If you're an IT exec, you're constantly dealing with putting out fires vs innovating, asking to do more with less budget, and stay a step ahead of the competition while attracting and retaining talent.
As an account executive working with top performing IT Innovators, I've noticed the winners of this arms race are able to slow down, reflect, realign, and envision - so they can ignite a bold direction for themselves and what they will bring to life over the next year (and beyond).
This podcast will help you unearth opportunities to do your Biggest, best and boldest work - and be the best and boldest version of yourself
How do we get there?
Twice a month I will be interviewing IT leaders on their Sources of Motivation, curiosity, and what brings fulfillment. We'll dive into their top priorities, challenges, and future plans
Too often the human element is left out of enterprise technology, and as we know it's people and their priorities that drive decisions.
So tune in and enjoy the Bigger, Better, Bolder IT Podcast
The Psychology of IT Leadership with Ken Widener, CIO
Episode description
Ken Widener, CIO and EVP of Do it Best Corp., started in psychology and planned a career in family counseling. He ended up leading IT for a major retail co-op. Ken talks about how he applies that background to leadership. He covers:
Treating a company like a living being with its own personality.
Starting with purpose before technology when integrating teams after an acquisition.
Leading people through change, and why it's okay for managers to say "I don't know."
Servant leadership and why leaders shouldn't become the bottleneck.
Key takeaways
Lead with purpose before technology. After the True Value acquisition, the first question was how to drive profitability for members, not which platform to use.
Repeat the same message and back it up with action. Leaders who say "this is our top priority" and then fund something else lose credibility fast.
Use "Challenge, Align, Commit." Challenge the premise and find the root cause. Align on how to execute. Then commit and run the play.
People worry about their own future during change. Train managers to listen first and admit what they don't know.
Servant leaders empower their team to decide and get out of the way. Otherwise they become the bottleneck.
Find a mentor, and define success for yourself before society does it for you.
Timestamps (optional)
0:28 Ken's path from psychology to IT
1:52 The company as a living being
3:16 Purpose first: Do it Best and the True Value merger
7:56 Keeping the message alive: all-hands, "Coffee with Ken," and the one-page plan
10:16 Change management and the human side of fear
12:08 Challenge, Align, Commit
14:00 Servant leadership
17:16 Lightning round: passion, curiosity, inspiration
19:08 Advice for early-career people, and legacy
22:24 One tip on communication
26 Mar 2026
Using Your Mom Skills to drive Innovation With Kathy Ogurek
This episode explores the human side of digital transformation, emphasizing building IT teams that drive change and enhance workplace experience. Kathy Ogurek shares insights on hybrid work, security, psychological safety, and leadership in tech.
Keywords
Digital Transformation, Workplace Experience, Hybrid Work, Security, Leadership, IT Teams, Psychological Safety, Technology Adoption
Key topics
Human side of digital transformation
Building IT teams that drive change
Hybrid work environment and future trends
Security, compliance, and risk management
Psychological safety and leadership in IT
Sound Bites
"You can't beat in-person creativity and innovation."
"Focus on the client and your employees equally."
"Helping the next generation is my legacy."
Chapters
00:00 Introduction to Digital Workplace Experience
02:14 Understanding End User Needs in Digital Transformation
03:52 Hybrid Work Environment and Future Trends
06:09 Generational Demands and Work-Life Balance
09:12 Balancing Business and Employee Needs
10:45 Security, Compliance, and Trust in IT
14:43 Hybrid Work Model and Flexibility
17:57 Psychological Safety in Transformation
19:17 Problem Solving and Innovation
20:25 Learning New Technologies and AI ROI
21:28 Stories of Resilience and Inspiration
23:24 The Power of Feedback and Listening
25:00 Legacy and Mentorship in Tech
26:26 Closing Remarks and Key Takeaways
13 Mar 2026
Moving Beyond Data Silos: The Future of AI-Driven Analytics with Abhi Singh
Discover how AI is revolutionizing data integration, breaking down silos, and empowering organizations with real-time insights. Join us as Abhi Singh, a seasoned analytics and AI leader, shares his insights on modern data architectures, the human element in AI adoption, and the exciting future of analytics over the next five years.
In this episode:
The historical evolution of data warehousing and what went wrong
Why connecting data is harder than collecting it
The human and cultural challenges in breaking silos
How AI tools like co-pilot and conversational analytics are changing the game
The key roles mentorship and curiosity play in AI progress
Future trends: from descriptive to transactional and autonomous AI systems
Real-world examples: supply chain automation and education systems
The importance of human in the loop for reliable AI outputs
Industry archetypes: AI Cowboys, Skeptics, and Frozen Executives
Emerging capabilities and the strategic bets for the next five years
Final thoughts: The legacy of curiosity and continuous learning
Timestamps:
00:00 - Welcome to the Bigger, Better, Bolder IT Podcast
01:30 - The history and pitfalls of data warehousing
03:00 - Why organizations struggle to connect data across silos
04:47 - Human vs. technological challenges in data integration
07:00 - Communication's role in successful analytics teams
09:56 - The shift towards AI-powered insights and the human element
13:58 - Ensuring trust: vetting AI outputs and avoiding hallucinations
16:14 - Industry archetypes: AI Cowboys, skeptics, and frozen executives
19:42 - The future of analytics in 5 to 10 years: big bets and trends
22:29 - Real-world applications: transactional analytics and education tech
25:05 - The power of curiosity, mentorship, and continuous learning
28:36 - Influences: Steve Wozniak and non-tech motivators
30:03 - The legacy of curiosity and learning
31:03 - Closing remarks and reflections
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
3.0 / 5
2 ratings
Spotify
3.0 / 5
2 ratings
Podcast Authority Score: 38 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
56
Social presence
0
YouTube
0
Engagement
51
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