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Outbound Squad

ChatGPT and reducing buyer friction & bias with Kyle Asay

Tue Jun 06 2023

The Use of Chat GPT in Sales

  • Kyle Assey, regional vice president of acquisition at MongoDB, shares his experience using chat GPT to build a persona matrix in less than five minutes.
  • The speaker used GPT to create a buyer persona matrix in just two minutes, which used to take two to three coaching sessions and 10 to 15 hours of work.
  • The speaker taught GPT the value propositions of MongoDB and the titles they should be selling to.
  • They then prompted GPT to identify what these titles care about, how they spend their time, what stresses them out, and how MongoDB can help them based on the value propositions.
  • The chatbot returned a table format with each persona as a row and columns for what they care about, how they spend their time, what stresses them out, and MongoDB Vive.
  • The chatbot also provided emotionally relevant first sentences, value propositions, and calls to action for four emails per persona.
  • The emails were short and easy to read at a fifth-grade reading level.
  • The advantage of using AI chatbots is that it can exponentially speed up the sales process by automating tasks that would take longer manually.

Improving Sales Calls and Reducing Friction

  • The conversation focuses on understanding buyer expectations and biases during sales calls, demos, and negotiations.
  • The podcast provides tactical tips for reducing unhealthy friction in the deal cycle and improving sales calls.
  • Using chat GPT can help reps get 80% of the way there in creating talk tracks, allowing them to focus on the incremental 10% that wins or loses deals.
  • Unnecessary friction in sales occurs when buyers are repeatedly asked for information they have already provided or when they are dragged through long discovery calls before a demo.
  • Sales strategies need to adapt based on where the buyer is at in their journey, and should focus on quickly determining if the seller can help the buyer and how.
  • Salespeople should be aware of the biases that buyers bring into sales processes and work to validate them as little as possible.
  • There is a time and place for friction in sales, but unnecessary friction should be avoided.
  • Healthy friction is when the seller guides the buyer through questions and challenges them to think bigger about their goals, even if it's uncomfortable.
  • Discovery should feel like a coaching call where the seller adds context for questions and explains why they're asking them.
  • Adding value to questions increases the buyer's desire to answer them.

Understanding Buyer Expectations and Biases

  • The podcast discusses the importance of being customer-centric in sales.
  • Understanding the buyer's point of view and biases is crucial for effective communication.
  • Salespeople have a history of being overly aggressive, dishonest, and misleading, which has led to buyers having their walls up during conversations.
  • Mentoring a discovery conversation or demo requires addressing the unspoken concerns that buyers have before they can hear the message.
  • Without understanding biases, even an excellent demo may not be retained by the buyer if their walls are up.
  • The speaker had an "aha" moment when they noticed unhealthy friction in deals due to challenging buyers without considering their perspective.

Effective Sales Presentations and Demos

  • The key to impacting buyer psychology is changing their mindset and adding context to questions.
  • Buyers often expect to be heavily interrogated and qualified in calls, but it's important to make sure they walk away with something valuable.
  • In demos and presentations, buyers are biased towards being bored and seeing the same high-level overview from competitors.
  • The seller should do the opposite of what the buyer is expecting.
  • Lead with something attention-grabbing and cut out most slides to avoid boring the buyer.
  • Use discovery slides to cover gaps in understanding, not as a product tour.
  • Label everything in the demo, including table stakes features, and differentiate from competitors by showing how your approach is better or unique.
  • Defend unique differentiators by explaining why only your company can offer it due to more resources or a different approach to the problem.
  • MongoDB has a challenger culture that emphasizes clear perspectives.

Using Customer Stories and Building Rapport

  • Sales training is often ineffective after 90 to 120 days.
  • There's a reinforcement component and playbooks that need to be implemented for effective sales training.
  • To convey a different perspective on the industry, start with the product features or solution features that are different than the competition.
  • Challenge customers to think differently about their needs and what a solution actually looks like.
  • Use customer stories as evidence to validate the differentiated solution.
  • Proof points are crucial in getting individuals motivated, enabled, and believing in the sales pitch.
  • Salespeople can use customer stories as proof points to make buyers believe in their product.
  • Many sales reps do not effectively use customer stories beyond mentioning big-name clients.
  • A good customer story evokes emotion and draws parallels between the buyer's situation and the successful outcome of a previous customer.
  • Sales reps should prioritize building their own arsenal of customer stories to convince buyers that their solution works.
  • Connecting with buyers on a human level, through humor or genuine conversation, can help build rapport and trust.
  • Sales reps should focus on connecting with the other person on a human-to-human level during calls.
  • Reps should aim to have a conversation and be curious, rather than just validating biases or asking self-serving questions.
  • It's important to find out how you can help the individual you're talking to and what their win is before trying to sell economic or business case victories.
  • Building rapport is crucial in sales, and some people may need more guidance in this area.
  • Sales leaders should model good behavior by having fun while getting things done.


  • Sales should be fun and productive at the same time.
  • Don't put unnecessary pressure on yourself, focus on what really matters.
  • If you're not having fun in your job, consider changing your environment.
  • Reframe every interaction with a buyer by thinking about their expectations and biases.
  • Add context to your questions and prove how you're different from competitors.
  • Reinforce customer stories to build trust.
  • Connect with the speaker on LinkedIn or visit for courses and resources.