5 Questions Every Leader Should Ask

Budgets are done, Financial year is starting and we are now in the count down towards the end of the year and Christmas. But do you ever stop and pause at the end of the month to reflect on how it went? Or do you simply push on with the next task?

Five questions leaders should ask themselves at the end of every month

In the rush of village life, it’s easy to move straight from one month to the next without stopping to consider what you’ve learned. Complaints are resolved, maintenance issues are completed, meetings are held, residents are supported, and before you know it, a new month has begun.

The most effective leaders, however, don’t just gain experience – they learn from it.

Taking just 10 to 15 minutes at the end of each month to reflect can help you recognise successes, identify opportunities for improvement, and make more intentional decisions in the weeks ahead.

Here are five simple questions to ask yourself before turning the calendar page.

1. What went well?

Start by acknowledging your wins.

Perhaps a resident event exceeded expectations, a difficult conversation had a positive outcome, or your team worked together particularly well. Maybe you simply managed to stay on top of competing priorities during a busy period.

Recognising what’s working helps you build on successful habits rather than constantly focusing on what needs fixing.

Ask yourself: What would I like to repeat next month?

2. What surprised me?

Every month brings something unexpected.

A resident may have reacted differently than anticipated. A new process might have worked better, or worse than expected. You may have received feedback that challenged your assumptions.

Rather than dismissing surprises, become curious about them. Unexpected moments often provide some of the most valuable learning opportunities.

Ask yourself: What would I like to repeat next month?

3. What was harder than it should have been?

Not every challenge is unavoidable.

Sometimes a task is difficult because a process isn’t working, communication wasn’t clear, information wasn’t available, or something simply took longer than necessary.

Identifying these friction points allows you to make small improvements that save time and reduce stress in the future.

Ask yourself: What would I like to repeat next month?

4. What did residents appreciate most?

Positive feedback isn’t just nice to hear – it tells you what’s making the biggest difference.

Think about the conversations, emails, thank you notes or casual comments you’ve received. Often it’s not the major projects that residents remember most, but the everyday acts of communication, responsiveness and genuine care.

When you understand what residents value, you can intentionally do more of it.

Ask yourself: What actions had the greatest positive impact on residents this month?

5. What's one thing I'll improve next month?

Avoid creating a long list of improvements.

Choose just one improvement that will make your work easier, strengthen resident experiences, or improve how you lead.

Small, consistent improvements are far more sustainable than trying to change everything at once.

Whether it’s improving communication, scheduling regular learning time or refining a process, one focused change can have a significant impact over time.

A Small Habit with Big Results

Reflection isn’t about dwelling on mistakes—it’s about turning experience into better decisions.

So, before August truly takes hold, block out just 15 minutes in your calendar (every month) and work through these five questions. You may be surprised how much clarity they provide and how many small improvements they inspire.

After all, continuous improvement doesn’t happen by accident. It starts by simply asking the right questions.

Before you turn the calendar page, ask yourself these five questions