When someone new joins your team, what do they see?

What opportunities or obstacles are they seeing that you have become oblivious to? What about the status quo surprises them?

What would your organization look like if it were rebuilt today?

The current setup was inherited. How can it be improved?

Are you busy, stressed, and working late without seeing real improvements?

A heavy workload can mask stagnation. If the pace is exhausting but nothing is improving, ask what would really make a difference.

What arrangement in your work exists mainly because no one wants to touch it?

Some problems are obvious to everyone. What are you treating as “good enough for now” that has quietly become permanent? What problem keeps reappearing no matter how often you fix around it?