Why Leadership Pipelines Can’t Wait for the “Right Time”

If you’ve been in hospitality long enough, you’ve probably heard some version of this: we’ll focus on leadership development once things settle down.

Once the peak period passes. Once recruitment stabilises. Once budgets feel less tight. Once we catch our breath.

But here’s what I’ve learned after years in this industry. There is no “right time”. There is only now, under whatever pressure you’re currently operating in.

Hospitality doesn’t calm down. It shifts. And if we keep postponing leadership development until conditions are perfect, we’ll be waiting forever.

What concerns me more is who carries the cost of that delay. And most of the time, it’s Gen X.

Gen X leaders are sitting right in the middle of our organisations. They are translating strategy into service. They are holding culture together on the floor. They are managing up, managing down, and often managing their own exhaustion quietly in the background.

They didn’t grow up with leadership frameworks or development pathways. Most of them learned by doing. By getting it wrong. By absorbing pressure and figuring it out without much guidance. In many cases, they came through workplaces where you didn’t question behaviour. You just got on with it.

Now they are expected to mentor the next generation while still delivering results in an industry that is faster, louder, and more scrutinised than ever.

At the same time, many of them are raising families or supporting ageing parents. They’re dealing with mortgages, cost of living pressures, and the emotional load that comes with being responsible both at work and at home. I often call them the “club sandwich generation” because they are layered with responsibility. They are holding A LOT.

And yet, when we talk about retention, we rarely talk about them.

We talk about attracting young talent. We talk about keeping Millennials and Gen Z engaged. All important conversations. But if we don’t build a leadership pipeline beneath our Gen X leaders, we are effectively asking them to carry the entire weight of culture and capability on their own.

That is not sustainable.

Leadership pipelines are not about succession charts or fancy HR strategies. They are about making sure that influence, decision making, and people capability are being built early and consistently, not only when someone resigns.

Waiting for the right time usually results in one of two things. We promote someone because we need to fill a gap, not because they are ready. Or we lose someone with real potential because they can’t see a future for themselves.

Neither option supports retention.

There is also a misconception that leadership development requires calm conditions. It doesn’t. In fact, if leadership capability only works when things are easy, it isn’t leadership capability at all.

Strong pipelines are built alongside pressure. They are built during busy seasons, not after them. They start when we ask better questions about the people already in our teams. Who is influencing others positively? Who takes ownership beyond their job description? Who seeks feedback instead of avoiding it?

Leadership development begins long before a title change.

And here is something I feel strongly about. When no one ever leaves an organisation, it’s not always stability. Sometimes it’s stagnation. Healthy organisations expect movement. They prepare for it. They see leadership as something that flows through the organisation, not something concentrated in a few overburdened individuals.

Research from Gallup consistently shows how much impact managers have on engagement. Engagement influences retention. Retention shapes culture. Culture shapes customer experience. It’s all connected. When we neglect the development of our middle leaders, we are not just risking future gaps. We are weakening the very part of the organisation that stabilises everything else.

Gen X leaders are often the calm presence in the room. They know how to read people. They know how to hold steady under pressure. But many of them were never formally developed, and now we expect them to develop everyone else.

If we want retention to improve in hospitality, we need to stop treating leadership development as something we will “get to”. We need to build capability despite the pressure, not after it.

That means identifying potential early. It means giving emerging leaders responsibility before they feel completely ready. It means allowing mistakes without humiliation. It means supporting middle managers so they are not mentoring in isolation.

When leadership is developed continuously, promotions feel like progression rather than survival. Transitions feel supported instead of chaotic. Gen X leaders are not left carrying the entire mentoring load alone. And younger team members can actually see a pathway forward.

So the real question isn’t whether now is the right time to build a leadership pipeline.

The question is whether you can afford not to.

Because hospitality will always be demanding. People will always move on. Pressure will always exist. The organisations that thrive are not the ones that waited for perfect conditions. They are the ones that chose to build leadership capability while the doors were open and service was in full swing.

If retention matters, the pipeline cannot wait. Reach out to discuss how Middle Management Movement can support your leaders (current and emerging) - TODAY!