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The (Really) Simple Contract Management Blog

The (Really) Simple Contract Management Blog

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    • Nobody Hates Contracts. They Hate Your Approval Process.

      Nobody Hates Contracts. They Hate Your Approval Process.

      April 2, 2026
      CLM Software, Contract Management

      I used to think sales hated legal. Turns out they just hated waiting three weeks for someone to approve a contract that should have taken two days. The frustration was real and it was specific. A sales rep would send over a new vendor agreement or a customer MSA, and it would disappear into a… (Read more →)

    • AI Read My Contracts. It Missed Some Stuff That Matters.

      AI Read My Contracts. It Missed Some Stuff That Matters.

      March 31, 2026
      CLM Software

      Last fall I decided to test something I’d been hearing about at every legal ops conference for two years: AI-powered metadata extraction. The pitch is simple. You upload your contracts, the AI reads them, and it spits out structured data: party names, effective dates, expiration dates, renewal terms, governing law, payment terms, the whole catalog.… (Read more →)

    • I Found 9 Different Versions of Our NDA Last Year. NINE!!!

      I Found 9 Different Versions of Our NDA Last Year. NINE!!!

      March 26, 2026
      Contract Management

      They were scattered across three departments, and not one of them matched the template I’d spent two weeks building with outside counsel. Sales had a version where someone had deleted the non-solicitation clause because a prospect pushed back on it once and the rep figured, why not just take it out? HR had a version… (Read more →)

    • How to Win the Game of “Where’s That Contract?”

      How to Win the Game of “Where’s That Contract?”

      March 24, 2026
      Contract Management

      Last year, our CFO needed the original MSA for a vendor we were about to renegotiate. Not the SOW. Not the last amendment. The original agreement, signed four years ago by someone who no longer worked at the company. I knew it existed. I’d seen it referenced in an email. But I couldn’t find it.… (Read more →)

    • Every Monday Morning, I Do *This* For 45 Minutes. It Saves Me Hours of Work.

      Every Monday Morning, I Do *This* For 45 Minutes. It Saves Me Hours of Work.

      March 19, 2026
      Contract Management

      I started doing this by accident. About six years ago, I walked into a Monday morning meeting and a VP asked me when the Aramark contract was up for renewal. I had no idea. I’d been managing the contracts for that org for over a year, and I couldn’t answer a basic question about one… (Read more →)

    • Signing the Contract Is the Easy Part. What Comes Next Is the Killer.

      Signing the Contract Is the Easy Part. What Comes Next Is the Killer.

      March 17, 2026
      CLM Software, Contract Management

      I can tell you the exact moment I realized how broken post-signature contract management is at most companies. I’d been at a mid-size manufacturing firm for about three months. Long enough to know where the contracts lived (mostly), who the key vendors were (roughly), and which ones had renewals coming up (barely). A project manager… (Read more →)

    • I Set Up a CLM in One Day, but the Six-Month One Failed. Here’s Why.

      I Set Up a CLM in One Day, but the Six-Month One Failed. Here’s Why.

      March 12, 2026
      CLM Software

      I’ve implemented contract management software five times across my career. One of those implementations took a single day. Another took the better part of six months and still wasn’t fully adopted a year later. The difference wasn’t the software. Not really. It was what we were trying to do with it. The day-long implementation was… (Read more →)

    • Every New Hire Gets the Same Advice: Read the MSA First!

      Every New Hire Gets the Same Advice: Read the MSA First!

      March 10, 2026
      Contract Management

      I’ve onboarded maybe a dozen people into contracts or legal ops roles over the years. Different companies, different industries, different levels of experience. And every single time, on day one or close to it, I say the same thing: “Before you read any SOW, read the MSA.” Most of them look at me like I’ve… (Read more →)

    • Your Contract Repository Is Probably Just a Fancy Folder. Here’s How to Fix It.

      Your Contract Repository Is Probably Just a Fancy Folder. Here’s How to Fix It.

      March 5, 2026
      CLM Software

      I’ve set up contract repositories at four different organizations. Three of them failed. Not because the software was bad (it wasn’t, mostly) but because nobody thought about what a repository actually needs to do before they bought something and started dumping files into it. The fourth one worked. It’s the one I still use. And… (Read more →)

    • What 200 Renewal Negotiations (Actually) Taught Me About Contract Management

      What 200 Renewal Negotiations (Actually) Taught Me About Contract Management

      March 3, 2026
      Contract Management

      The first renewal negotiation I ever handled, I lost before the conversation started. I just didn’t know it yet. It was a document management platform. Annual contract, about $38,000. The vendor’s account rep emailed me six weeks before the renewal date with a “quick update” that included a 12% price increase and a note that… (Read more →)

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