Why Apprenticeships Matter for Leadership Pipelines in Hospitality, Travel, Leisure (HTL), and Retail.
One of the conversations I find myself having more and more often with leaders across HTL and retail is about readiness.
Not readiness in the sense of filling roles today, but readiness for what the sector will demand from its leaders in the years ahead.
When I discussed this with Tea Colaianni, Founder and Chair of WiHTL & Diversity in Retail, we quickly aligned on a shared concern: the way leadership has historically been developed in these sectors is no longer keeping pace with the demands being placed on it.
For decades, these industries have been strong at developing leaders through experience. Many of the most successful CEOs began their careers on the floor, learning the realities of service, operations, and customer expectations firsthand. But the context those leaders are now operating in has changed significantly.
Many organisations are now grappling with whether their current pathways are capable of producing the next generation of leaders fast enough, and with the right capabilities.
The future of hospitality, travel and leisure will demand leaders who are commercially sharp, digitally fluent and culturally intelligent.
–Tea Colaianni
This is where apprenticeships are starting to take on a more strategic role, not just as an entry point into the industry, but as a deliberate way of building leadership capability earlier and more effectively.
Tea Colaianni
Founder and Chair of WiHTL & Diversity in Retail
So, what’s changed in HTL and Retail, and why does this matter now?
Customer expectations have continued to evolve. Technology has reshaped service delivery. And operational leaders are expected to combine commercial judgement, digital awareness, and strong people leadership far earlier in their careers than before.
When I spoke with Tea, what came through clearly is just how much the context has shifted. Many of today’s leaders were developed in a more stable, pre-AI environment. What they are now being asked to lead through is fundamentally different. It requires digital fluency, confidence in interpreting data, and the ability to adapt continuously as operating conditions change.
AI and automation are becoming foundational to service delivery.
–Tea Colaianni
As Tea put it, AI and automation are no longer something on the horizon. They are already embedded in how these businesses operate, often moving faster than teams are being equipped to keep up.
At the same time, in many businesses, supervisors are stepping into leadership roles earlier than organisations traditionally planned, often without the preparation required. The result is a growing gap between the demands of leadership and the development pathways designed to prepare people for those responsibilities.
How Talent Is Entering the Industry Is Changing
For many years, HTL and retail businesses relied on a relatively predictable flow of graduates entering the industry through management programmes. That route provided structure to early leadership development and helped maintain a steady pipeline of future leaders.
The perception of university as a default pathway is changing.
– Tea Colaianni
However, with rising concerns around student debt and increasing scrutiny on the return of university education, more young people are questioning whether the traditional academic pathway is the right one for them.
As Tea put it:
The graduate pipeline that employers have historically relied on is no longer guaranteed as many young people are opting for debt free pathways
– Tea Colaianni
For boards and executive teams, this creates both a pipeline risk and a competitive opportunity.
When you remove financial barriers and redesign learning around real jobs, you unlock the potential of individuals who might never have seen themselves as future leaders in our industries. Inclusion then becomes a competitive advantage.
– Tea Colaianni
Apprenticeships can play a critical role here, not only as an alternative pathway, but as a more structured way of building a leadership pipeline.
Done well, they combine the lived experience these industries have always valued with structured development that builds commercial judgement, leadership capability, and strategic thinking from the outset.
Tea emphasised that embedding learning into real roles accelerates both confidence and capability in a way traditional pathways often cannot.
Why Apprenticeships Are Still Misunderstood
Apprenticeships are increasingly being used, and not just at entry level. Yet in many organisations, they are still not delivering the leadership impact they are capable of.
Too often, they sit within HR or compliance discussions, rather than being treated as part of a broader leadership and workforce strategy. As a result, they’re managed as programmes rather than used as a deliberate mechanism for building capability.
One of the biggest barriers is the complexity of the current apprenticeship system.
