A Procurement Checklist for School Leaders Evaluating New Software

If you’re at the point of comparing providers seriously, you’re past the question of whether to switch and onto the question of which one. Different problem. Different stress. And in some ways, harder, because the answer isn’t obvious.

Procurement for school software has a few specific challenges. The decision affects multiple stakeholders with different priorities. The criteria are often unclear. The features all look similar in the demo. And the consequences of a bad choice are long-lasting and expensive.

We’ve spent two decades helping schools navigate this stage, both as a provider and as a sounding board. The thing that separates good procurement from bad procurement isn’t the size of the budget or the seniority of the people involved. It’s the quality of the questions being asked.

Here’s the structured set we recommend working through. You don’t have to use every question, but the categories matter, and the bias should be toward asking too much rather than too little.

Before You Even Look at Vendors

This is the bit schools skip most often, and the one that costs the most when it’s missed.

Before you start running demos, you need internal clarity. Otherwise you’ll find yourself evaluating five providers without an objective benchmark for what “good” means in your context. Every demo will feel impressive. Every conversation will leave you reassured. And the decision will end up being made on instinct rather than fit.

The questions to settle internally before vendor conversations begin:

• Who owns this project? Not the committee. The named individual.
• What are the three to five outcomes we’re actually trying to achieve?
• What are the current workflows in this area, and where do they break?
• How clean is our existing data? Be honest.
• What’s our realistic timeline, given our academic and fiscal calendars?
• Who needs to be in the decision, and who just needs to be informed?
• What’s the budget envelope, including implementation and ongoing costs?

The answers don’t all need to be settled before you talk to anyone. But they do need to be settled before you sign anything. The order matters.

What Can the Platform Actually Do?

This is the section schools usually overweight. Features matter, but they’re the easy bit to evaluate, and they’re rarely what determines success.

That said, you do need to know whether the platform genuinely solves your problem. The questions worth asking, and worth asking specifically rather than generally:

• Does the platform handle our specific use cases, not just the standard ones?
• What does the workflow look like for the people who’ll use it most?
• How customisable is it? And what does customisation cost in time and money?
• What does reporting look like, and can leadership get the views they need without IT involvement?
• How does the platform handle role-based permissions and access?
• What happens when we grow, add a new programme, or change our model?

A note on demos. They’re useful, but they’re rehearsed performances. The platform always looks great in the demo because the data is clean, the workflows are simplified, and the person running it has done this hundreds of times. Don’t decide on the demo alone. Ask for a sandbox environment, get your own data in there, and let your team poke at it. That’s a much better signal.

How Will It Talk to Everything Else You Use?

In a fragmented stack, the joins are where the cost lives. A new platform that doesn’t integrate cleanly with the rest of your ecosystem can create as much overhead as it removes.

The questions:

• Which of our existing systems need to integrate with this one?
• Is the integration native, via API, or via middleware?
• Is data synced one-way or both ways? And how often?
• What happens when there’s a conflict between sources?
• Does the platform support single sign-on (SSO)?
• What are the known limitations of the integrations, and are they documented?
• Who owns the integration work, and who’s responsible if it breaks?

A specific warning. “Yes, we integrate with X” can mean many things. It can mean a clean, two-way, real-time integration. It can also mean an export-import workflow that runs nightly with manual reconciliation when it fails. Ask for the technical detail. Vague answers here usually translate to expensive surprises later.

What Happens after You Sign?

We’ve covered this in more depth elsewhere, but it belongs in any procurement framework, because it’s the area where procurement decisions most often go wrong.

The short version of what to ask:

• Who specifically will run our implementation?
• How many other projects are they running concurrently?
• What does the implementation plan look like, end to end?
• How is data migration structured, and what’s our role in preparing for it?
• How is training delivered, and is it role-based?
• What does support look like during go-live week, and for the two weeks after?
• What’s the handover process from implementation to ongoing account management?

Are You Building a Partnership or a Transaction?

The final category is the one most procurement processes underweight, because the questions feel softer and harder to score. They matter more than they look.

You’re not just buying software. You’re entering into a multi-year relationship with a company whose decisions will shape how your school operates day to day. The character of that relationship affects almost everything that happens after the contract is signed.

The questions:

• What does ongoing support actually look like, with response times and channels specified?
• What are the service level agreements, and are they meaningful?
• How does the provider handle product improvements?
• Are they driven by customer feedback or imposed top-down?
• How often do you get a meaningful conversation with someone who knows your account?
• Is there strategic consultancy available if you need it, separately from the support function?
• How does the provider handle issues when they arise? Reactively, or with structured ownership?
• What do other schools in your sector say about working with them long-term, not just at go-live?

That last question is the most useful one in this section. A two-year-old customer relationship tells you more about what life with a provider actually looks like than any sales conversation can.

A Quick Note on Scoring

A lot of procurement processes use scoring matrices to compare providers. They have their uses, particularly when multiple stakeholders are involved and you need a defensible record of how the decision was made.

Two cautions, though.

The first: don’t let the matrix do your thinking for you. Scoring can give a precise-looking answer to an imprecise question. If two providers score within five percent of each other, the matrix isn’t telling you which one to pick. It’s telling you the criteria you used weren’t sharp enough to distinguish them.

The second: weight the categories thoughtfully. Features tend to get overweighted because they’re easiest to evaluate. Implementation support and long-term partnership tend to get underweighted because they’re harder to score. Adjust accordingly. The categories that matter most for your school’s success aren’t always the ones that matter most on a spreadsheet.

So What Should You Walk Away With?

By the end of a serious procurement process, you should be able to answer four questions confidently.

Does this platform solve the specific problems we’re trying to solve, not the generalised version of them?

Will it integrate cleanly with the rest of our ecosystem, with the limitations clearly documented?

Do we trust the people running the implementation to actually deliver, based on evidence rather than promises?

Are we comfortable being a customer of this company for the next five years, given what we’ve seen of how they operate?

If you can answer yes to all four with specific evidence behind each answer, you’re ready to sign. If you can’t, the work isn’t finished.

We’ve put together a full guide on how to approach the whole switching process, including more on the procurement and implementation stages, what the five-phase framework looks like in practice, and how to set the project up for success from the inside.

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The procurement stage is the one where you have the most leverage. Use it.