Seven questions to ask before approving a technology investment

Look beyond the software demonstration

The demonstration looks convincing. The monthly subscription fits the budget. The supplier says the new platform will save your team time. Before you approve it, a few questions remain: who will move the records, train staff, connect the existing systems, and deal with problems after launch?

Those tasks affect both the cost and the benefit of the purchase. Use the seven questions below to review a proposal with your team and supplier. The aim is a clear decision: proceed, test a smaller change, ask for more evidence, or defer.

1. What business problem will this solve?

Describe the work you want to improve. “Replace the CRM” names a purchase. “Reduce repeated data entry between an inquiry and client onboarding” gives the team a problem to investigate.

Identify who experiences the problem, how it affects their work, and why it matters now. Compare the proposal with improving the current process or making better use of tools you already have.

Ask to see: A short problem statement, a measure of current performance, and the alternatives considered.

2. Who will make the change work?

Name the person who approves the spending and the person responsible for everyday use. They may be different people. Agree who will train users, change working practices, and check whether the expected benefit appears.

Give that owner enough time and authority to do the job. Include training and adoption work in the plan and budget.

Ask to see: A named business owner and a plan for training, adoption, and performance reviews.

3. Will it fit our existing systems and workflows?

Map where the new system fits into the way work gets done. Identify which existing tools it will replace, which it must connect to, and who will manage the handoffs.

Ask the supplier to demonstrate the important connections using the versions and subscriptions your organization actually has. Confirm any extra licenses, custom development, or changes to staff routines.

Ask to see: A simple system-and-workflow map, with required connections, limitations, and responsible people.

4. What must happen to our data?

Identify the information the change needs, who owns it, and whether it is accurate enough to use. Decide which system will be the main source of each important record and who can view or change it.

Plan how records will be cleaned, moved, and checked. Include duplicate records, missing information, access permissions, and a recovery plan if the move goes wrong. Agree what information must be retained or removed.

Ask to see: A data preparation and migration plan covering ownership, access, validation, and recovery.

5. What could go wrong, and how would we respond?

List the assumptions that could change the decision: supplier availability, staff capacity, a difficult data move, or a connection that has not been tested. Name an owner and a response for each significant risk.

Consider how you would leave or reverse the arrangement. Confirm how to export your information, what happens if costs rise, and how the business would keep operating during an interruption.

Ask to see: A short risk list with owners, response plans, and workable exit or rollback options.

6. What will it cost to set up, run, and eventually replace?

Look beyond the subscription price. Include setup, connections to other systems, data migration, training, staff time, security, support, and eventual replacement or closure. Separate one-time costs from recurring costs over an agreed period.

Ask which estimates are uncertain and what would happen if usage, support demand, or supplier prices increased. The U.S. GAO’s Cost Estimating and Assessment Guide supports documenting assumptions, examining risk, and updating estimates with actual costs. Apply that discipline at a level that suits your organization.

Ask to see: A cost breakdown covering setup, operation, staff time, and exit, with assumptions clearly stated.

Sources: U.S. GAO Cost Estimating and Assessment Guide

7. How will we know it worked?

Choose a few measures tied to the original problem. Record today’s performance, the improvement you want, who will measure it, and when you will review it. For an onboarding project, you might track completion time, repeated data entry, and staff effort per case.

Agree approval checkpoints before spending more. A small pilot should answer a specific question. Decide in advance what evidence would support a wider rollout, another test, a change of approach, or a stop.

Ask to see: Success measures with a baseline, target, review date, and owner, plus criteria for the next approval.

Example: deciding whether to replace a scheduling tool

Imagine a maintenance business considering a new scheduling platform because appointments are being missed. The supplier demonstrates automatic reminders and staff allocation. This is an illustrative example, not a reported client result.

Before approving the purchase, the team reviews missed appointments, checks how customer and job details would move, and names an operations owner. It compares the platform with improving the existing booking process, including training, setup, and ongoing support costs.

If incomplete job details cause most missed visits, fixing the booking questions may be the first useful investment. If staff still cannot allocate work reliably, a limited trial can test the proposed scheduling features against actual needs. The purchase decision follows those findings.

Bring a one-page decision brief to the meeting

Use the answers to prepare a short record that everyone approving or delivering the work can understand. Include these five items:

• Decision: what you are approving now, which alternatives you considered, and what remains outside the scope.
• Expected outcome: the business problem, current performance, and the improvement you want.
• Accountable owner: who will make the change work and review its results.
• Full cost: setup, ongoing operation, staff time, and exit costs, including uncertain estimates.
• Evidence for the next commitment: what must be demonstrated, by whom, and when before more funding or wider rollout.