became Stars

Here’s the messy truth: I’ve hired the wrong people, promoted folks just because they were talented cooks (or had been around forever), and lost some amazing employees because we never really stopped to think about what they wanted, or if they were ready.

The two-step interview process Kim suggested? Game-changer. We used to hire fast, regret it even faster. Now, we let someone with people-reading skills handle round one, put candidates through a second interview if they seem right, and (miracle!) turnover dropped. Suddenly, we weren’t training someone just to have them quit a week later, saving money AND headaches.

One of my favorite stories: Shirley remembered hiring a kid everybody thought was the local “bum,” he just needed a little direction and a pencil. That guy turned into a star employee. Goes to show you can’t always judge by appearances, but you DO have to give people a fair shot (and honest feedback).

Don’t Make Every Molehill Into a Mountain (Seriously, Stop It)

Raise your hand if you’ve ever changed an entire system just because of one complaint. Been there. We’ve all turned little one-off issues into sweeping policy changes that backfire with everyone else. Kim nailed it: Most of the time, we just need to slow down, see if it’s a real pattern or someone having a weird day, and avoid panic-fixing things.

But sometimes, ignoring change bites you. What worked 20 years ago can suddenly fall apart, especially as your customers evolve. (Trust me, we talked about self-checkout, and while I hate it, our younger customers love it. Lesson: you are NOT your customer.)

Lead By Listening (Not Just Yelling Instructions)

Want to guess the number-one thing I wish I’d learned sooner? LISTENING. Early on, I thought leading was barking out instructions and expecting results. Now, I know explaining the “why” isn’t just feel-good talk, it actually gets better results, faster.

Turns out, my best moments as a “boss” are when I shut up and let people talk. You’d be amazed how fast a business runs when your team is on board because you actually heard them.

Advice I’d Give Myself (or Anyone Starting Out)

  1. Use every learning tool out there - podcasts, books, YouTube, even ChatGPT. There’s no excuse for “figuring it out in the dark” anymore.

  2. Stay calm - Most stuff isn’t as urgent as it feels.

  3. Remember you’re not your customer - Be open to doing things differently, especially as people change.

  4. Listen twice as much as you talk - (Big one. Still learning.)

Running a family business isn’t about getting everything right, it’s about learning, laughing, and rolling with the punches together. Our processes and our people, keep changing. That’s the fun (and challenge) of it. Thanks for being part of the ride.

Drop your stories or questions at [email protected] I’d love to hear where you’re at in this wild business world. Until next time, keep learning, keep listening, and don’t forget to laugh at yourself now and then.

Make sure to give the full episode a listen here!

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