AI Strategy Gap Between Business Leaders and Engineers Breaking Companies with Craig Heile

Why CTOs Fail in the Boardroom for Engineers to Turn Technical Work Into Strategy With Rob Seolas

In this episode of The Dark Arts of Team Optimization Podcast, hosts Kyle Johnson [https://www.linkedin.com/in/kyleclaytonjohnson/] and Franz Aliquo [https://www.linkedin.com/in/franz-aliquo/] talk with Robert Seolas [https://www.linkedin.com/in/robertseolas/], Certified Executive Team Coach at Petra Coach [https://www.linkedin.com/company/petra-coach/], Senior Advisory Consultant at Gears Sports [https://www.linkedin.com/company/gears-sports/], Founder & Advisor at Motrix and Co-Founder & Board Member at ObservePoint [https://www.linkedin.com/company/observepoint/], about the gap between technical expertise and strategic influence. The conversation explores how engineers and technical leaders can move beyond being “right” to being effective, by developing emotional intelligence, mastering storytelling, and translating technical work into business value. Robert Seolas is a seasoned entrepreneur and leadership advisor with over 20 years of experience operating in high-stakes business environments. As the co-founder of ObservePoint, he scaled the company to over $15M ARR, raised venture funding, and worked closely with enterprise clients. Rob focuses on coaching leaders, especially technical leaders on how to bridge the gap between deep technical thinking and executive-level communication. Expect To Learn: * The difference between IQ and EQ in engineering leadership * Why being technically correct can still lead to failure * How to translate technical work into strategic business impact * The role of storytelling in influencing executives and boards * Common mistakes engineers make in board meetings * How to build executive presence without faking it Timestamps: [00:00] - Teaser [01:09] - Intro & guest background [04:18] - IQ vs EQ in engineering leadership [07:36] - Translating technical work for the boardroom [10:14] - Turning technical debt into a compelling narrative [14:04] - Why storytelling is essential for leaders [17:04] - Building executive presence as an introvert [22:22] - Coaching engineers into high performers [25:54] - Common boardroom mistakes (and how to avoid them) [34:46] - Why coaching accelerates growth [35:40] - Closing Thoughts 📱 Follow the Guest Robert Seolas: 👉 LinkedIn: https://www.linkedin.com/in/robertseolas/ [https://www.linkedin.com/in/robertseolas/] 👉 Instagram: https://www.instagram.com/rseolas/ [https://www.instagram.com/rseolas/] Company LinkedIn: - Petra Coach: https://www.linkedin.com/company/petra-coach/ [https://www.linkedin.com/company/petra-coach/] - Gears Sports: https://www.linkedin.com/company/gears-sports/ [https://www.linkedin.com/company/gears-sports/] - ObservePoint: https://www.linkedin.com/company/observepoint/ [https://www.linkedin.com/company/observepoint/] Company Website: - Petra Coach: https://petracoach.com/ [https://petracoach.com/] - Gears Sports: https://www.gearssports.com/ [https://www.gearssports.com/] - ObservePoint: https://www.observepoint.com/ [https://www.observepoint.com/] Company Instagram: - Petra Coach: https://www.instagram.com/petra_coach/ [https://www.instagram.com/petra_coach/] - Gears Sports: https://www.instagram.com/gears.sports/ [https://www.instagram.com/gears.sports/] - ObservePoint: https://www.instagram.com/observepoint [https://www.instagram.com/observepoint] 📱 Follow the Hosts Kyle Johnson and Franz Aliquo: 👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/ [https://www.linkedin.com/in/kyleclaytonjohnson/] 👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/ [https://www.linkedin.com/in/franz-aliquo/] 📱 Follow Holonic: 👉 Website: https://www.becomeholonic.com/ [https://www.becomeholonic.com/] 👉 LinkedIn: https://www.linkedin.com/company/becomeholonic/ [https://www.linkedin.com/company/becomeholonic/]

How Engineering Teams Fail Without Trust, Leadership and Psychological Safety with Tom Holt

