Hiring a Chief Legal Officer (CLO) is one of the most consequential decisions an organization can make. The right CLO becomes a trusted advisor who protects the company, enables growth, and shapes corporate culture. The wrong hire can result in mismanaged risks, missed opportunities, and eventual turnover. Instead of asking generic questions that fail to reveal whether a candidate can truly excel in the role, you may want to include questions that provide much more perspective. 

Here are nine interview questions that will help you identify a CLO who can drive your organization forward: 

1. How do you communicate complex legal issues to executives or board members who may not have a legal background?

As the saying goes, communication is the foundation to business’ success. For a CLO, this means translating complex legal concepts into language every stakeholder can understand. When working alongside colleagues unfamiliar with regulatory nuances or jargon, the CLO must articulate the issue clearly and accessibly. Without this skill, transparency suffers, and distinctions are lost, potentially leading to an unintentional decision.

2. Tell me about a time you recommended a course of action that carried significant risk. How did you justify it?

This question offers a window to your candidates’ decision-making process and how they weigh risk and opportunity. You may be seeking a confident CLO who can support strategic risks that create competitive advantage, but you don’t need a leader who approves of reckless or unethical actions. A strong CLO embraces well-informed, calculated risk while maintaining clear guardrails around compliance.

3. How have you leveraged technology or data analytics to improve legal operations or decision-making? 

Many people assume legal is inherently traditional and don’t expect innovation. The legal function can leverage technology to reduce costs, mitigate risks, and enable faster business decisions. When used appropriately, the continuous emergence of new technology and generative AI in the workplace can transform legal operations. Appointing a CLO who leverages legal expertise and technology can be a valuable addition to your C-suite. 

4. How do you measure the effectiveness of your legal team beyond closing cases or reviewing contracts?

Every high-performing team is more than the work they complete and the boxes they check. You need confidence that your legal team operates cohesively, maintains clear communication, and is supportive during crises. This question reveals the candidate’s philosophy on team building and team culture, impacting whether their team is an asset or a liability.

5. How do you approach ethics and compliance culture, outside of policies and training?

Compliance culture goes beyond written rules. A CLO should recognize that culture is shaped through informal mechanisms like how leaders respond to bad news, whether people feel safe speaking up, and what behaviors get rewarded versus punished. You should ask a question that distinguishes CLO candidates who will create genuine ethical accountability from those who will merely manage compliance paperwork.

6. How do you prioritize when everything feels urgent?

Legal officers constantly face competing urgent demands. This includes regulatory inquiry, a major contract dispute, a board request, and an employee crisis, all of which are occurring simultaneously. Impressive candidates articulate clear prioritization frameworks based on factors like financial exposure, regulatory risk, reputational impact, and strategic importance.

7. How do you stay ahead of legal and regulatory changes that could potentially impact our business?

This question will help you assess how proactive and forward-thinking your candidates are and reveals their systematic approach to regulatory monitoring. A reliable candidate should view themselves as more of a business partner who can anticipate and plan for change, rather than a reactive and compliant function in the company.

8. How do you handle situations where you’re asked for legal advice on a topic outside your expertise?

There’s an inherent tension in the CLO position: you’re expected to be the organizational expert on learning and development, yet the field itself is constantly evolving. Although you may expect a CLO to be all-knowing, it’s important that they balance intellectual humility and resourcefulness rather than leaving a dangerous blind spot. Drawing from current practices or trends, catching up on legal literature, or meeting with their legal network are great methods to approach unfamiliar territory.

9. What’s your approach to managing legal matters that cross international borders?

International legal matters can be some of the most multi-layered and overwhelming situations a CLO can face. It requires them to navigate conflicting laws, manage jurisdictional disputes, and coordinate across different legal systems and cultures. An appropriate answer will reference current trends, demonstrate that the candidate stays informed about evolving international legal landscapes, and show that the candidate can handle international matters with cultural sensitivity.

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In Closing

These nine questions are designed to move past rehearsed answers and reveal the qualities that distinguish exceptional CLOs from competent ones. They identify strategic thinking, cultural intelligence, technological adaptability, and the ability to balance risk with opportunity. The candidates who provide thoughtful, specific answers, while drawing on real examples and self-awareness, are those who will protect your organization from legal pitfalls and empower it to grow with confidence.

How Should I Find a Chief Financial Officer?

Partnering with an executive search firm like TalentRise can help ensure your organization is developing the right job description, promoting it in the right places, and asking the best questions during the interview process, all while delivering excellent candidate experience.

If you’re ready to find the right Chief Legal Officer for your organization, contact us today.