The worst job I ever had, and what it taught me about being a better leader

Four lessons that I still use today

I’ve been working since I was 15, almost continuously. I’ve had a variety of jobs and a few different career pivots: nanny, receptionist, wedding photographer, concierge, lifestyle journalist, paid blogger, medical equipment buyer, barmaid, deli counter server, plus many retail and customer service jobs and one gig as a housesitter to a b-list celebrity.

And yet, when someone asks what the worst job I ever had was, it’s an easy answer for me: Supermarket cashier.

When I was 19, I worked for a large chain of grocery stores, one that didn’t have self checkouts at the time. And to be quite frank, I hated it. I only lasted a few months and got out as soon as I felt I could. I still have the apron because it’s a good apron and a good reminder of how grateful I am not to work there anymore.

Not my store; stock image from rw rogers company

It sounds like a fairly normal, uncontroversial job, no? But even today, I get anxious thinking about it. Here’s why:

1 — The only metric that mattered was speed

I was told that the supermarket I worked in was the busiest in Western Canada, and I have no idea if that was legit or not, but this “Fact” was used as evidence that the speed of the checkout was the only thing that matters; people were busy! We needed to be on top of our game.

We had this metric called items per minute, and it was tracked on every till and shared. Our IPM number was our main goal and focus each day— it was rewarded or shamed depending on where you were at that day. Our bosses didn’t even seem to care whether the cash in our till matched our cash-out receipts. IPM was all that mattered, at that time.

Being a cashier is already a pretty joyless job, but when you make speed the only metric that matters, it takes any hints of delight out of the day. We didn’t have a chance to properly engage with people, because we were taught to be solely focused on our scanning.

Now that I work in Service Design, I have to wonder: Did they ever actually ask their customers if speed was more important to them than a friendly cashier? Or did they just assume that’s what people wanted? Yes, a lot of people are in a hurry, but what about the people who are isolated, lonely, grieving, anxious — the ones for whom seeing a friendly face might change their whole day?

Those interactions matter. But we were taught that they don’t.

Lesson: Experience should never be forgotten for the sake of efficiency. You must find ways to optimize both.

2 — Toxic team culture

Working as a cashier for this supermarket meant mandatory union membership, and the culture that arose from that union was one where seniority was the only thing that mattered. The more senior you were, the more power you had: Seniors got higher wages, better shifts and were given different opportunities (like working at the customer service counter with another cashier instead of alone on a till.)

Within our team of cashiers, there was a feeling of intense competition. We had no control over where we sat in the seniority ladder, so people would find other ways to compete and exert their power. I have vivid recollections of being bullied by someone who had only been at the job a few weeks longer than me, but held that seniority over me like some kind of feudal lord.

I’m in a mandatory union now, too. But I’ve never experienced the kind of culture I experienced at the supermarket. I suspect there was more going on that I didn’t understand at the time to make it such an extremely hostile environment.

Lesson: Teams need to prioritize psychological safety and understand power imbalances, if they want to have a happy, engaged workforce that will stick around.

3 — Shortcuts were not allowed

Before I started working at a till, I had to spend a couple of weeks in full-time training to learn the PLU (price look up) codes for every single non-barcoded item in the store. I also had to pass an exam on these with an 85% or higher score, or risk being let go before I even started. Do you know how many kinds of apples there are, all with a unique code? How many types of nuts in the bulk aisle? Can you identify them all based on sight? It’s mind boggling.

I thought (and still think) this was unnecessary overkill and I said as much in the training; I remember asking the instructor why, when all the fruits and veggies had stickers, did we need to remember everything? Not to mention, we also had books with the codes at every till, and a look-up tool on our cash registers. She told me that the stickers were probably wrong and we couldn’t trust them, which was a lie because here we all are in 2022, using the stickers at the self-checkouts.

Here’s what I don’t get: If the stickers are wrong, doesn’t it make more sense to change the stickers or software than to change the people? It’s a known fact that human memory is fallible. And yet, we were explicitly told we weren’t allowed to look things up unless absolutely necessary. We were called out and shamed when we looked for items in the book and on the register, items which were both designed for looking things up.

Here’s another interesting tidbit: I always found the cashier job to be physically exhausting, because I was on my feet on a concrete floor for 6–8 hours a day. We weren’t allowed to sit or stretch as long as we were in the customer’s view, even when it wasn’t busy. We were told off if we so much as leaned on on the counter for a bit of a break for our knees.

But when I moved to the UK, I discovered something that blew my mind: all cashiers in supermarkets sit down. Why was that never an option for us?

Lesson: Look for and embrace easier ways of doing something. See your staff as real, complex people who also deserve to have an easy experience in doing their job.

4 — We had to stay in our lanes

In this supermarket, the people I interacted with fell into three distinct groups: Cashiers (like me), the ‘floor’ people (those who stocked shelves and helped customers in the aisles and produce section, plus those who bagged and carried groceries) and the managers. I don’t think it’s a coincidence that all the floor people and managers were men. We had a few male cashiers, but there were no females in the other groups that I knew of.

Floor people and managers could go where they wanted and work on different things. But we cashiers had to quite literally stay in our lanes at all time, until someone relieved us for a break or end of shift.

This wasn’t my only cashier job — I also spent a couple of years working at an office supplies store. The difference in that job was that, when cash wasn’t too busy, I could do other jobs: I could stock shelves, I could collect the trolleys from the parking lot, I could help out in the copy centre (my favourite.)

It’s telling that I stayed in that cashier job for much longer than I lasted at the supermarket. I found that I actually enjoyed the cashier job when I was allowed to do other things.

Lesson: Don’t pigeonhole staff into one task or duty. Empower them and allow them the chance to try different tasks, and to contribute in different ways.

A summary

There’s nothing intrinsically wrong with the job of being a cashier. It’s a decent, solid way to make a living with lovely people working in supermarkets around the world. It’s also a job that will be around for a while; many things come and go but we’re always going to need groceries.

But what was wrong with this job in particular wasn’t the job itself but the culture of the organization I was working for, where efficiency and business needs took precedence over the customer and employee experience. It was a culture where power imbalances were perpetuated and managers turned a blind eye to the bullying that happened when low ranking employees were pitted against each other. It was a culture without psychological safety, where people were not empowered or encouraged to think or work differently.

There are four things I learned from this job that I still use today:

• Customer and employee experience matter more than efficiency. Find ways to optimize both but don’t sacrifice experience for speed
• Prioritize psychological safety, and understand and work to fix power imbalances
• Embrace easier ways of doing something; accept that employees are real, complex people who deserve to have an easy experience of doing their job
• Empower staff to try different things and contribute in new ways

Is your organization someone’s worst job?

If you’re a boss — and even if you’re not — it’s worth asking yourself honestly whether the experience of working in your organization, business or team is a good one. It’s also necessary to look at the structures of power in your org: Who has is? Who doesn’t? How can we make things more equitable?

And then, when you’re done asking yourself that question, ask your team members:

• What’s the experience of working here? How can we make this better?
• What are the best and worst parts of working here, and why? What can we learn from that?
• What things and processes can we let go of, that are no longer serving us?
• Do people in this org truly feel comfortable surfacing problems? Do we know that for sure, or are we just guessing?

It always pays off to ask these questions, and to be reflective on what’s working and what’s not. Your employee experience matters too, more than you think.

I’ll end this with a tweet about corporate culture that I think is so important: