Technology Due Diligence: What Buyers Actually Look For in 2026

In every PE transaction I've worked on, technology has been the domain where buyers find the risk that management didn't know they had. Not because portco leadership teams are careless, but because the questions buyers ask are increasingly specific, and the answers require preparation. Here's a structured view of what a buyer's technology due diligence team actually scrutinises in 2026, and how portco CEOs and CFOs can prepare 12–18 months before the process begins.

Why technology DD matters more than it used to

Technology used to be a checkbox item in buyer due diligence. Assets on the balance sheet, contracts in place, no immediate crises, signed off in a few days by a junior on the deal team.

That has changed. Buyers now treat technology as a value driver or a value risk, and the DD process reflects that. A specialist technology DD firm typically spends two to four weeks probing the estate, interviewing management, and looking specifically for the risks that could reduce enterprise value or delay integration.

The reasons are worth naming. First, businesses now run on their technology in a way that they didn't ten years ago. A SaaS-heavy operating model means the vendor stack IS the business. Second, buyers have been burned. Undisclosed technical debt, single-person dependencies, and unmanaged supplier risk have caused enough post-close surprises that buyers now expect to find them proactively. Third, AI has entered the DD conversation. Any credible business over a certain size is now expected to have a defensible position on it.

The consequence for portcos is straightforward: technology DD is no longer a formality, and the risks it surfaces are increasingly priced into the transaction: either as valuation discounts, remediation escrows, or delayed close.

The six pillars buyers scrutinise

Across recent transactions, buyer technology DD tends to concentrate on six specific areas. Not every buyer covers all six with the same depth, but a comprehensive DD process will touch all of them. The pillars below are the same six used in the DD Readiness Scorecard we publish, not by coincidence, but because the scorecard was structured to mirror the questions buyers actually ask.

Pillar 1 — Technology Landscape and System Architecture

Buyers want to understand the estate: what the systems are, how they relate to each other, who owns them, and what happens when something breaks. Specifically, they probe for:

• A current, defensible inventory of business-critical systems, including ownership and purpose
• Documented architecture diagrams that show how the core systems connect
• Clarity on which system is the source of truth for customer, product, and financial data
• Evidence of active simplification, including retirement of legacy systems and consolidation of overlapping tools, rather than organic growth of the estate
• Named single-points-of-failure and the plans to mitigate them

The absence of any of these is not fatal, but the pattern matters. A buyer's DD team will read the estate documentation before the interviews. If it's incomplete or hard to interpret without verbal explanation, the follow-up questions get sharper.

Pillar 2 — Integration and Automation

The integration layer is where most technical debt hides. It's the plumbing that keeps operations flowing between systems (quote to cash, order to invoice, customer to CRM), and it's usually built organically over years by people who left the business two managers ago.

Buyers probe for:

• Documentation of all business-critical integrations — data flows, transformation logic, error-handling rules
• Knowledge of which integrations would cause immediate business disruption if they failed
• Active monitoring, alerting, and investigation of integration errors, rather than reactive fire-fighting when a user complains
• Named owners for each critical integration or automation, with a clear escalation path
• Version control and change management on the integration layer

This pillar is where I see the most common surprise. Portco leadership teams often don't realise how much of the business runs on informal Zapier flows, undocumented middleware, or a single engineer's shell scripts. Buyer DD surfaces this fast.

Pillar 3 — Governance, Decision-Making, and Ownership

Buyers care less about whether you have a governance framework and more about whether it reflects how decisions actually get made. The two are often different.

Specifically, they probe for:

• A defined technology decision-making process, with clarity on who approves what
• Total annual technology spend visibility across the business — the central IT budget plus every departmental SaaS purchase
• Whether new technology purchases are evaluated centrally or bought independently by departments (the "shadow IT" question)
• Whether technology has a strategic voice at leadership level, or is treated purely as a cost centre
• Regular executive review of technology risks with clear ownership and resolution timelines

A common finding: businesses spend materially more on technology than they think because they're only tracking the IT budget. Marketing has its own SaaS stack, Sales has HubSpot and Salesforce and Gong, Finance has three reporting tools, and Product has a dozen developer subscriptions. When a buyer's DD team asks for total technology spend, the number is usually higher than management expected. The discovery process itself signals governance immaturity.

Pillar 4 — Security, Access, and Compliance

The policy stack is the easy target, but it's also the one that gets refreshed most often, so buyers now look beyond the documents. They want to see the reality.

Specifically:

• Are the core policies (Information Security, Incident Management, Third Party Risk, AI Usage) documented, current, and actually applied in practice?
• Is admin and privileged access reviewed regularly? Is there a defensible process for granting and revoking access?
• Is there a documented and rehearsed incident response process, with named responsibilities?
• Is offboarding of leavers structured and prompt, with all access removed within an audited timeframe?
• Is device management (laptops, mobiles, admin machines) coordinated centrally, rather than left to individuals?
• Can the business demonstrate compliance with the security expectations of its customers, suppliers, and where relevant, regulators?

