This Former CIO Felt Like He Could Write and Publish a Book, and Did

Don Tennant

How many times has someone asked you about the craziness of dealing with the challenges of being in the IT profession, and “I could write a book” was your natural response? The fact is, you probably could, and it would probably be a valuable resource for your peers. Unfortunately, those potential goldmines of information generally don’t get written.

One that did was authored by Dewey Ray, the former CIO I wrote about last week. Ray’s book, “The IT Professional’s Merger and Acquisition Handbook,”  was a mammoth undertaking, a 491-page tome that covers in extraordinary detail the crucial role that IT plays in a successful merger or acquisition, and serves as an indispensable how-to guide for any IT professional who finds himself in an M&A situation.

Ray, who began his IT career as an analyst/programmer in 1973, founded Cognitive Diligence LLC last fall to provide M&A consulting services based on the book, and to market the book itself. During our conversation, Ray shared the story of what inspired him to write it:

Back around 2000, I was the CIO for a company here in Atlanta, a virtual distributor of truck parts for over-the-road trucks. One of my competitors on the West Coast was interested in acquiring us, so they sent a team of folks to do their due diligence. And on the team there were a couple of IT people. They came, and they asked questions, and they looked at our IT assets, and they took notes, and they went on their way. I realized as it was happening that they were not asking the right questions. At that point in time I had just been brought on board to fix IT for this firm that had best-of-breed everything, but the integration of the assets had been done poorly, so there were some serious structural weaknesses in IT. They failed to uncover those, because they didn’t ask the right questions. I’ve been in IT for over 30 years, so I have this broad perspective—I stepped back and said, “There’s got to be a better way to do this, because if they acquire us and they don’t come back and take a closer look, they’re going to be taking on some risk that they wouldn’t necessarily need to take on. Or they could make a different offering price—there are a lot of different ways you can mitigate the risk.” So that was the inspiration for the book. I went looking across the marketplace for content that would help a senior IT executive like myself to do due diligence in an M&A scenario, and couldn’t find it. There are a half-dozen consulting firms that do it, but they haven’t published how they do it—just a few white papers here and there. But of course, I was busy—I had my career, I couldn’t sit down and write the book. But I did begin developing my methodology for how to approach that, and outlining what it would look like. I really got serious about it about four years ago.


Interestingly, Ray chose to self-publish the book. He shared his reasons for making that decision:

About three years ago, as the book was really beginning to take shape and I had some content, I was approached by a company I have a relationship with, a major IT book publisher in New York. They said, “Send us an abstract, we’d like to see what you’re doing.” I sent them a 20-page abstract, they put it before their committee, and they came back and sent me a formal proposal to publish the book. I looked at the contract, and it bothered me—the big thing that bothered me is they would own the copyright to all the content. There’s some intellectual property and some innovative thinking, and one of my longer-term goals is to offer training based on the book. I immediately saw all kinds of problems trying to do that if someone else owned the content. I put the contract in front of an attorney friend, and he advised me against signing it. So that totally changed my approach. If I was going to build a business based on the book, and do the things I wanted to do with toolkits and training, I had to own the copyright. That was the deciding factor. The downside is that I am having to market it myself. But that’s the route I chose—I didn’t see an alternative.

As an aside, I asked Ray what the biggest mistake he ever made as an IT professional in an M&A situation was, and what he learned from it that he could pass along to other IT professionals. He was characteristically candid in his response:

I was a practice director for an IT consulting firm here in Atlanta, and we acquired a boutique firm over in North Carolina. I was dispatched to go meet with those folks to assuage their anxiety, and let them know they were going to be part of the new firm. I don’t think I handled that well, and my shortcoming was in the communication area—I’m at IT person. This was in the nineties, and I don’t think at that point in time I fully appreciated how important handling that first encounter with those folks was, and I think I lost some of them in that process. If I had it to do over again, I would be much more purposeful and thoughtful, and I think I would do a better job.



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