Effective Work Sample Exercises for Hiring a Deal Desk Manager

The Deal Desk Manager serves as a critical bridge between sales, finance, legal, and product teams, ensuring that complex deals move efficiently from quote to contract while maintaining pricing integrity and compliance. This pivotal role requires a unique blend of analytical prowess, cross-functional collaboration skills, and meticulous attention to detail. Traditional interviews often fail to reveal whether candidates truly possess these capabilities in practical scenarios.

Implementing well-designed work samples during your hiring process allows you to observe candidates applying their skills to realistic challenges they'll face in the role. For Deal Desk Managers, this means evaluating how they analyze pricing structures, optimize workflows, navigate cross-departmental communication, and maintain compliance—all while under the time constraints and pressures similar to those they'll experience on the job.

Research consistently shows that performance on job-relevant tasks is one of the strongest predictors of future job success. By incorporating the following work samples into your interview process, you'll gain valuable insights into how candidates approach the specific challenges of deal desk management, helping you identify those who can truly drive efficiency, compliance, and revenue growth through effective deal structuring.

These exercises are designed to be both practical for your hiring team to implement and insightful for evaluating candidates. Each activity targets core competencies required for success in the Deal Desk Manager role, providing a comprehensive view of a candidate's capabilities beyond what traditional interviews or resume reviews can reveal.

Activity #1: Complex Deal Pricing Analysis

This exercise evaluates a candidate's analytical thinking, attention to detail, and ability to optimize pricing strategies while maintaining compliance with company policies. Deal Desk Managers must regularly analyze complex pricing scenarios to ensure profitability while supporting sales teams in closing deals.

Directions for the Company:

• Create a realistic but anonymized deal scenario with multiple products/services, various discount levels, and non-standard terms.
• Include a pricing sheet with standard rates, discount thresholds, and margin requirements.
• Provide a brief company policy document outlining approval requirements for different discount levels and non-standard terms.
• Allow 45-60 minutes for this exercise.
• Prepare specific questions about the candidate's approach to analyzing the deal.

Directions for the Candidate:

• Review the provided deal scenario, pricing information, and policy documentation.
• Analyze the proposed deal structure and identify any pricing issues, compliance concerns, or approval requirements.
• Prepare recommendations for optimizing the deal structure to improve margins while maintaining competitiveness.
• Create a brief summary (1 page maximum) outlining your findings and recommendations.
• Be prepared to explain your analysis process and defend your recommendations.

Feedback Mechanism:

• After the candidate presents their analysis, provide specific feedback on one aspect they handled well (e.g., thoroughness of analysis, creative solution to a pricing challenge).
• Offer one constructive suggestion for improvement (e.g., missed opportunity for bundling, overlooked approval requirement).
• Ask the candidate to revise one portion of their recommendation based on the feedback, giving them 5-10 minutes to adjust their approach.

Activity #2: Cross-Functional Deal Review Simulation

This role play evaluates the candidate's communication skills, ability to collaborate across departments, and effectiveness in facilitating deal approvals. Deal Desk Managers must regularly coordinate with multiple stakeholders to resolve complex deal issues.

Directions for the Company:

• Assemble 2-3 interviewers to play the roles of stakeholders from different departments (Sales, Legal, Finance).
• Create a scenario involving a complex deal with specific issues that each stakeholder would be concerned about (e.g., non-standard payment terms for Finance, custom contract language for Legal, aggressive discounting for Sales).
• Provide the candidate with basic deal information and stakeholder concerns 24 hours before the exercise.
• Prepare each role player with specific objections or concerns to raise during the meeting.

Directions for the Candidate:

• Review the deal information provided and prepare to facilitate a 20-minute deal review meeting.
• Your goal is to address stakeholder concerns, identify solutions to potential roadblocks, and move the deal toward approval.
• Come prepared with questions to understand each stakeholder's perspective and potential compromise solutions.
• Document key action items and next steps that emerge from the discussion.
• Focus on finding a balance between maintaining deal momentum and ensuring compliance with company policies.

Feedback Mechanism:

• After the role play, each stakeholder should provide feedback on how effectively the candidate addressed their concerns.
• Highlight one aspect of the candidate's facilitation that was particularly effective.
• Identify one area where the candidate could improve their approach to stakeholder management.
• Give the candidate 5 minutes to explain how they would adjust their approach based on the feedback.

Activity #3: Deal Desk Workflow Optimization

This exercise assesses the candidate's ability to identify inefficiencies in deal processes and implement improvements—a core responsibility for Deal Desk Managers who must continuously optimize workflows to enhance sales velocity.

