Decision guides
Short answers to technology decisions I'm often asked about, with what to check before you decide.
- The system is live and people still won't use it. What do we do?
Find out what the system makes harder for the people avoiding it, because resistance usually points at a real problem.
- How far should we let AI agents act and write code unsupervised?
Set an agent's authority by the consequence and reversibility of what it can do.
- Should we let AI influence credit, clinical or safety decisions?
Define first what the AI is allowed to do: present information, draft for a person, or decide.
- Which AI models should we use, and can we afford them at scale?
Settle model choices with a test on your own evaluation set and real traffic, measuring quality and cost together by request type.
- Our AI pilot or product is not delivering. Fix, scale or drop it?
Find out why it stopped short before you decide on the product, the vendor or the team.
- Should our startup add AI, and what do we keep if providers copy it?
Start with a customer task and a buying decision, then build only if the evidence says it matters.
- How should leadership set AI direction and oversight without writing a blank check?
Approve the direction with conditions: a short list of problems worth solving, an owner for each AI decision, and evidence before more money.
- Should we trust a vendor's AI accuracy claim before we sign?
Not yet.
- What should an AI vendor contract say about data, liability and model changes?
Require terms on four things: use of your data, visible performance, what happens when the model fails or degrades, and what you own at exit.
- The project delivered, but the promised savings never appeared. What happened?
Projects often succeed on delivery and fail on the step from delivered system to changed cost, which nobody owned.
- How does the board know our cyber protection works beyond the paperwork?
Ask for a few measures the board can track every quarter, backed by evidence that the controls actually operate.
- How should our board oversee technology without being technical?
Ask for a short set of facts in plain terms: critical systems, major projects, key vendors, security posture and recent incidents.
- Should we build this ourselves or buy a product?
Build only what makes you different and what you can fund and staff for the system's whole life.
- Our data would be hosted abroad or in the cloud. What must we verify?
Know where the data is stored, backed up and supported from, who can read it, whether it is used beyond your service, and how you get it back.
- Should we move this system to the cloud, and what will it really cost?
Decide per system, rather than one answer for everything.
- The contract keeps growing through change orders. How do we control the spend?
Change orders grow when the vendor is the only party who can price and build changes, and when nobody sees the total.
- Security and the business are deadlocked on a project. Who decides, and how?
Put both sides on the same page: one list of what the first version does, the risks and the controls each needs, with the reason for each.
- The security budget request is large. What should we fund first?
Fund the basics that stop most attacks and the recovery that limits the rest: strong login, patched systems, limited access, backups that restore, and a plan everyone knows.
- A vendor or partner wants our data. What should we give, and how?
Keep ownership of your data and license the other party only what its service needs, for a defined purpose and period, with return or deletion at exit.
- Nobody trusts our data. New data platform or fix the basics first?
Fix the basics first in most cases: agreed definitions, an owner with authority over each source, and a traceable path from every number to its source.
- A large enterprise customer wants terms we can't easily meet. What should we agree?
Measure what your product can actually do, then commit to that plus a margin.
- How do we choose between ERP offers when nobody in-house can judge them?
Agree the criteria first.
- Our ERP vendor is forcing a cloud move or new version. Should we follow?
Treat the vendor's date as one input rather than the decision.
- How do we evaluate charging platforms and sites before we commit?
Judge charging commitments on evidence you can test: protocol support checked on your own chargers, connection capacity under its documented conditions, and service outcomes.
- Systems are making errors. Should we pause the rollout or push on?
Cap growth at what you can handle correctly today, and fix the cause before you copy it to the next site, customer or process.
- The vendor says we are ready to go live. Are we?
Readiness is a set of tests your organization runs, with the vendor's report as one input.
- The group wants to centralize or split our IT. What should we require?
Treat a group IT change as a contract with you as the customer.
- Large consultancy or small specialist: how do we choose an implementation partner?
Choose the people who will actually do the work and the terms that keep them there, whichever firm they belong to.
- After an outage or breach, how do we know the response was adequate?
Ask for evidence on how it got in or broke, why detection took that long, and why recovery took that long.
