What are the top 3-5 questions you ask senior leadership during an annual risk assessment interview?

Some examples:

What are the key strategic objectives for the upcoming year, and how have they evolved since the last assessment?

Can you identify any emerging risks that we should be aware of?

What key performance indicators (KPIs) or metrics should we monitor to track the effectiveness of risk management efforts?

Here are my questions that I used to ask as GC to assess the company's risk profile in the first 30-90 days:

"If our company were a ship, where do you see the potential leaks?"

This metaphorical question encourages leaders to think creatively about vulnerabilities and areas of concern, framing them in a way that's more visual and intuitive.

"Imagine it's a year from now, and we're on the cover of a major business magazine due to a risk we didn't foresee. What's the headline?"

This question prompts leaders to envision worst-case scenarios in a tangible way, helping to identify potential blind spots.

"Which fictional character or historical figure do you believe our company should emulate in its approach to risk, and why?"

By referencing characters or figures, leaders can draw upon stories or traits that can provide unique insights into how the company might approach risk.

"If you had to describe our company's risk appetite using a type of cuisine, what would it be and why?"

This question uses the analogy of food to gauge how adventurous or conservative the company's risk stance is. For example, "spicy" might indicate a higher tolerance for risk, while "bland" might suggest caution.

"If our company were to throw a 'Risk Party,' what theme would you suggest and who are the three most important guests we should invite?"

These whimsical questions can reveal key stakeholders and external factors that leadership considers crucial in the risk landscape.