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/

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#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
Discomfort and Leadership [not-audio_url] [/not-audio_url]

Duration: 10:26
Rule 1 of leadership is helping the team operate better.Rule 2 is that even if Rule 1 is uncomfortable - you are still responsible to do it.This episode dives into Rule 2.Yes, you can :-)
Leaders Are Not Trusted [not-audio_url] [/not-audio_url]

Duration: 6:55
This is a sad reality of leadership. So many negative stories (and experiences) about managers/supervisors/leaders who do not take good care of their teams.
Overcoming Introversion with Felix Boecker [not-audio_url] [/not-audio_url]

Duration: 48:31
I'm a fan of anyone working on introversion. Felix is doing excellent work.Learn more about Felix at http://brokesurgeon.com#40pb
The Initiative Advantage [not-audio_url] [/not-audio_url]

Duration: 8:27
How did you do that?I've been asked repeatedly by colleagues and execs. Across all the other mental models and skills - initiative is critical.
Leadership as a System [not-audio_url] [/not-audio_url]

Duration: 9:21
Smart leadership is a system.It works the same over and over again.And it starts with first level leaders/supervisors/managers.
Talking With Strangers - 40PB Episode 5 [not-audio_url] [/not-audio_url]

Duration: 9:55
Every employee engagement journey starts with communication.I spent decades struggling with social anxiety - but now I talk with strangers every day and enjoy public speaking.The difference - learning and practicing skil…
Persuasion Wins [not-audio_url] [/not-audio_url]

Duration: 15:11
Being friends with your boss is nice - but often times ineffective for making change happen. What you need are the models and skills for persuasion. Persuasion means translating what you know into language that resonates…

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