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The (Really) Simple Contract Management Blog

The (Really) Simple Contract Management Blog

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    • Are Your Vendor’s “AI Terms” a Blank Page? (You Should Probably Check…)

      Are Your Vendor’s “AI Terms” a Blank Page? (You Should Probably Check…)

      February 19, 2026
      CLM Software

      Six months ago, I started a project I’d been putting off: going through every vendor contract in our repository that involves any kind of AI or machine learning functionality and checking what the agreements actually say about it. Sixteen contracts. SaaS platforms, analytics tools, an HR screening product, a couple of document processing services. All… (Read more →)

    • “Digital Transformation” Is Just a $4 Trillion Word for… Getting Organized

      “Digital Transformation” Is Just a $4 Trillion Word for… Getting Organized

      February 17, 2026
      CLM Software

      Last year, I sat through a webinar where a vendor described their contract management platform as “an end-to-end digital transformation solution for the modern legal enterprise.” I looked at the demo. It was a searchable database with alerts and some reporting. Which is great. That’s what I use every day. But calling it a “digital… (Read more →)

    • Your Spreadsheet Isn’t the Problem. Your Spreadsheet *at Scale* Is the Problem.

      Your Spreadsheet Isn’t the Problem. Your Spreadsheet *at Scale* Is the Problem.

      February 12, 2026
      CLM Software

      I need to say something that might surprise you, coming from a guy who writes about contract management software for a living: your spreadsheet is probably fine. If you have 30 contracts, a decent Excel tracker, and the discipline to open it every Monday morning, you’re doing better than a lot of people I’ve met… (Read more →)

    • Nobody Used to Ask Me About Contract Data. Now the Board Does.

      Nobody Used to Ask Me About Contract Data. Now the Board Does.

      February 10, 2026
      Contract Management

      I’ve been doing contract management for over fifteen years, and for most of that time, nobody above my direct manager cared what was in the contracts database. As long as nothing blew up, the data quality of our contract records was my problem and mine alone. That’s changed. In the last two years, I’ve been… (Read more →)

    • 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 →)

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