Discovery conversations are where B2B engagements are won or lost. Done well, discovery is a collaborative diagnostic process where you and the prospect build the solution together—so the proposal becomes simply a review of what you’ve already agreed to. Done poorly, it becomes a free consulting session that goes nowhere.
Coaches have natural strengths for discovery: the ability to listen deeply, ask incisive questions and create trust quickly. But B2B discovery requires strategic discipline. You need to probe for business pain and consequences, address budget and timeline early, and assess whether this opportunity is actually viable—all while staying relational and collaborative.
This session teaches the art and discipline of B2B discovery conversations. Attendees will learn how to use their coaching skills strategically, what questions to ask to properly qualify an opportunity, and how to lead the conversation while building the solution together with the prospect.
Learning objectives
By the end of this session, participants will be able to:
- Use coaching skills strategically in discovery by asking powerful questions focused on business pain, stakeholder impact and organizational consequences rather than individual transformation
- Structure discovery with commercial discipline by probing three critical areas: current pain and cost, consequences of inaction, and budget/timeline/decision-making realities
- Lead collaborative diagnosis that builds the solution with the prospect while maintaining expertise and avoiding free consulting
- Assess opportunity viability by distinguishing between prospects who are engaged in conversation and prospects who are actually qualified to close
Meet the Host
Mary Dombrowski
Mary is the founder of Strategic Inflection Advisory, where she is a strategic advisor on creating business development systems, consultative sales conversations and pricing strategy to boutique consulting, coaching and advisory firms. With over 20 years of marketing and business development experience at large organizations including Time Inc. and Condé Nast, as well as smaller founder-led firms, she specializes in helping professional services founders build systematic approaches to business development, pricing and client acquisition.
Mary’s work focuses on helping founders move from founder-dependent revenue to scalable business systems. She has presented workshops at business incubators including 1871 in Chicago and currently speaks on panels with organizations including XPX (Exit Planning Exchange) on topics related to revenue growth, outcome based pricing and business development strategy.