Contracts Manager Interview: Work Sample Exercises & Role Plays for Hiring Success

Practical work samples and role plays are essential for evaluating Contracts Manager candidates because the role requires a unique blend of legal expertise, business acumen, and interpersonal skills that can't be fully assessed through traditional interviews alone. Contract management involves complex negotiations, meticulous attention to detail, and the ability to balance legal requirements with business objectives. By observing candidates in realistic scenarios, hiring teams can evaluate how candidates apply their knowledge to actual contract situations, assess their negotiation style, and determine their ability to identify and mitigate risks. These practical assessments reveal a candidate's thought process, communication skills, and problem-solving abilities in contexts directly relevant to the day-to-day responsibilities of a Contracts Manager.

Activity #1: Contract Redlining Exercise

This exercise evaluates the candidate's ability to review, analyze, and negotiate contract terms while balancing legal protection and business objectives.

Directions for the Company:

• Provide the candidate with a sample contract (e.g., a software license agreement, vendor agreement, or customer contract) with intentional issues that need addressing.
• Include a brief business context explaining the company's priorities and non-negotiables.
• Allow 45-60 minutes for the exercise.
• Prepare a "model answer" highlighting key issues that should be identified.

Resources to provide:

• Sample contract in Word format with track changes enabled
• Business context document (1 page)
• Instructions document

Best practices:

• Use a realistic but simplified contract (5-7 pages maximum)
• Include a mix of obvious issues (unfavorable liability clauses) and subtle problems (ambiguous language)
• Ensure the exercise reflects the types of contracts the candidate will regularly handle

Directions for the Candidate:

• Review the provided contract and business context document.
• Using track changes, edit the contract to address problematic terms and improve language clarity.
• Add comments explaining your rationale for significant changes.
• Prepare a brief summary (bullet points) of the top 3-5 issues you identified and how your changes protect the company while maintaining business objectives.
• Be prepared to discuss your approach and reasoning.

Feedback Mechanism:

After reviewing the candidate's work, provide specific feedback on:

1. Something done well (e.g., "Your identification of the ambiguous payment terms was excellent")
2. An area for improvement (e.g., "Consider how the indemnification clause could be further refined")

Allow the candidate 10-15 minutes to revise their approach to the improvement area and explain their new solution.

Activity #2: Contract Negotiation Role Play

This role play assesses the candidate's negotiation skills, ability to think on their feet, and effectiveness in balancing legal protection with business relationship management.

Directions for the Company:

• Designate an interviewer to play the role of a vendor/customer representative.
• Create a scenario with 2-3 specific contract points that are under negotiation.
• Provide the candidate with background information 24 hours in advance.
• Allocate 20-25 minutes for the role play followed by 10 minutes for discussion.

Resources to provide:

• Scenario brief with company position and priorities
• Draft contract sections under negotiation
• Brief description of the counterparty's known priorities

Best practices:

• Script key objections for the interviewer to ensure consistency across candidates
• Focus on realistic points of contention (pricing structure, liability caps, termination rights)
• Have the interviewer maintain a slightly difficult but professional demeanor

Directions for the Candidate:

• Review the provided materials before the interview.
• During the role play, represent your company in negotiating the specified contract terms.
• Balance protecting your company's interests with maintaining a positive business relationship.
• Be prepared to propose alternative solutions when faced with resistance.
• After the role play, explain your negotiation strategy and reasoning behind key decisions.

Feedback Mechanism:

After the role play, provide feedback on:

1. A strength demonstrated (e.g., "Your creative solution to the pricing structure addressed both parties' concerns")
2. An area for improvement (e.g., "Consider how you might handle objections more diplomatically")

Give the candidate an opportunity to re-approach one of the negotiation points incorporating the feedback.

Activity #3: Contract Process Improvement Case Study

This exercise evaluates the candidate's ability to develop and implement scalable contracting solutions to improve efficiency.

Directions for the Company:

• Create a case study describing current contract management challenges (e.g., lengthy approval times, inconsistent templates, poor visibility into contract status).
• Include relevant data points (average time to execution, bottlenecks, etc.).
• Provide 45-60 minutes for the candidate to analyze and develop recommendations.

