26: Microsoft Insider Reveals The Biggest Leadership Mistakes with Dave Wascha

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David Wascha is a seasoned product and tech leader with experience at Microsoft, MOO, Travelex and Zoopla.



In this episode, you're going to learn when to combine product and tech leadership roles and when not to, why the distinction between tech-enabled and deep tech businesses matters for leadership structure, how to avoid tension and misalignment between product and tech teams, the importance of representing and advocating for all functions as a leader, and practical strategies for new CTOs to build trust and effectively lead cross-functional teams.

Timestamps:

[08:23] Lessons learned from mistakes at Microsoft

[11:00] Transitioning to product-focused roles

[13:45] Adopting customer-focused strategies at Microsoft  

[16:10] Moving to the UK and joining MOO  

[17:32] Differences in product management between the US and UK  

[19:08] Expanding MOO’s product lines and markets  

[20:44] First combined product and tech leadership role  

[23:13] When to combine product and tech roles  

[24:35] Distinguishing between tech-enabled and deep tech businesses  

[25:31] Avoiding tension between product and tech teams  

[27:09] Challenges with re-platforming

[29:12] Handling legacy systems and updates  

[31:04] Balancing product and tech priorities  

[32:27] The importance of titles and team representation  

[34:16] Managing relationships with other executives  

[36:25] Challenges of stakeholder management  

[37:46] The cost of misalignment in leadership  

[39:12] Tips for avoiding executive misalignment  

[40:27] Building trust as a new tech leader  

To learn more from Dave, connect with him on LinkedIn.

Resources Mentioned:

MOO | Website

Photobox | Website

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.