profile

Dr. Oliver Degnan

Join 64k professionals and transform yourself and learn from the trenches of a CIO about leadership, productivity, and career growth.

Subscribe to get all my latest posts

#68 When you miss detail, you risk damaging your reputation

Why Your Big Executive Brain Can't Count Anymore (And How I Fixed Mine) Read time: 5 minutes TL;DR: That Thursday I quoted $320K instead of $3.2 million to our board nearly ended my career as CIO. Turns out, your promotion literally rewires your brain to miss details. Here's the science behind why executives make dumb mistakes and my ZOOM framework to catch them before they catch you. 👇 Let me tell you about the most humiliating 30 seconds of my career. I'm standing in front of our board,...
READ POST

#67 Stop Hiding Behind "We"

Stop Hiding Behind "We"(Your Career Depends On It) Read time: 3 minutes TL;DR: Using "we" when describing your accomplishments makes you invisible in leadership conversations. Learn to articulate your specific contributions without sounding like a credit-stealing jerk. I watched a director get passed over for VP three times. Same story every promotion cycle. "We increased revenue by 40%." "We launched the new product line." "We restructured the entire department." The hiring committee had no...
READ POST

#66 Your Boss Is Playing Favorites (And Here's How to Become One of Them)

The RISE Framework: How to Build Upward Influence Without Being a Brown-Noser Read time: 6 minutes TL;DR: Stop waiting for your boss to notice your hard work. Use the RISE Framework - Read the Room, Invest in Relationships, Show Strategic Value, Execute Consistently - to systematically build influence with executives. It's not about politics; it's about positioning yourself as indispensable through proven psychological principles. You know that sinking feeling when your less-qualified...
READ POST

#65 The Corporate Dropouts, Misfits, and Rejects

The Three Types of People Quitting Their Corporate Jobs (And Which One Will Actually Succeed) Read time: 6 minutes TL;DR: Research reveals three distinct types of corporate leavers: Dropouts (85% success rate), Misfits (65% success), and Rejects (35% success). Knowing which type you are determines whether your career escape will be brilliant or a disaster. Your most successful friend just quit their executive job to become a life coach. Again. And you're thinking, "Is this another midlife...
READ POST
Dr. Oliver Degnan's Executive Playbook

#64 Your First 100 Days: The Executive Playbook

Your First 100 Days: The Executive Survival Guide Nobody Gave You Read time: 4 minutes (Some of what I am sharing here will shock you.) TL;DR: Most executives blow their first 100 days by moving too fast, trusting too quickly, or getting sucked into operational quicksand. Here's the framework I developed after watching dozens of leaders crash and burn (including myself once or twice). This isn't about making friends—it's about setting yourself up, actually, to deliver the transformation you...
READ POST

#63 The AI Job Apocalypse is Coming Your Way

The AI job apocalypse is coming (and your LinkedIn profile won't save you) Read time: 4 minutes TL;DR: By 2026, AI will be finding and hiring talent by scanning the entire internet. If you're not creating content now, you're invisible. Start with one YouTube video weekly, turn it into 20+ pieces of content across platforms, and become unfindable. Listen up. If you're not building your online brand RIGHT NOW, you're basically telling AI recruiters in 2026 to swipe left on your career. Here's...
READ POST
Don't protect your team!

#62 You shouldn't protect your team

The Leadership Myth That's Burning Out Your Team Read time: 4 minutes TL;DR: If you're constantly protecting your team from work challenges, you might be creating weakness instead of strength. Strong teams don't need shields – they need strategic clarity and the freedom to manage themselves. The real problem isn't the workload; it's the lack of accountability and poor expectation management that creates a culture of learned helplessness. The Protection Trap Last week, I got a call from a VP...
READ POST

#61 The Pitfalls of Singling out Heroes

The Hidden Trap in "Thank You": Why Singling Out Heroes Damages Teams Read time: 4 minutes TL;DR: When managers single out individuals for praise, they undermine team cohesion and create unsustainable hero cultures. True leadership acknowledges collective effort while still recognizing individual contributions in balanced, thoughtful ways. Have you ever watched a manager praise a "star performer" during a team meeting while everyone else sits awkwardly silent? Or sending an email to the group...
READ POST

#60 AI Can Get You Fired (If you don't master it)

AI Will Get You Fired If You Don’t Master It (And Why That’s Burning You Out) Read time: 4 minutes TL;DRAI isn’t just some shiny new tech—it’s the difference between getting ahead or getting cut. If you’re drowning in tasks, overwhelmed by demands, or waking up with that familiar pit in your stomach, AI might be the lifeline you’re ignoring. Here's how failing to embrace it leads straight to burnout—and how mastering it can pull you out. The Productivity Trap That’s Killing You Let’s cut the...
READ POST