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AI Without The Ick: Thoughtful Ways to Use AI in Sales

AI Without The Ick: Thoughtful Ways to Use AI in Sales

So I’m a bit of an “Anti Sales AI” kinda dude.

Most applications of AI people tend to use for sales involve using AI to replace their calls, emails, and thoughtfulness with watered down generic AI drivel.

Which is the exact OPPOSITE of what buyers want.

But working with several of my students I have found a pretty reliable way to use it to PROMPT thoughtfulness vs. replacing it.

Here’s how I do that.

Train Your GPT

First off, train your ChatGPT to better understand your solution/value prop/problems you solve, give it links and documents so it has a full understanding of your ICP, their challenges, and your solution.

I work in sales for a company called Mentimeter, you can see our website here for a better overview: https://www.mentimeter.com/ We sell to learning and development teams and higher education to help them with the following problems: Lack of feedback from learning programs & online meetings which leads us to question our decisions and make improvements Lack of participation and engagement from students and employees during learning which means time is wasted, student satisfaction is lowered, and employees don't improve We solve these issues with interactive presentations that allow participants to engage with the presentation in real time on their mobile phones & collect anonymous feedback data for teams Typically the status quo for our customers is using Zoom meetings/Google slides/Canva for presentations and Typeform or other learning tools for feedback

Now your ChatGPT has a better understanding you can begin to ask it questions to prompt ideas.

Ideas For Outbound Prospecting Triggers

If you want to find new ways to prioritize or target accounts that will also allow you to hypothesize that a problem is happening in your cold outbound messaging you can ask ChatGPT to suggest signs/triggers that make an account more likely to struggle with a problem.

If were to want to prospect into companies, what are 20 signs that might I be able to find online that could indicate a school or organization are more likely to be facing the issues mentioned above?
Signs of Feedback Challenges Glassdoor Reviews Mentioning Lack of Communication: Reviews indicating employees feel unheard or that feedback isn't implemented. Complaints About Decision-Making Processes: Online reviews or testimonials noting poor decisions due to lack of data. Frequent Job Postings in Learning & Development: Indicates a focus on training programs but potentially lacking tools to measure their effectiveness. High Turnover Rates in Training or Teaching Roles: Suggests dissatisfaction potentially linked to ineffective feedback mechanisms. Seeking Feedback Tools on RFPs: Schools or companies issuing RFPs for learning tools or feedback systems. Articles or Posts About Struggling to Improve Outcomes: Public discussions about challenges in decision-making for learning or development programs. Use of Older Tools (e.g., PowerPoint or PDF Materials): Evidence of outdated technology that doesn't facilitate feedback collection. References to Compliance-Based Training: Indicates a check-the-box approach, often lacking feedback loops for quality improvement. Unanswered Student/Employee Feedback Surveys: Complaints or public posts indicating surveys aren’t yielding actionable results.
Signs of Engagement Challenges Online Complaints About Boring Presentations: Feedback on forums or reviews about dull or monotonous training sessions. Low Employee/Student Satisfaction Ratings: Published satisfaction scores indicating disengagement during training or educational activities. Frequent Discussions About Remote Work Challenges: Blogs, webinars, or posts highlighting remote participation issues. High Dropout Rates in Training Programs: Schools or organizations discussing retention issues in learning programs. Low Event Attendance or Engagement Metrics: Publicly shared concerns about underwhelming engagement in online events or classes. LinkedIn Posts About Seeking New Engagement Strategies: L&D teams openly exploring or asking for ways to make training more interactive. Use of Static Platforms for Presentations: Evidence of reliance on tools like Google Slides or Canva without live interactivity. Push for Employee-Led Workshops: Indicates efforts to boost engagement but may lack the proper tools to facilitate interaction. Complaints About Meeting Fatigue: Posts or reviews discussing "Zoom fatigue" and the lack of stimulating content in online meetings. Presence of Polls/Surveys Without Actionable Follow-Up: Feedback mechanisms that don’t lead to visible improvements in learning or workplace initiatives. Rebranding or Reworking Training Programs: Indicates a need to modernize engagement methods, often prompted by declining satisfaction or effectiveness.
How to Find These Signs Monitor social media (LinkedIn, Twitter, etc.) for relevant keywords or discussions. Review Glassdoor, Indeed, or other job review platforms for employee sentiments. Look at public-facing reports or case studies highlighting organizational challenges. Research RFP postings and procurement announcements. Analyze LinkedIn profiles of L&D professionals for certifications or activities that hint at the adoption of new strategies or tools.

