Practical Work Samples to Evaluate AI Conversation Intelligence Skills for Sales Teams

AI-powered conversation intelligence has revolutionized how sales organizations analyze, learn from, and improve their customer interactions. Companies implementing these tools gain unprecedented visibility into sales conversations, uncovering patterns, coaching opportunities, and revenue insights that were previously impossible to capture at scale. However, finding team members who can effectively leverage these powerful AI tools requires careful evaluation of specific skills.

The intersection of sales expertise and AI technology creates a unique skill set that's difficult to assess through traditional interviews alone. Candidates may claim proficiency with conversation intelligence platforms, but without seeing them in action, it's challenging to determine their true capabilities. Work samples provide a window into how candidates actually approach the analysis of sales conversations, their ability to extract meaningful insights, and their skill in translating those insights into actionable recommendations.

Effective AI conversation intelligence specialists must demonstrate technical competence with the tools, analytical thinking to identify meaningful patterns, communication skills to convey insights to sales teams, and strategic thinking to connect conversation data to business outcomes. The following work samples are designed to evaluate these critical capabilities in a practical context.

These exercises simulate real-world scenarios that conversation intelligence specialists encounter daily. By observing candidates as they work through these challenges, hiring managers can make more informed decisions about which individuals will truly drive value from their conversation intelligence investments. The right hire will not only understand the technology but will also know how to make it actionable for sales improvement.

Activity #1: Call Analysis and Insight Extraction

This activity evaluates a candidate's ability to analyze AI-processed sales call data and extract meaningful, actionable insights. This skill is fundamental to the role as it demonstrates whether the candidate can interpret AI-generated conversation intelligence and translate it into valuable business insights that can drive sales performance improvements.

Directions for the Company:

• Provide the candidate with a transcript and AI analysis from a real sales call (with sensitive information redacted). Include AI-generated metrics such as talk-time ratios, question counts, topic analysis, sentiment scores, and competitor mentions.
• The sample should include enough complexity to allow for meaningful analysis (ideally 15-30 minutes of conversation).
• Prepare a document explaining the context: what stage of the sales process this call represents, basic information about the product/service being sold, and the typical sales cycle.
• Allow the candidate 30 minutes to review the materials and prepare their analysis.
• Have a sales leader available to receive the insights and ask follow-up questions.

Directions for the Candidate:

• Review the provided sales call transcript and AI analysis.
• Identify 3-5 key insights from the conversation that would be valuable for the sales representative or sales leadership.
• Prepare specific, actionable recommendations based on these insights.
• Present your findings in a 10-minute briefing as if you were sharing them with the sales representative who conducted the call.
• Be prepared to explain how you determined which insights were most important and how you would prioritize follow-up actions.

Feedback Mechanism:

• After the presentation, the interviewer should provide feedback on one aspect the candidate did well (such as identifying a non-obvious insight or providing particularly actionable guidance).
• The interviewer should also provide one piece of constructive feedback about an area for improvement (such as missing an important pattern or providing too general recommendations).
• Give the candidate 5 minutes to incorporate the feedback and revise one portion of their analysis or recommendations.

Activity #2: Conversation Intelligence Implementation Planning

This activity assesses the candidate's ability to strategically plan the implementation of AI conversation intelligence in a sales organization. It demonstrates their understanding of change management, technical integration considerations, and how to align the technology with business objectives.

Directions for the Company:

• Create a fictional scenario of a sales organization looking to implement AI conversation intelligence for the first time.
• Provide details about the organization: team size, current sales processes, existing tech stack, key sales challenges, and business goals.
• Include information about stakeholders (sales leadership, reps, operations, etc.) and their potential concerns or priorities.
• Allow the candidate 45 minutes to develop their implementation plan.
• Have a panel of 2-3 interviewers representing different stakeholders (e.g., Sales VP, Sales Enablement Director, IT Manager) to review the plan.

Directions for the Candidate:

• Develop a 90-day implementation plan for rolling out AI conversation intelligence to the described sales organization.
• Your plan should include:
• Key milestones and timeline
• Technical integration considerations
• User adoption strategy
• Training approach
• Success metrics and how you'll measure ROI
• Potential challenges and how you'll address them
• Create a simple one-page visual representation of your implementation plan.
• Present your plan in a 15-minute briefing to the stakeholder panel.
• Be prepared to answer questions about your approach and defend your recommendations.

Feedback Mechanism:

• After the presentation, one interviewer should highlight a strength in the candidate's implementation plan (such as a particularly thoughtful adoption strategy or creative solution to a potential challenge).
• Another interviewer should provide constructive feedback on an area that could be improved (such as overlooking a key integration consideration or missing an important success metric).
• Give the candidate 10 minutes to revise one section of their plan based on the feedback received.

Activity #3: Sales Coaching Using AI Insights

This activity evaluates the candidate's ability to use AI-derived conversation intelligence to coach sales representatives effectively. It demonstrates their skill in translating data insights into practical coaching that improves sales performance.

Directions for the Company:

• Prepare a scenario with AI conversation intelligence data for a fictional sales rep showing specific patterns across multiple calls (e.g., low question rate, interrupting customers, not discussing certain product features, poor handling of objections).
• Include trend data showing how this rep compares to team averages on key metrics.
• Create a brief profile of the fictional sales rep including their experience level, recent performance, and personality traits.
• Schedule 30 minutes for the candidate to review the materials and prepare, followed by a 20-minute role play.
• Have an interviewer play the role of the sales rep receiving coaching.