– Tea Colaianni
Tea pointed to complexity as a key barrier. Funding rules, standards, compliance requirements, and delivery structures can make apprenticeships feel overly bureaucratic, particularly for leaders focused on pace and performance.
That perception is often reinforced by programme design. Fixed durations and structured training models can feel misaligned with fast-moving operational environments.
As Tea described, the system is often out of sync with how businesses now operate. Skills need to evolve quickly, but training structures and standards have not always kept pace.
Senior leaders often want learning solutions that can be deployed quickly, scaled easily, and adapted to different roles. The current apprenticeship framework can make that harder because organisations must fit their needs into predefined standards and delivery models.
– Tea Colaianni
In reality, the challenge is not just the system itself, but how organisations choose to engage with it.
How to Design Apprenticeships to Develop Future Leaders
For apprenticeships to stand alongside university as a credible leadership pathway, they must go beyond building role-specific capability. They need to develop the commercial judgement, perspective, and adaptability that leadership roles now demand.
When apprentices are encouraged to question, suggest improvements and understand why decisions are made, they develop the mindset leaders need in a fast-moving sector
– Tea Colaianni
At their best, apprenticeships accelerate this by combining structured learning with real-world experience from the outset.
As Tea emphasised, their impact depends on how deliberately they are positioned.
Apprenticeship programmes enable employers to build resilient internal talent pipelines and develop the skills their organisations will depend on in the years ahead.
– Tea Colaianni
In practice, this requires organisations to focus on six key areas:
01
Treat apprenticeships as part of leadership strategy
If apprentices are viewed primarily as operational support, the development they receive will reflect that. When organisations instead position apprenticeships as a core part of their leadership strategy, it changes how programmes are designed, prioritised and measured.
As Tea highlighted, this is also a cultural signal.
When leaders demonstrate that they value non-traditional routes into the business, it reshapes organisational culture.
– Tea Colaianni
02
Build leadership capability from the outset
If apprenticeships are to develop future leaders, they need to focus early on the capabilities leadership roles actually require.
Commercial fluency:
Future leaders need earlier exposure to how the business really makes money, not just how their role operates.
Without this, organisations risk building leadership pipelines that are misaligned with how the business actually runs.
In HTL and Retail, commercial awareness is not theoretical, it is lived. Apprentices should be exposed early to the realities of margin management, occupancy rates, supply chain pressures, and customer lifetime value.
– Tea Colaianni
Cross-functional exposure:
Tea and I discussed the value of structured experience across operations, marketing, and finance. This broader perspective is critical in environments where leaders are expected to make decisions across increasingly complex and interdependent systems.
Real responsibility early on:
Leadership capability is built through doing, not observing. Giving apprentices meaningful, “safe-to-fail” responsibility develops judgement, resilience, and confidence far faster than classroom learning alone.
Giving apprentices ownership of real projects, whether improving guest experience scores or leading a small team during peak season, builds confidence and decision-making capability.
– Tea Colaianni
Digital and AI capability:
Tea and I discussed the value of structured experience across operations, marketing, and finance. This broader perspective is critical in environments where leaders are expected to make decisions across increasingly complex and interdependent systems.
The next five years will demand digital fluency, and confidence in using and interpreting data. But many teams lack the skills or training to use AI and automation tools effectively.
– Tea Colaianni
Judgement as the differentiator:
As technical knowledge becomes more accessible, judgement becomes the defining leadership capability.
As Tea highlighted, technology can support decision-making, but it cannot replicate the judgement that comes from actual experience. Leaders need to know not just how to use AI, but when to challenge it, particularly in environments where customer interaction, nuance, and real-time decision-making matter.
AI can generate textbook answers quickly, but it cannot replicate the human touch, the judgement that comes from navigating real situations in real environments.
– Tea Colaianni
03
Connect apprenticeships to leadership pipelines
If apprenticeships are to produce future leaders, they need to be explicit about how progression happens and where these individuals sit within the organisation’s future leadership bench.
