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Guest Resources

Website – Rainy Day Trust

Website – Mason Foundation

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279: Empowering Performance: Building a Coaching Culture from the Ground Up with Anna Skeats

In this Episode

Host, Rosie Nice, speaks with Anna Skeats, CEO of the Rainy Day Trust and former CEO of The Mason Foundation. From her early career supporting vulnerable communities to building a national charity from scratch, Anna’s leadership has always centred on empowerment over direction.

Anna challenges the myth that coaching cultures tolerate underperformance, sharing how coaching approaches actually create high-performing, effective and motivated teams by encouraging the skills and strengths already within individuals and teams. Drawing on her experience at the Mason Foundation, she explores how trust, psychological safety, and clear expectations work together to drive inclusion, accountability, and impact.

Throughout the conversation, Anna reflects on the realities of embedding a coaching culture in practice, the importance of listening and responding to real needs, and the incredible results she’s experienced. Her insights offer practical guidance for leaders seeking to create sustainable organisations without losing focus on performance, accountability, or impact.

You Will Learn

How coaching cultures enhance performance and empower teams
How psychological safety and trust unlocks capability
Leadership starts with listening – Responding to real needs, rather than assumptions

Guest Bio

Anna Skeats is CEO of the Rainy Day Trust, supporting the home improvement workforce in times of need. Previously founding CEO of the Mason Foundation, she scaled the organisation from zero to national reach, supporting neurodivergent people into employment across the UK.

With 20+ years across NHS, public health, corporate, and charity sectors, Anna champions coaching cultures rooted in her early community work. A neurodivergent leader and parent to neurodivergent children, Anna prides herself on rolling up her sleeves and gets stuck in.