I’ve stood at more airport gates than I care to admit, watching the same moment unfold.
Most recently on a trip to the US, I arrived with a confirmed seat, boarding pass in hand, everything aligned. Then came the announcement no frequent flyer ever wants to hear: “Sorry, we’ve overbooked this flight.”
A 300 seat plane. 340 passengers. Everyone with a valid ticket. Everyone expecting to travel. And yet, in that moment, some people simply are not getting on.
What follows is never chaotic in the way you might expect. It is structured. Familiar. Almost rehearsed. Gate agents negotiating. Volunteers being asked to step aside. Upgrades quietly offered. Standbys reshuffled. A system optimising itself in real time while people absorb the consequences.
No one is shocked. That is the strange part. Everyone knows how it ends, even as it unfolds.
This is exactly what the Ambition–Reality Trap looks like in transformation. Major corporates and organisations investing in change that go through the same dance every year.
There is nothing subtle about the Ambition–Reality Trap. It doesn’t creep in quietly. It shows up like an overbooked flight.
Not because people don’t care. Because the system rewards promise over proof.
The Annual Planning Race
This dynamic almost always starts in the annual planning cycle.
What should be a disciplined exercise in prioritisation becomes a boarding gate under pressure. A finite pool of funding. Multiple strategic narratives. Every executive making the case for why their initiative deserves a seat on the plane.
I’ve run these cycles globally and advised or sat through countless more. The conditions are almost perfectly designed to create overbooking:
- A fixed pool of money
- Competing priorities
- Compressed timelines
- Variable data and confidence levels
- Decisions shaped as much by influence as by evidence
Business cases become tools to win, not to inform. Commitments are made before the full picture is understood. Numbers are stretched, shaved, and negotiated until decisions land. A lot of the decisions live in the corridors of these organisations.
Everyone gets a boarding pass often with invisible conditions of entry. Very few are told they aren’t getting on the plan at the start.
The Overpromise Zone
As pressure builds, the same questions come every time:
- How fast can we do this?
- What will it cost?
- Can you commit?
Teams are forced to answer before they are ready. Complexity that would take months to understand is compressed into weeks. Uncertainty is pushed aside in favour of momentum.
And so they comply. Not because they are reckless. Because the system leaves no room to say, we don’t know yet. They are forced to into a corner to try and get a seat on the plane.
That pressure does create movement. But it also locks in assumptions that haven’t been tested. And this is where overbooking is locked in.
The Stretch–Cut–Hope Dynamic
Once funding starts to land, the dynamic intensifies.
Give everyone a stretch.
Apply a haircut.
Fund less. Deliver the same.
Now you have more initiatives than capacity, all starting at once, all competing for the same constrained resources. Without enough money to delivery. To use a different analogy we just entered The Hunger Games
Teams look for support from functions that are already full.
Leaders cannot scale capacity due to headcount constraints. The system begins to strain immediately.
What follows is predictable. Bottlenecks. Stop-start delivery. Exhaustion. A surge of activity at the same points in the year, followed by slowdowns elsewhere and bizarrely often underspend which no-one understands but common due to the planning cycles itself creating a slow down often for months.
And then the inevitable question:
Why can’t we deliver?
This Is a System Problem
This is not about effort. Or intent. It is the system working exactly as designed. Every actor is behaving rationally within it:
- CFOs push for cost discipline
- Vendors compete to win work
- Teams try to meet expectations with incomplete information or not enough cash in the first place
- Project managers commit to timelines tied to funding cycles
- Leaders balance ambition with optics
- Executives are measured on outcomes, not feasibility
And at the centre, the organisation commits to more than it can absorb or deliver.
No-one has a clear view of total demand versus real capacity. So the overbooking continues.
The Invisible Maths
Ironically, I once worked with a major international airline to help them step back and do the maths.
They were committing to roughly four times more change than they could realistically deliver with the people they had.
That is not unusual.
Look closer in most organisations and you will find: teams oversubscribed many times over; critical digital and data capabilities saturated; operational areas hit at the worst possible moments; and delivery plans that assume capacity that does not exist. Yet the commitments stand.
Just like the flight.
Everyone Can See It
Most people can feel it. They can see it. They can predict how it will play out. The quiet reshuffling. The trade-offs. The initiatives that slip. The ones that never quite leave the ground.
And yet no one calls it at the start. Because by then, everyone already has a ticket.
So how do you actually solve the Ambition–Reality Trap?
It is not a simple problem, because it is not caused by one decision point. It is the accumulation of many small optimisms that harden into commitments before anyone truly understands what delivery will require.
But if you step back and look at where the pressure actually shows up, it is not at the point of funding approval. It is immediately after.
Once money is allocated, whether as seed funding, full funding, or continuation funding, the system often assumes the work is now “set.”
Funding must be treated for what it really is a hypothesis. A belief that a certain level of investment can achieve a defined outcome. And like any hypothesis, it should be tested continuously.
If the funding cannot deliver the outcome, then something has to give. Scope. Time. Ambition. Those trade offs should be surfaced early, not buried until it is too late. So in reality, this is exactly the moment where the most important question should be asked again: what is actually doable?
That is where I think the shift needs to happen.
The sponsor role becomes critical here. Not as an approver of status updates, but as the person who actively forces a re-evaluation of reality once funding has been assigned. What is genuinely achievable with what we now know? What assumptions have changed? What did we not understand at the point of commitment?
I am a strong believer in early do-ability assessments. Not as a one-off exercise, but as a structured reset of vision, roadmap, and expectations once delivery begins to meet reality. This is the principle behind approaches like Jumpstart, where the goal is not to defend the plan, but to re-test and realign against what is actually possible.
The key shift is this. Stop treating delivery as the execution of a fixed plan, and start treating it as a continuous confidence building process.
At each stage, ask simple but uncomfortable questions. How much do we really know now. What has changed. What would need to be true for this to succeed. And most importantly, how confident are we really in the shape of delivery ahead.
Not once, but repeatedly.
Because confidence is not a starting condition. It is something you earn through evidence.
Calling all Sponsors
Sponsors then need to play a more active role in surfacing trade-offs early. If something is not achievable within the envelope, that needs to be visible quickly, not after months of sunk effort. That means being willing to reshape scope, extend timelines, or reset expectations rather than silently absorbing risk into delivery teams.
And at executive level, there needs to be a different expectation set from the outset. Not that plans will be perfect once funding is approved, but that they will be wrong in important ways once delivery begins. That is not failure, it is reality.
Which means governance should not just track progress. It should continuously test whether the original assumptions still hold. Not to penalise teams, but to actively recalibrate scope, sequencing, and expectations based on what is now known.
Because the real problem is not ambition. It is the lack of structured reality injection after ambition has been set.
A final thought
If there is one shift that matters most, it is this. Build systems that continuously re-ground delivery in reality after the plan has been approved, rather than assuming the plan was ever fully real in the first place.