Hire Learning with Oz Rashid

In this episode of Hire Learning, host Oz Rashid sits down with Lin Cherry, a powerhouse executive with experience as Chief Legal Officer and Chief People Officer in fast-growing tech and media companies. From her early days at MySpace to building high-impact legal and HR teams at Wiseline, Lin shares a career filled with bold transitions, leadership insights, and instinct-led decision-making.

🔥 Topics Covered:

• The surprising connection between legal strategy and people leadership
• What she learned at MySpace during the Facebook takeover
• The Reed Hastings quote that changed how she viewed media
• How startups should think about building culture at scale
• The real impact of trusting your gut during hiring decisions
• Why she values athletes and first-job hustle when building teams
• Tips for creating aligned, global cultures across multiple time zones

Timestamps:

0:00 - Intro: Meet Lin Cherry

2:12 - New Year’s Resolutions & Family Reflections

4:45 - From CLO to CPO: How Legal Led to People Leadership

7:18 - Legal Strategy Meets People-Centric Culture

9:44 - Why Wiseline Handpicked Lin to Lead HR

13:06 - Lessons from MySpace vs. Facebook: Tech & UX

17:48 - Reed Hastings’ Quote That Nailed Media’s Future

20:55 - Why Tech Companies Win at Content Distribution

25:34 - Creating HR & Legal Harmony in Startups

28:56 - Lin’s Hiring Philosophy: Mindset > Skillset

32:12 - What First Jobs Teach You About Grit

35:47 - A Memorable Interview Mistake

38:18 - Creating a Great Candidate Experience

41:05 - Best Hire She Ever Made—And Why

43:22 - Wicked, Hamilton & Content That Changes Perception

45:39 - Book Recommendation: Amy Edmondson on Failure

47:30 - Advice to Her 20-Year-Old Self

49:12 - Florida Speed Round: Food, Travel, and Disney Picks

53:15 - Wrap-Up & Final Thoughts

Plus, Lin reflects on the biggest lesson she’d give her 20-year-old self: trust your instincts—even when you're the only woman in the room.

🎯 Whether you're in HR, legal, or leadership, this episode will give you an edge in building smarter, more human-centric teams.

🔗 Don’t forget to rate, review, and subscribe on Apple, Spotify, or YouTube!

In this episode of Hire Learning, host Oz Rashid sits down with Andrew Tidwell, Chief Human Resources Officer at Wineshipping, to discuss what it takes to build high-performing teams. 

Andrew shares his unique hiring philosophy — prioritizing culture fit over experience — and why that approach is crucial for long-term success.

From unforgettable interview moments to insights on improving the candidate experience, Andrew reveals what companies often get wrong when attracting top talent. He also introduces his powerful team-building framework — I SOAR — and explains how fostering interdependence, shared purpose, and risk-taking can unlock true team potential.

💬 Key Takeaways:

✅ Why hiring for culture fit matters more than experience (15:32)

✅ The unexpected power of asking candidates, "What would you rather be doing right now?" (22:10)

✅ How to spot red flags — and avoid hiring the wrong people (30:45)

✅ Why your onboarding experience can make or break employee retention (41:15)

✅ Andrew’s unforgettable interview story — and the shocking answer he once received about collective bargaining (7:40)

Don't miss Andrew's candid advice for HR leaders and founders navigating today’s competitive talent landscape.

In this episode of Hire Learning, host Oz Rashid sits down with Skyler Mattson, CEO of Wongdoody, to discuss her incredible 20+ year journey from assistant account executive to global CEO. 

Skyler shares how Wongdoody transformed from a traditional ad agency into a cutting-edge digital experience company, and what it took to successfully integrate with tech giant Infosys.

🔍 Key Takeaways:

⏲️ [00:02:10] - The surprising origin story behind the name “Wongdoody” and how it breaks the ice

⏲️ [00:05:45] - Why Wongdoody’s acquisition by Infosys was a game-changing move

⏲️ [00:11:30] - Skyler’s mindset-first hiring philosophy — and why it’s better than hiring for skill alone

⏲️ [00:18:20] - How embracing change and the value of “being like water” has driven growth

⏲️ [00:24:00] - Why AI is revolutionizing content creation and the customer experience

⏲️ [00:31:45] - The role of empathy, storytelling, and mindset in building a winning team

Skyler also opens up about her leadership journey, the power of resilience, and the advice she’d give her 22-year-old self. Plus, she reveals the fascinating role of AI-generated humans in advertising and how Wongdoody is using cutting-edge tech to create hyper-personalized brand experiences.

In this episode of Hire Learning, host Oz Rashid sits down with Michael Fowler, former CIO of Florida Power & Light (FPL), to discuss his incredible career journey, lessons in leadership, and what retirement really looks like for a lifelong innovator.

Michael shares insights from his time leading large-scale tech transformations, his approach to building high-performing teams, and why empathy is his #1 hiring trait. He also reveals the unconventional interview question that helps him spot red flags — and why trusting your gut is critical in hiring.

Plus, you'll hear fascinating stories from Michael’s post-retirement adventures — including an eye-opening trip to Iraq and a near-disaster in Guinea.

Episode Highlights & Timestamps

🔹 (00:00) Intro – Oz introduces Michael and kicks off with an unexpected travel story

🔹 (05:21) Why Michael retired — and why the decision was harder than you'd think

🔹 (11:42) Michael’s new projects in retirement, including mentoring and culture building

🔹 (15:08) The inspiring story behind Michael’s leadership book, Letters from Leaders

🔹 (20:55) Michael’s proudest achievement: Modernizing legacy systems to drive innovation

🔹 (26:14) The interview question that reveals everything about a candidate

🔹 (31:32) Why empathy is the most underrated hiring skill

🔹 (37:05) The time Michael’s travel plans turned chaotic — and how he navigated a crisis

🔹 (44:10) Why Michael’s #1 piece of advice is to "Do Big Things" — and what that means

🎧 Listen now to hear Michael’s powerful insights on leadership, hiring, and embracing new challenges.

AI is changing the game—but most companies are playing by the wrong rules. 

In this episode of Hire Learning, host Oz Rashid sits down with Sol Rashidi, one of the world’s leading AI and data experts, to break down why businesses aren’t ready for AI—and how they can fix it.

Sol has done it all—she’s been a Chief Data & AI Officer at Fortune 100 companies, an Amazon tech exec, and a 10-time patent holder. 

She’s been in the trenches, building AI strategies long before it was mainstream. 

And now, she’s sharing her no-BS playbook on AI, hiring, and leadership.

🔥 In this episode, we cover:

✔️ Why most companies are set up to fail with AI (07:15)

✔️ The biggest AI misconceptions that are costing businesses millions (13:42)

✔️ How to build an AI-ready workforce—before it’s too late (21:09)

✔️ The one interview question Sol swears by to spot top talent (36:45)

✔️ The truth about AI replacing jobs—and what the future really looks like (45:20)

✔️ How Sol’s rugby career shaped her leadership style (56:33)

This is the AI reality check every leader needs. If you want to stay ahead, don’t miss this one.

Get Sol's Bestelling Book here: https://www.amazon.co.uk/Your-Survival-Guide-Real-World-Deployments/dp/1394272634