Data Driven Leadership

In this episode, Jess Carter sits down with Nicola Smith, senior AI advisor at Southwest Airlines, to explore how organizations can operationalize AI strategically and build a workforce ready for the future. Nicola shares her insights on AI literacy, human-centered design, and creating a mindset of abundance that empowers employees rather than creating fear. 
 
In this episode, you'll learn:
How to develop an enterprise AI strategy that works across departments

The importance of building AI literacy programs

How AI can enhance creativity, innovation, and decision-making

 
Things to listen for:
(00:00) Introduction to the episode with Nicola Smith
(04:44) Building enterprise and departmental AI strategies
(07:30) Bottom-up innovation and employee-driven AI use cases
(09:51) Adoption through AI literacy programs
(13:24) Combating fear and cultivating a mindset of abundance
(22:22) Storytelling and transparency in AI-driven organizations
(27:49) Future AI initiatives and emerging technologies

Nicola's LinkedIn: https://www.linkedin.com/in/nicolasmith22/

How can business and IT leaders align on AI and make smarter decisions together?
Jess Carter reflects on conversations with business, IT, and data leaders across industries, sharing common themes she has observed around AI adoption. She discusses the disconnect between technical teams and business stakeholders, and offers practical advice on how to bridge that gap, build confidence with AI, and focus on real business value.
In this episode, you'll learn:
How data leaders can better connect AI initiatives to business outcomes

Why developing hands-on experience with AI tools is critical

How business leaders can experiment with AI while managing risk and cost

 
Things to listen for:
(00:00) Introduction to the episode
(02:16) The two types of IT and data leaders approaching AI
(06:25) Prompt engineering and AI experimentation
(09:20) Managing data security and tool limitations
(14:06) Why AI adoption looks different for every organization


Jess's LinkedIn: https://www.linkedin.com/in/jessicaccarter/ 

Not sure if your AI efforts are actually paying off? Take this free quiz and find out where your business stands: https://info.resultant.com/ai-value-scorecard

When times get tough, we rely on leaders to make the hard decisions. That's why their character is so critical—it can make or break a team, a company, or even an entire organization. 
In this episode, Jess Carter sits down with Ernest O'Boyle to explore the "dark triad" of leadership and how these toxic traits can quietly sabotage a workplace. Professor Ernest shares his research on how these traits often go unchecked, leading to manipulation and a toxic culture. They discuss how leaders with dark triad traits can distort data, influencing outcomes and undermining trust in data-driven decisions.

In this episode, you'll learn:
How toxic leadership traits impact team performance

The effects of narcissism and Machiavellianism in leadership dynamics

How to build and maintain a positive workplace culture despite challenging behaviors

 
Things to listen for:
(00:00) Introduction to the episode with Ernest O'Boyle
(02:00) The dark triad traits in leadership
(06:45) How narcissism and psychopathy show up in the workplace
(10:25) Leadership in high-pressure environments
(14:10) Managing manipulative behaviors in teams
(18:00) How organizational culture shapes leadership behavior
(22:15) Ethical dilemmas in decision-making
(27:30) Can toxic leadership traits be reformed?
Ernest's LinkedIn: https://www.linkedin.com/in/ernest-o-boyle-4547a729/

AI can make decisions fast. But weak data foundations still slow everything down.
In this episode, Jess Carter sits down with Senior Director of Data Platform & Governance at Hungryroot Ben Ganzfried to discuss what it takes to build trust in data as companies grow. At Hungryroot, data does more than support reporting. It informs recommendations, recipes, and inventory decisions.
Ben shares lessons on building data foundations that help teams move faster with more confidence. He explains why governance should reinforce accountability, not create friction, and why unclear ownership becomes a bigger risk when more decisions depend on data. 


In this episode, you'll learn:
Why data governance is crucial for business growth

Best practices for managing data security and accessibility

How to foster a data-driven culture within your organization


Things to listen for:
(00:00) Introduction to the episode with Ben Ganzfried
(02:41) How Hungryroot uses data to personalize the customer experience
(08:39) Making faster decisions through better governance
(14:15) The rise of data and AI leadership roles
(19:23) Why ambiguity becomes a risk as systems scale
(23:38) Curiosity as part of data-driven leadership

Ben's LinkedIn: http://linkedin.com/in/ben-ganzfried-1a5a8620a/?skipRedirect=true
Links from the episode - 
https://www.cdomagazine.tech/opinion-analysis/lessons-in-ambiguity-data-ai-and-the-limits-of-informal-coordination 
https://benganzfried.com/f/the-nature-of-data-the-foundation-we-forgot-and-why-it-matters 
https://benganzfried.com/f/the-year-the-margin-for-error-disappeared 
https://www.cdomagazine.tech/opinion-analysis/lessons-in-ambiguity-data-ai-and-the-limits-of-informal-coordination

Some moments define the kind of leader you are. When the stakes are high and the data is incomplete, your character becomes the strategy.
In this episode, former FBI agent Herbert Stapleton joins Jess Carter to explore the role of integrity, decision-making, and leadership in high-stakes environments. Drawing from his two decades of experience in federal law enforcement, Herb shares his insights on how character and effective leadership are essential when the stakes are life and death. He discusses the importance of honesty, accountability, and the challenges of making tough decisions with incomplete information.


In this episode, you'll learn:
How to lead with integrity under intense pressure

The importance of humility and confidence in leadership

Ways to foster trust and loyalty within your team during crises



Things to listen for:
(00:00) Introduction to the episode with Herbert Stapleton
(02:20) Herb's journey from law school to the FBI
(06:34)  Leadership development in the FBI
(10:03) Decision-making with incomplete information
(14:32) How to deal with crises in corporate settings
(17:35) Prioritizing wellness in your team
(22:21) Developing character in the age of AI
(28:33) Can integrity be taught?
Herb's LinkedIn: https://www.linkedin.com/in/herb-stapleton-b94a19126/ 
https://www.dinsmore.com/