Before choosing a technology solution, ask every vendor the same questions and require specific evidence: how the product meets your needs, handles and protects data, works with your systems, serves users accessibly, performs in realistic conditions, and fits your full lifecycle budget. Put important promises into measurable acceptance criteria and contract terms.
Prepare before you meet vendors
Write down your requirements, priorities, and evaluation criteria before demonstrations begin. This makes it easier to compare products on your needs rather than on whichever features a presentation emphasizes. For an uncertain or high-impact purchase, consider a prototype or pilot that tests feasibility against agreed scenarios. U.S. federal acquisition guidance identifies prototyping and post-implementation reviews as possible ways to manage IT acquisition risk; the specific rules apply to federal agencies, while the planning techniques can help other buyers too. FAR Part 39
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- Separate must-haves from preferences.
- Choose realistic workflows and sample data for demonstrations.
- Decide in advance what evidence and results will count as acceptable.
- Identify the people who will evaluate product fit, security, accessibility, operations, and cost.
Questions about requirements and fit
Ask the vendor to respond to your requirements one by one, including gaps and dependencies—not just to present a general product tour.
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1Clear out junk files and repair common Windows errors2Scan for outdated or missing drivers - takes under a minute3Repair Windows errors before they cause bigger problems- Which of our stated requirements does the solution meet, and where does it fall short?
- Can you demonstrate our highest-priority workflows using realistic sample data and scenarios?
- What assumptions, configuration, customization, integrations, or third-party products are needed for the demonstration to reflect production use?
- What acceptance criteria can we agree on before purchase?
- How will the solution behave when our expected usage, data volume, or workflows change?
Ask for a demonstration to use the same scenarios across all contenders. If the vendor cannot show a requirement directly, record whether it depends on planned work, a workaround, or an unverified claim.
#1 Best Overall
- Keep track of everything from attendance to test scores
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Questions about security, privacy, and suppliers
Understand not only the direct vendor, but also what happens to your information and which other organizations or services may be involved.
- What information will you collect, access, store, process, or share, and for what purposes?
- Where is the data handled, and which subcontractors or suppliers can access it?
- Which security controls protect the service and customer data? What evidence can you provide, and what is its scope and date?
- How do you detect, report, investigate, and recover from security incidents?
- What incident-notification timelines, cooperation duties, and remedies can be included in the contract?
- How do you assess supplier risks, product provenance, resilience, ownership or control, and security practices?
- How do you manage vulnerabilities, patches, and changes to the product or its suppliers?
NIST’s July 2026 SP 1326 frames ICT supplier due diligence around foreign ownership, control, or influence; provenance; resilience; foundational cybersecurity practices; and supply-chain tiers. CISA’s small-business vendor guidance also highlights supplier security and privacy policies, contractual protections, incident detection, and recovery. Ask for evidence that is relevant to the specific service and data you plan to use, rather than relying on a broad assurance without scope or date.
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Questions about compatibility, portability, and future choices
A solution can meet today’s needs but become costly or restrictive if it does not work with your existing systems or makes it difficult to move later.
- Which of our existing systems, identity providers, data formats, interfaces, and standards does the product support?
- How will data move into and out of the solution? Which export formats are available, and are there fees or limits?
- Which product components and third-party services does the solution depend on?
- What would migration away from the product involve, and what support is available at termination?
- Could choosing this product limit future integrations, product choices, or upgrades?
- How long will the product and its components receive support, and how are end-of-life changes communicated?
Test the important data flows and integrations during evaluation where possible. NIST SP 800-36 is an older security-product selection guide, but its prompts about lifecycle support, scalability, interoperability, testing, vulnerabilities, dependencies, and future improvements remain useful as a checklist. Its referenced tools or standards should not be assumed to be current without checking. NIST SP 800-36
Questions about accessibility and usability
Accessibility should be assessed before selection, not left as an informal promise to address after purchase.
- Which users and accessibility needs were included in product testing?
- Can you provide current, product-specific accessibility documentation and explain known limitations?
- Can our users test the product with their actual workflows before we commit?
- Which accessibility criteria can be included in evaluation and acceptance documents?
- Who is responsible for remediation, and how will changes or updates be checked?
U.S. federal buyers can use Section508.gov’s guidance on requesting accessibility information and its ICT procurement roadmap, which recommends assessing accessibility information before selection and specifying evaluation factors, contract provisions, and acceptance criteria. These sources address federal procurement; other buyers should determine which accessibility laws and standards apply to their organization and location.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Questions about cost, support, resilience, and contracts
Compare the cost and operational commitments over the expected term, not just the initial license price.
- What is the full cost over the expected term, including licensing, implementation, integrations, training, support, upgrades, storage, and exit?
- Which support channels are included, and what response or resolution commitments are measurable?
- What are the service’s recovery arrangements, and how can we validate them?
- What happens to our data, configurations, and access when the contract ends?
- Which outcomes and benefits will we measure after implementation, and when will we review them?
- Which vendor commitments can be written into the contract, and what happens if they are not met?
U.S. federal agencies must analyze IT acquisition risks, benefits, and costs before contracting under FAR Part 39; that framework also describes planning, ongoing risk assessment, prototyping, and post-implementation review of actual costs and benefits. Other organizational buyers can use the same questions without treating federal acquisition rules as universally applicable. FAR Part 39
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- Used Book in Good Condition
Compare vendors with a shared scorecard
When you have multiple genuine contenders, use the same criteria and evidence standards for each. Weight the criteria according to business impact and risk instead of giving every feature equal importance.
| Evaluation area | What to compare |
|---|---|
| Requirements and workflows | Must-have coverage, demonstrated scenarios, gaps, dependencies, and acceptance criteria |
| Security, privacy, and supplier risk | Data practices, control evidence, supplier access, incident commitments, and supply-chain assessment |
| Integration and exit | Compatibility, data movement and formats, dependencies, migration effort, and termination support |
| Accessibility | Product-specific evidence, user testing, applicable requirements, and remediation commitments |
| Lifecycle value | Total expected cost, credible benefits, implementation effort, and review measures |
| Operations and resilience | Support commitments, recovery arrangements, product lifecycle, and implementation risks |
Keep the scorecard tied to evidence: distinguish what was demonstrated, what is documented, what is contractually committed, and what remains an assumption. NIST SP 800-36 recommends considering overall requirements and vendor reliability alongside product testing; FAR Part 39 supports quantifiable measures and reviews of actual costs and benefits for federal IT acquisitions. NIST SP 800-36 FAR Part 39
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