What separates great companies from the rest isn’t just technology… it’s clarity.
In this episode of Leadership Lens, Taylor Robinson sits down with Ken Widner, EVP & CIO at Do It Best, to break down how top leaders align mission, technology, and people to drive real results.
From leading large-scale acquisitions to navigating the hype around AI, Ken shares a pragmatic approach to leadership, decision-making, and organizational change.
If you’re a founder, operator, or leader trying to scale without losing clarity, this conversation is packed with insights you can actually apply.
⏱️ Chapters:
00:00 Introduction to Ken Widner
01:52 Why purpose matters more than execution
03:09 What happens when success isn’t clearly defined
05:31 Communicating vision during acquisitions
09:40 “Coffee with Ken” and leadership accessibility
10:13 Why leadership is about people, not just tech
11:32 Ken’s unconventional path into IT
14:03 From music store to psychology mindset
15:39 Treating IT like a “dysfunctional family”
16:27 Why technical skills aren’t his superpower
17:57 Making IT approachable across the business
20:40 How leaders evaluate new technology
21:56 “I’m not the department of no”
24:01 Why companies can’t handle too much change
26:01 The reality of AI and where money is actually made
27:31 FOMO and bad tech decisions
30:10 The real challenge: user adoption
31:38 Why adoption matters more than implementation
32:01 Defining success before choosing tools
33:54 Change management and driving adoption
35:03 Why timing matters more than the tech itself
36:31 Final thoughts on leadership and vision
