How to Ask Better Interview Questions for Strategic Roles in Financial Services

“Tell me about yourself.”

“Why do you want this role?”

“Talk me through your CV.”

These aren’t wrong, they’re just not revealing. For strategic roles, you need to understand:

• How someone makes decisions
• How they handle pressure
• How they balance commercial ambition with risk
• How they influence senior stakeholders

That requires sharper questioning.

Control functions in financial services are no longer back-office safeguards – they sit at the centre of growth strategy.

Instead of:

“How do you manage regulatory risk?”

Ask:

“Tell me about a time you pushed back on a commercially attractive opportunity because of risk concerns. How did you handle it?”

What strong candidates demonstrate:

• Confidence to challenge
• Commercial fluency
• Measured judgement under pressure
• Clear stakeholder management

In regulated environments, particularly payments and fintech, the ability to protect growth without stalling it is critical.

Senior legal hires should shape business direction, not just review contracts.

Instead of:

“What regulatory frameworks have you worked with?”

Ask:

“Describe a situation where your legal advice materially influenced business strategy.”

Look for:

• Strategic awareness
• Board-level communication
• Ability to prioritise under time pressure
• Commercial judgement alongside technical accuracy

You’re hiring a partner to leadership, not a technical gatekeeper.

Enterprise leaders must adapt to market shifts and long sales cycles.

Instead of:

“What were your targets?”

Ask:

“Describe a time market conditions changed and you had to adjust your commercial strategy.”

Strong candidates will reference:

• External market drivers
• Data-led adjustments
• Clear ownership of outcomes
• Reflection on lessons learned

Senior commercial hires need adaptability as much as delivery.

Chief of Staff hires sit between strategy and execution – and weak questioning won’t reveal if they can bridge that gap.

Instead of:

“How do you support leadership?”

Ask:

“Tell me about a time you identified a gap between strategy and execution. What did you change?”

You’re assessing:

• Systems thinking
• Cross-functional influence
• Comfort with ambiguity
• Measurable impact

The strongest candidates bring clarity, not just coordination.

Regardless of function, these consistently separate strong from average candidates:

1. “What’s a decision you made that turned out to be wrong?”
   Reveals humility and learning capacity.
2. “How do you decide what not to prioritise?”
   Reveals judgement – often more important than capability.
3. “If you joined tomorrow, what would you focus on in your first 30 days?”
   Reveals structured thinking and commercial awareness.