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Lessons From an IT Mentor: Navigating Software Licensing and Management


Understand Your Termination Requirements

Your need for certain products or services will inevitably change across time. When the time comes to part ways, it’s crucial to fully understand your termination requirements.

For some vendors, you’re obligated to issue an official notice of termination within a specific timeframe. Failure to do so can result in automatic renewals, locking you into another year of service or requiring payment for additional months that you no longer need, just to fulfill your contractual obligations. Always be clear on the termination clauses in your contracts to avoid unexpected costs and unnecessary commitments.

Vendor Policy

As your mentors, we want to emphasize that vendors often try to enforce their internal policies as if they are contractual obligations—but they are not. These policies can artificially inflate the cost of software for the end customer.

It’s essential to thoroughly understand your contract and distinguish between what’s truly required versus what the vendor presents as “policy.” By knowing your actual obligations, you can push back when needed and avoid unnecessary expenses.

URL Links in Your Contract

Hyperlinks are embedded in everything, from marketing brochures to contracts. As your mentors, we strongly advise you to save a copy of any URL links and the content they reference as soon as you execute a contract—then file them securely.

For example, Oracle includes a URL link to the Processor Core Factor Table in its contracts. In just 1 year, that link changed three times. These changes can have significant implications for your compliance and costs, so it’s critical to preserve the original content referenced at the time you agreed to the terms.

Vendor Audits

All software vendors reserve the right to audit your use of their products. While these protections were originally intended to ensure compliance, today’s audits are largely driven by revenue generation. As your mentors, we would caution you that many audits are designed not merely to check compliance but to uncover opportunities for the vendor to increase revenue.

The departments within software companies that position themselves as offering a “helping hand” are often covert sales organizations, fully incentivized like any other sales team.

Recognizing this dynamic is a critical insight that will save you significant headaches in the future. It’s crucial to thoroughly understand and manage your organization’s software usage. Expect audits every few years, and always be prepared. Software licensing mistakes can be extremely costly, so proactive management and audit readiness are key.

Nothing Lasts Forever

In November 2023, Broadcom completed its acquisition of VMware. Soon after, it introduced a new licensing model. Similarly, in January 2010, Oracle finalized its acquisition of Sun Microsystems, gaining control of Java. It took Oracle nearly a decade before customers were required to license Java for commercial use, but this move eventually became one of Oracle’s most profitable strategies.

As your mentors, we would remind you that companies get bought and sold, and software vendors hold the right to charge what they want for their products. The landscape can change quickly, and what seems stable today may look entirely different tomorrow.

In our article, “The Weaponization of Software License Audits,” we introduced a new term: “software licensing troll.” These are unscrupulous vendors who weaponize software audits to extract money from their customers. However, if you diligently manage your software usage and stay compliant, you’ll be much less susceptible to these predatory tactics.

So, please, younger selves—don’t be distracted by our white hair, expanding waistlines, or fancy cars. Understand that we didn’t see any of this coming back in 1975, but the knowledge we’re sharing now could make all the difference in your career. Oh, and by the way, the Red Sox do finally win a few World Series titles.

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