Renting software vs owning it: what to ask before you sign up

Most business software today is rented. You pay every month, often for every person who uses it, and you use it for as long as you keep paying. Sometimes that's exactly right. Sometimes the monthly fees add up to far more than you ever meant to spend.

This post is the list of questions we'd ask before signing up for anything. They work for any software company, and they work for us too. We've put our own answers at the end.

When renting is the right call

Renting is often the sensible choice. It usually is when:

• the need is the same for every business, like email, accounting or payroll;
• only one or two people will use it;
• you're trying something out and may stop in a few months;
• the tool already fits how you work, without changes.

If that's you, rent, and don't look back.

When owning starts to make sense

Owning is worth a look when:

• the way you work is part of why customers choose you;
• you pay for many people, every month, with no end date;
• your team works around the tool instead of with it;
• you'd be stuck if the company raised its price or closed.

Questions about your data

Can I export all of it, in a format I can open?

Ask for a sample export before you sign. "You can export your data" can mean everything, or it can mean one table at a time. Check that it includes history, files and notes, not only the main list.

Where is it stored, and who can see it?

Ask which country it's stored in, who at the company can read it, and whether they use it to train their AI tools. Ask for the answer in writing.

What happens to it if I stop paying?

Some services keep your data for a while, some delete it, and some lock you out until you pay again. Find out which, and for how long.

Questions about price

What will this cost my whole team over three years?

Multiply the monthly price by the number of people, then by 36. Add the extras you'll need, like more storage, add-ons or a higher plan for one feature. That number is the real price.

What makes the price go up?

Usually it's more people, more usage, or a feature that's only on the next plan. Ask which of these you're likely to hit as you grow.

Can the price change while I'm on it?

Ask how much notice they give before a rise, and whether your price is fixed for a term.

Questions about leaving

How do I leave, and how long does it take?

Ask what you'd get on the way out and in what form. Then ask what you'd have to rebuild somewhere else: your templates, your automations, your reports and the habits your team has built around them.

Is anything I set up mine to keep?

The custom fields, automations and connections you've paid someone to set up usually only work inside that service. If you leave, they stay behind.

Questions about fit

Will we change how we work to fit the tool?

A little is fine. If the answer is "a lot", count the time that costs your team every day.

Who can change it when our needs change?

If only the vendor can, you wait for their roadmap. If you can, ask how hard it is and who would do it.

The questions to ask us

We build software that the business owns. That's a different deal, so it needs the same scrutiny. Here are the questions, with our answers.

The short version

Renting is a fine deal when the tool fits and the price over time makes sense. Owning is worth it when your way of working matters and the monthly fees never end. Whichever you choose, ask about your data, the real price, how to leave, and who can change it, before you sign.

If you'd like to see what owning looks like in practice, read how it works, or see the examples we've built on sample data.