In this episode of The Dark Arts of Team Optimization Podcast, hosts Kyle Johnson [https://www.linkedin.com/in/kyleclaytonjohnson/] and Franz Aliquo [https://www.linkedin.com/in/franz-aliquo/] talk with Tom Holt [https://www.linkedin.com/in/tomholtstl/], Principal Consultant & Founder of OtterWorks Consulting [https://www.linkedin.com/company/otterworks-consulting/], Adjunct Instructor of Data Analytics & Python at Savvy Coders [https://www.linkedin.com/school/savvy-coders/] and Sr. Delivery Consultant at Accelerance [https://www.linkedin.com/company/accelerance-inc/], to explore what it really takes to build high-performing engineering teams across startups and distributed environments. Tom brings over 40 years of software experience, including two decades leading distributed teams across the US, China, and Latin America. The conversation moves from hands-on coding to leadership philosophy, focusing on how engineers become multipliers, why psychological safety matters, and how trust shapes everything from estimation to execution. At its core, this episode is about shifting from building software to building the conditions for people to build software well. EXPECT TO LEARN - Why engineering leadership is about multiplying team impact, not just managing work - How to help engineers connect their day-to-day coding to real user outcomes - What psychological safety looks like in high-performing engineering teams - Why bad news needs to travel early, especially around estimates and deadlines - How team structure, communication, and process need to evolve as organizations scale TIMESTAMPS [00:00:00] – Teaser [00:01:09] – Introduction to Tom Holt [00:02:20] – From coding to leadership [00:05:47] – Helping engineers “look up” from code [00:10:53] – Building environments that sustain motivation [00:15:55] – Why bad news must travel fast [00:19:42] – Death march projects and unrealistic deadlines [00:20:02] – Estimation, ownership, and sustainable pace [00:28:42] – Scaling teams and what breaks first [00:31:23] – Right-sizing process vs. over-process [00:39:34] – Leading distributed teams globally [00:42:09] – Body, mind, and performance in knowledge work [00:48:17] – Closing thoughts 📱 Follow the Guest Tom Holt: 👉 LinkedIn: https://www.linkedin.com/in/tomholtstl/ [https://www.linkedin.com/in/tomholtstl/] Company LinkedIn: - OtterWorks Consulting: https://www.linkedin.com/company/otterworks-consulting/ [https://www.linkedin.com/company/otterworks-consulting/] - Savvy Coders: https://www.linkedin.com/school/savvy-coders/ [https://www.linkedin.com/school/savvy-coders/] - Accelerance: https://www.linkedin.com/company/accelerance-inc/ [https://www.linkedin.com/company/accelerance-inc/] Company Website: - OtterWorks Consulting: https://www.otterworksllc.com/ [https://www.otterworksllc.com/] - Savvy Coders: https://savvycoders.com/ [https://savvycoders.com/] - Accelerance: https://www.accelerance.com/ [https://www.accelerance.com/] Company Instagram: - Savvy Coders: https://www.instagram.com/savvy_coders [https://www.instagram.com/savvy_coders] - Accelerance: https://www.instagram.com/accelerance/?hl=en [https://www.instagram.com/accelerance/?hl=en] 📱 Follow the Hosts Kyle Johnson and Franz Aliquo: 👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/ [https://www.linkedin.com/in/kyleclaytonjohnson/] 👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/ [https://www.linkedin.com/in/franz-aliquo/] 📱 Follow Holonic: 👉 Website: https://www.becomeholonic.com/ [https://www.becomeholonic.com/] 👉 LinkedIn: https://www.linkedin.com/company/becomeholonic/ [https://www.linkedin.com/company/becomeholonic/]

AI Strategy Gap Between Business Leaders and Engineers Breaking Companies with Craig Heile

In this episode of The Dark Arts of Team Optimization Podcast, hosts Kyle Johnson [https://www.linkedin.com/in/kyleclaytonjohnson/] and Franz Aliquo [https://www.linkedin.com/in/franz-aliquo/] talk with Craig Heile [https://www.linkedin.com/in/craig-heile/], Head of GTM AI Solutions at Ascend AI Labs [https://www.linkedin.com/company/ascendailabs/], also the Co-founder and Advisor at Launch GTM [https://www.linkedin.com/company/launchgtm/]. With AI technology advancing at an unprecedented pace, there is often a significant gap between the expectations of business leaders and the technical capabilities of engineers. Craig shares his expertise on how to bridge this gap, ensuring that AI can be effectively integrated into business operations to create lasting value. From understanding AI’s transformative potential to addressing fears among engineers about job displacement, this conversation covers the strategic and operational challenges companies face as they adapt to a rapidly changing technological landscape. Craig also discusses how engineers can evolve into internal advisors, working alongside business teams to optimize workflows and drive innovation. Expect to Learn: - The challenges business owners face when communicating AI needs to engineers. - How to align business strategies with AI integration. - Insights into the evolving role of engineers and AI in organizations. - Practical steps for creating sustainable AI strategies in business. TIMESTAMPS: [00:00] - Teaser [01:29] - Introduction [03:00] - The Gap Between Business Owners and Engineers [07:10] - The AI Knowledge Gap [10:55] - Identifying Early Signs of AI Disconnect [13:30] - Managing Shadow AI in Organizations [15:26] - Engineers’ Fear of AI Integration [18:06] - The Changing Role of Middle Management [19:55] - Building a Durable AI Strategy [24:11] - Preparing for AI Transitions: What’s Next? [35:53] - Conclusion 📱 Follow the Guest Craig Heile: 👉 LinkedIn: https://www.linkedin.com/in/craig-heile/ [https://www.linkedin.com/in/craig-heile/] Company LinkedIn: - Ascend AI Labs: https://www.linkedin.com/company/ascendailabs/ [https://www.linkedin.com/company/ascendailabs/] - Launch GTM: https://www.linkedin.com/company/launchgtm/ [https://www.linkedin.com/company/launchgtm/] Company Website: - Ascend AI Labs: https://ascendlabs.ai/ [https://ascendlabs.ai/] - Launch GTM: https://launchgtm.com/ [https://launchgtm.com/] Company Instagram: - Ascend AI Labs: https://www.instagram.com/ascendlabs.ai [https://www.instagram.com/ascendlabs.ai] 📱 Follow the Hosts Kyle Johnson and Franz Aliquo: 👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/ [https://www.linkedin.com/in/kyleclaytonjohnson/] 👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/ [https://www.linkedin.com/in/franz-aliquo/] 📱 Follow Holonic: 👉 Website: https://www.becomeholonic.com/ [https://www.becomeholonic.com/] 👉 LinkedIn: https://www.linkedin.com/company/becomeholonic/ [https://www.linkedin.com/company/becomeholonic/]

