Why Do Founders Keep Losing Deals, Even When They Have Great Products with Stephen Steers

In this episode of Leaders of the WoT, Host Steve Miksta sits down with Stephen Steers, President of Steers Consulting Group, program facilitator and trainer at Mindracer Consulting, mentor at TinySeed, and author of Superpower Storytelling, to discuss sales strategy, context, storytelling, and how organizations can build trust through clearer messaging. They cover Stephen’s move from construction into sales, the gaps he saw in startup sales training, his Context Selling methodology, and how AI raises the need for better human intent and stronger context. Stephen shares how early experiences selling ice pops, T-shirts, and furniture shaped his view of business before a near-miss accident in construction pushed him toward entrepreneurship. He explains why sales teams need training, shared context, measurable outcomes, and authentic founder stories, while also connecting his consulting work to lessons from standup comedy, iteration, and accountability. ## **Key Takeaways** - Strong sales systems need clear training and context, not just a list of prospects and a request to book meetings. - Buyers respond to outcomes and stakes such as revenue, savings, efficiency, or risk reduction more than product features. - Founders and leaders can build trust by sharing the real mission and human story behind the business. - A reverse sales demo helps teams establish current reality before choosing sales coaching, consulting, or training. - AI can speed up research, summaries, proposals, and iteration, but people still need experience to judge outputs. - Human intent drives AI value; better context and deliberate execution improve each next iteration. ## **Episode Timestamps** \[00:00] - Trailer \[01:45] - Stephen’s sales origin story in Jamaica, Queens \[03:05] - Construction work on major New York projects and a near-miss accident \[05:28] - Starting as an SDR with no training and learning through cold calls \[06:20] - Working remotely and learning sales process from Scott Sambucci \[08:09] - Seeing broken sales systems through limited training and startup patterns \[09:37] - Selling outcomes instead of features and making stakes measurable \[12:05] - Clarifying Superpower Storytelling and the Context Selling methodology \[16:31] - Starting client engagements with a reverse sales demo and sales elevation roadmap \[21:23] - AI as a tool that requires experience, judgment, and context \[28:51] - Where to find Stephen’s resources, book, and LinkedIn **Disclosure**: *Portions of this episode (such as the introduction or promotional segments) use AI-generated voice narration produced under human editorial review.* Find Stephen Steers' resources on book writing, sales calls, and discovery: https://stephensteers.com ## **🔗 Connect with the Guest Stephen Steers:** 👉 LinkedIn: https://www.linkedin.com/in/stephen-steers/ ## **🔗 Connect with the Guest Companies:** 👉 Steers Consulting Group - Website: https://www.stephensteers.com/ 👉 Steers Consulting Group - LinkedIn: https://www.linkedin.com/company/steers-consulting-group/ 👉 Mindracer Consulting - Website: https://www.mindracerconsulting.com/ 👉 Mindracer Consulting - LinkedIn: https://www.linkedin.com/company/mindracernyc 👉 TinySeed - Website: https://tinyseed.com/ 👉 TinySeed - LinkedIn: https://www.linkedin.com/company/tinyseed ## 🔗**Follow the podcast:** 👉Spotify: https://open.spotify.com/show/033rjH7T2gSv9KyUs4uC4x?si=db0aed8e99f84fc8 👉Apple Podcast: https://podcasts.apple.com/us/podcast/leaders-of-the-workplace-of-tomorrow/id1896864216 👉 YouTube: https://www.youtube.com/@opptyunlimited9222 ## **🔗 Connect with the Host Steve Miksta:** 👉 LinkedIn:https://www.linkedin.com/in/stevemiksta/https://www.linkedin.com/in/stevemiksta/ ## **🔗 Connect with the Host Company, Oppty Unlimited:** 👉 LinkedIn:https://www.linkedin.com/company/opptyunlimited/https://www.linkedin.com/company/opptyunlimited/ 👉 Website:https://www.opptyunlimited.com/https://www.opptyunlimited.com/