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300 Leaders Later: What Actually Breaks During Transformation | LFC Ep. 263 Most transformations fail not because the strategy is wrong — but because the leader can't see what's actually breaking. After 30 years and 300+ leaders coached, Jennifer Selby Long knows exactly where the cracks form, and how to close them before the whole thing collapses. In this episode: • Why the biggest barrier to leading transformation sits between your own ears — and how to move it • What really breaks during hypergrowth at companies like Airbnb and LinkedIn (it's not what the press release says) • When post-acquisition integration stops being a logistics problem and becomes a leadership crisis • The "mini-me hiring trap" that quietly kills team diversity and strategic thinking • How to lead across cultures without over-rotating into stereotypes — and what most global leadership programs get wrong • The one thing to do this week if your transformation is six months in and not going as planned Jennifer Selby Long is the Founder and CEO of Selby Group LLC, an executive coaching firm she has built over 28 years into a proudly small, highly focused practice. She has coached more than 300 individual leaders and shaped leadership culture at companies including Airbnb, LinkedIn, and Cisco during some of their most turbulent and explosive growth periods. Her work lives at the intersection of behavioral change, organizational transformation, and the messy human realities that no project plan ever captures. Chapters: 0:00:00 Introduction & Guest Welcome 0:03:00 How Rejection Built a 28-Year Coaching Practice 0:09:00 Does HR Still Deserve a Seat at the Table? 0:16:00 The Hidden Cost of Promoting Your Best Technical Person 0:24:00 Hypergrowth, Airbnb, LinkedIn, and Barely Controlled Chaos 0:30:00 What Got You Here Won't Get You There — AI and Leadership Literacy 0:39:00 Post-Acquisition Integration: Logistics Problem or Leadership Crisis? 0:47:00 Leading Across Cultures Without Stereotyping 0:54:00 Founding Your Own Company Later in Career 1:01:00 One Thing to Do When Your Transformation Is Off Track Find Jennifer Selby Long: Website: https://www.selbygroup.com LinkedIn: Search Jennifer Selby Long Email: [email protected] Newsletter: The Leadership Edit — subscribe at selbygroup.com Hosted by Robin Ayoub | Localization Fireside Chat Podcast: 263 episodes, 200K+ downloads Blog: robinayoub.blog Network & Fractional Leadership: N49 Networks AI Exchange: Weekly networking event — connect with Robin on LinkedIn to join More Related Tags: transformation leadership, business transformation, organizational transformation, leadership lessons, change management, transformation strategy, business leadership, organizational change, leadership challenges, transformation failure, executive leadership, business growth, scaling organizations, leadership insights, change leadership, transformation management, business strategy, #leadership #leadershipdevelopment #businesstransformation #transformation #changemanagement #executiveleadership #businessleadership #organizationalchange #leadershiplessons #businessstrategy #futureofleadership #management #ceoleadership #leadership #leadershippodcast #businessgrowth #changeleadership #organizationaltransformation #lfc #leadershipinsights

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