How I Improved My COBBLESTONE SOFTWARE In One Day

I remember the day it hit me. We’d been using Cobblestone Software, specifically Cobblestone Contract Insight, for a little over a year. The initial implementation was a whirlwind of new fields, workflows, and a seemingly endless list of features. We got the basics down, and for the most part, it did what it was supposed to do: it got our contracts out of scattered network drives and email inboxes and into a central repository. It was a useful tool, but I wouldn’t have called it a game-changer. It was a piece of software, nothing more.

Then came a particularly challenging week. A critical contract renewal with a major vendor was looming, and I was spending hours manually chasing down approvals, verifying key dates, and trying to track down a specific clause that I knew was buried somewhere in the system. The beautiful dashboards I’d been shown during the demo were stagnant, the automated alerts were going to my spam folder, and I was feeling every bit of the manual work I thought we had left behind.

In a moment of sheer frustration, I decided something had to change. I wasn’t just going to accept the system as it was; I was going to master it. I set aside an entire day—just one day—to dive deep and figure out how to transform Cobblestone from a simple document repository into the powerful, intelligent engine it was promised to be. This is the story of how I did it, and the lessons I learned that can help anyone unlock the full potential of their Cobblestone platform in a single, focused effort.

Hour 1-2: Reconnecting with the Foundation – The Dashboard and Workflows

I started at the most obvious place: the homepage. My dashboard was a mess of default widgets that didn’t provide any meaningful insights. My first task was to customize it.

1. Deconstructing the Dashboard: I removed every widget I didn’t use. Then, I added the ones that mattered most to my daily tasks. This included a “Contracts Nearing Expiration” list, a “My Open Tasks” chart, and a “Vendor Scorecard” summary. This simple act immediately transformed my homepage from a cluttered landing page into a personalized command center. I could see the most critical information at a glance, and I knew exactly what I needed to tackle first.
2. Unleashing Workflow Notifications: I went into my user settings and the workflow configuration area. The key was to move beyond the default email alerts. I configured my workflows to send notifications directly to my dashboard and also to trigger a task assignment if an approval was overdue. For that critical vendor contract, I set a specific notification to escalate to my manager if I didn’t act on it within 48 hours. This created a safety net that ensured nothing would fall through the cracks. It wasn’t about micromanagement; it was about building a system that had a built-in sense of urgency.

Hour 3-4: The Data is King – Optimizing Fields and Reports

A system is only as good as the data you put into it. Our initial setup had been rushed, and many of our contract records were missing crucial information. I knew this was the root of my search and reporting frustrations.

1. Cleaning Up Custom Fields: I reviewed our custom fields. Some were redundant, others were formatted incorrectly, and some were simply not being used. I worked with my team to agree on a standardized set of fields that were mandatory for every new contract. This meant that from that day forward, every contract record would have consistent, searchable data.
2. Building a Smart Search: Cobblestone’s search functionality is incredibly robust, but I hadn’t been using it to its full potential. I created a series of “Saved Searches” for my most common queries, such as “Contracts in Negotiation with a Value over $100k” or “Vendor Agreements with an Indemnification Clause.” This eliminated the need to manually re-enter search criteria every time and gave me instant access to the information I needed.
3. Harnessing Ad-Hoc Reports: The reporting module, which I had previously found intimidating, suddenly became my new best friend. I created an ad-hoc report that tracked our contract cycle times. By analyzing the data, I could see where our biggest bottlenecks were (hint: it was the legal review stage). This wasn’t just about getting a report; it was about gaining a strategic insight that I could use to improve our overall process.

Hour 5-6: The AI Revolution – Befriending VISDOM® and IntelliXtract™

This was the part I had been most intimidated by, but it turned out to be the most rewarding. Our system had VISDOM® AI and IntelliXtract™ enabled, but we were barely using it. I took a deep breath and decided to let the AI do the heavy lifting.

1. Re-Running IntelliXtract™ on Existing Contracts: I didn’t have time to manually go through every contract, so I took a sample of our most important agreements and re-ran the IntelliXtract™ feature. The results were astounding. It automatically pulled key dates, party names, and critical clauses that had been missed during the initial, manual data entry. It wasn’t perfect, but it was 90% of the way there, saving me hours of work.
2. Activating ConfigAI™: I turned on the ConfigAI™ feature for new contract uploads. Now, when a contract is added, the system proactively suggests metadata fields and values based on the document’s content. This was a game-changer for my team, who often struggled to remember which fields to fill out. It turned data entry from a chore into a guided process.
3. Using Clause and Template Management: Our legal team had a pre-approved clause library, but it was rarely used because it wasn’t integrated into our process. I worked with the legal team to sync the library to the Cobblestone platform. Now, during contract drafting, the system’s “Auto-Redline” feature could automatically insert approved language, ensuring compliance and significantly speeding up the negotiation process.

Hour 7-8: The Secret Weapon – Mass Actions and User Permissions

By the afternoon, I was moving fast, filled with a newfound confidence. I had a few last tricks up my sleeve that I knew would save time in the long run.

1. The Mass Transfer Tool: This was a hidden gem. My team was undergoing a reorganization, and contracts needed to be re-assigned. Instead of doing it one by one, a process that would have taken a full day, I used the “Mass Transfer” tool. In a single screen, I was able to transfer hundreds of contracts and their associated tasks from one user to another. The efficiency was mind-boggling.
2. Refining User Permissions: Our user permissions were either too broad or too restrictive. Some users had access to contracts they shouldn’t see, while others couldn’t get the information they needed without asking me. I spent some time reviewing and refining the permission groups. I created a new “Read-Only” role for our finance team and a “Full Access” role for our legal department. This not only improved security but also empowered my colleagues by giving them access to the data they needed while keeping sensitive information protected.

The Result: A New Relationship with Our Software

By the end of the day, I was exhausted but exhilarated. I had come to the office with a feeling of dread and was leaving with a sense of mastery. The Cobblestone system was no longer a burden; it was a powerful partner.

The contracts were organized. The workflows were running smoothly. My dashboard provided a clear, actionable overview of my priorities. I had armed my team with better tools and had leveraged the platform’s AI to do the work that had once been a manual grind.

The lesson I learned that day was simple yet profound: no matter how robust a software platform is, its true potential lies not in its features, but in how you configure and use them. Cobblestone Software, with its deep configurability and powerful AI, is a tool that rewards a little time and effort. It’s a system designed to be molded to your business, not the other way around. My one-day deep dive transformed it from a simple repository into a strategic asset that has since saved my team countless hours, mitigated risk, and unlocked a level of efficiency I didn’t think was possible. If you’re using Cobblestone and feel like you’re only scratching the surface, take one day. Just one day. You’ll be amazed at what you can accomplish.