Debbie Shotwell
Chief People and Culture Officer
Stack Overflow
Episode 294
Navigating AI & Culture: The Essential Role of Transparent Leadership
Current chapter: Covering monthly expenses is the number one concern for employees in 2024
Built By PeopleFebruary 20, 2025 · 14:29
Thesis
“A thriving company culture, effective learning & development, and successful technological transformations (like AI adoption and M&A integrations) are fundamentally driven by strong, transparent leadership, clear values, continuous communication, and proactive employee engagement that fosters psychological safety and adaptability.”
Show notes
Stack Overflow serves millions of developers worldwide — and its Chief People and Culture Officer has had to build the kind of culture that earns their trust from the inside. Debbie Shotwell knows something most CPOs are reluctant to say plainly: culture isn't built by HR. It's built by everyone, every day, through leadership that models the values it claims to hold.
Debbie's experience spans M&A integrations, AI adoption, and the particular challenge of L&D in a company whose entire audience is the developer community. She's watched culture fail in acquisitions when companies tried to integrate systems before integrating people — and she's clear on why that sequence is backwards. Successful M&A comes down to two things: clear values and transparent communication. Not just at announcement, but sustained through every ambiguous month that follows. Her framework: employees can handle uncertainty far better than they can handle silence.
On AI in HR, Debbie has moved past the theoretical. She describes how AI is already enabling more personalized learning and development — allowing employees to chart their own skill paths rather than defaulting to generic training catalogs. The measurement challenge has shifted accordingly: completion rates are nearly meaningless. What matters is whether the learning changed behavior and moved a business metric. She's also direct about the psychological dimension of AI adoption: employees fear it, and HR's job is to proactively address that fear — not with reassurance, but with transparency about what will change, what won't, and how the company will support the transition.
- Culture as a leadership practice, not an HR program — what it actually takes to build culture that outlasts any initiative
- AI-enabled personalized L&D — moving from generic training catalogs to individualized skill development paths
- Measuring L&D impact that matters — why completion rates are lagging indicators and what to track instead
- AI adoption and employee fear — how to address anxiety with transparency, not platitudes
- M&A culture integration — why values and communication must come before systems, not after
- Mentorship as career infrastructure — why continuous learning relationships accelerate professional development
Built by People is sponsored by Previ, the private pricing network that saves employees an average of $2,200/year on essentials like cell phone and auto insurance — free for companies to launch and maintain.
What you'll take away
- 1A thriving company culture is built on a clear mission, strong leadership modeling values, transparent communication, feedback loops, and employee recognition.
- 2Learning & Development has evolved significantly with AI, enabling personalized skill development and internal career opportunities through platforms like 'My Academy' and 'Opportunities Module'.
- 3Successful AI integration requires proactive, transparent communication, addressing employee fears, empowering employees by automating repetitive tasks, and investing in upskilling/reskilling.
- 4Measuring culture and L&D success goes beyond basic metrics, now relying heavily on employee engagement surveys, inclusion surveys, and eNPS, with transparency even when scores decline.
- 5Culture is the primary reason mergers and acquisitions fail; early culture audits, leadership engagement, fostering trust, and structured onboarding are critical for successful integration.
What most organizations get wrong
- •Many view M&A as purely a business decision, but Debbie asserts that 'the biggest reason why mergers fail is culture clashes.'
In Debbie's words
“Culture requires a combination of leadership, values, and daily practices that align with the organization's mission.”
This defines the foundational elements of a strong company culture.
“The most important thing about L&D at Stack and how it's been really lucky for me is a core value of our company is learn, share, and grow.”
This highlights how deeply L&D is integrated into their company values.
“The most important thing is to communicate and be transparent and be proactive. Be very clear on the why. Explain how AI will enhance business processes and not replace employees because there is a fear there.”
This emphasizes the critical communication strategy needed for AI adoption.
“Today, so much easier when you can utilize tools like employee engagement and measure engagement from an engagement survey. And then what actions you've taken based on that employee engagement survey and continue to measure that.”
This showcases the modern shift in how HR measures success and impact.
“Culture plus L&D equals a successful merger.”
This concisely states the intertwined importance of culture and L&D in M&A success.
The problems this episode addresses
- •Companies struggle with culture clashes during mergers and acquisitions, leading to prolonged integration difficulties (e.g., 'taken more than, you know, 12 to 18 months').
- •Organizations face employee fear and resistance during technological transformations like AI integration due to concerns about job security and role changes.
- •HR teams need robust methods beyond basic metrics (like turnover/hiring) to effectively measure employee engagement, inclusion, and the impact of L&D initiatives.
- •Establishing and maintaining a clear company mission, vision, and values that employees truly understand and align with is a challenge for leaders.
- •Ensuring leaders consistently model company culture and values is critical but often difficult to achieve.
In this episode
Covering monthly expenses is the number one concern for employees in 2024
Built by People
You've been in human resources for more than 20 years
Lucky in HR: Susan Flannery
What do you believe are the key elements that create a thriving company culture
What Makes a Well-Developed Company Culture?
Debbie has a passion for learning and development at Stack
Teaching at Stack: Learning & Development
How do you balance maintaining company culture during technological transformation while addressing employee concerns
How To Manage Company Culture During AI Integration
How do you measure and track success of your culture and L&D initiatives
How to Track the Success of Your Culture and L&D Initi
A well-managed culture integration ensures alignment, engagement, and productivity
What Role Does Culture Play in Merger Integration?
Debbie has worked in human resources for more than 20 years
A Human Resources Professional's Last Words
Topics covered
Organizations and entities mentioned
Full transcript
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