Technology Vendor Selection Advice from Experienced CTOs

Selection supports the purchase decision: requirements, a shortlist, evidence and a recommendation. IT vendor management covers performance against the contract, spend, risk and renewal after signing. The two connect when selection criteria become the yardsticks you manage against, so write criteria you can assess later. Reopen selection at renewal or when your use changes materially.

One workflow, current baseline, candidate products and plans, material requirements, permitted data, a common cost horizon, acceptance reviewers and an exit owner.

Include licenses and usage, but also preparation, source checking, correction, repeated review, integration, training, support and maintenance. Show setup and migration separately from recurring operation. Include the effort to leave, restore a manual path or transfer to another provider.

Use the same workload and time horizon across candidates. Distinguish existing committed spend from incremental or genuinely avoidable spend. Mark unestimated exit work as unknown and use your own workload baseline.

Where AI is involved, compare accepted outputs and full review effort—not drafting time alone. Keep elapsed waiting time distinct from active person-time. The finance owner in your organization accepts the cost assumptions and their interpretation.

Keep product, plan, configuration and evidence date attached to findings. Separate supplier claims, documented scope, authorized observations and an accepting owner's decision. Unknown means the requirement remains unestablished.

Data rights: establish permitted submission, reuse, storage, export and downstream use for the actual product and plan; route contractual interpretation to qualified owners.

Acceptance: define useful output and required support, then evaluate permitted ordinary and difficult cases with the responsible process, domain and security owners.

Exit: identify sources, outputs, review history, templates, settings and custom work the receiving team needs, together with usable formats, rights, migration dependencies and continuing access.

Keep essential rights and access conditions explicit. For the detailed AI-specific questions, use the AI vendor due diligence checklist.

Treat your current route as Option C and ask what a candidate must show to beat it. If a current tool meets the requirement through straightforward configuration, test that route first. If the gap is narrow, consider a bounded integration or configuration first. Agree who configures, operates and supports any combination.

For your existing architecture, use technology assessment; for the wider commitment and roadmap, use CTO consulting. If the tool is an AI workflow, first decide whether the workflow is ready for a pilot; see AI readiness.

Your organization. The recommendation memo, observed evaluation result and accepted purchasing conditions remain distinct records.

Ask any provider, including an introducer, how it is compensated and about relationships with candidates or implementation providers. Resolve material interests before relying on a recommendation; disclosure alone does not resolve a conflict.

Before agreeing the engagement, ask about current or past supplier relationships and implementation interests. If a proposed expert has worked for or with a candidate supplier, ask them to say so and how it would be handled.

The experience shown, from Jerome MacGillivray's profile, is an attributed adjacent delivery and due-diligence contribution. Ask what the proposed expert personally examined, recommended and owned in a comparable selection.

Agree one output, one team and the decision the review must support. Candidate count, systems and data flows touched, requirement clarity, acceptance owners, documentation versus authorized testing, available rights/exit evidence and the handover needed determine scope. Timing and commercial terms follow the agreed contribution.

Agree documentation review, evaluation design, test execution and handover separately from procurement, implementation and adoption support. Expert participation, scope and commercial terms are confirmed for the actual inquiry.

Procurement, implementation, contract interpretation and specialist domain conclusions have separate owners and scopes. A review memo grants neither purchase authority nor permission to submit confidential data. Grand Rounds is an initiative of Dinarys, and a conversation may lead to cooperation with Dinarys.