2026: The Most Expensive Tech Debt You Haven’t Booked Yet
The investments you approve in 2026 will either make you agent-ready, or turn you into a high-friction supplier that agentic platforms quietly route around
Your 2026 roadmap is likely funding the next wave of stranded assets.
Most tech debt isn’t just old code. It’s structural.
It’s the “modern” platform you just bought that has an API, but requires a human to email support to get a token.
It’s the governance model that technically allows automation, but practically requires a human to click “Approve” for every exception.
It’s the data model that is optimised for human reporting, not machine reasoning.
We usually book tech debt as a line item for later. But in the agentic economy, this debt is existential.
If an external agent (buying on behalf of a customer) hits your friction, it doesn’t complain. It just goes to your competitor who has an API that actually works.
In Part 3 of this series, I breakdown:
Why your 2026 roadmap might be funding the next wave of stranded assets.
The “Agentic Test” for new investments: Does this increase or decrease our structural optionality?
How to stop buying “Performance Theatre” (nicer dashboards) and start buying leverage.
A challenge for this week:
Look at the biggest tech investment on your desk for 2026 and ask one question:
“If a third-party AI agent needed to use this system to buy from us without a human, could it?”
If the answer is no, you might be buying a legacy asset.
If you aren’t sure, hit reply (or DM me). I’m opening a few spots for “Red Pen” reviews to stress-test your 2026 roadmap before you sign the cheque.
Read the full analysis below. 👇
2026: The Most Expensive Tech Debt You Haven’t Booked Yet
Most leadership teams don’t experience tech debt as a line item. They experience it as:
growth that’s slower than it should be,
transformation that costs more and delivers less,
and “strategic platforms” nobody wants to touch.
Looking backwards, it’s easy to see how this happened:
big bets on systems that never really integrated,
operating models that hardened around stopgap processes,
AI and data projects that made slideware promises and operational headaches.
Looking forwards, 2026 is shaping up to be another big investment year:
refreshed digital and AI roadmaps,
new data and agent platforms,
consolidation of bloated SaaS stacks,
rethinking customer and employee journeys.
All of this is happening just as agentic interfaces start to emerge:
browsers and sidecars that scan dozens of sites and services at once,
orchestration layers that compare providers on speed, reliability, and friction,
domain-specific agent apps that sit between buyers and entire supply markets.
The question is simple:
Are you about to fund the foundations of your agentic future, or the next wave of stranded assets that external agents learn to avoid?
The invisible tech debt you are about to create
Tech debt is usually framed as:
old code,
unsupported systems,
delayed upgrades.
Over the next few years, a more structural form of tech debt will matter far more:
Operating models that are too rigid for agents to work inside.
Processes designed around manual control and human gatekeepers.Capabilities that external agents can’t easily consume.
Limited or inconsistent APIs, no real-time events, opaque pricing and SLAs.Governance models that assume a human in every loop.
Every decision treated as bespoke, every exception routed through committees.
You can modernise the front-end and still end up here.
In fact, many “modernisation” programmes accidentally increase this kind of debt:
multiple SaaS platforms with overlapping capabilities,
integration patterns that lock you into brittle, point-to-point dependencies,
data models optimised for reporting, not for real-time decisioning by agents.
On a slide, everything looks connected.
In reality, nothing moves without heavy manual effort.
To an external agent, the kind your customers will increasingly rely on, you show up as: slow, opaque, and hard to work with.
The agentic test for 2026 investments
If the cost of transactions, coordination, decisions, and actions, really does trend towards zero in the wider economy, then your internal and external transaction costs become the constraint.
The agentic test for any major 2026 investment is straightforward:
Does this reduce our internal transaction costs?
fewer approvals,
fewer handoffs,
fewer systems for the same outcome.
Does this make us easier for external agents to work with?
clear, well-documented APIs,
reliable events that reflect real-world state,
machine-readable pricing, SLAs, and constraints.
Does this increase or decrease our structural optionality?
can we re-route flows,
introduce new agents,
or swap out components without rewiring the whole organisation?
If an initiative fails that test, you’re likely buying performance theatre:
nicer dashboards,
more automation layered over broken systems,
but no real shift in how work flows inside, or how you present yourself to external agents.
That’s the kind of asset that looks great in a press release and painful when you realise that the better external agents simply stop choosing you.
How stranded assets will show up in the agentic economy
Stranded assets in this context won’t look like abandoned factories.
They’ll look like:
“modern” platforms nobody can integrate with cleanly,
processes that are too bespoke for agents to navigate,
data that is high-volume but low-context and unusable in real time.
As agentic interfaces mature, this will show up in conversations like:
“The customer’s automation keeps dropping us from its shortlist.”
“Our APIs technically exist, but external agents time out or get inconsistent states.”
“We’re being excluded from new agent-driven marketplaces because we can’t meet their integration bar.”
Meanwhile, the rest of the market will be:
exposing cleaner, composable capabilities,
letting agents negotiate, schedule, and transact directly,
reducing internal and external friction at the same time.
You’ll be stuck playing defence inside your own four walls while demand flows through lower-friction providers.
What to do before you sign the 2026 cheques
This is not an argument to freeze investment. It’s an argument to change how you make investment decisions.
Three practical moves before you sign:
1. Add an “agent-readiness” lens to your business cases
For every major initiative, include a simple section:
Internal: How will this reduce internal friction and expose clearer states and capabilities?
External: How will this make it easier for external agents to discover, compare, and consume what we do?
Be specific:
Which APIs or events will exist that don’t exist today?
What will a third-party agent be able to do end-to-end without human intervention?
How will we measure “friction” from an external agent’s perspective?
If the answers are vague, or buried under generic promises, press harder.
2. Tie platform decisions to ecosystem decisions
Don’t treat platforms as neutral infrastructure.
Every platform decision is:
an operating model decision (how work flows internally), and
an ecosystem decision (how easy it is for others to plug into you).
Make that explicit:
When you buy a new system, define not just the internal journey, but the external touchpoints and contracts.
When you redesign a process, define which capabilities will be callable by external agents, under what guardrails.
When you introduce AI, define where it sits relative to external agent flows: will it broker, respond, verify, or all three?
3. Reserve capacity for simplification, not just addition
Most roadmaps are biased towards adding:
more data sources,
more use cases,
more capabilities.
Make simplification a funded workstream, not an afterthought:
consolidate overlapping tools,
retire zombie processes,
reduce configuration and policy sprawl.
Every simplification you deliver now reduces the cost of integrating with agentic platforms later – and makes you a more attractive node in their networks.
A different question for your board
Instead of asking “How much are we investing in AI and digital in 2026?”, ask:
“Of the money we’re investing in 2026, how much is honestly reducing internal transaction costs, increasing our readiness for internal and external agents, and decreasing our structural tech debt?”
If you can’t answer that clearly, you’re flying blind.
The agentic economy won’t reward the organisations that spend the most on AI slideware.
It will reward the ones that:
consciously design for lower internal friction,
expose capabilities that external agents can reliably consume,
and treat every 2026 investment as either a step towards that future – or a cost they refuse to carry.
You don’t control the pace of model innovation.
You do control whether you turn 2026 into the year you quietly funded your next wave of stranded assets, or the year you started to re-architect for a world where agents, not just humans, decide who gets the work.