My first document automation deployment was for a sales team of 70 people who would use the system to generate customer NDAs, quotes, orders, and contracts. We started with about 15 templates, stocked with one thousand pages of text ranging from contract terms to product descriptions.

Salespeople must focus on getting deals signed. Unlike the rest of us, they don’t pay their bills unless they close a new business. Internal bureaucracy, approval loops, compliance requirements, and lengthy contracts are unwelcome. It was a salesperson who first introduced me to the phrase: “It’s easier to get forgiveness than permission.”

Introducing document automation into a team that previously had the ‘freedom’ to use its own pet texts was necessary for many good business reasons, but not obviously compelling for the salespeople. And yet, by the time that system was replaced after ten years, they missed it. Meanwhile, some team members went to other organizations and asked them to adopt similar tools. Why?

At the first automated documents launch, we (the contract management team) made a deal with the sales team. It was simple: “You must use this system. In return, we must make sure the system is usable.” We imposed the new documents and associated changes, but it was our job to make sure the new system covered all their needs, was relatively easy to use, and that the system didn’t get in the way of closing new business. When gaps emerged, or when the business evolved, we filled the gaps, and we evolved the templates. If the documents caused problems with customers, we looked at ways to improve them. If the system was awkward to use, we adapted it. Instead of being a burden on the sales function, the tool became a resource they relied on to close complex sales (our contracts were typically 40-80 pages for a business-critical service of a technical nature). We gave them a tool, not an administrative overhead.

The document automation system could be influenced by the finance team (making sure pricing was correctly formulated), the product team (making sure services were correctly specified), and the executive team (making it easier to approve deals). Instead of creating lengthy policy documents or sales handbooks, we built the rules into the automation. We made it easier for sales teams to do their work correctly by default.

We measured the benefits of automation to win support from the sales management team, and to check that we were not kidding ourselves. We also looked for opportunities to reiterate the bargain we declared, to acknowledge that we had an ongoing duty to manage the system and keep it tuned. 

Winning hearts and minds is easier than it used to be. Modern systems like Legito are better, nicer to use, do more, and are used by a generation that prefers to use technology to perform repetitive work.

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