Effective Work Sample Exercises for Hiring a Deal Desk Analyst

The Deal Desk Analyst role serves as a critical bridge between sales, finance, legal, and operations teams, ensuring that deals are structured optimally while maintaining compliance with company policies. When hiring for this position, traditional interviews alone often fail to reveal a candidate's true capabilities in analyzing complex deals, identifying potential issues, and collaborating effectively across departments.

Work sample exercises provide a window into how candidates actually perform the core responsibilities of a Deal Desk Analyst. By observing candidates as they analyze contracts, structure pricing, communicate with stakeholders, and optimize deal processes, hiring managers can make more informed decisions based on demonstrated skills rather than self-reported experience.

The best Deal Desk Analysts combine analytical rigor with practical business acumen and excellent communication skills. These qualities can be difficult to assess through standard interview questions but become readily apparent when candidates engage with realistic work scenarios. Additionally, work samples reduce hiring bias by focusing evaluation on objective performance rather than subjective impressions.

The following exercises are designed to evaluate the essential competencies required for success as a Deal Desk Analyst: analytical thinking, attention to detail, communication, collaboration, and problem-solving. By implementing these work samples as part of your hiring process, you'll be better equipped to identify candidates who can truly excel in this multifaceted role.

Activity #1: Contract Analysis and Deal Structure Review

This exercise evaluates a candidate's ability to analyze contract terms, identify potential issues, and make recommendations to optimize deal structure. It tests analytical thinking, attention to detail, and understanding of contract elements that impact profitability and compliance.

Directions for the Company:

• Prepare a sample sales contract with intentionally included issues such as non-standard terms, pricing inconsistencies, missing clauses, or compliance concerns.
• Include a basic customer profile and deal context (industry, size, strategic importance).
• Allow 45-60 minutes for the candidate to review and analyze the document.
• Prepare evaluation criteria focusing on the candidate's ability to identify key issues, prioritize concerns, and provide practical recommendations.
• Have a sales operations leader or deal desk manager available to review the candidate's analysis and provide feedback.

Directions for the Candidate:

• Review the provided sales contract and customer profile.
• Identify any issues, risks, or opportunities for improvement in the contract structure.
• Prepare a brief analysis document (or use a provided template) that outlines:

1. Key issues identified and their potential impact
2. Recommendations for addressing each issue
3. Questions you would ask the sales team to better understand the deal context
4. Suggested changes to optimize the deal structure for both the company and customer

• Be prepared to discuss your analysis and reasoning.

Feedback Mechanism:

• After the candidate presents their analysis, the interviewer should provide specific feedback on one strength (e.g., "You did an excellent job identifying the non-standard payment terms and their financial impact") and one area for improvement (e.g., "You might have missed how the auto-renewal clause could create future compliance issues").
• Give the candidate 10-15 minutes to revise their recommendations based on the feedback, focusing specifically on the improvement area identified.
• Observe how receptive the candidate is to feedback and how effectively they incorporate it into their revised approach.

Activity #2: Deal Pricing Scenario and Financial Impact Analysis

This exercise assesses the candidate's ability to evaluate pricing structures, calculate financial impacts, and make data-driven recommendations. It tests quantitative analysis skills, understanding of pricing strategies, and business acumen.

Directions for the Company:

• Create a realistic pricing scenario with a complex deal structure (e.g., multi-year contract, volume discounts, service tiers, or add-on options).
• Provide relevant company pricing guidelines, discount thresholds, and margin requirements.
• Include a spreadsheet template for the candidate to use for calculations.
• Allow 30-45 minutes for the candidate to complete the analysis.
• Have a finance team member or pricing specialist available to evaluate the candidate's work.

Directions for the Candidate:

• Review the deal scenario and pricing information provided.
• Using the spreadsheet template, calculate the financial impact of the proposed deal structure, including:

1. Total contract value
2. Annual recurring revenue
3. Gross margin percentage
4. Impact of proposed discounts

• Identify any pricing elements that don't align with company guidelines.
• Recommend an optimized pricing structure that balances customer value with company profitability.
• Prepare a brief summary explaining your analysis and recommendations.

Feedback Mechanism:

• The interviewer should review the candidate's calculations and recommendations, providing specific feedback on one strength (e.g., "Your margin analysis was thorough and accurately identified the problematic service tier") and one area for improvement (e.g., "Your alternative discount structure doesn't account for the strategic importance of this customer").
• Ask the candidate to revise their pricing recommendation based on the feedback provided.
• Evaluate how well the candidate balances competing priorities (revenue, margin, customer relationship) in their revised approach.

Activity #3: Cross-Functional Communication Role Play

This exercise evaluates the candidate's ability to communicate effectively with different stakeholders and navigate potentially conflicting priorities. It tests communication skills, stakeholder management, and the ability to find collaborative solutions.

