.jpg)
It's a question most employers can answer for this year, and very few can answer with confidence for the next five. Our 2026 snapshot survey of 482 contractors and hiring managers points to a succession gap building quietly beneath the day-to-day scramble to recruit, one that recruitment alone won't fix.
The middle is where it hurts most
Ask hiring managers which roles are hardest to fill, and the answer isn't the most senior positions or the entry-level ones. It's the middle. Middle management is the single hardest level to source, cited well ahead of both senior management and junior roles.
That's the layer that quietly holds delivery together: experienced enough to run complex work independently, senior enough to make decisions, and close enough to the ground to mentor the people coming up behind them. When it's thin, everything above and below it feels the strain and around 88% of employers already find specialist contractors difficult to source.
The pipeline isn't ready to step up
A shortage of experienced people would be manageable if there were a strong pipeline behind them. There often isn't. More than a quarter of hiring managers (28%) report a significant gap before early-career and mid-level contractors are ready to move into senior or management roles.
At the same time, the contractor workforce is ageing. In some sectors, such as town planning, well over half of contractors are in the later stages of their careers, with only a small fraction early in theirs. More people are approaching retirement than are coming through to replace them and the experience that makes a good middle manager takes years to build.
Why recruitment alone won't solve it
The instinct is to hire the gap away. But if every organisation is competing for the same shrinking pool of experienced specialists, recruitment becomes a bidding war that raises cost without increasing supply. And when a late-career contractor leaves, they take scarce specialist and leadership knowledge with them knowledge no job advert can replace.
James Fernandes, Co-Founder and Managing Director at Carrington West, puts it directly: "The hardest roles to fill are almost always in that experienced middle layer, the people who hold projects together and bring everyone around them on. When they retire, they take years of knowledge with them, and you can't simply recruit that back overnight. The employers who come through this well will be the ones planning for it now: identifying where critical knowledge sits and giving their mid-level people a clear path to grow into those roles before the gap opens up."
Start before the gap opens
Succession planning rarely feels urgent until it's too late. The organisations best placed for the next few years are treating it as a live priority now, mapping where critical knowledge sits, identifying who could step up, and building deliberate pathways for early and mid-level contractors to develop before senior people leave.
It's a multi-year task, not a quick fix. But it's the only reliable answer to the question in the headline.
Our 2026 snapshot survey explores succession risk and the ageing workforce, alongside four other culture shifts reshaping the UK contract workforce. Download the report to see the full findings.