Effective Work Sample Exercises for Hiring a Deal Desk Senior Manager

The Deal Desk Senior Manager serves as a critical bridge between sales, finance, legal, and product teams in high-growth organizations. This strategic role requires a unique blend of analytical prowess, business acumen, and interpersonal skills to navigate complex enterprise deals effectively. When hiring for this position, traditional interviews alone often fail to reveal a candidate's true capabilities in structuring deals, managing cross-functional relationships, and optimizing processes.

Practical work samples provide invaluable insights into how candidates approach real-world challenges they'll face in the role. For a Deal Desk Senior Manager, these exercises should evaluate their ability to analyze complex deal structures, navigate approval processes, communicate effectively with stakeholders, and implement process improvements. The right candidate must demonstrate not just theoretical knowledge but practical skills in balancing sales objectives with financial and legal considerations.

The following work samples are designed to simulate the day-to-day responsibilities of a Deal Desk Senior Manager. They assess candidates' abilities to quarterback non-standard deals, provide strategic consultation, manage approval processes, and optimize deal structures. By observing candidates in action through these exercises, hiring teams can make more informed decisions about which individuals possess the right combination of skills, experience, and adaptability to excel in this multifaceted role.

Implementing these exercises as part of your interview process will help identify candidates who can truly drive business growth by streamlining deal cycles, increasing average deal size, and ensuring compliance with company policies. The exercises also provide candidates with a realistic preview of the role, helping ensure alignment between their expectations and the actual responsibilities they'll encounter if hired.

Activity #1: Complex Deal Structure Analysis

This exercise evaluates a candidate's ability to analyze a non-standard deal, identify potential issues, and recommend an optimized structure. It tests their strategic problem-solving skills, business acumen, and understanding of pricing strategies and contract terms—all essential competencies for a Deal Desk Senior Manager who must balance sales objectives with financial and legal considerations.

Directions for the Company:

• Create a detailed case study of a complex enterprise deal with multiple products/services, non-standard pricing requests, and unique contract terms.
• Include a mock sales opportunity summary, customer requirements document, pricing sheet, and relevant company policies.
• Provide information about standard margins, approval thresholds, and common deal structures.
• Allow candidates 45-60 minutes to review materials and prepare their recommendations.
• Have a panel representing sales, finance, and legal teams to review the candidate's proposal.

Directions for the Candidate:

• Review the provided materials for a complex enterprise deal opportunity.
• Identify potential issues, risks, and opportunities in the current deal structure.
• Prepare a revised deal structure that balances customer needs, sales objectives, and company policies.
• Create a brief presentation (5-7 slides) outlining:

1. Key issues with the current deal structure
2. Recommended changes and rationale
3. Financial impact analysis
4. Required approvals and next steps

• Be prepared to present and defend your recommendations to a cross-functional panel.

Feedback Mechanism:

• After the presentation, the panel should provide specific feedback on one aspect the candidate handled well (e.g., creative solution to a pricing challenge) and one area for improvement (e.g., missed a compliance requirement).
• Give the candidate 10 minutes to revise their approach based on the feedback.
• Observe how receptive they are to feedback and their ability to quickly adapt their thinking.

Activity #2: Cross-Functional Stakeholder Role Play

This role play assesses the candidate's ability to navigate challenging conversations with different stakeholders—a critical skill for Deal Desk Senior Managers who must influence without authority and balance competing priorities across departments. It evaluates their communication skills, stakeholder management abilities, and adaptability in real-time situations.

Directions for the Company:

• Prepare a scenario involving a time-sensitive deal with conflicting stakeholder interests.
• Create role descriptions for three stakeholders:

1. An aggressive sales executive pushing for approval of non-standard terms
2. A risk-averse legal counsel raising compliance concerns
3. A finance leader concerned about margin impact

• Assign experienced team members to play these roles, with specific talking points and objections.
• Allow the candidate 15 minutes to review the deal details before the role play.
• Schedule three consecutive 10-minute meetings with each stakeholder.

Directions for the Candidate:

• Review the details of a pending enterprise deal requiring urgent resolution.
• Your goal is to find a path forward that addresses key concerns while keeping the deal on track.
• You will meet with three stakeholders in sequence, each with different priorities and concerns.
• For each meeting:

1. Listen to the stakeholder's perspective
2. Ask clarifying questions
3. Propose potential solutions
4. Work toward alignment on next steps

• After all three meetings, prepare a brief summary of your recommended approach and rationale.

Feedback Mechanism:

• After the role play, provide feedback on the candidate's strongest communication technique and one area where their approach could be more effective.
• Give the candidate an opportunity to reflect on how they would handle one specific challenging moment differently based on the feedback.
• Ask them to demonstrate their revised approach in a brief follow-up conversation.

