Chief Legal Officer Work Samples: Practical Exercises to Evaluate Your Top Legal Candidates

The Chief Legal Officer (CLO) serves as the cornerstone of an organization's legal strategy and risk management framework. This executive-level position requires a unique blend of legal expertise, business acumen, leadership capabilities, and strategic thinking. Finding the right CLO is critical, as this individual will not only oversee all legal matters but also serve as a key advisor to the executive team and board of directors.

Traditional interviews often fail to reveal how candidates will actually perform in the complex, high-stakes environment of a CLO role. While resumes and references can provide insights into a candidate's background, they rarely demonstrate how candidates approach real-world legal challenges or how they balance legal risk with business objectives.

Work samples and role-playing exercises offer a window into a candidate's practical skills, thought processes, and leadership style. By observing candidates tackle realistic scenarios, hiring teams can assess their ability to analyze complex legal issues, communicate effectively with stakeholders, and make sound judgments under pressure. These exercises also reveal how candidates prioritize competing demands and navigate ambiguity—essential skills for any successful CLO.

The following four activities are designed to evaluate the most critical competencies for a Chief Legal Officer. Each exercise simulates a real-world challenge that CLOs commonly face, allowing candidates to demonstrate their capabilities in a practical context. By incorporating these exercises into your hiring process, you'll gain deeper insights into each candidate's potential for success in this pivotal leadership role.

Activity #1: Legal Risk Assessment and Strategic Recommendation

This exercise evaluates a candidate's ability to identify legal risks, analyze their potential impact on the business, and develop strategic recommendations that balance legal protection with business objectives. A strong CLO must be able to translate complex legal issues into clear guidance for executive decision-making.

Directions for the Company:

• Prepare a fictional but realistic business scenario that presents multiple legal risks (e.g., a potential acquisition, new product launch in a regulated industry, or international expansion).
• Include relevant background information such as company size, industry, regulatory environment, and business objectives.
• Provide the scenario to candidates 24-48 hours before the interview to allow for thoughtful analysis.
• Allocate 20 minutes for the candidate's presentation and 10 minutes for questions.
• Ensure the evaluation panel includes both legal and business stakeholders.

Directions for the Candidate:

• Review the provided business scenario and identify the key legal risks and opportunities.
• Prepare a 15-20 minute presentation that:
• Outlines the most significant legal risks and their potential business impact
• Prioritizes these risks based on likelihood and severity
• Recommends specific strategies to mitigate each risk
• Explains how your approach balances legal protection with business objectives
• Be prepared to answer questions about your analysis and recommendations.
• Consider how you would communicate these issues to both legal and non-legal stakeholders.

Feedback Mechanism:

• After the presentation, provide specific feedback on one aspect the candidate handled particularly well and one area for improvement.
• Ask the candidate to revisit their recommendation for the area identified for improvement, giving them 5 minutes to adjust their approach based on the feedback.
• Observe how receptively they incorporate the feedback and their ability to adapt their thinking.

Activity #2: Executive Communication Role Play

This exercise assesses a candidate's ability to communicate complex legal issues to non-legal executives and influence decision-making. The CLO must be able to translate legal concepts into business terms and serve as a trusted advisor to the C-suite and board.

Directions for the Company:

• Develop a scenario where the CLO must brief the CEO and CFO on a significant legal issue with business implications (e.g., a potential regulatory investigation, major litigation risk, or compliance concern).
• Assign company representatives to play the roles of CEO and CFO, providing them with character briefs that include their priorities, concerns, and communication styles.
• The CEO character should be focused on growth and innovation, while the CFO should be concerned with financial risk and cost management.
• Allow 15-20 minutes for the role play.

Directions for the Candidate:

• You will role-play a meeting where you, as CLO, must brief the CEO and CFO on a significant legal issue.
• Your objectives are to:
• Clearly explain the legal situation and its business implications
• Provide strategic recommendations
• Answer questions and address concerns from both executives
• Build consensus on a path forward
• Focus on communicating in business terms rather than legal jargon.
• Be prepared to handle pushback and competing priorities from the executives.

Feedback Mechanism:

• After the role play, the "executives" should provide feedback on the candidate's communication effectiveness and strategic thinking.
• Identify one specific aspect of the communication that could be improved.
• Give the candidate a second scenario (a follow-up issue or question) and ask them to incorporate the feedback in addressing this new challenge.
• Evaluate how well they adapt their communication approach based on the feedback.

Activity #3: Contract Negotiation Simulation

This exercise evaluates a candidate's contract negotiation skills, including their ability to identify key terms, protect the company's interests, and find creative solutions to impasses. Effective contract negotiation is a fundamental skill for any CLO.

Directions for the Company:

• Create a mock contract scenario (e.g., a vendor agreement, partnership deal, or licensing arrangement) with several problematic clauses.
• Prepare a brief on the company's priorities, non-negotiable points, and areas of flexibility.
• Assign a skilled negotiator to play the counterparty, with clear instructions on their priorities and concession limits.
• Allow 30 minutes for preparation and 30 minutes for the negotiation.
• Record the session if possible for later review.

