The (Really) Simple Contract Management Blog

The (Really) Simple Contract Management Blog

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    • 5 Numbers. That’s All Your CFO Wants from You.

      5 Numbers. That’s All Your CFO Wants from You.

      February 5, 2026
      Contract Management

      I’ve sat through a lot of leadership meetings. Probably too many. And if there’s one thing I’ve learned about presenting contract management data to a CFO, it’s this: they do not care about your KPIs. I don’t mean they don’t care about performance. They care deeply about performance. What they don’t care about is your (Read more →)

    • A Vendor Ghosted Me… And It Was the Best Thing That Ever Happened to My Contract Portfolio!

      A Vendor Ghosted Me… And It Was the Best Thing That Ever Happened to My Contract Portfolio!

      February 3, 2026
      Contract Management

      I want to tell you about the time a vendor rep just stopped answering my emails during a renewal negotiation. Not a polite “let me get back to you.” Not a “we need to run this up the chain.” Just silence. Three emails over two weeks, zero replies. At the time, I was furious. This (Read more →)

    • How I Got Sales to Stop Slacking Me Contracts at 4:47 on a Thursday

      How I Got Sales to Stop Slacking Me Contracts at 4:47 on a Thursday

      January 29, 2026
      Contract Management

      The Slack message came in at 4:47 PM on a Thursday. It said: “Hey, can legal look at this vendor contract? They want to start Monday.” Attached was a forwarded email chain. No scope of work. No dollar amount. No explanation of what the vendor would actually be doing. Just a sales rep who needed (Read more →)

    • The Part of Contract Management That’s Falling Apart (and Why Regulators Care Now)

      The Part of Contract Management That’s Falling Apart (and Why Regulators Care Now)

      January 27, 2026
      Contract Management

      I spend most of my time on post-signature contract management. The stuff that happens after the deal is done. Tracking obligations, monitoring vendor performance, making sure deadlines don’t slip, chasing down deliverables, confirming that what we agreed to is actually what we’re getting. It’s the least glamorous part of this work. Nobody writes conference keynotes (Read more →)

    • 8.6% of Your Contract Value Is Disappearing. I Can Show You Where It Goes.

      8.6% of Your Contract Value Is Disappearing. I Can Show You Where It Goes.

      January 22, 2026
      Contract Management

      There’s a stat that gets cited at every contract management conference, dropped into every vendor whitepaper, and referenced in every pitch deck for CLM software. It comes from World Commerce & Contracting (WorldCC, formerly IACCM), and it goes like this: organizations lose an average of 8.6% of their contract value to poor management. That number (Read more →)

    • I’ve Never Had a 6 Figure CLM Budget. I’ve Never Needed One.

      I’ve Never Had a 6 Figure CLM Budget. I’ve Never Needed One.

      January 20, 2026
      CLM Software

      I’ve spent my entire career at companies with fewer than 500 employees. The kinds of places where “legal department” means one attorney and someone like me. Where “procurement” is a person, not a floor. Where the idea of spending $200,000 a year on contract management software would get you laughed out of a budget meeting (Read more →)

    • 4 CLM Platforms in 15 Years…  Here’s What I Actually Learned.

      4 CLM Platforms in 15 Years… Here’s What I Actually Learned.

      January 20, 2026
      CLM Software

      I’ve been through four CLM platforms in my career. Two I inherited. One I picked. One I picked after learning from all the mistakes I made with the other three. I’m not going to name the first three, because this isn’t a product review. The problems I ran into weren’t really about the software being (Read more →)

    • I Found AI Clauses in 23 Vendor Contracts!!! I Wasn’t Looking for Most of Them.

      I Found AI Clauses in 23 Vendor Contracts!!! I Wasn’t Looking for Most of Them.

      January 15, 2026
      CLM Software

      Six months ago, I renewed a marketing analytics platform and noticed something new in the vendor’s terms: a three-paragraph section on artificial intelligence that hadn’t been there before. It covered how the vendor uses AI in their product, what happens to data that gets processed through their AI features, and whether they retain the right (Read more →)

    • AI in Contract Management: Is It All Just B.S.???

      AI in Contract Management: Is It All Just B.S.???

      January 13, 2026
      CLM Software

      Every CLM vendor on the planet has added “AI-powered” to their marketing page in the last two years. Some of them mean it. Some of them added a chatbot and called it artificial intelligence (looking at you, Concord Horizon!!!) And almost all of them are making promises that sound a lot bigger than what the (Read more →)

    • Why Most CLM Platforms Fail (Guess What! It’s Not the Software!)

      Why Most CLM Platforms Fail (Guess What! It’s Not the Software!)

      January 8, 2026
      CLM Software

      I’ve watched three CLM implementations fail. Not “fail to deliver ROI” in some abstract consulting-report sense. Fail as in: the company bought the platform, spent months setting it up, and twelve months later almost nobody was using it. The contracts were still in email. The renewals were still getting missed. The software was just sitting (Read more →)

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