CTO Podcast – Insights & Strategies for Chief Technology Officers Navigating the C-Suite while Balancing Technical Strategy Etienne de Bruin (7CTOs)

Join Etienne in this episode as he interviews Allan Stewart, the lead engineer at SynkedUP, a groundbreaking startup focused on bridging the technological gaps in today’s digital world. Together, they unravel the threads of storytelling in The Lord of the Rings, explore the implications of Conway’s Law on organizational design and software development, and discuss coding challenges that leave even seasoned developers hesitant.

Allan touches upon his lifelong journey with Tolkien's work, showcasing how the tales have influenced his personal and professional life, and his unique perspective illuminates the profound impact of literature on technological creativity and problem-solving. The conversation also dissects Conway's Law and its profound influence on the architecture of software systems, mirroring the communication patterns within organizations.

Etienne and Allan also delve into a common dilemma in the tech world: the fear of modifying legacy code. Allan recounts tales from the trenches, revealing strategies to address the untouchable parts of a codebase that developers dread to alter. Their discussion serves as a critical reminder of the importance of fostering a culture that encourages innovation, transparency, and resilience in the face of technological challenges.

Allan’s insights offer a fresh perspective on the relationship between team dynamics and code quality, shedding light on how team structure can shape the final product, for better or worse. Whether you're a fan of Middle Earth, an aspiring engineer, and/or a seasoned CTO, this episode promises a treasure trove of wisdom and intriguing discussions that run the gamut of software development and beyond.




Time Stamps:

[1:43] - Allan discusses his love for The Lord of the Rings.

[3:45] - Allan explores Middle-earth's history through Christopher Tolkien's posthumous works, finding it rewarding.

[6:34] - Allan's reading habits are sporadic, recently focusing on the fifth volume of The History of Middle Earth.

[8:45] - Conway's Law suggests team dynamics shape software, stressing the importance of communication in development.

[10:58] - Software mirrors its development context, with team practices and incentives affecting the codebase's quality.

[12:22] - Etienne argues that hasty incentives can lead to poor coding practices and duplicated work to meet deadlines.

[14:07] - Financial motives of offshore teams often overlook comprehensive codebase care, highlighting the importance of aligning team incentives with quality goals.

[16:58] - Allan values trust in software audits and reiterates the importance of aligning developer incentives with principal goals.

[18:44] - Allan highlights how attitudes towards automated testing mirror Conway's Law, impacting developer confidence and code quality.

[20:50] - Allan critiques the dynamics between QA and developers, leading to defensive coding and diminished collaboration.

[24:39] - Understanding software complexity is challenging; relying on trusted opinions and monitoring development are important.

[27:12] - Etienne observes prolonged development times, suggesting collaborative code reading sessions for improved quality.

[29:14] - Allan emphasizes collaboration through pair and mob programming, involving all teams for active participation.

[31:42] - Hear why Allan prioritizes principles such as collaboration and automated testing over vague "best practices."

[33:46] - In large developer meetings, Allan points out, some may not speak up due to overcrowding, hindering valuable input.

[35:50] - Effective collaboration doesn't require everyone to do the same tasks simultaneously but involves coordination and acknowledgment of specialties.

[39:04] - Addressing fear and context changes requires transparency, incentives, and adaptable code structures.

[42:02] - Etienne shares how his hackathon competition helped alleviate his developers’ fears around touching code.




We have 200+ CTOs in peer gro

Jennifer shares insights into her unique lifestyle as a technologist and baroness of Texas, where she navigates the balance between rural tranquility and technological challenges.

Joining Etienne this week on the podcast is Sean Nam, the CTO of Ivy Energy. Etienne engages in a multifaceted conversation with Sean, and they touch upon the intricacies of supporting founders during fundraising to reflections on technology giants like Apple and Uber.

Sean provides insights into IV Energy's mission to revolutionize shared energy usage through solar platforms, shedding light on the challenges and innovations in the field, and as the conversation delves deeper, Sean and Etienne explore the dynamics of team management, fundraising endeavors, and the evolving role of a CTO. Sean's reflections on American democracy, viewed through the lens of a South African and a Korean immigrant, also add a thought-provoking layer to the discussion.

Sean also offers a candid exploration of the challenges of participating in a democracy amidst distractions and complexities, resonating with both disappointment and a call for collective action. Tune in for a compelling dialogue that blends technical expertise with societal insights, offering a glimpse into the complexities of modern leadership and civic engagement.




Time Stamps:

[1:25] - What are Sean’s thoughts on Apple Vision Pro?

[4:35] - Sean describes Ivy Energy’s mission.

[7:30] - Learn about Sean’s team dynamics.

[9:21] - Sean finds David Farley's insights refreshing, bridging software engineering with other technical disciplines.

[10:42] - Learn how Sean's journey to leadership at Ivy Energy stemmed from seizing unexpected opportunities and challenges.

[12:16] - Sean reflects on some of the lessons that he has been learning.

[13:24] - Reflecting on venture capital dynamics through media like "Super Pumped" informs Sean's approach.

