The role of a Deal Desk Manager is crucial in orchestrating complex deals and ensuring smooth collaboration between sales, finance, and legal teams. Drive is particularly relevant for this position as it fuels the persistence and determination needed to navigate challenging negotiations, meet tight deadlines, and continuously improve deal processes.

When evaluating candidates for this role, it's essential to look for evidence of self-motivation, resilience in the face of obstacles, and a proactive approach to problem-solving. The questions below are designed to assess these qualities through past experiences, allowing candidates with some relevant experience to showcase their skills and traits.

Remember that while Drive is a critical competency, it should be balanced with other skills such as attention to detail, strategic thinking, and the ability to work effectively across different departments. For more insights on conducting effective interviews, check out our blog post on how to conduct a job interview.

Interview Questions for Assessing Drive in Deal Desk Manager Roles

Tell me about a time when you faced a particularly challenging deal that seemed unlikely to close. How did you approach it, and what was the outcome?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. What specific obstacles did you encounter during this process?
2. How did you maintain your motivation throughout the challenge?
3. If you were to face a similar situation now, what would you do differently?

Describe a situation where you had to balance multiple high-priority deals simultaneously. How did you manage your time and energy to drive all of them forward?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you prioritize your efforts across the different deals?
2. Were there any tools or systems you used to stay organized?
3. How did you communicate progress and challenges to stakeholders?

Share an example of when you identified an inefficiency in the deal process and took initiative to improve it. What steps did you take, and what was the impact?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you identify this inefficiency?
2. What resistance, if any, did you face when implementing the change?
3. How did you measure the success of your improvement?

Tell me about a time when a deal fell through despite your best efforts. How did you handle the setback, and what did you do next?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you communicate the news to your team and stakeholders?
2. What specific lessons did you take away from this experience?
3. How have you applied these lessons to subsequent deals?

Describe a situation where you had to push back against unreasonable demands from a client or internal stakeholder during a deal negotiation. How did you handle it?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you prepare for this challenging conversation?
2. What strategies did you use to maintain a positive relationship while standing firm?
3. How did this experience influence your approach to future negotiations?

Share an example of when you had to quickly learn and adapt to a new technology or process to close a deal. How did you approach the learning curve?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. What resources did you use to get up to speed quickly?
2. How did you balance learning with your other responsibilities?
3. How has this experience shaped your approach to learning new skills?

Tell me about a time when you had to motivate a cross-functional team to meet a tight deadline for a complex deal. What strategies did you employ?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you ensure everyone understood their roles and responsibilities?
2. What challenges did you face in keeping the team motivated?
3. How did you celebrate successes along the way?

Describe a situation where you had to go above and beyond your normal duties to ensure a deal closed successfully. What drove you to put in the extra effort?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you manage your time and energy during this period?
2. What impact did this extra effort have on the deal outcome?
3. How did you recover after this intense period?

Share an example of when you had to maintain momentum on a long, complex deal process. How did you keep yourself and others engaged over an extended period?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. What milestones or checkpoints did you establish to track progress?
2. How did you handle periods of low activity or setbacks?
3. What strategies did you use to prevent burnout in yourself and your team?

Tell me about a time when you had to quickly pivot your strategy on a deal due to unexpected changes. How did you adapt and drive the new approach forward?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you communicate the need for change to stakeholders?
2. What challenges did you face in implementing the new strategy?
3. How did this experience influence your approach to deal planning?

Describe a situation where you had to drive a deal forward despite facing significant internal resistance. How did you navigate the organizational challenges?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you identify and address the root causes of the resistance?
2. What strategies did you use to build consensus?
3. How did this experience shape your approach to internal stakeholder management?

Share an example of when you had to take a calculated risk to move a deal forward. How did you assess the situation and decide to proceed?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you communicate the risks and potential rewards to stakeholders?
2. What contingency plans did you put in place?
3. How has this experience influenced your risk assessment process in subsequent deals?

Tell me about a time when you had to manage multiple competing priorities while driving a critical deal to closure. How did you balance your responsibilities?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. How did you determine which tasks to prioritize?
2. What strategies did you use to stay focused and productive?
3. How did you communicate your priorities and progress to stakeholders?

Describe a situation where you had to maintain your drive and motivation during a particularly slow or frustrating deal process. How did you stay engaged and keep things moving forward?

Areas to Cover:

• Details of the situation
• Actions taken
• How those actions were decided on
• Who the candidate got help or support from
• Results of the actions
• Lessons learned
• How the lessons have been applied

Possible follow-up questions:

1. What specific challenges did you face during this period?
2. How did you keep other stakeholders engaged and motivated?
3. What techniques or habits did you develop to maintain your focus and energy?

FAQ

Q: How many of these questions should I ask in a single interview?A: It's recommended to ask 3-4 questions per interview, allowing time for follow-up questions and in-depth discussions.

Q: Should I ask these questions in a specific order?A: The order can be flexible, but it's often good to start with a more general question and then move to more specific or challenging scenarios.

Q: How can I ensure I'm getting authentic responses rather than prepared answers?A: Use follow-up questions to dig deeper into the candidate's responses, asking for specific details and examples. This helps to verify the authenticity of their experiences.

Q: What if a candidate doesn't have a specific example for one of these questions?A: If a candidate doesn't have a directly relevant example, you can ask them to describe a similar situation or how they would hypothetically approach the scenario. However, be aware that hypothetical answers are generally less reliable indicators of future performance than actual past experiences.

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