The Leverage Point

In this episode we cover:Why technical excellence is a poor predictor of management successThe four failure modes of accidental managersWhy organizations are structurally complicit in this problemA practical framework for making the transition deliberatelyReferenced: CEB/Gartner research on IC-to-manager transitions | High Output Management — Andrew GroveFollow the show: | Connect with Timi Ogunjobi: SPONSORSHIP: The Leverage Point reaches senior technology leaders—CTOs, engineering managers, and Staff+ professionals—engaged in high-stakes decisions around AI, strategy, and execution. It offers sponsors a focused, credibility-driven channel to connect with an audience that influences real budgets and technology direction. If your product serves serious technical leaders, this is where your message lands with impact. To explore sponsorship opportunities and position your brand where serious conversations happen, let’s connect. Email [email protected]

In this episode we cover:Three misconceptions that corrupt the decision before it startsAn honest account of what Staff Engineering actually demandsAn honest account of what Engineering Management actually demandsA five-question framework for making the decision with full informationThe hybrid path and what to do if you choose wrongReferenced: Will Larson — Staff Engineer: Leadership Beyond the Management TrackFollow the show: | Connect with Timi Ogunjobi:SPONSORSHIP: The Leverage Point reaches senior technology leaders—CTOs, engineering managers, and Staff+ professionals—engaged in high-stakes decisions around AI, strategy, and execution. It offers sponsors a focused, credibility-driven channel to connect with an audience that influences real budgets and technology direction. If your product serves serious technical leaders, this is where your message lands with impact. To explore sponsorship opportunities and position your brand where serious conversations happen, let’s connect. Email [email protected]

In this episode we cover:Why a gap exists between public AI confidence and private CTO realityFive things technology leaders are privately wrestling with right nowThe ROI measurement problem nobody is solving cleanlyWhat the best CTOs are actually doing to navigate this momentWhat this means for engineering managers, Staff engineers, and senior leadersKey themes: AI governance · Enterprise AI strategy · Technical leadership · Build vs. buy · AI ROIFollow the show: | Connect with Timi Ogunjobi: ⁠https://www.linkedin.com/in/timiogunjobi/⁠SPONSORSHIP: The Leverage Point reaches senior technology leaders—CTOs, engineering managers, and Staff+ professionals—engaged in high-stakes decisions around AI, strategy, and execution. It offers sponsors a focused, credibility-driven channel to connect with an audience that influences real budgets and technology direction. If your product serves serious technical leaders, this is where your message lands with impact. To explore sponsorship opportunities and position your brand where serious conversations happen, let’s connect. Email [email protected]

In this episode we cover:Key themes: Product-engineering alignment ·Roadmap planning · Technical estimation · Cross-functional trust · Engineering leadershipThe question to take into your next planning cycle:Did engineering contribute input before the priorities were set — or after?Who to share this with: Your product manager.Your engineering manager. Anyone who has sat in a roadmap review and felt the gap between what was on the slide and what was real.Follow the show: | Connect withTimi Ogunjobi: ⁠ Timi Ogunjobi | LinkedIn⁠

In this episode we cover:Key themes:Technical debtEngineering cultureIncentive designKnowledge managementEngineering leadershipRetentionThe one question to take into your next planning cycle: What did we sustain this quarter — and did we recognize the people who did it?Who to share this with: Any engineering leader who has had the tech debt conversation more than twice. Any product leader who has ever wondered why delivery keeps slowing down. Any engineer who has been told "we'll address that next quarter" for the last four quarters.Follow the show: | Connect with Timi Ogunjobi: ⁠Timi Ogunjobi | LinkedIn