Mid-Year Reset

Six Powerful Questions to Shape Your Legacy

As we move into the second half of the year, it’s the perfect time to pause, reflect, and reset.

Mid-year offers a natural opportunity to step back from the day-to-day and consider the bigger picture — especially for those of us in senior leadership roles where the pace is fast and the demands are high.

Whether you're leading transformation, navigating organisational change, considering your next chapter, or simply want to lead with more intention, a reflective reset can be incredibly powerful.

Here are six questions I often use in legacy coaching conversations with senior leaders. They’re designed to help you reclaim clarity, reconnect with your purpose, and realign your energy for meaningful impact.

1️⃣ What were your top three wins from the first half of the year?

We often move quickly from one challenge to the next without taking time to celebrate success. Pause to acknowledge what you’ve achieved so far.
What worked? What are you proud of? What deserves a quiet moment of celebration?

2️⃣ What were your biggest challenges — and what did they teach you?

Some of our most valuable lessons come through discomfort. What stretched you? Where did you grow?
Reflection here can uncover insights that strengthen your leadership moving forward.

3️⃣ What unfinished business do you need to complete this year?

Loose ends drain energy.
Is there something you’ve been putting off? A decision to make, a conversation to have, a commitment to fulfil? Clearing the decks protects your momentum and your integrity.

4️⃣ If someone replaced you tomorrow, what would they start doing — and stop doing?

This is a bold question, but it’s one of my favourites. A fresh perspective can highlight what’s become stale or misaligned.
Are there ‘sacred cows’ you’re holding onto? What would a new leader shift immediately?

5️⃣ If you had to achieve your 10-year vision in the next 6 months, what would you do differently?

This challenge disrupts comfortable thinking.
Who could help you move faster? What bold moves might you make?
It’s not about rushing — it’s about reimagining your pace and potential.

6️⃣ What are your three biggest goals for the rest of 2025 — and what’s the biggest obstacle for each?

Clarity comes from focus. Define what matters most for the remainder of the year, and name the barriers. Then create the plan that helps you overcome them — with support, not just strategy.

Whether you’re planning a promotion, preparing for retirement, or leading through complexity, these six questions can reset your direction and reignite your purpose.

So carve out a little time. Grab a cuppa (or a glass of something stronger), find a quiet space, and work your way through them. Your future self — and those you lead — will thank you.