Directions for the Candidate:

• Review the provided contract and company brief.
• Identify the problematic clauses and develop a negotiation strategy that protects the company's interests while achieving the business objectives.
• During the 30-minute preparation time, make notes on:
• Key issues to address
• Your proposed revisions
• Fallback positions and potential compromises
• Questions to clarify the counterparty's concerns
• Conduct the negotiation with the goal of reaching an agreement that meets the company's core needs.
• Focus on both the legal protections and the relationship aspects of the negotiation.

Feedback Mechanism:

• After the negotiation, provide feedback on the candidate's effectiveness in identifying key issues and negotiating favorable terms.
• Highlight one specific negotiation tactic or approach that could be improved.
• Present a new challenging clause and ask the candidate to demonstrate how they would negotiate it differently based on the feedback.
• Evaluate their ability to incorporate the feedback and adjust their approach.

Activity #4: Legal Department Leadership Case Study

This exercise assesses a candidate's leadership philosophy, team management approach, and ability to structure a legal department to support business objectives. A successful CLO must be an effective leader who can build and develop a high-performing legal team.

Directions for the Company:

• Create a case study that describes a legal department with specific challenges (e.g., high turnover, inefficient processes, poor business partnership, or budget constraints).
• Include information about the department structure, key personnel, current workload, and business feedback.
• Provide relevant company information such as growth plans, industry, and regulatory environment.
• Give candidates the case study 24 hours before the interview.
• Allocate 20 minutes for presentation and 15 minutes for questions.

Directions for the Candidate:

• Review the case study and develop a comprehensive plan to address the legal department's challenges.
• Prepare a 15-20 minute presentation that covers:
• Your assessment of the key issues facing the department
• Your proposed organizational structure and resource allocation
• Specific initiatives to improve department effectiveness and business partnership
• Your leadership approach and how you would implement change
• How you would measure success
• Be prepared to discuss your leadership philosophy and experience building effective legal teams.

Feedback Mechanism:

• After the presentation, provide feedback on the candidate's leadership vision and practical implementation plan.
• Identify one aspect of their approach that could be strengthened or reconsidered.
• Ask the candidate to spend 5 minutes explaining how they would adjust their plan based on this feedback.
• Evaluate their receptiveness to feedback and ability to refine their thinking.

Frequently Asked Questions

How should we weight these exercises relative to traditional interviews?

These work samples should complement, not replace, traditional interviews. We recommend allocating approximately 50% of your evaluation to these exercises, with the remaining 50% divided between experience-based interviews, reference checks, and cultural fit assessments. The work samples provide objective data on capabilities that are difficult to assess through conversation alone.

Should we use all four exercises for every CLO candidate?

While using all four exercises provides the most comprehensive assessment, time constraints may make this impractical. At minimum, we recommend using the Legal Risk Assessment and Executive Communication exercises, as these evaluate core competencies for any CLO. Choose additional exercises based on specific priorities for your organization.

How should we adapt these exercises for remote interviews?

All of these exercises can be conducted virtually. For the negotiation and role play exercises, use video conferencing with breakout rooms for preparation. For presentations, have candidates share their screen. Consider providing slightly more preparation time for remote exercises to account for potential technology challenges.

What if a candidate has limited experience in one of these areas?

Focus on evaluating the candidate's approach and thinking process rather than specific knowledge. A strong candidate might not have extensive experience in every area but should demonstrate sound judgment, quick learning, and effective problem-solving. Consider providing additional context for areas where a candidate has less experience.

How do we ensure these exercises don't disadvantage candidates from different backgrounds?

Review all scenarios to ensure they don't require industry-specific knowledge that would unfairly advantage certain candidates. Provide clear instructions and equal preparation time to all candidates. Consider having diverse evaluators assess the exercises to minimize unconscious bias in the evaluation process.

How much detail should we provide in the scenarios?

Provide enough detail to make the scenario realistic and actionable, but leave room for candidates to ask clarifying questions and make reasonable assumptions. This tests their ability to navigate ambiguity—a critical skill for CLOs. The best scenarios mirror the complexity and incomplete information of real-world situations.

Finding the right Chief Legal Officer is a critical decision that impacts your organization's risk profile, governance structure, and strategic capabilities. By incorporating these practical work samples into your hiring process, you'll gain deeper insights into each candidate's abilities and fit for your specific needs. These exercises go beyond traditional interviews to reveal how candidates actually approach the complex challenges of the CLO role.

For more resources to optimize your hiring process, explore Yardstick's comprehensive tools for creating AI-powered job descriptions, interview questions, and interview guides. Our platform helps you design and execute the very best candidate interviews, turning your hiring process into a competitive advantage. Learn more about the Chief Legal Officer role at Yardstick's CLO job description.

Ready to build a complete interview guide for your Chief Legal Officer search? Sign up for a free Yardstick account today!