They’re the most powerful people in your company… and the most overlooked.
In this episode, we sit down with Chelsea, Head of People at Tomorrow, whose approach to middle management has transformed team performance and culture. From scaling challenges to personal breakthroughs, Chelsea reveals what most leaders get wrong about middle managers and what to do about it.
Here’s what you’ll learn
Why middle managers shape your company culture more than your CEO
The real reason managers burn out (and how to stop it)
How Tomorrow built one of the UK’s top workplaces by focusing on its “squeezed middle”
The three powerful qualities Chelsea looks for when identifying future leaders
This isn’t theory. It’s a masterclass in the people strategy most companies ignore, until it’s too late.
👉 Subscribe for more honest, unfiltered conversations with the people rewriting the rules of work.
Chapters
00:00:00 – From Retail Floors to Head of People
00:03:16 – Learning Business From the Inside Out
00:05:13 – Why Middle Managers Hold the Power
00:07:10 – The Hidden Cost of Neglecting Managers
00:09:01 – Embedding Culture Through the Squeezed Middle
00:10:32 – From High Turnover to Top 10 Workplace
00:12:18 – The Mistakes We Made Scaling
00:13:51 – The Power of Monthly Reflection
00:15:36 – Fixing Feedback and Growth Conversations
00:16:55 – Why Radical HR Experiments Sometimes Fail
00:18:53 – Becoming a Manager is a Career Change
00:20:41 – No Training for Micro-Moments
00:22:33 – Avoiding Burnout Through Small Wins
00:24:25 – Building Great Leaders from Within
00:26:09 – The Three C’s of Great Management
00:27:44 – Creating Paths Beyond Management
00:29:35 – Essential Skills, Not Soft Skills
00:31:00 – Growth Plans That Actually Grow People
00:33:03 – Making Purpose Tangible
00:34:43 – The Manager’s Impact on Retention
00:36:33 – Advice to Her Younger Self