AI Reliability in Legal Tech for Law Firms to Build Trustworthy Automation with Adam Paulisick

In this episode of The Dark Arts of Team Optimization, hosts Kyle Johnson [https://www.linkedin.com/in/kyleclaytonjohnson/] and Franz Aliquo [https://www.linkedin.com/in/franz-aliquo/] talk with Adam Paulisick [https://www.linkedin.com/in/paulisick/], Chief Executive Officer at Skilly [https://www.linkedin.com/company/skillyai/], Distinguished Service Professor, Lead Instructor, and Occasional Founder of Executive Education at Carnegie Mellon University School of Computer Science [https://www.linkedin.com/school/cmuscs/]. He is also Founder and maad Scientist at maad labs [https://www.linkedin.com/company/maad-labs/], Advisor of Sales and Product at ViralMoment [https://www.linkedin.com/company/viralmoment/] and Advisor of Sales and Go-To-Market at BlastPoint [https://www.linkedin.com/company/blastpoint/]. Adam brings a wealth of knowledge from his experience in AI, product entrepreneurship, and human-computer interaction. He is currently building Skilly, a company deploying AI agents that onboard and train employees in a human-like manner. In this engaging conversation, Adam dives into the challenges and opportunities that AI brings to teams, the dynamics of acquisitions, and how leaders can thrive in the fast-changing tech landscape. Adam Paulisick is a seasoned entrepreneur, having led three companies through successful acquisitions. With a background in AI, human-computer interaction, and entrepreneurship, Adam has also taught at Carnegie Mellon for over a decade. He’s passionate about blending technology with human interaction, and he's currently building Skilly AI agents that train and onboard employees. Adam's career has intersected various domains, from tech to psychology, providing him with a unique perspective on innovation, leadership, and team dynamics. EXPECT TO LEARN: - Insights into the effects of acquisitions on teams and the challenges of integrating human talent with AI. - How AI is reshaping job descriptions and team structures, and how curiosity and soft skills are more valuable than ever. - The importance of interdisciplinary thinking and collaboration in fostering innovation. - The role of AI in augmenting human capabilities and its impact on employee productivity and decision-making. - How personal routine and self-awareness play a crucial role in maintaining balance while navigating the entrepreneurial journey. EPISODE BREAKDOWN WITH TIMESTAMPS: [00:00:00] – Teaser [00:01:24] – Adam’s experience with acquisitions. [00:05:28] – Distribution vs. differentiation. [00:07:19] – Integrating AI with humans. [00:11:12] – Proactive change management. [00:13:32] – Skilly’s “AI Fridays.” [00:21:05] – Job descriptions evolve with AI. [00:26:12] – Curiosity and soft skills matter. [00:30:08] – Empathy + AI = success. [00:41:02] – Skilly’s AI agents. [00:52:07] – AI enhances customer journeys. [00:52:46] – Adam’s routine and avoiding burnout. [00:58:25] – Conclusion 📱 Follow Guest Adam Paulisick: 👉LinkedIn: https://www.linkedin.com/in/paulisick/ [https://www.linkedin.com/in/paulisick/] 👉Instagram: https://www.instagram.com/paulisick/ [https://www.instagram.com/paulisick/] 👉Company LinkedIn: - Skilly: https://www.linkedin.com/company/skillyai/ [https://www.linkedin.com/company/skillyai/] - Carnegie Mellon University School of Computer Science: https://www.linkedin.com/school/cmuscs/ [https://www.linkedin.com/school/cmuscs/] - maad labs: https://www.linkedin.com/company/maad-labs/ [https://www.linkedin.com/company/maad-labs/] - ViralMoment: https://www.linkedin.com/company/viralmoment/ [https://www.linkedin.com/company/viralmoment/] - BlastPoint: https://www.linkedin.com/company/blastpoint/ [https://www.linkedin.com/company/blastpoint/] 👉Company Website: - Skilly: https://www.skillyai.com/ [https://www.skillyai.com/] - Carnegie Mellon University School of Computer Science: https://www.scs.cmu.edu/ [https://www.scs.cmu.edu/] - maad labs: https://maadlabs.io/ [https://maadlabs.io/] - ViralMoment: https://viralmoment.com/ [https://viralmoment.com/] - BlastPoint: http://www.blastpoint.com/ [http://www.blastpoint.com/] 👉Company Instagram: - Skilly: https://www.instagram.com/skillyai/ [https://www.instagram.com/skillyai/] - Carnegie Mellon University School of Computer Science: https://www.instagram.com/scsatcmu/ [https://www.instagram.com/scsatcmu/] - maad labs: https://www.instagram.com/maadlabs/ [https://www.instagram.com/maadlabs/] - ViralMoment: https://www.instagram.com/getviralmoment/ [https://www.instagram.com/getviralmoment/] 📱 Follow the Hosts Kyle Johnson and Franz Aliquo: 👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/ [https://www.linkedin.com/in/kyleclaytonjohnson/] 👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/ [https://www.linkedin.com/in/franz-aliquo/] 📱 Follow Holonic: 👉 Website: https://www.becomeholonic.com/ [https://www.becomeholonic.com/] 👉 LinkedIn: https://www.linkedin.com/company/becomeholonic/ [https://www.linkedin.com/company/becomeholonic/]