Directions for the Company:

• Create a visual representation of your current (or a fictional) quote-to-contract process, including approval workflows, handoffs between departments, and common bottlenecks.
• Include relevant metrics such as average deal cycle time, approval wait times, and common reasons for deal delays.
• Provide sample deal desk tickets or requests that illustrate typical challenges.
• Allow 45-60 minutes for this exercise.Directions for the Candidate:
• Review the provided workflow documentation and metrics.
• Identify 3-5 key inefficiencies or bottlenecks in the current process.
• Develop specific recommendations for process improvements that would:
• Reduce deal cycle time
• Maintain or enhance compliance
• Improve the experience for sales teams
• Create a brief presentation (5-7 slides) outlining your findings and recommendations.
• Be prepared to explain the expected impact of your proposed changes and how you would measure success.

Feedback Mechanism:

• After the candidate presents their recommendations, provide feedback on one aspect that demonstrated strong process thinking.
• Offer one suggestion for how they might enhance their approach to process optimization.
• Ask the candidate to select one of their recommendations and elaborate on how they would implement it, incorporating the feedback provided.

Activity #4: Non-Standard Deal Term Evaluation

This exercise evaluates the candidate's contract review skills, understanding of risk management, and ability to balance sales enablement with company policy compliance—essential skills for a Deal Desk Manager who must regularly evaluate non-standard terms.

Directions for the Company:

• Prepare a sample contract with 5-7 non-standard terms highlighted (e.g., custom payment terms, unique SLA requirements, non-standard cancellation clauses).
• Create a document outlining company policies regarding contract terms, approval requirements, and risk thresholds.
• Include a brief description of the customer and deal context (size, strategic importance, etc.).
• Allow 30-45 minutes for this exercise.

Directions for the Candidate:

• Review the contract and identify which non-standard terms require special attention or approval.
• Evaluate each term for:
• Potential financial impact
• Legal/compliance risks
• Operational feasibility
• Precedent concerns for future deals
• Prepare a concise evaluation document (1-2 pages) that:
• Categorizes each term by risk level (high, medium, low)
• Recommends approval paths for each term
• Suggests alternative language where appropriate
• Be prepared to explain your reasoning and how you would communicate these issues to the sales team.

Feedback Mechanism:

• After reviewing the candidate's evaluation, highlight one aspect of their analysis that was particularly thorough or insightful.
• Provide one suggestion for how they might improve their approach to evaluating contract terms.
• Ask the candidate to revise their recommendation for one specific term based on the feedback, giving them 5-10 minutes to adjust their approach.

Frequently Asked Questions

How long should we allocate for these work samples in our interview process?

Each exercise requires approximately 45-60 minutes, including time for setup, execution, feedback, and candidate revision. We recommend selecting 1-2 exercises that best align with your specific needs rather than attempting all four in a single interview process. The cross-functional role play (Activity #2) works particularly well as a final-round exercise.

Should we provide these exercises to candidates in advance?

For Activities #1, #3, and #4, providing the basic scenario 24 hours in advance allows candidates to come prepared, which more accurately reflects the real job where they would have time to review materials. For Activity #2 (the role play), providing basic information in advance but reserving some details for the live exercise creates a realistic balance of preparation and adaptability.

How can we adapt these exercises for remote interviews?

All four activities can be conducted remotely with minimal adjustments. Use screen sharing for presentations, collaborative documents for real-time analysis, and video conferencing for role plays. Consider using digital whiteboarding tools for workflow optimization discussions. Ensure all materials are shared in advance through secure channels.

What if our company doesn't have established pricing policies or workflows to share?

Create simplified versions based on industry standards or your aspirational processes. The goal is to evaluate how candidates approach these scenarios, not to test their knowledge of your specific company procedures. This can actually provide valuable insights into how they might help establish these processes at your organization.

How should we weight these exercises compared to traditional interviews?

Research shows that work samples are highly predictive of job performance. We recommend giving these exercises significant weight (40-50%) in your overall evaluation, with traditional experience and behavioral interviews comprising the remainder. The candidate's ability to incorporate feedback should be particularly noted as it demonstrates coachability.

Can these exercises be customized for different industries or company sizes?

Absolutely. The core activities remain relevant across industries, but you should customize the specific scenarios, pricing structures, and compliance requirements to reflect your industry and company size. For example, enterprise software companies might focus more on complex multi-product deals, while services firms might emphasize custom SOW terms.

The Deal Desk Manager role is pivotal in optimizing your sales operations and ensuring deal integrity. By incorporating these practical work samples into your hiring process, you'll gain deeper insights into candidates' abilities to handle the complex challenges of the position. This approach not only helps you identify the most qualified candidates but also gives applicants a realistic preview of the role, leading to better hiring decisions and improved retention.

Ready to take your hiring process to the next level? Yardstick offers comprehensive tools to help you design and execute exceptional candidate interviews. From creating tailored job descriptions with our AI Job Description Generator to developing targeted interview questions with our AI Interview Question Generator and building complete interview guides with our AI Interview Guide Generator, we provide everything you need to make informed hiring decisions. Check out our Deal Desk Manager job description for more insights into this critical role.

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