[16:38] - Sean argues that effective collaboration between visionaries and their teams, like Steve Jobs with engineers, shapes success.

[18:04] - Sean touches upon the significance of risk assessment.

[20:01] - Balancing sales and marketing with product development ensures delivering on the promised vision.

[22:51] - Transitioning from software engineer to CTO, Sean has honed communication skills and adapted to delayed feedback in leadership.

[24:49] - Sean explains how giving feedback in a PR setting versus individually has a significant impact on individuals.

[26:01] - Sean recently saw a news story involving a lack of attention leading to bribery in West Virginia.

[28:30] - Etienne discusses how participating in democracy is challenging due to complexities; simpler systems are desired for all.

[30:02] - The flaw in the US voting system lies in its historical complexity and lack of modernization.

[33:10] - Sean asserts that politics becoming a show has led to exhaustion and disengagement and that systemic change requires collective effort.

[36:02] - Sean feels that restricting information and education perpetuates autocracy.




Resources and Links Mentioned:

David Farley - Modern Software Engineering: Doing What Works to Build Better Software Faster

We have 200+ CTOs in peer groups: Quick Testimonials Video

Contact Etienne: Website / YouTube / LinkedIn / X / Instagram / The CTO Podcast Website

Contact Sean: LinkedIn

Schedule a meeting with Etienne on Calendly

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Etienne is thrilled to sit down with Tracie Hlavka, former CTO of Flyhomes, to discuss the tumultuous journey of rapid scale and the poignant process of winding down a company. Tracie reflects on her experience navigating the job market amidst layoffs and shifting funding landscapes, shedding light on the challenges of finding the right fit in a tough market.

Tracie and Etienne also delve into the complexities of managing a tech team during rapid growth and downsizing, highlighting the delicate balance between building scalable systems and adapting to changing circumstances. Tracie shares insights into the intricacies of hiring and team organization, emphasizing the importance of aligning technology with business objectives and fostering a culture of resilience.

The conversation also touches on the emotional toll of layoffs and the significance of empathetic leadership in times of transition. As Tracie explores her journey of self-discovery and career exploration, she also reflects on the lessons learned from the book Designing Your Life and the value of embracing possibility amidst uncertainty. Join Etienne and Tracie as they navigate the highs and lows of the tech industry, offering valuable insights for CTOs and aspiring leaders alike.




Time Stamps:

[1:59] - Tracie finds the current market tough, especially for series B/C startups and consumer-facing ventures.

[3:44] - Tracie sees a challenging cycle in rapid scaling, grappling with evolving processes and clinging to past achievements.

[6:21] - Hear how Tracie finds rapid scaling exhilarating, despite its challenges, embracing the process of hiring and growth.

[8:21] - Tracie relishes the challenge of building systems and teams to support rapid company growth.

[10:59] - For each hire, Tracie conducts around ten interviews, with approximately 100 applicants for consideration.

[13:30] - Tracie argues that hiring can initially be inefficient, requiring time for new hires to integrate and become productive.

[16:57] - Tracie advocates for yearly adjustments in team structure to match business needs, balancing deep expertise with innovation.

[20:02] - Managing code boundaries and team dynamics becomes challenging when splitting teams to match organizational growth.

[23:40] - Tracie points out that educating about realistic technology expectations involves managing the desire to scale prototypes instantly.

[24:44] - Tracie argues for the importance of handling layoffs with empathy.

[26:24] - Adapting to rapid changes requires adjusting systems.

[29:35] - Tracie shares that she found solace in taking time off and exploring the book Designing Your Life to navigate career choices.

[30:49] - Exploring alternative scenarios and milestones through exercises fosters openness to new possibilities and insights.




Resources and Links Mentioned:

Bill Burnett & Dave Evans - Designing Your Life: How to Build a Well-Lived, Joyful Life

We have 200+ CTOs in peer groups: Quick Testimonials Video

Contact Etienne: Website / YouTube / LinkedIn / X / Instagram / The CTO Podcast Website

Schedule a meeting with Etienne on Calendly

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Etienne is very happy to be sitting down with Matt Van Itallie, founder of Sema, a company that develops software to help engineering leaders manage AI in software development. As they delve into their shared experiences of learning to code on vintage machines, they explore Matt's journey from studying philosophy to founding Sema.

The conversation takes a philosophical turn, discussing pragmatism in decision-making and the importance of clarifying outcomes, and Etienne and Matt also dissect the complexities of C-suite dynamics and the challenges of resolving conflicts within leadership teams. Matt shares insights on the significance of developer retention and the metrics that matter most on a CTO dashboard, and the discussion touches on the art of listening, empathy, and the power of effective communication within organizations.

As they plan a session on pivot tables, Matt also emphasizes the value of community, highlighting the support and inspiration found in groups like 7CTOs. Tune in for a thought-provoking conversation on leadership, problem-solving, and the human side of technology!




Time Stamps:

[2:09] - Learn how Matt’s academic journey expanded with a focus on law's evolution and late 19th-century pragmatism.

[4:56] - Matt argues that our brains seek to make sense of things.