Directions for the Company:

• Develop a scenario involving a complex deal with competing stakeholder interests (e.g., sales pushing for aggressive discounts, legal concerned about terms, finance worried about margins).
• Assign team members to play the roles of different stakeholders (sales representative, legal counsel, finance manager).
• Provide the candidate with deal details and stakeholder concerns 24 hours before the exercise.
• Allow 20-30 minutes for the role play.
• Brief the role players on their positions, concerns, and personality traits to portray.

Directions for the Candidate:

• Review the deal scenario and stakeholder information provided.
• Prepare for a meeting where you'll need to address concerns from sales, legal, and finance teams regarding a pending deal.
• During the role play:

1. Facilitate a productive discussion among stakeholders
2. Demonstrate active listening to understand each perspective
3. Identify areas of compromise and potential solutions
4. Work toward a resolution that addresses key concerns
5. Clearly communicate next steps and action items

• Your goal is to find a path forward that balances stakeholder needs while optimizing the deal structure.

Feedback Mechanism:

• After the role play, the interviewer should provide feedback on one communication strength (e.g., "You effectively acknowledged each stakeholder's concerns and found creative compromises") and one area for improvement (e.g., "You could have been more assertive in redirecting the conversation when it went off-track").
• Give the candidate an opportunity to reflect on how they would approach a specific moment in the conversation differently based on the feedback.
• Ask them to demonstrate this improved approach in a brief follow-up interaction with one of the stakeholders.

Activity #4: Deal Process Optimization Exercise

This exercise assesses the candidate's ability to analyze inefficient processes, identify bottlenecks, and recommend improvements. It tests problem-solving skills, process thinking, and understanding of deal desk operations.

Directions for the Company:

• Create a case study of a problematic deal process with clear inefficiencies (e.g., lengthy approval times, redundant steps, communication gaps).
• Include process flow diagrams, average processing times, and stakeholder pain points.
• Provide relevant constraints (system limitations, compliance requirements, team structure).
• Allow 45-60 minutes for the candidate to analyze and develop recommendations.
• Have an operations or process improvement specialist available to evaluate the candidate's work.

Directions for the Candidate:

• Review the current deal process documentation and identified pain points.
• Analyze the process to identify:

1. Key bottlenecks and inefficiencies
2. Root causes of delays or errors
3. Opportunities for automation or streamlining
4. Potential process improvements

• Create a revised process flow that addresses the issues identified.
• Prepare a brief presentation (3-5 slides) outlining your analysis, recommendations, and implementation considerations.
• Be prepared to discuss the potential impact of your proposed changes and any challenges to implementation.

Feedback Mechanism:

• After the candidate presents their recommendations, the interviewer should provide feedback on one strength (e.g., "Your identification of the redundant approval steps was insightful and your solution is practical") and one area for improvement (e.g., "Your solution doesn't address how the legal review process would integrate with the new workflow").
• Ask the candidate to spend 10-15 minutes refining their recommendation to address the improvement area.
• Evaluate how well the candidate incorporates the feedback while maintaining the overall integrity of their solution.

Frequently Asked Questions

How long should we allocate for these work sample exercises?

Each exercise is designed to take 30-60 minutes, with additional time for feedback and revision. We recommend scheduling separate sessions for each exercise or selecting the 2-3 most relevant exercises for your specific needs. The entire battery would typically require a half-day assessment if conducted sequentially.

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

We recommend using at least one work sample (typically the Contract Analysis exercise) earlier in the process to screen candidates before investing in full interviews. The more time-intensive exercises like the Cross-Functional Communication Role Play are best reserved for final candidates.

How should we weight these exercises compared to traditional interviews?

Work samples are typically more predictive of on-the-job performance than traditional interviews. We recommend giving work sample results significant weight (40-60% of the overall evaluation) in your hiring decision, particularly for the exercises most relevant to your specific deal desk operations.

Can these exercises be conducted remotely?

Yes, all of these exercises can be adapted for remote administration. For the Contract Analysis and Deal Pricing exercises, use screen sharing or collaborative documents. For the Communication Role Play, video conferencing works well. Just ensure candidates have access to necessary tools and templates before the session.

How do we ensure these exercises don't disadvantage candidates without specific industry experience?

Focus evaluation on the underlying skills rather than industry-specific knowledge. Provide sufficient context about your products/services and typical deal structures. The exercises are designed to test analytical thinking, communication, and problem-solving rather than pre-existing knowledge of your specific business.

Should we compensate candidates for completing these exercises?

For exercises requiring significant preparation or time commitment (particularly if assigned as "homework"), consider offering compensation, especially for more senior roles. This demonstrates respect for candidates' time and expertise while potentially increasing completion rates and effort quality.

In conclusion, implementing these work sample exercises will significantly enhance your ability to identify top Deal Desk Analyst talent. By observing candidates as they perform realistic job tasks, you'll gain valuable insights into their analytical abilities, communication skills, and problem-solving approaches that traditional interviews simply cannot reveal.

For more resources to optimize your hiring process, explore Yardstick's suite of AI-powered tools, including our AI Job Description Generator, AI Interview Question Generator, and AI Interview Guide Generator. You can also find more information about the Deal Desk Analyst role in our comprehensive job description guide.

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