BAM-OSBAM-OSBAM-OSCareer timeline with key transitions and pivots
Lesser-known facts most interviewers miss
Contradictions or tensions in the public narrative (good interview pressure points)
Recent news, projects, or developments
Connections to broader trends or movements
Potential controversial or sensitive topics to be aware of
If you want, I can add a “prep pack” section next: 10 lightning-round opener questions, 5 “polite traps” to get past rehearsed answers, and 8 episode title options tailored to Beyond a Million.
From the guest (intake form)
### OPENER 1. Dean, I heard that at just 16 you chose an IBM PC over a car. What was it about technology that captured your imagination so early on? 2. You co-founded Infragistics with $25,000 at age 23. Can you paint a picture of those early days and what it was like starting with Don Preuninger? ### SECTION 1: REINVENTION AND RESILIENCE 1. Moving from those beginnings, you've rebuilt products from scratch. What was the pivotal moment that made you realize this approach was necessary for Infragistics? 2. How did you navigate the internal debates when it came time to end a profitable legacy product? 3. Balancing cash flow and innovation is no easy feat. How did you manage to fund reinvention without risking the core business? 4. Can you share a story about a time when Infragistics nearly became irrelevant, and how you turned it around? ### SECTION 2: CUSTOMER INSIGHTS AND PRODUCT STRATEGY 1. Transitioning to customer influence, how have your customers shaped your strategic roadmap, especially when their needs went against internal assumptions? 2. Your claim of working with “100% of the S&P 500” is impressive. Can you clarify what that means in terms of direct customers versus users through OEMs? 3. In launching Reveal and Slingshot, what unexpected lessons did your customers teach you? 4. What signals help you determine if a new product idea is a strategic rebuild or simply a distraction? ### SECTION 3: LEADERSHIP AND CULTURE 1. Shifting to leadership, your book argues that grit alone isn't enough. What specific leadership behaviors do you believe truly change outcomes? 2. How do you foster a culture that encourages the risk-taking necessary for constant reinvention? 3. Slingshot promises alignment and productivity. How do you ensure it changes behavior rather than becoming just another app? 4. Can you share a time when your leadership approach had to drastically change to meet new challenges? ### SECTION 4: AI AND THE FUTURE OF WORK 1. Let’s explore AI. With Slingshot at the intersection of AI and work management, what trends do you see as pivotal for the future of work? 2. As the host of the AI & Data Driven Leadership podcast, what recent insight or guest perspective challenged your thinking? 3. How do you address skepticism that all-in-one platforms might be too shallow in the crowded AI tools market? 4. If you were starting Infragistics today, what platform shift signals would you monitor more closely? ### VIRAL MOMENT 1. In a world dominated by tech giants, how do you maintain the confidence to rebuild from scratch rather than follow trends? 2. What’s the most unconventional decision you’ve made that paid off against common entrepreneurial wisdom? ### CLOSER 1. Looking ahead, what are you most excited about building or achieving with Infragistics in the next few years? 2. Finally, what advice would you give to entrepreneurs aiming to scale their business beyond a million dollars?