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CTO Leadership: Navigating Startup Realities and Inspiring Teams with Krijn Van der Raadt

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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.

Krijn van der Raadt
Krijn van der RaadtProduct Developer, CTO Mentor / Coach, Startup Advisor
From software engineer to Product- and Engineering executive, I’ve spearheaded ambitious projects at startups like AppFolio, MindTouch, and GreatCall, which we transformed from a single-product venture into a multi-product powerhouse. My expertise in lean product strategies and my leadership roles at various stage startups and scaleups position me as a trusted figure in product development and leadership.
Throughout my 20-year career, I’ve passionately coached emerging product and engineering talent, both inside and outside the companies I’ve served. My commitment to fostering a culture of growth and support has been a cornerstone of my coaching philosophy, ensuring that every individual I guide reaches their fullest potential.
I’ve worked closely with pre-revenue and VC-funded startups, helping them get off the ground and overcome challenges on their way to success. My guidance has often centered on simplifying their approach, understanding their customers better, and instilling the confidence they need to take decisive action. Through this hands-on support, they have successfully secured funding and refined their vision.

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.

Episode Resources:

Jane McGonigal – Imaginable

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