Resources to provide:

• Case study document (1-2 pages)
• Current process flowchart
• Sample metrics dashboard or data points

Best practices:

• Base the case study on actual challenges your organization has faced
• Include cross-functional considerations (legal, sales, procurement)
• Ensure the complexity level matches the seniority of the role

Directions for the Candidate:

• Review the case study materials.
• Identify key inefficiencies in the current contract management process.
• Develop a structured improvement plan that includes:
• Short-term actions (implementable within 30 days)
• Medium-term solutions (1-3 months)
• Long-term strategic improvements (3+ months)
• Consider technology, template standardization, approval workflows, and training needs.
• Prepare a brief presentation (5-7 minutes) outlining your recommendations.

Feedback Mechanism:

After the presentation, provide feedback on:

1. A strength demonstrated (e.g., "Your phased approach shows excellent prioritization skills")
2. An area for improvement (e.g., "Consider how you might address potential resistance to change")

Allow the candidate 10 minutes to refine one aspect of their plan based on the feedback.

Activity #4: Contract Risk Assessment Exercise

This exercise evaluates the candidate's ability to identify, analyze, and mitigate contractual risks while providing strategic counsel.

Directions for the Company:

• Prepare a complex contract scenario with multiple risk factors (e.g., a high-value international agreement with unusual terms).
• Include business context explaining why the deal is strategically important.
• Provide 30-40 minutes for the candidate to review and assess.

Resources to provide:

• Contract summary or excerpts highlighting key provisions
• Business context document explaining strategic importance
• Risk assessment template (optional)

Best practices:

• Include a mix of obvious and subtle risk factors
• Ensure the scenario requires balancing risk mitigation with business objectives
• Make the exercise realistic for your industry and typical contract types

Directions for the Candidate:

• Review the provided contract scenario and business context.
• Identify and prioritize the top 5-7 contractual risks.
• For each risk:
• Assess potential impact (high/medium/low)
• Propose specific mitigation strategies
• Indicate whether you would recommend proceeding with the contract and under what conditions
• Prepare to explain your risk assessment approach and how you balanced legal protection with business needs.

Feedback Mechanism:

After reviewing the candidate's assessment, provide feedback on:

1. A strength demonstrated (e.g., "Your identification of the regulatory compliance risks was thorough and insightful")
2. An area for improvement (e.g., "Consider how you might better quantify the financial impact of the identified risks")

Allow the candidate 10 minutes to revise their approach to one of the risks based on the feedback.

Frequently Asked Questions

How long should these work samples take in total?

The complete set of four activities would take approximately 3-4 hours of candidate time, including preparation. We recommend selecting 1-2 activities most relevant to your specific needs rather than using all four. The Contract Redlining Exercise and Negotiation Role Play are particularly effective for evaluating core contract management skills.

Should we provide these exercises to all candidates or only finalists?

These exercises are most appropriate for candidates who have passed initial screening. The Contract Redlining Exercise can be used earlier in the process to screen for basic contract review skills, while the more involved activities like the Negotiation Role Play and Process Improvement Case Study are better suited for final-round candidates.

How should we evaluate candidates who have experience in different industries or contract types?

Focus on evaluating transferable skills rather than industry-specific knowledge. You can customize the contract examples to be generic enough that industry experience isn't a determining factor. Alternatively, provide additional context documents to level the playing field for candidates from different backgrounds.

Can we modify these exercises for a remote hiring process?

Yes, all of these exercises can be adapted for remote interviews. The Contract Redlining Exercise and Risk Assessment can be completed asynchronously, while the Negotiation Role Play can be conducted via video conference. For the Process Improvement Case Study, candidates can present their recommendations virtually.

How do these exercises align with the job description for a Contracts Manager?

These exercises directly assess the key responsibilities and competencies outlined in the Contracts Manager job description, including drafting and negotiating agreements, developing scalable contracting solutions, managing the contract lifecycle, collaborating cross-functionally, providing strategic counsel, and ensuring compliance.

Should we share our evaluation criteria with candidates in advance?

Providing general guidance about what you're looking for helps candidates prepare appropriately and reduces anxiety. However, keep specific evaluation criteria confidential to ensure authentic responses. For example, you might tell candidates you're evaluating their analytical skills and business judgment, but not share the specific issues you expect them to identify.

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