The hard conversation dilemma

Sometimes it’s the smallest moments - a single sentence, a quick decision - that reveal the real state of leadership in a workplace.The other day, I saw something in a store that made me pause.

I found myself wondering:“What would I have done in the first five years of my working life?”

I was in a well-known liquor store, grabbing a bottle of wine. The place was empty, and as I browsed, I overheard the two staff talking. From what I could pick up, it sounded like they were discussing a new team member and their first days on the job.

In just a few minutes, I could tell the person telling the story was someone who valued giving people opportunities, supporting their growth, and helping them through challenges.

(Don’t ask me how I know that—it’s just one of those weird instincts I have 😉)

I needed help finding something, so the storyteller kindly stopped to assist me and walked with me to the counter to complete the sale.

By now, two other groups of customers had entered the store. As I was being served, the other staff member walked past and said:“I’m just ducking out for a quick cigarette break.”

I was surprised, and I caught the brief flash of disbelief on the face of the person serving me. I knew that this moment wasn’t just about a smoke break. It was about timing, safety, and teamwork.

If I were to rate workplaces by risk, liquor stores—especially at night—would be fairly high on the list. I’m certain there are safety protocols around not leaving staff alone when customers are present.

So, the question to myself was:Would I have…

A) Let it go, because confronting it felt too hard.

B) Had a conversation about the timing of breaks and the risks of leaving staff alone.

C) Said nothing, but complained to others later, quietly losing confidence in that person.

Early in my career, my answer probably would have been A or C. Now, with years of leadership experience, I’d choose B - addressing it politely but firmly in the moment

(“If you can wait a few minutes until the customers have gone, that’d be great”) and following up afterwards.

This experience was a reminder that leadership isn’t just for people with “manager” in their job title. It's a skill that should be developed at every level. If both team members had shared an understanding of expectations, the situation likely wouldn’t have arisen in the first place.

Those micro-moments, where we choose how to act, are what shape the culture of a workplace.

They’re about showing up for yourself, your teammates, and your organisation.

They’re about values, ethics, empathy, and support.

That’s why ongoing leadership coaching and development are so important. Because not everyone knows what’s appropriate - and even when they do, having the hard conversations can feel harder than it should.