One of the things I did not fully appreciate before stepping into a CIO role is how much vendor management shows up in the work.

As a software architect, I was used to reviewing code, architecture decisions, data flows, and implementation details. That kind of review made sense to me. I knew what to look for. I knew where risk usually lived.

Contract review is different.

It is slower. It is less exciting. Honestly, I still find code review less boring than contract review.

I did have a college subject related to negotiations and contracts, at least I think that was the name. That was decades ago, and I vaguely remember the subject title, much less the details of what I learned from it.

What I do remember is that I found the law-related subjects boring.

But I am learning that contract review is part of protecting the organization. Before a system is implemented, before a renewal is signed, and before a vendor relationship becomes harder to unwind, someone has to slow down and understand what is actually being agreed to.

The Advice That Sounded Too Simple

When I started looking more closely at contracts, I asked Mark Ruma, my former boss and mentor at Epitec, for advice.

His first response was simple:

Print them.

At first, I did not fully understand why that was the first tip.

Print them?

It sounded almost too basic. I spend most of my day on a computer. I read technical documentation, pull requests, emails, reports, and project notes on a screen. I assumed contracts would be the same.

But I tried it.

I downloaded the document, printed it, highlighted sections, and wrote my questions in the margins. That changed the way I read it.

Why Paper Helped

Reading the contract on paper made me slow down.

On a screen, I tend to scan. I jump between windows. I search for terms. I move quickly because that is how most digital work feels.

On paper, I read differently. I noticed terms I might have skipped. I circled language that felt unclear. I wrote questions near the sections that created the questions. I could see the whole agreement as something I needed to understand, not just a file I needed to get through.

Maybe that is old school, but it worked for me.

I grew up reading on paper more than on screens. For certain types of work, especially work that carries risk, I still focus better that way.

Where AI Helped

Mark also suggested using AI to help review the contract.

The idea was not to let AI make the decision. It was to use AI to help me understand the document better.

I used AI to look at areas like:

• Duration
• Payment terms
• Termination language
• Issue resolution
• Important timeframes
• Insurance requirements
• Places where risk might be shifted to the organization

That helped me identify terms I did not understand and questions I needed to ask.

The important part is that we still had legal review. AI did not replace the lawyers. It helped me become a better participant in the conversation with them.

Instead of just asking, “Is this okay?” I could ask more specific questions.

What happens if we need to terminate early?

Is this renewal language standard?

Are we accepting risk here that we should push back on?

Does this agreement limit our options later?

That was the real value. AI helped me prepare. Legal helped us understand the risk properly.

The Signature Is Not A Formality

One lesson came from a renewal that looked routine at first.

It would have been easy to treat it like a normal subscription renewal and move it through the signing process. But after downloading the file and reviewing it more carefully, the structure looked closer to a lease or agreement than a simple software subscription.

That mattered.

Had we treated it as routine, we may have accepted terms that limited our options later. Reviewing the actual document before signing gave us a chance to ask better questions and avoid unnecessary lock-in.

That experience changed how I look at signing workflows.

When something comes through an e-signature process, I do not treat the signature step as the review. Before I sign anything, I download the file, print it if needed, read it, mark it up, and make sure the right people have reviewed it.

The convenience of signing electronically is helpful. But the speed of the process can make it too easy to move past the actual agreement.

What I Am Learning

Vendor management starts before the signature.

It starts when you ask what problem you are solving, what terms you are accepting, what risk is being shifted, what options you are preserving, and what obligations you are creating for the organization.

This is one of the differences I am feeling in the move from software architecture into CIO leadership.

As an architect, I was often focused on whether the solution worked.

As a CIO, I still care whether the solution works, but I also have to ask what it commits us to, what it costs over time, how it affects operations, and whether it protects the organization.

That is a different kind of review.

It may not be as interesting as reviewing code, but it matters.

Takeaway

Print the contract.

Read it slowly.

Write down the questions.

Use AI carefully to understand unfamiliar terms and prepare for the conversation.

Bring legal into the review.

And do not let the convenience of a signature workflow make the decision feel smaller than it is.