One of my coaching clients said something on a discovery call that took serious guts: "From my selfish standpoint of wanting to sell you services, I can absolutely bring you a proposal. But I don't think you're going to be ready to buy. I'm not seeing a big enough problem for us to solve." That one candid line completely changed the dynamics of the deal. The prospect opened up, revealed the CIO's days were numbered, that he was spending $340K a year across three internal IT people, and that the CIO had been slow to respond despite the owner pushing the initiative. All roads lead to discovery—and this is what I mean by that. Every question I get from sellers about stalled deals, pricing objections, unexpected decision makers, or lack of urgency can be traced back to what we didn't learn in discovery. Most sellers stop at the surface level. They ask their scripted questions, get standard answers, and move on to the next checkbox. They never pull on the thread. This episode breaks down why digging deeper in discovery requires emotional intelligence and courage that most sellers never develop, how being candid and challenging a prospect who gives surface-level answers can completely reframe the problem you're solving—from IT issues to a fundamental business problem worth hundreds of thousands—and why the seller who gets to the real pain differentiates themselves from everyone else competing for the same deal. If you don't know the real problem you're solving, your prescription won't be credible. Keep digging.
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Welcome to The Ray J. Green Show, your destination for tips on sales, strategy, and self-mastery from an operator, not a guru.
About Ray:
→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.
→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.
→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com
→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.
→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com
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