The Art of Managing Diverse Personalities | Oscar Hedaya

The Art of Managing Diverse Personalities | Oscar Hedaya

Author: Bill March 6, 2026 Duration: 1:04:16
Serial entrepreneur Oscar Hedaya, founder of SPACE and The Space Safe, joins Bill Lennan on the 40% Better podcast for a wide-ranging conversation on what real leadership looks like across industries. Oscar's career has taken him from visual merchandising in New York to touch-screen gloves, electric mobility, and now the world's first smart safe with a built-in camera, touchscreen, tamper sensors, and app connectivity. Along the way, he's built and led teams of 25+ people across hardware, software, firmware, and design, and he shares the hard-won lessons that came from managing very different personalities under one roof. The conversation digs into the messy, human side of leadership: how to handle conflict without letting it fester, why getting quiet team members to speak up can completely transform a team's output, and how psychological safety and employee happiness aren't soft extras but core performance drivers. Oscar and Bill also unpack the challenge of getting cross-functional teams speaking the same language, the power of extreme ownership when things go wrong, and why small gestures like better coffee or Friday pizza often matter more than a pay rise. Key Takeaways
  • Leaders who come from under-resourced backgrounds often develop stronger creative problem-solving instincts early on
  • Managing larger teams means spending significant time on interpersonal issues, not just the work itself
  • Bringing clashing team members together socially is often the most effective way to defuse conflict
  • Getting promoted doesn't mean doing more of the same job; the role fundamentally changes
  • Quiet, high-performing team members need time and consistent encouragement before they'll speak up in group settings, but it's worth the investment
  • Cross-functional teams (hardware, firmware, software, design) each speak a different language; a good leader bridges that gap
  • When something goes wrong, blame-minimising and accountability-taking from the top changes the entire team culture
  • Employee happiness is a business metric: appreciated employees go beyond their job description, stay longer, and produce better work
  • Small perks (better coffee, free lunch, a nearby hotel room for late nights) create disproportionate goodwill and loyalty
  • Upgrading team equipment is one of the highest-ROI investments a leader can make
Connect with Oscar Hedaya: LinkedIn: https://www.linkedin.com/in/oscar-hedaya-b1a76b3/ Website: https://www.thespacesafe.com If you found this episode useful, hit subscribe and leave a review. It really helps the show reach more leaders who want to build better teams.
I hope you enjoy this episode! Give it a like, share, and subscribe to not miss the content coming your way weekly. – Bill and the 40 % Better podcast team

Connect with Bill on LinkedIn: https://www.linkedin.com/in/wblennan/ 
Visit the 40 Percent Better website here: https://40pb.com/

Listen to 40 % Better on these podcast platforms:
Spotify: https://open.spotify.com/show/6qkqdMPkR9BqYPM7UPa4P0
Apple Podcasts: https://podcasts.apple.com/us/podcast/40%25-better---engineering-leadership/id1709546347 
Amazon Podcasts: https://music.amazon.com/podcasts/01ad162e-7a33-4df4-8c29-04c4af0405fc/40-better---engineering-leadership

#40PercentBetter #BillLennan #Leadership #TeamPerformance #EmployeeEngagement #PsychologicalSafety #BusinessGrowth #Kaizen #EngineeringLeadership #Coaching The 40% Better podcast with Bill Lennan unlocks previously unheard-of performance levels in teams and leaders. Bill Lennan, founder of 40 Percent Better, interviews experts on employee engagement, psychological safety, engineering leadership, and actionable mental models. Learn...

Hosted by Bill, 40% Better-Engineering Leadership is a conversation for those who build and guide technical teams. This isn't about abstract theory; it's a practical dialogue focused on the tangible mechanics of morale, motivation, and output. Each episode features a single expert in employee engagement, and together we dissect the specific strategies that lead to measurable leaps in performance. You'll hear detailed explorations into what actually moves the needle for engineers and their managers, translating research and experience into actionable leadership techniques. The goal is straightforward: to provide the insights that can help your team operate at a significantly higher level of effectiveness and satisfaction. Tune in for a focused, deep-dive podcast that cuts through the noise of generic management advice, offering concrete ideas you can apply directly to the unique challenges of engineering leadership.
Author: Language: English Episodes: 100

40% Better - Engineering Leadership
Podcast Episodes
Mistakes, psychological safety, and leadership clarity | Rob Zuber [not-audio_url] [/not-audio_url]

Duration: 1:05:23
Welcome to the 40% Better podcast with your host, Bill Lennan!In this episode, we sit down with Rob Zuber to explore his candid journey into leadership—from the trial by fire of the startup world to managing complexity i…
Episode - AI Doesn't Replace Your Thinking It Amplifies It Jimi Li [not-audio_url] [/not-audio_url]

Duration: 46:17
What does it actually take to get real business value from AI? Jimi Li, CTO at ALM Media, has spent the last three years running AI initiatives inside a company that just went through a successful private equity exit — a…
Jiu Jitsu Changed My Life and Leadership | Jeremy Hass [not-audio_url] [/not-audio_url]

Duration: 40:43
In this episode of the 40% Better Podcast, Jeremy Hass shares powerful insights from his leadership journey, shaped by his experiences in the military, startups, and Brazilian Jiu Jitsu.Jeremy dives into the importance o…
The Risk Mindset That Changes Everything | Tamara Laine [not-audio_url] [/not-audio_url]

Duration: 41:59
In this episode of the 40% Better Podcast, Tamara Laine shares her unconventional leadership journey from teaching dance at a young age to working in documentaries, journalism, and eventually leading in the tech world.Ta…
Why Employee Loyalty Has Nothing to Do With Salary | Ian Watts [not-audio_url] [/not-audio_url]

Duration: 51:41
In two decades of coaching leaders across startups to multi-billion dollar corporations, Ian Watts discovered that companies lose talented people not because of compensation, but because they treat employees like replace…
From Dial-Up Belarus to 350 Engineers | Andrei Yurkevich [not-audio_url] [/not-audio_url]

Duration: 52:41
In 2002, a 25-year-old Andrei Yurkevich started a software outstaffing business in Belarus with internet speeds under 100 kilobits per second for the entire country—slower than a dial-up modem. Twenty-two years later, he…
SE1E94 - From Dial-Up Belarus to 350 Engineers | Andrei Yurkevich [not-audio_url] [/not-audio_url]

Duration: 52:41
In 2002, a 25-year-old Andrei Yurkevich started a software outstaffing business in Belarus with internet speeds under 100 kilobits per second for the entire country—slower than a dial-up modem. Twenty-two years later, he…
Run to the Inevitable: High-Trust Engineering Teams | Josh Carroll [not-audio_url] [/not-audio_url]

Duration: 52:53
When Josh Carroll tells his engineers not to bring him their hard problems, he's actually doing the opposite—he's making sure they feel resourced enough to tackle anything. As an engineering leader with 20+ years of expe…
How Failure Made Her a Better Engineer | Sairan Aqrawi [not-audio_url] [/not-audio_url]

Duration: 57:16
When Sairan Aqrawi decided to become a swimming coach as a teenager in Iraq, she discovered something critical about leadership: passion alone isn't enough. You need skills, responsibility, and the willingness to take ac…