How to Build Reliable AI Systems: When Hallucinations Are Inevitable with Justin Waltrip

In this episode of The Dark Arts of Team Optimization, hosts Kyle Johnson [https://www.linkedin.com/in/kyleclaytonjohnson/] and Franz Aliquo [https://www.linkedin.com/in/franz-aliquo/] talk with Justin Waltrip [https://www.linkedin.com/in/justin-waltrip-53082b17b/], Co-founder & Data Scientist at SQUARY AI [https://www.linkedin.com/company/squary-ai/]. Justin has been at the forefront of AI development since 2015, well before the current AI boom took hold. With a deep background in data science and machine learning, he has spent years building AI solutions that tackle complex problems in various industries. Justin focuses on leveraging AI to streamline and enhance the legal industry’s often cumbersome document review processes. Under his leadership, SQUARY AI is developing tools that help law firms and legal departments improve productivity, reduce time spent on manual tasks, and ensure more reliable, efficient outcomes. In this episode, Justin shares his journey, the challenges of building AI for legal tech, and how he and his team are rethinking how technology can support legal professionals. Expect to Learn: - Insights into the challenges of building AI for legal tech - The importance of testing in AI development - How AI tools can reduce tedious work for lawyers while maintaining high standards of accuracy and reliability - The evolving role of AI in the legal field and potential for future automation Timestamps: [00:00] - Teaser [01:13] - Introducing Justin Waltrip [02:15] - AI Engineering Challenges and Overlooked Disciplines [04:05] - Managing AI Unpredictability and Reliability [06:24] - Hallucinations in AI: Can They Be Eliminated? [08:42] - SQUARY AI's Pivot into Legal Tech [14:33] - Engineering for 100% Reliability [17:40] - Pushback from the Legal Industry on Efficiency Tools [23:12] - Managing a Small Startup Team [25:19] - Hiring for Culture and Vision Fit at SQUARY AI [30:58] - Navigating Investor Expectations and Growth [33:48] - Future Plans for SQUARY AI'S Product Development [38:19] - How to Learn More About SQUARY AI 📱 Follow Guest Justin Waltrip: 👉LinkedIn: https://www.linkedin.com/in/justin-waltrip-53082b17b/ [https://www.linkedin.com/in/justin-waltrip-53082b17b/] 👉Instagram: https://www.instagram.com/justin.waltrip8408? [https://www.instagram.com/justin.waltrip8408?igsh=MTVoMnJvcTZwaDM0bg==] 👉Company LinkedIn: https://www.linkedin.com/company/squary-ai/ [https://www.linkedin.com/company/squary-ai/] 👉Company Website: https://www.squary.ai/ [https://www.squary.ai/] 👉Company X: https://x.com/CognistX [https://x.com/CognistX] 📱 Follow the Hosts Kyle Johnson and Franz Aliquo: 👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/ [https://www.linkedin.com/in/kyleclaytonjohnson/] 👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/ [https://www.linkedin.com/in/franz-aliquo/] 📱 Follow Holonic: 👉 Website: https://www.becomeholonic.com/ [https://www.becomeholonic.com/] 👉 LinkedIn: https://www.linkedin.com/company/becomeholonic/ [https://www.linkedin.com/company/becomeholonic/]