The (Really) Simple Contract Management Blog

The (Really) Simple Contract Management Blog

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    • Healthcare Contract Management Is Just Contract Management (With Higher Stakes & Less Forgiveness)

      Healthcare Contract Management Is Just Contract Management (With Higher Stakes & Less Forgiveness)

      April 16, 2026
      Contract Management

      I’m not a healthcare contracts specialist. I should say that up front. I’ve spent my career in commercial contract management across multiple industries, and healthcare has only been one of them. But the year I spent helping a regional health system get its contract house in order taught me something I think about a lot: (Read more →)

    • I Stopped Letting People Redline Without Rules. It Saved My Sanity!

      I Stopped Letting People Redline Without Rules. It Saved My Sanity!

      April 14, 2026
      CLM Software, Contract Management

      I once watched a vendor contract go through nine rounds of redlines over six weeks. Nine rounds. The final version had exactly three material changes from the first draft. The other six rounds were people on both sides editing the same clauses back and forth, losing track of what had already been agreed, and reopening (Read more →)

    • The Audit Question I Wasn’t Ready For: “Show Me How Your CLM Is Configured”

      The Audit Question I Wasn’t Ready For: “Show Me How Your CLM Is Configured”

      April 9, 2026
      CLM Software, Contract Management

      Two years ago, our external auditors came in for the annual review and asked me something nobody had ever asked me before. They didn’t want to see a contract. They wanted to see how my contract management system was set up. Specifically, they wanted to know: Who can edit contract records after they’re finalized? What (Read more →)

    • The Spreadsheet That Found Us $200K (and Why Nobody Believed Me at First)

      The Spreadsheet That Found Us $200K (and Why Nobody Believed Me at First)

      April 7, 2026
      Contract Management

      Last year I pulled up a vendor contract because someone in operations was complaining about response times. The SLA said four-hour response for priority incidents. I asked the vendor for their performance reports. They sent over a PDF that showed 99.2% compliance. Sounded great. Except it wasn’t. When I matched their report against our internal (Read more →)

    • 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 →)

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