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Lead, Actually with Jess Pressland

Lead, Actually with Jess Pressland

Jess Pressland 6 Episodes Aug 19, 2026

Lead, Actually with Jess Pressland is a leadership podcast hosted by Jess Pressland, a leadership expert. The show offers honest stories, practical insights, and a candid look at corporate leadership, cutting through jargon to provide actionable strategies. Each episode covers common pitfalls leaders make and shares proven management frameworks from Pressland's proprietary JP Learning Loop. The podcast aims to help managers at all levels improve their leadership skills and drive business performance.

Episodes

Managing Different Generations: Are We Focusing On The Wrong Thing?
Managing Different Generations: Are We Focusing On The Wrong Thing? Aug 19, 2026 391 Baby Boomers, Gen X, Millennials, Gen Z… are the generational gaps in your workplace truly as wide as the internet makes them seem?In this episode, Jess Pressland challenges the modern corporate trend of partitioning employees by generation and argues that while it's easy to blame "generational friction" for communication breakdowns or workplace tension, managers are often focusing on
Why Purpose Matters More Than Ever
Why Purpose Matters More Than Ever Aug 12, 2026 457 In a world facing serious talent shortages and retention challenges, how do you keep your team truly motivated and engaged? In this episode, Jess Pressland breaks down why true workplace purpose isn’t just a slogan written on an office wall, it is a deeply felt connection to the business’s future. Sharing a brilliant real-world example from a five-star London hotel, Jess illustrates how redefining
Developing Others Is Your Real Job
Developing Others Is Your Real Job Aug 5, 2026 487 Many managers see themselves as the ultimate problem solvers of their team, but true leadership isn't about doing everything yourself or just dictating tasks.In this episode, Jess Pressland challenges the traditional top-down leadership style and explores why developing the people around you is an absolute necessity. Using a modern coaching approach, Jess breaks down the realistic ways people
Recognition : The Underestimated Leadership Tool
Recognition : The Underestimated Leadership Tool Jul 22, 2026 426 Telling your team members they are doing a great job costs absolutely nothing, yet intentional recognition remains one of the most underutilized strategies in modern business.In this episode, Jess Pressland breaks down why a generic "good job, team" does more harm than good and reveals the exact three-part formula leaders must use to make their employees feel genuinely seen, valued, and mo
The Art Of Difficult Conversations
The Art Of Difficult Conversations Jul 22, 2026 441 We’ve all avoided them: the awkward conversations we put off because we want to maintain peace, remain friends, or simply hope the problem will miraculously vanish.In this episode, Jess Pressland reveals why sweeping issues under the rug backfires drastically, affecting your entire team dynamic. Using a powerful real-world logistics example, Jess shares a practical blueprint to strip the fear out
Kind Leadership Is Not Weak Leadership
Kind Leadership Is Not Weak Leadership Jul 22, 2026 357 Is being a "kind" leader making you a soft target, or is it actually the toughest path to success?In this episode, Jess Pressland busts the widespread myth that kind leadership is "soft" or weak.Through a surprisingly common and awkward real-world workplace scenario, Jess illustrates how avoiding difficult conversations is actually the unkind route.She breaks down the "3 Fs&#34
Why Emotional Intelligence Is Every Leader's Greatest Advantage
Why Emotional Intelligence Is Every Leader's Greatest Advantage Jul 22, 2026 515 Many leaders focus on their intentions, but true leadership is defined by your impact.In this episode, Jess Pressland breaks down why emotional intelligence (EQ) is a leader's ultimate competitive advantage. Through a hilarious and eye-opening real-world training story, Jess reveals the common pitfalls of "box-ticking" relationship building and outlines the four core pillars of EQ need
Becoming A Leader, Why Leadership Is More Than A Job Title
Becoming A Leader, Why Leadership Is More Than A Job Title Jul 22, 2026 445 What is the actual difference between management and leadership?In this debut episode, Jess Pressland breaks down the core definition of leadership: it isn’t a title or a position of authority; it’s about having people choose to follow you.Jess shares real-world stories and insights on what it takes to step up as a true leader, focusing on the fundamental behaviors required to build trust, navigat
Welcome to Lead, Actually
Welcome to Lead, Actually Jul 16, 2026 64 Get ready for Lead, Actually, the leadership podcast with Jess Pressland, CEO of The JP Group.

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