26 minutes | Apr 12, 2019

Scaling Leadership in a Growing Tech Organization with Nick Caldwell, Chief Product Officer @ Looker

In this episode of CTO Connection, host Peter Bell sits down with Nick Caldwell, Chief Product Officer of Looker, to discuss the challenges of scaling leadership in a growing tech organization. 

Nick shares his experience moving from a 15-year career at Microsoft into the world of Bay area startups, his approach for finding and developing tech leaders, and some of the hard lessons he learned early in his management career. 

  • [00:53] Fundamental challenge of scaling leadership in pace with the business
  • [01:33] Nick’s career journey from Microsoft to Reddit to Looker
  • [04:00] Thinking about career progression and training in a growing business
  • [06:26] Balancing priorities of product delivery and people management
  • [09:34] What resources to provide managers for their career development
  • [11:09] The MBA experience as a ‘forcing function’ for exiting your comfort zone
  • [13:06] Is this an engineering manager or is it a replicant?
  • [15:13] Different traits desired from an engineering manager versus director
  • [17:07] Cringeworthy lessons from early days in management
  • [21:25] View of opportunities in the Bay area and tapping talent across the country
  • [23:51] What Nick gets out of attending the CTO Summits

You can hear more at The 2019 Chicago CTO Summit, coming up May 1, 2019, where Nick Caldwell will be presenting his talk - Ignite the Fire: How Managers Can Spark New Leaders.

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Podcast episode production by Dante32.

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