A short policy stack that's actually applied is more defensible than a long one that isn't. Buyers can tell the difference within one or two interviews.

Pillar 5 — Training, Adoption, and Ways of Working

This is the pillar most under-prepared for because it feels soft. It's rising up the buyer's list. The question underneath it is: does the technology you deployed actually deliver the value that was assumed when it was bought?

Specifically:

• Does onboarding embed core systems consistently, so that new joiners are productive quickly?
• Is there structured, current training content for the systems the business relies on, and is it actually used?
• Is system adoption consistent across teams, or do you see wide variability in how (or whether) tools are used?
• Are communication tools rationalised, with clear defaults for where different types of conversation happen, or fragmented across Slack, Teams, email, WhatsApp, and half a dozen other places?
• Do you have visibility of adoption metrics: are the tools you deployed actually being used?

This is the pillar where the human dimension matters most. Programmes don't fail because of technology; they fail because of misaligned people, cultural friction, and change no one owns. That's true during transformation, and it's equally true in the aftermath: the residual state a buyer inherits.

Pillar 6 — AI Readiness and Opportunity

Two years ago, AI wasn't a standard DD pillar. Today it is. Buyers ask about it in almost every process, and the absence of a defensible position is now itself a signal: of management maturity, of forward-thinking, or the absence of it.

Specifically, buyers probe for:

• A documented AI Usage Policy that has been reviewed and approved by leadership
• Clear guidance for employees on which AI tools they can use, for what purposes, and with what data
• Specific AI use cases identified for the business, with commercial value quantified and named owners
• Data readiness for AI adoption — accessible, structured, and of sufficient quality to be useful
• Any AI-enabled improvements already delivered, with documented outcomes
• The ability to give a buyer a defensible answer to the question: what is your position on AI, and what value is it creating?

The right answer here is rarely a 47-slide AI strategy deck. Two or three pragmatic AI wins with named owners, a defensible policy, and a clear-eyed view of what's realistic in the next 12 months beats a comprehensive strategy that has never left the shared drive.

When to start preparing

The pragmatic window is 12–18 months before an expected transaction. Earlier is stronger.

Why 12–18 months? Because most of the risks buyers surface in DD are solvable. Not on the timeline the process demands. Capability transfer takes 8–12 weeks minimum. Policy refresh, review cycles, and board approval take 2–3 months. Supplier renegotiation takes 3–6 months. Architecture clarity, when it requires actual work rather than just documentation, takes longer still.

Businesses that start preparation in the 12–18 month window typically have time to close the risks that would trigger valuation discounts. Businesses that start under 6 months out are usually in damage-control mode: evidencing what exists defensibly, preparing management narratives, and hoping the buyer's DD team doesn't push too hard on the areas that couldn't be fixed in time.

The self-assessment starting point

If you're reading this and thinking about your own portfolio or portco, the fastest way to get a defensible view is a structured self-assessment against the same six pillars.

We publish a Technology DD Readiness Scorecard: a 30-question self-assessment covering all six pillars, with scoring bands that indicate whether the business is Strong (120–150), Adequate (90–119), At Risk (60–89), or Urgent (below 60). It takes about 20 minutes to complete honestly, and it's freely shareable across your network. No lead capture, no obligation.

The scorecard is designed to be useful across three audiences: portco CEOs and CFOs as an honest self-assessment, PE Operating Partners as a portfolio-level diagnostic, and recruiters and advisers as a conversation starter with clients considering interim CTO/CIO engagement.

What happens after the scorecard

If the scorecard surfaces risks you weren't aware of, or confirms concerns you already had, there are three common next steps:

A focused DD readiness assessment, a 3-to-5-day engagement scored against the specific questions buyers ask. Outputs a prioritised remediation plan with named owners and delivery horizons. Best for businesses within 12–18 months of a transaction.

A full technology audit, a broader 2-to-4-week review across the six pillars, going deeper than the DD-specific variant. Best for businesses further from exit, or those where the broader picture matters more than the specific transaction lens.

Interim technology leadership, where the risks identified need active closure over 3–12 months. Best for businesses without permanent CTO/CIO capacity, or where a defined mandate can be shaped as an interim engagement.

All three have the same underlying method and structure. What differs is scope, depth, and duration.

The through-line

Buyer technology due diligence in 2026 is more structured, more specific, and less forgiving than it was five years ago. The good news: nearly every risk buyers surface is solvable if identified 12–18 months out. The bad news: portco leadership teams often don't realise how the questions have evolved until the process begins and the surprises start.

The mitigation is preparation. Structured self-assessment, honest scoring, and a phased remediation plan starting well before buyer engagement. Not glamorous, not expensive, but the single most reliable way to protect enterprise value at exit.

James Scott is the founder of The Clarity Partnership, an interim and fractional practice for PE-backed and privately-owned businesses at inflection points. Nearly thirty years of transformation, integration, and enterprise programme delivery across Unilever, Gravity Media, Samsung, General Mills, and PE-backed portfolio companies.