People often ask me what it’s like to be an analyst at Gartner, and for me, the answer is, “It’s a life of constant client conversations.” Over the course of a typical year, I’ll do something on the order of 1,200 formal one-on-one conversations (or one-on-small-team, if the client brings in some other colleagues), generally 30 minutes in length. That doesn’t count the large number of other casual interactions at conferences and whatnot.

While Gartner serves pretty much the entire technology industry, and consequently I talk to plenty of folks at little start-ups and whatnot, our bread-and-butter client — 80% of Gartner’s revenue — comes from “end-users”, which means IT management at mid-market businesses and enterprise.

Over the years, I have learned a lot of important things about dealing with clients. One of them is that they generally aren’t really interested in best practices. They find best practices fascinating, but they frequently can’t put them to use in their own organizations. They’re actually interested in good practices — things that several other organizations like them have done successfully and which are practically applicable to their own environment.

More broadly, there’s a reason that analysts are still in business — people need advice that’s tailored to their particular needs. You know the Tolstoy line “Happy families are all alike, but every unhappy family is unhappy in its own way” that starts Anna Karenina? Well, every corporate IT department has its own unique pathology. There are the constraints of the business (real and imagined) and the corporate culture, the culture in IT specifically, the existing IT environment in all of its broken glory and layers of legacy, the available budget and resources and skills (modified by whether or not they are willing to hire consultants and other outside help), the people and personalities and pet peeves and personal ambitions, and even the way that they like to deal with analysts. (Right down to the fact that some clients have openly said that they don’t like a woman telling them what to do.)

To be a successful advisor, you have to recognize that most people can’t aim for the “ideal” solution. They have to find a solution that will work for their particular circumstances, with all of the limitations of it — some admittedly self-imposed, but nevertheless important. You can start by articulating an ideal, but it has to quickly come down to earth.

But cloud computing has turned out to be an extra-special set of landmines. When clients come to me wanting to do a “cloud computing” or “cloud infrastructure” project, especially if they don’t have a specific thing in mind, I’ve learned to ask, “Why are you doing this?” Is this client reluctant, pushed into doing this only because someone higher-up is demanding that they do ‘something in the cloud’? Is this client genuinely interested in seeing this project succeed, or would he rather it fail? Does he want to put real effort into it, or just a token? Is he trying to create a proof of concept that he can build upon, or is this a one-shot effort? Is he doing this for career reasons? Does he hope to get his name in the press or be the subject of a case study? What are the constraints of his industry, his business, his environment, and his organization?

My answer to, “What should I do?” varies based on these factors, and I explain my reasoning to the client. My job is not to give academic theoretical answers — my job is to offer advice that will work for this client in his current circumstances, even if I think it’s directionally wrong for the organization in the long term. (I try to shake clients out of their complacency, but in the end, I’m just trying to leave them with something to think about, so they understand the implications of their decisions, and how clinging to the way things are now will have business ramfiications over the long term.) However, not-infrequently, my job involves helping a deeply reluctant client think of some token project that he can put on cloud infrastructure so he can tell his CEO/CFO/CIO that he’s done it.

Cloud providers dealing with traditional corporate IT should keep in mind that not everyone who inquires about their service has a genuine desire for the project to be a success — and even those who are hoping for success don’t necessarily have pure motivations.