When a software renewal hits your inbox, it’s easy to treat it like routine admin. Click, renew, move on.

But every renewal is a high-value negotiation opportunity — and when it’s handled poorly, the long-term consequences can be significant. Locked-in costs. Inflexible terms. Features you never use. And no room to pivot when your business evolves.

At 2Data, we’ve reviewed hundreds of software contracts, and the same mistakes come up again and again. Here are the five biggest ones to avoid:

1. Leaving It Too Late

The closer you get to the renewal deadline, the less power you have. Vendors know this — and they’ll use it to pressure you into accepting terms you haven’t had time to fully evaluate.

Start planning your renewal six to nine months in advance. That gives you time to review usage, align internally, and negotiate from a place of control, not urgency.

2. Focusing Only on Discounts

Yes, pricing matters. But a 15% discount on the wrong licensing model is still a bad deal.

Too many companies focus only on shaving down the top-line cost without reviewing whether the structure even fits their environment. Are you buying too many licenses? The wrong types? Are there cheaper alternatives the vendor isn’t offering?

Optimize the deal structure first. Then negotiate the price.

3. Taking the Vendor’s Word for It

Your account rep may be helpful, but they’re also working toward a sales target. That means they’re incentivized to upsell, bundle more, and downplay alternatives.

We see this all the time — companies get steered into packages that sound great but don’t match their actual usage or roadmap.

Trust, but verify. Always ask for documentation, licensing guides, and usage reports — and question assumptions.

4. Ignoring the Terms and Conditions

Many organizations go straight to the pricing page and skip the fine print. That’s where vendors include auto-renewal clauses, vague audit rights, usage limitations, and termination fees.

These legal details can quietly lock you into an inflexible position for years.

Redline what doesn’t serve you. Don’t assume the standard terms are non-negotiable — they’re not.

5. Going in Without Independent Advice

The licensing models for SAP, Microsoft, Oracle, and Salesforce are incredibly nuanced. If you don’t understand the ins and outs — and how those vendors typically negotiate — you’re at a disadvantage.

This is especially true for complex environments with multiple products or global usage.

Bringing in a vendor-neutral advisor levels the playing field. Someone who knows the playbook, understands your rights, and can help you avoid traps that only show up after you’ve signed.

Final Thoughts

Software vendors are experts at structuring deals in their favor. But that doesn’t mean you have to play along.

Avoid these mistakes, and your next renewal becomes more than a routine process — it becomes a strategic opportunity to reduce costs, increase flexibility, and future-proof your software environment.

And if you want someone in your corner who does this every day? That’s where we come in.