Anna Hislop is a Leadership certified professional coach and facilitator, with a background of 15 years as a teacher. Anna works with a range of organisations to help facilitate better communication and internal relationships, ensuring all generations are catered to and engaged.
Her particular focus is on communicating with Gen Z, coaching the next generation of leaders and talent. The Retail Hive’s Ed Lawson sat down with Anna to discuss the “generational melting pot” and how leaders can navigate this…
Anna Hislop
Ed Lawson
You’ve described retail, and many industries, as a “generational melting pot.” What do you mean by that?
Right now, we often have four—sometimes even five—generations working side by side. That brings incredible richness of experience, but it also creates tension, because expectations, communication styles, and motivations can look very different depending on the life stage and generation you’re in. This has always been true, but the arrival of Gen Z has really surfaced it. They’re more outspoken, they expect clarity and feedback, and they are willing to leave if they don’t find it. That makes the gaps between generations much more visible.
You work with leaders across sectors, from retail to law and finance. What challenges are you seeing most often?
The themes are remarkably similar. In law firms or accountancy, where hierarchy and tradition run deep, younger generations often push back on “command and control” leadership. They want purpose, involvement, and coaching. In retail and hospitality, you see the same dynamic. If Gen Z don’t feel seen, they disengage or leave quickly. Older generations might tolerate misalignment longer, but Gen Z has raised the stakes. They’re not afraid to demand workplaces that actually deliver on their values.
How has your background shaped your perspective?
Before stepping into leadership development, I spent 15 years in education, working as a teacher and Deputy Head. That gave me a front-row seat to Gen Z before they even entered the workplace. I learned how traditional methods often failed to engage them, and how curiosity, clarity, and care could unlock energy and commitment. Later, working with parents, social services, and policymakers gave me a deeper understanding of how the environment shapes behaviour. Today, those same young people are in our offices and shops, and leaders face many of the same challenges teachers faced in classrooms a decade ago.
Don’t assume the playbook that worked before will work now. Leadership today is about adaptability.”
What’s the key for leaders trying to navigate this generational mix?
I’d say three things: communication, clarity, and care. Firstly, we want to go back to basics and communicate more, with curiosity and without judgment. Secondly, leaders need to set crystal-clear expectations, but also show they care, not just in grand gestures, but in everyday conversations. Onboarding is critical too. Too many organisations treat it as a checklist when it should be a cultural handshake: “this is who we are, this is how you belong here.” Get that right, and you set the foundation for trust, motivation, and retention.
How do you bring this to life in your work?
My work spans keynotes, workshops, and leadership coaching, always with a focus on bringing Generational Intelligence to life in practical ways. I work a lot with middle managers, because they’re often the ones caught in the middle: expected to motivate younger employees who demand clarity, purpose, and feedback, while also meeting the expectations of more senior leaders who may be rooted in traditional ways of working.
I also design programmes for younger managers and early-career talents, helping them build confidence, self-leadership, and resilience at an earlier stage than previous generations ever did. And at the other end of the spectrum, I support senior leaders to adapt their leadership so they can connect across generations with credibility and impact.
If you could leave leaders with one piece of advice, what would it be?
Don’t assume the playbook that worked before will work now. Leadership today is about adaptability—asking better questions, giving feedback more often, and creating cultures where every generation feels seen and valued. Generational Intelligence isn’t “nice to have”—it’s what future-proofs your leadership and your organisation.
Want to know more?
Join our upcoming Digital Café with Anna Hislop to learn how to avoid alienating the younger generations in your workforce!
When? 20th November 2025 (1pm GMT)
Where? Taking place on Zoom, so you can dial in from the comfort of your home or desk!
Who? All of our Cafés are informal, retailer-only sessions. Get involved below…