Visible progression pathways:
Employees need to see from day one how an apprenticeship can take them to the next level. Organisations should map pathways from entry-level roles through to management and leadership positions.
– Tea Colaianni
Integration into talent and succession processes:
When leaders regularly review internal talent and see apprentices represented in those discussions, it signals that these pathways are not peripheral but are core to future leadership supply.
– Tea Colaianni
04
Make sponsorship part of the model
Apprenticeships do not translate into leadership pipelines by design alone. They depend on active leadership ownership.
When leaders treat apprenticeships as long-term capability investments, hold teams accountable for progression, and ensure apprentices are part of broader talent conversations, it shapes how individuals are supported, developed, and progressed.
Where apprenticeship schemes thrive, the CEO and executive team speak about them as strategic investments. They visit cohorts, mentor participants, and hold their direct reports accountable for progression outcomes. Being visible and ‘walking the walk’ changes everything.
– Tea Colaianni
Tea also drew a clear distinction between mentoring and sponsorship. Mentoring provides guidance. Sponsorship drives progression.
She highlights that its sponsorship – where senior leaders actively advocate for individuals in promotion and stretch opportunities – that accelerates movement into leadership roles.
05
Translate access into diverse leadership outcomes
Apprenticeships are often positioned as a tool for improving access and diversity. From a leadership perspective, access is only the starting point. Progression defines success.
Leaders need clear criteria for identifying potential that do not rely solely on confidence, style, or prior educational background. Structured assessment of behaviours such as curiosity, resilience and collaborative mindset can help surface talent that might otherwise be overlooked.
– Tea Colaianni
Tea also drew a clear distinction between mentoring and sponsorship. Mentoring provides guidance. Sponsorship drives progression.
She highlights that its sponsorship – where senior leaders actively advocate for individuals in promotion and stretch opportunities – that accelerates movement into leadership roles.
06
Measure progression into leadership roles
For apprenticeships to be taken seriously as a leadership strategy, organisations need to measure outcomes, not just participation.
Tea stressed that organisations often focus too heavily on participation metrics. In her view, what really matters is visibility on completion, progression, and long-term outcomes, without which apprenticeships risk remaining an entry-level diversity initiative rather than a true leadership pipeline.
This doesn’t just mean reporting but actually understanding whether apprenticeships are genuinely translating into leadership capability over time.
The Risk of a Missing Generation of Leaders
With more young people questioning the value of traditional university pathways, organisations face a structural risk if they fail to rethink how leadership capability is developed.
And without alternative routes that combine experience with structured development, the sector risks narrowing its future leadership pipeline.
More broadly, there is a real opportunity to invest in the thousands of young people who are currently outside the workforce. With the right incentives and support from Government, apprenticeships can create meaningful pathways into our industry, strengthening both capability and social mobility at the same time.
– Tea Colaianni
Apprenticeships offer a way to address this, providing a route that broadens access, strengthens capability, and builds leaders who understand the business from the ground up.
Organisations that overlook apprenticeships risk higher costs, weaker leadership pipelines, and missed access to funding, all while falling behind on capability, diversity and long-term resilience.
– Tea Colaianni
How Redgrave Helps Build Future-Ready Leadership Teams
At Redgrave, we work with founders, investors, and leadership teams across the sector to identify and develop the leaders who will shape its future.
If you’re thinking about how to build stronger leadership pipelines in hospitality, travel or leisure, I’d be very happy to exchange perspectives.
My thanks to Tea Colaianni for the thoughtful conversation and for sharing her perspective on how apprenticeships can help shape the next generation of leaders in our industries. Learn more about WiHTL’s great apprenticeship programme.
As Head of Redgrave’s Hospitality, Travel & Leisure practice, Imogen Seear partners with boards, investors and leadership teams to identify and develop senior talent across global markets, helping organisations build leadership teams capable of delivering long-term growth.
