The (Really) Simple Contract Management Blog

The (Really) Simple Contract Management Blog

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    • 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 →)

    • My Entire Renewal Tracking System Fits on One Screen. Here’s How I Do It.

      My Entire Renewal Tracking System Fits on One Screen. Here’s How I Do It.

      February 26, 2026
      CLM Software

      I almost cost my company $87,000 once because I missed a renewal by four days. It was a facilities management contract. Three-year term, auto-renewal clause with a 60-day notice window. I knew the contract existed. I’d even flagged it when I first organized the repository. But I hadn’t set an alert, because at the time (Read more →)

    • I Stopped Asking People to “Read the D@%$ Contract.” Here’s What I Do Instead!

      I Stopped Asking People to “Read the D@%$ Contract.” Here’s What I Do Instead!

      February 24, 2026
      Contract Management

      Last year I sat in a meeting where our VP of Sales waved a contract at me and said, “Dave, this vendor is saying we owe them for an extra year. Is that right?” I pulled up the agreement. The auto-renewal clause was on page fourteen, paragraph 8(b), buried in a sentence that ran nine (Read more →)

    • 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 →)

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