Directions for the Candidate:

• Review the conversation intelligence data for the sales representative.
• Identify 2-3 key areas for improvement based on the patterns in the data.
• Prepare for a coaching conversation with this sales rep that addresses these areas.
• During the role play, demonstrate how you would:
• Open the conversation constructively
• Share insights from the conversation intelligence platform
• Provide specific guidance for improvement
• Handle potential resistance or defensiveness
• Create accountability for implementing changes
• Your goal is to deliver coaching that is data-driven, specific, and actionable while maintaining a positive, supportive approach.

Feedback Mechanism:

• After the role play, the interviewer should highlight one aspect of the coaching conversation that was particularly effective (such as how the candidate presented data without making the rep defensive).
• The interviewer should also provide one piece of constructive feedback about how the coaching approach could be improved.
• Give the candidate 5 minutes to reflect on the feedback and demonstrate how they would adjust their coaching approach based on this input.

Activity #4: Conversation Intelligence Platform Evaluation

This activity assesses the candidate's technical understanding of AI conversation intelligence platforms and their ability to evaluate solutions based on business requirements. It demonstrates their knowledge of the technology landscape and strategic thinking about tool selection.

Directions for the Company:

• Create a scenario where your company is evaluating new or additional conversation intelligence platforms.
• Provide information about:
• Current sales processes and challenges
• Specific business objectives for implementing conversation intelligence
• Technical requirements and constraints
• Budget considerations
• User personas who will be using the platform
• Prepare profiles of 3-4 fictional conversation intelligence vendors with different strengths, weaknesses, and pricing models.
• Allow the candidate 45 minutes to review materials and prepare their analysis.

Directions for the Candidate:

• Review the company scenario and vendor information provided.
• Develop a structured evaluation framework for assessing the conversation intelligence platforms.
• Analyze each vendor against your framework, identifying strengths and weaknesses relative to the company's specific needs.
• Prepare a recommendation for which platform(s) would best meet the company's requirements, with clear justification.
• Create a simple comparison matrix or scorecard to visualize your evaluation.
• Present your analysis and recommendation in a 15-minute briefing as if you were presenting to the executive team making the purchasing decision.
• Be prepared to defend your methodology and recommendation with specific references to the company's requirements.

Feedback Mechanism:

• After the presentation, the interviewer should highlight one particularly strong aspect of the candidate's evaluation approach (such as a thoughtful evaluation criterion or insightful vendor analysis).
• The interviewer should also provide constructive feedback on one area that could be improved (such as overlooking an important consideration or not sufficiently justifying a recommendation).
• Give the candidate 10 minutes to revise one portion of their evaluation or recommendation based on the feedback received.

Frequently Asked Questions

How should we modify these exercises if we use a specific conversation intelligence platform?

If your company already uses a particular platform (like Gong, Chorus, Salesloft, etc.), you can adapt these exercises to focus on that specific tool. For Activity #1, use actual data from your platform. For Activity #3, have the candidate demonstrate how they would use your platform's specific features for coaching. For Activity #4, you might replace it with an exercise focused on advanced use cases for your existing platform.

What if we don't have real call data to share with candidates?

If sharing real call data isn't possible due to privacy concerns, you have several options. You can create synthetic data that mimics real patterns, use anonymized data with all identifying information removed, or have team members role-play a sales call that you record and analyze specifically for this exercise. Some conversation intelligence vendors also provide sample data for training purposes.

How technical should candidates be with AI concepts?

The level of technical AI knowledge required depends on the specific role. For roles focused on using the insights to coach sales teams, a general understanding of how AI analyzes conversations is sufficient. For roles involved in platform administration, implementation, or customization, deeper technical knowledge is valuable. Adjust the complexity of the technical questions in Activities #2 and #4 accordingly.

Can these exercises be conducted remotely?

Yes, all of these exercises can be adapted for remote interviews. For remote assessments, provide materials in advance through secure sharing methods, use video conferencing for presentations and role plays, and consider extending time allowances slightly to account for potential technical issues. Collaborative tools like Google Docs or Miro can be helpful for the planning exercises.

How long should we allocate for these exercises?

Plan for approximately 1-2 hours per exercise, including preparation time, the activity itself, feedback, and discussion. You may choose to spread these across multiple interview sessions or select the 1-2 most relevant exercises based on the specific role requirements. The implementation planning exercise (Activity #2) typically requires the most time.

Should we provide access to AI tools during these exercises?

For most candidates, providing sample outputs rather than requiring them to use the actual tools during the interview is sufficient. However, for roles heavily focused on platform administration or for candidates claiming advanced expertise, having them demonstrate navigation of a conversation intelligence platform can be valuable if feasible within your interview structure.

AI conversation intelligence is transforming how sales organizations operate, coach, and improve. Finding team members who can effectively leverage these powerful tools requires evaluating both technical understanding and practical application skills. The work samples outlined above provide a comprehensive framework for assessing candidates' abilities to extract insights, implement solutions, coach effectively, and make strategic decisions about conversation intelligence technology.

By incorporating these exercises into your hiring process, you'll be able to identify candidates who not only understand the technology but can translate AI-generated insights into tangible business value. The right hire will help your organization fully capitalize on the potential of conversation intelligence to improve sales performance, enhance customer experiences, and drive revenue growth.

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