- When do we need an independent technology review, and is it truly independent?
Commission one when a finding would matter and the usual sources have a stake in the answer.
- Predictive maintenance and digital twins: will they change decisions on the plant?
Start from the plant decisions the system must change, with a named owner and a real consequence.
- Should we bring this in-house or hand it to an outsourcing partner?
Keep in-house the people who hold knowledge and judgment: architecture, product ownership, and customer and operational knowledge.
- Is it time to hire a CIO or CTO, and how do we choose?
Hire when technology decisions now shape the business and nobody can own them.
- Upgrade, modernize or replace our legacy system: how do we decide?
Start with what specifically fails, at what load, with evidence.
- We are asked to approve a long-term technology contract. What should we ask first?
Ask four things: what was compared, what you take with you at exit, what the vendor owes if it underperforms, and the full cost over the term.
- After the merger we still run two sets of systems. What now?
Go back to the savings list and ask which savings actually need systems integration.
- How do we keep control when we outsource IT or operations?
Keep the knowledge, the data and the right to leave, and measure the provider on the outcomes your customers and regulator care about.
- Our program is behind plan. Should we continue, change scope, pause or stop?
Decide on the remaining work and what it is worth, and leave money already spent out of it.
- The program reports on track. How do we verify that independently?
Ask for evidence instead of status: what was tested and accepted, what was spent against plan, and what the next milestone needs to pass.
- What should a public body require from framework and tender suppliers?
Make the order define what the framework or tender leaves open: deliverables and acceptance, named staff, milestones, data and exit for this system.
- The ministry wants a digital service fast. What must we insist on?
Commit to a first version you can deliver on the date, with the rest conditional.
- Could we keep operating if a critical system or provider failed?
Judge readiness on tested recovery of your most critical services, measured in hours, under realistic conditions.
- The vendor wants a share of revenue or exclusivity. Is it a good deal?
Price the deal at your growth plan over the full term and compare it with owning or licensing.
- Do we need new software, or should we fix how we work first?
Find where the cost or delay actually comes from before you choose a tool.
- Software and cloud costs keep rising at renewal. What are our options?
Start from what you actually use, measured by product or workload.
- Do we really own the software and technology rights we depend on?
Map each system the business needs to operate to the evidence that you own it or may keep using it.
- One suite or specialist products: which serves us better?
Decide on the work rather than the vendor count.
- Before we invest or acquire, how do we check the technology is real?
Sort the claims into what runs for paying customers, what is built but untested, and what is planned.
- IT sent a large budget request. How do we judge whether it is right?
Ask for the request split into keeping existing systems running, obligations such as security and regulation, and new projects.
- We are bidding with technology commitments. What should we check first?
Check the delivery plan behind each technology commitment: who delivers, on what evidence, with what fallback, and what the penalties could cost.
- A technology dispute may end in litigation. How strong is our technical position?
Get an independent technical picture before the legal strategy is fixed.
- How do we write requirements we can test, and accept delivery on evidence?
Write each requirement with the test that would pass or fail it, and score bids on demonstrations with your own data.
- How much access should vendors have to our networks and control systems?
Start with an inventory of who connects, to what and why, and remove the access nobody can justify.
- Our traceability failed an audit. Fix the system or the supply chain data?
Find where the trace broke before you buy or replace anything.
- The vendor says switching is too hard. Should we renew, renegotiate or leave?
Test the switching claim before you accept it.
- Our key vendor or developer may disappear. How do we protect the company?
Secure what you're entitled to now: code or configuration, documentation, data, environments and credentials, under the company's control.
- The vendor guarantees savings or uptime. Does the guarantee cover what matters?
A guarantee is worth what its conditions allow.
- How do we compare technology vendors fairly when everyone has a favorite?
Write the criteria before anyone assesses a vendor, then test every candidate the same way on your own data and real conditions.
- The vendor and our team blame each other. Who is right?
Usually each side shows only the half of the evidence that clears it.
- Vendor upgrades and model changes keep breaking things. How do we control them?
Breaks usually come from untested interfaces, reports and behavior rather than from the upgrade itself, so change what you test and with which data.