[7:24] - Etienne reflects on navigating conflicting perspectives among C-Suite members, highlighting the challenge of coherence.

[10:23] - Focus on critical outcomes, not just outputs.

[12:25] - Matt emphasizes fostering understanding through clarifying outcomes and promoting inclusive dialogue and contributions.

[15:58] - Matt suggests identifying underlying causes of communication issues and resolving conflicts promptly for organizational success.

[16:40] - Hear how Matt prioritizes organizational goals over personal interests, advocating for a values-based decision-making approach.

[18:46] - Matt explains how Sema goes about making decisions pragmatically.

[21:07] - The opposite of pragmatism might be scrutiny, but pragmatism focuses on moving forward effectively.

[24:45] - Mastering pivot tables symbolizes problem-solving prowess, transforming decision-making with raw data access.

[28:03] - Discover how pivotal moments led to Sema's inception in 2015, spurred by tech challenges and leadership insights.

[30:50] - Matt explains how, inspired by a Bloomberg article, he delved into tech research in 2015, seeking innovation.

[32:25] - Matt pursued tech research, seeking licenses from 250 professors; one acceptance birthed Sema.

[34:40] - Matt discusses developer retention, a pivotal metric, and how it holds 25 points on Sema's 100-point scale.

[37:40] - Etienne shares a story in which a key developer's silence flagged a possible departure, highlighting the important role of product vision clarity.

[39:16] - Matt asserts that effective people management discerns subtle shifts in participation, vital for organizational success and cohesion.

[41:49] - Matt encourages us to prioritize listening qualitatively to one's team before relying solely on data-driven tools.

[43:44] - Etienne agrees, adding that mastering listening is as complex as it is crucial, often underestimated despite its profound impact.




We have 200+ CTOs in peer groups: Quick Testimonials Video

Contact Etienne: Website / YouTube / LinkedIn / X / Instagram / The CTO Podcast Website

Contact Matt: Sema Website / LinkedIn / X

Schedule a meeting with Etienne on Calendly

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Etienne sits down with Krijn van der Raadt, a seasoned CTO with a rich history of steering both startups and established tech giants toward successful exits. Krijn, now a fractional CTO and advisor to startups, shares insights gained and collaborative problem-solving experiences with fellow CTOs. They explore the challenges of transitioning from a technical role to a leadership position and the common pitfalls faced by startups when scaling their engineering teams.

Dive into the conversation as Krijn reflects on his journey from Great Call to Health App Folio, discussing leadership styles, organizational structures, and the Goldilocks rate of growth. The episode unfolds with a fascinating discussion on managing budgets in different scenarios, exploring the nuances of constrained vs. surplus spending and the impact on team motivation.

Krijn also sheds light on his passion for preparedness and frugality, drawing parallels between his Dutch background and his approach to leadership. Etienne and Krijn delve into the significance of scarcity as an inspiration for quality work, touching on the dynamics of team motivation and purpose.

The episode takes a turn into the realm of simulations and imagination, where Krijn recommends Jane McGonigal's Imaginable. Discover how the lessons from simulations can transform leadership approaches, enhance team collaboration, and prepare for unforeseen challenges.

Krijn wraps up with insights into tools like ChatGPT and Jupyter notebooks, offering practical tips for effective utilization. Tune in to explore the multifaceted world of leadership, technology, and the human element with Krijn and Etienne in this engaging and insightful episode.




Time Stamps:

[2:57] - Krijn highlights the challenges of evolving from a founding engineer to an effective CTO in startups.

[4:33] - Etienne and Krijn discuss the fascination of transitioning from a technical role to a leadership position.

[6:46] - Krijn shares his experiences with constrained spending and the motivation it provides for quality work.

[9:11] - The discussion turns to the impact of excessive funds on team motivation and product success.

[11:37] - Krijn relates his passion for preparedness, fiscal responsibility, and strategic planning.

[13:19] - Krijn reflects on Jane McGonigal's Imaginable and its influence on leadership and team collaboration.

[17:39] - Etienne delves into the importance of bringing stakeholders along through scenario painting.

[20:53] - Listen as Krijn highlights the value of ChatGPT and AI tools in enhancing productivity and problem-solving.

[23:19] - Krijn advocates for the widespread adoption of tools like Copilot and ChatGPT for increased productivity.

[26:23] - Krijn explores the role of a Python library.

[29:05] - Krijn shares his concern about the prevalence of poor leadership and the need for sincerity and humility.

[30:49] - Etienne reflects on the challenges of leadership and the importance of staying connected to the purpose.

[33:51] - The discussion touches on the disconnect between leadership positions and the tactical understanding required.

[36:09] - Etienne discusses the importance of recognizing and reconciling different perspectives within the organization.

[38:35] - Krijn emphasizes the significance of leaders inspiring trust through sincerity, humility, and a lack of ego.




Resources and Links Mentioned:

leadcto.com

Jane McGonigal - Imaginable

We have 200+ CTOs in peer groups: Quick Testimonials Video

Contact Etienne: Website / YouTube / LinkedIn / X / Instagram / The CTO Podcast Website

Schedule a meeting with Etienne on Calendly

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.