The questions to ask before you buy new software

Software is easy to buy and surprisingly hard to get rid of. A free trial turns into an annual contract, the one person who championed it leaves, and two years later you’re paying for something half the office has never logged into. A few questions before you sign head most of that off.

What should you ask before buying business software?

Ask what problem it solves, what it really costs, what you already have that does the same thing, and how you’d leave. The rest of this post breaks those into specific questions you can put to yourself and to the vendor, with what a good answer sounds like.

What problem are we actually solving?

Write it in one sentence before you look at any product. “We keep double-booking the service van” is a problem. “We need a scheduling platform” is a solution, and it skips the step where you check whether a simpler fix exists. If you can’t state the problem plainly, you’re not ready to compare tools, and a salesperson will happily define the problem for you.

Do we already own something that does this?

Check before you buy, because the answer is often yes. Microsoft 365 and Google Workspace both include far more than most businesses use: file sharing, video calls, forms, basic automation, and more. Your accounting, payroll, or practice-management software may also have features nobody has switched on. Overlap is one of the most common kinds of software waste: two file-sharing services, two video tools, three places where customer information lives.

What will it really cost over three years?

Add up licenses, setup, training, add-ons, and price increases, not just the monthly price on the website. Ask the vendor directly:

• Is the listed price per user, and is it billed monthly or annually?
• What’s included at this tier, and which features we’d actually need are only on a higher tier?
• Is there a setup or onboarding fee?
• How much has the price gone up in the past, and is our rate locked for the contract term?
• What happens to the price when we add users or pass a usage limit?

Then multiply it out for three years at your realistic headcount. That’s the number to compare, not the monthly sticker.

How long is the contract, and how do we get out?

Prefer month-to-month or a one-year term, and find out exactly how cancellation works before you sign. Look for auto-renewal clauses and notice periods, since some contracts require notice sixty or ninety days before renewal. Put the renewal date and the notice deadline on a calendar the day you sign.

Can we get our data out if we leave?

You should be able to export all of your data, in a standard format, whenever you want. Ask what format exports come in (a spreadsheet or CSV is good; a proprietary file only their software can read is not), whether exports include attachments and history, and whether there’s a fee. Then test it during the trial. Being unable to leave cleanly is how businesses end up stuck with tools they’ve outgrown. A usable export also matters if you later need to consolidate data from several systems.

Does it work with what we already use?

Check for built-in connections to your email, calendar, and accounting system, or at least support for tools like Zapier. Software that doesn’t talk to your other systems creates retyping, and retyping creates errors. Ask for specific integrations by name, and ask whether they’re included or cost extra. When built-in connections stop short, focused automation work can sometimes bridge the gap without replacing the tools that already work.

Who will own it inside the business?

Name one person who’s responsible for setting it up, training others, and managing who has access. Tools without an owner drift: nobody removes former employees’ access, nobody learns the features you’re paying for, and nobody notices when it stops being useful. If there’s no one with time to own it, that’s worth knowing before you buy.

What happens to our data and security?

Know where your data is stored, who can see it, and how people log in. At minimum, the tool should support two-factor sign-in and let you remove someone’s access in one step when they leave. If you handle health, financial, or other sensitive information, ask whether the vendor will sign the agreements your industry requires, such as a business associate agreement for health data under HIPAA.

Will people actually use it?

Run a real trial with the people who’ll use it every day, doing their real work. A demo shows the product at its best; a two-week trial with your actual staff shows whether it fits how you work. If the people who’ll live in it every day don’t like it, adoption will stall no matter how good the features look.

What’s the smallest version we could start with?

Start with the fewest users and the lowest tier that solves the problem, and upgrade once it’s proven. Vendors often push annual plans for every seat up front. It’s usually better to pay a little more per month for flexibility while you find out whether the tool sticks.

Where does this leave you?

A one-page answer to these questions, written before you sign, will prevent most software regret. It doesn’t need to be formal. It just needs to exist, so the decision is made on purpose rather than at the end of a sales call.

Reviewing software choices, and periodically checking what a business is already paying for, is part of our fractional CTO retainer for businesses in Southeastern Pennsylvania. If you’ve got a purchase decision coming up, we’re glad to talk it through.