Most IT and software contracts don't get decided — they get renewed. The invoice shows up, the auto-renew clause has already fired, and another year is locked in before anyone asks whether it's still the right deal. That's how businesses end up paying for seats they retired, tools nobody opens, and terms that quietly got worse.
A renewal is a decision. Here are the seven questions I run through before signing one — the same ones I'd ask if it were my own money, because as a fee-only advisor it effectively is: I earn nothing from what you buy.
1. What are we actually paying, per unit, versus a year ago?
Get the real number: total spend divided by active users or devices. Then compare it to last year. Price creep hides in bundles and "list price adjustments" that never get questioned. If the per-seat cost went up, the vendor should be able to explain exactly why — and "inflation" isn't an explanation.
2. How many licenses are we paying for but not using?
Pull the actual usage report. It's routine to find 15–30% of licenses assigned to people who left, changed roles, or never logged in. Every one of those is pure margin for the vendor and pure waste for you. Right-size before you renew, not after — the renewal is your leverage.
3. When does it auto-renew, and what's the cancellation window?
Find the auto-renewal date and the notice period — often 30, 60, or 90 days before the term ends. Miss it and you're locked in regardless. Put that date on a calendar today, with a reminder two weeks ahead of the deadline. This single habit saves more money than any negotiation.
4. What would it cost to leave — and could we?
You don't have to switch to benefit from knowing you can. Ask: is our data exportable in a usable format? Are there early-termination fees? How long would a migration take? A vendor who knows you're genuinely willing to walk negotiates very differently from one who knows you're stuck.
5. Are we on the right tier, or one sold to us?
Products get sold at the tier that's easiest to sell, not the one that fits. Review what the current tier actually includes versus what you use. Sometimes you're overpaying for an enterprise tier you don't need; sometimes a cheaper tool covers 100% of your real usage. Match the plan to reality.
6. What's the true all-in cost — including the add-ons?
Sticker price is rarely the price. Add per-integration fees, storage overages, "premium" support, onboarding charges, and the internal time to manage the thing. A cheaper tool with three paid add-ons can quietly cost more than the "expensive" all-inclusive one. Compare totals, not headline rates.
7. If we were choosing from scratch today, would we pick this?
The most important question, and the one nobody asks at renewal time. Incumbency is not a reason to stay — it's just inertia. If the honest answer is "no, but switching is a hassle," that's worth a real look, not an automatic re-up. Renewal is the one moment a year you're allowed to reconsider. Use it.
The one-page version
Before any renewal, know: real per-unit cost vs. last year, unused licenses, the auto-renew and cancellation dates, your exit options, whether the tier fits, the all-in total, and whether you'd choose it fresh. If you can answer those seven, you're renewing on purpose.
If a big renewal is coming up and you'd rather have an independent set of eyes on it, that's exactly what a second opinion or a technology assessment is for — no commission, no stake in what you decide. Book a call and bring the contract.