Activity #3: Deal Process Optimization Exercise

This exercise evaluates the candidate's ability to identify inefficiencies in deal processes and implement improvements—a key responsibility for Deal Desk Senior Managers tasked with reducing cycle times and increasing sales productivity. It tests their process thinking, analytical skills, and ability to translate insights into actionable recommendations.

Directions for the Company:

• Prepare a detailed flowchart of your current deal approval process, including average time spent at each stage.
• Include sample data showing deal cycle metrics, common bottlenecks, and escalation patterns.
• Provide anonymized examples of deals that experienced significant delays.
• Create a brief on company objectives (e.g., reduce approval time by 30%).
• Allow candidates 60 minutes to review materials and prepare recommendations.
• Have a panel representing sales, finance, and legal teams to review the candidate's proposal.

Directions for the Candidate:

• Review the provided materials on the current deal approval process.
• Analyze the data to identify key bottlenecks, inefficiencies, and root causes of delays.
• Develop a comprehensive plan to optimize the process, including:

1. Specific process changes and their expected impact
2. Required technology or tool enhancements
3. Policy modifications or clarifications
4. Implementation timeline and change management approach
5. Key metrics to track success

• Prepare a one-page executive summary and supporting documentation.

Feedback Mechanism:

• Provide feedback on the most valuable insight or recommendation the candidate identified and one area where their analysis could be more thorough.
• Give the candidate 15 minutes to expand on the area needing improvement.
• Evaluate their ability to quickly deepen their analysis and refine their recommendations.

Activity #4: Non-Standard Deal Approval Simulation

This simulation tests the candidate's ability to make sound decisions under pressure when evaluating non-standard deal requests—a daily responsibility for Deal Desk Senior Managers. It assesses their knowledge of deal policies, business judgment, and ability to balance risk management with business growth objectives.

Directions for the Company:

• Create a queue of 5-7 mock deal desk requests of varying complexity and urgency.
• Each request should include:

1. Deal summary (customer, products, total value)
2. Requested exception or non-standard term
3. Sales justification
4. Relevant company policies
5. Approval deadline

• Include a mix of pricing exceptions, contract term modifications, and approval process requests.
• Provide a template for documenting decisions and rationale.
• Allow candidates 45 minutes to process the queue.

Directions for the Candidate:

• You will receive a queue of deal desk requests requiring your review and decision.
• For each request, you must:

1. Determine if you can approve, reject, or need to escalate
2. Document your decision and rationale
3. Specify any conditions or modifications to your approval
4. Identify which stakeholders need to be informed or consulted
5. Prioritize which requests to handle first based on urgency and impact

• Balance the need for speed with proper risk assessment and policy compliance.
• Be prepared to explain your decision-making process for each request.

Feedback Mechanism:

• Provide feedback on one decision the candidate handled particularly well and one where their approach could be improved.
• Ask the candidate to reconsider the decision that needs improvement and explain their revised approach.
• Evaluate their ability to incorporate feedback while maintaining their independent judgment.

Frequently Asked Questions

How long should we allocate for these work sample exercises?

Each exercise requires approximately 1-2 hours of total time, including preparation, execution, and feedback. We recommend spreading them across different interview stages rather than conducting all four in a single day, which would be overwhelming for candidates.

Should we use our actual company data in these exercises?

While using realistic scenarios is important, we recommend creating mock data that resembles your actual deals but doesn't contain sensitive information. This protects confidentiality while still providing an authentic experience.

What if we don't have team members who can effectively role-play the stakeholders?

The stakeholder role play is most effective with experienced team members, but if unavailable, you can simplify by having one interviewer play multiple roles or provide written stakeholder perspectives instead. The key is testing how candidates navigate competing priorities.

How do we evaluate candidates consistently across these exercises?

Create a standardized rubric for each exercise that maps to the key competencies in your job description. Have multiple evaluators use the same criteria, and conduct a calibration session before beginning interviews to ensure alignment on expectations.

Should we share these exercises with candidates in advance?

For Activities #1 and #3, providing materials 24 hours in advance allows candidates to prepare thoughtful responses, which is realistic for the role. For Activities #2 and #4, which test real-time decision-making, share only basic context in advance.

What if a candidate has limited experience with our specific industry or products?

Focus evaluation on their process, reasoning, and adaptability rather than specific industry knowledge. Provide sufficient context in the exercise materials to enable candidates from adjacent industries to demonstrate their transferable skills.

The Deal Desk Senior Manager role requires a unique combination of analytical thinking, stakeholder management, and process optimization skills. By incorporating these practical work samples into your hiring process, you'll gain deeper insights into candidates' abilities to handle the complex challenges they'll face in this critical position.

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