In episode 286 of the IDEAS+LEADERS Podcast, I’m joined by Thanos Diacakis, Software Delivery Coach, Fractional CTO, and business growth expert. With more than 25 years in software development, Thanos has worked with startups and global tech companies like Uber, where he led the integration of the JUMP Bikes acquisition, scaling the platform to 45,000 vehicles and over 2 million monthly trips.

We explore why so many organizations struggle to scale despite strong teams, and how misalignment between business leaders and engineering creates hidden bottlenecks, technical debt, and burnout. Thanos shares how leaders can communicate more clearly with tech teams to increase speed, quality, and outcomes.

In this episode, we discuss:

• How to align business goals with engineering reality

• Why “doing Agile” often fails to deliver results

• The hidden cost of technical debt and quick fixes

• How leaders can spot and fix real bottlenecks in delivery

Tune in for a grounded, practical conversation on scaling technology teams without chaos.

You can connect with Thanos here: Thanos Diacakis' infrequently updated page

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