Why do so many B2B deals stall? It’s often not the product, but the questions you didn’t ask. Host Peter Meyers and founder Jen Kelly explore why curiosity is a B2B leader’s most critical competitive advantage in an AI-driven world. Learn how to move beyond generic questions , mentor the “craft” of questioning in your team , and stop making the one assumption that kills deals. This episode delivers the Portage framework for asking questions that uncover true motivations and get buyers to sell themselves.
About This EpisodeIn a world increasingly driven by AI, the human skill of curiosity is what separates top performers from the rest. But how do you train this “craft”? Host Peter Meyers sits down with Jen Kelly, Founder of New Initiatives Marketing, to unpack a practical framework for asking better questions. They discuss how introversion can be a sales “secret weapon” , why you must have a non-negotiable list of questions , and the one “Future Question” that gets prospects to sell themselves.
Actionable Takeaways for Revenue Leaders
- Stop “Winging It”: Even experts forget key questions in the flow of conversation. Create a visible checklist of your non-negotiable questions (e.g., timing, budget, decision-makers) and use it on every call.
- Ask the “Obvious” Questions: Stop assuming your buyer knows what you know or has a clear decision process. A deal was lost because the host assumed the buyer knew how to move forward. Always ask what it will take to make a decision.
- “Load” Your Questions: Generic questions get generic answers. Build credibility and momentum by sharing an observation first, then asking for your prospect’s thoughts (e.g., “I’m noticing X… what do you think about that?”).
About Our GuestJennifer Kelly is the Founder of New Initiatives Marketing and a fractional CMO who partners with B2B CEOs to drive growth. She has deep experience connecting strategy with execution for global brands like Motorola and the Financial Times.