Ideas For Discovery Questions

If you’re having a hard time coming up with insightful questions to ask in your discovery process then prompt ChatGPT to suggest questions that align with your preferred Sales Methodology (Gap Selling in this case)

If I were in an introduction/discovery conversation with a Learning and Development Leader what are some questions I could ask to uncover what challenges they are having with participation/feedback, the impacts of those challenges on their business, and the root cause of those challenges?
Participation Challenges Current State: "How do you currently measure engagement during your training sessions or workshops?" "What tools or methods do you use to ensure participants stay engaged?" "What signs do you typically see when engagement is high or low in your programs?" Perceived Challenges: "What challenges have you faced in keeping employees/students actively involved during learning sessions?" "Are there specific groups or types of sessions where engagement is particularly difficult?" Efforts to Address: "What strategies have you tried to boost participation? How well have they worked?" "Do you feel your current tools allow you to create interactive, dynamic sessions?"
Feedback Challenges Current State: "How do you currently collect feedback after sessions?" "Are participants comfortable providing honest feedback? How do you know?" Perceived Challenges: "What types of feedback are you not getting that you wish you had?" "How often do you find feedback to be incomplete or unhelpful in shaping future programs?" Efforts to Address: "Have you tried different methods to encourage more detailed or honest feedback? What has worked or not worked?"
Impact of Challenges On Business Objectives: "What happens when participants aren’t fully engaged during your programs?" "How does low engagement impact key metrics like retention, productivity, or satisfaction?" On Stakeholders: "How do participants typically respond when programs don’t feel engaging or interactive?" "What feedback have you received from leadership about the effectiveness of your programs?" On Time and Resources: "How much time does your team spend revising or improving programs based on limited feedback?" "Do you feel you’re investing more resources than necessary because of these issues?"
Root Causes Content: "Do you feel the content itself could be contributing to disengagement? Why or why not?" "How often do you refresh or adapt your content to make it more engaging?" Delivery Tools: "Are your current tools meeting your needs for interactivity and feedback collection?" "What limitations have you noticed with the tools or platforms you’re using?" Audience Dynamics: "Do you notice differences in engagement based on audience type (e.g., remote vs. in-person, employees vs. students)?" "What feedback do you get from participants about what’s missing or not working for them?"
Vision for Improvement Ideal State: "If you could solve these issues, what would an ideal training session or learning program look like?" "What would success look like in terms of engagement and feedback?" Alignment with Goals: "How would solving these challenges align with your team’s goals or the organization’s objectives?" "What priorities or initiatives would become easier to achieve with better engagement and feedback?" Readiness for Change: "What’s stopping you from addressing these challenges today?" "How open are you to exploring new tools or strategies to improve these areas?"

Prospect Research / Call Prep

If you have a key account try dig up a document of theirs (like a plan, investor report, or financial 10k), input it into ChatGPT and ask it what issues the account could be facing that tie to your solution. This will allow you to arrive to the call or write a cold email that includes a well researched hypothesis.
I am targeting the University of Cambridge with outbound messaging, what problems/initiatives do they suggest in this document that Mentimeter could help with?
Challenges and Opportunities: Inclusive Teaching, Learning, and Assessment: The university is working on inclusive teaching practices and curriculum enhancement to address gaps in attainment, particularly for underrepresented groups such as Black and disabled students. Engagement in Student Learning: Cambridge seeks to enhance participation and engagement through inclusive teaching methods and diverse assessment modes. Feedback and Assessment Improvements: The university emphasizes better feedback practices, including diversifying assessment methods and aligning learning outcomes with assessments. Mental Health and Wellbeing: Addressing mental health and its impact on academic performance, the university aims to create a supportive learning environment. Reducing Attainment Gaps: Focus on eliminating unexplained gaps in outcomes, such as between students of different ethnicities or those with mental health disabilities. Widening Participation and Outreach: Enhancing access and participation for underrepresented groups by using innovative teaching tools to foster inclusivity.
How Mentimeter Could Help: Real-Time Feedback Mechanisms: Use Mentimeter’s interactive features (polls, quizzes, and Q&A sessions) to provide instant feedback and foster inclusivity in lectures and workshops. Boosting Participation and Engagement: Enable active participation by allowing students to engage anonymously via their devices, addressing barriers such as fear of judgment or lack of confidence. Inclusive Learning Practices: Support curriculum enhancement projects by facilitating interactive, data-driven discussions and assessments aligned with inclusivity goals. Enhancing Mental Health Support: Provide a safe space for students to express concerns or feedback anonymously, contributing to the university’s mental health strategies. Data Collection and Insights: Enable the collection of data on participation and engagement to track progress toward reducing attainment gaps and ensuring equality.

It’s Prompting You, Not The Other Way Around

The goal of these types of exercises isn’t to take what it says and use it all.

Rather it might come up with a trigger, question, or observation that you may have missed while also speeding up your prospect research.

Control the AI, don’t let it control you.

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