by
Rob Enderle, President and Principal Analyst, Enderle Group
If IT carefully assembles the right planning team, and the team plans carefully and candidly, the team can vastly improve the probability of a successful implementation — and avoid costly and time-consuming rework.
Based on the large and growing number of cloud implementations over the last few years, IT is learning some valuable lessons about how to successfully plan a cloud project and how to avoid catastrophe. This article summarizes the most valuable lessons.
Who belongs on the planning team?
Cloud projects can range from the very small (a departmental project, financed on a credit card) to the very large (conversion of an Oracle implementation to a cloud structure, requiring CEO approval). Compare this to a construction project: It takes only a few people to build a house, many more to build a hotel, and many more than that to build a skyscraper. Your cloud project will require different expertise depending on what you’re moving, what hardware it’s going to reside on, how secure it needs to be, what sign-offs and approvals are necessary, and the budget available.
However, generally speaking, here are the people who should be on the planning team:
All the key parties should be involved to ensure success.
Obstacles to good planning
One obstacle to good planning is fear. Every group and almost every person on the planning team may have an unspoken fear. For example, an IT organization might feel threatened by an external cloud project because it looks like outsourcing, which removes control and budget from the IT organization. A line manager might resent a forced private cloud over a public cloud because it looks like a power grab by IT.
You have to build trust by reconciling and defusing these fears. If all the parties can reach a high degree of trust on the front end of the project, there’s a much better chance they won’t be fighting on the back end.
Another obstacle to good planning is a lack of communication on the front end. For example, one company hired a software consulting firm to plan and implement a cloud project. The consultant was inexperienced; he spent fifteen or twenty minutes talking to a few salespeople — and did no further research. Then he spent a year drafting a plan and implementing it. Because the implementation did not reflect the company’s real needs, it was completely unusable. The company brought in another firm. The new firm had to discard everything, redo the research, write a new plan, and implement the plan — adding another year to the project.
Measure twice, cut once
In your planning, follow the carpenter’s motto: “Measure twice, cut once.” In the construction business, people often get impatient during the planning phase. They figure they can gain some time by beginning the execution while they plan. But they soon discover that they have to redo a massive amount of work because of something they had not fully thought through. And, of course, they run over budget.
If the work is going to be outsourced, the danger of starting work too early is even greater. For example, many companies give contracts before they can coherently state what they want. So the vendors have to guess what the companies want — and they may guess wrong.
In IT project planning, as in construction, there are three absolutes:
How conflicts arise
The biggest source of conflict is the eternal tension between line organizations and staff organizations. (IT, of course, is a staff organization.) The conflict is natural, because most people want some degree of power and control. Specifically, line wants power and control over the projects it manages, and IT wants power and control over its assets.
What’s worse, the two sides rarely speak the same language. Each side can leave a meeting thinking that its view is absolutely right and that the other side’s view is absolutely wrong. When this happens, the result is almost always catastrophic.
Line may even want to fire IT. The usual reason is that IT hasn’t been treating line managers as customers. IT should constantly be doing customer satisfaction studies, but usually they don’t. Then they act surprised when line managers outsource or bypass IT.
In past decades, the CFO handed out the money and IT controlled its own budget. Everyone outside IT just assumed that IT would magically create productivity improvements. Everyone assumed this because no one really understood technology.
That changed a lot during the last decade, when profit-and-loss responsibility was pushed down to line managers. Now the budgets in most companies, especially large ones, are controlled by line managers. In many companies, IT has not fully grasped the implications of this change — that they must serve their customers directly.
End-runs around IT
One implication is that now it’s easier to circumvent IT. And the cloud makes it easier still. Line managers can go shopping for cloud services with their company credit cards. Granted, if the auditing organization finds that any line managers have exceeded their authority, those line managers will suffer for it. But otherwise, most line managers are feeling confident that they can circumvent IT when they want to do so.
Also, line managers no longer have to worry about inadequate security. There are cloud services that can meet robust security requirements, because they were designed to do so. They may not be the least expensive options, but they are auditable. And they take credit cards.
For example: In one company, the IT manager wanted to use a third-party cloud resource, so the company’s senior management brought in the security team to do an audit. Security concluded that the third-party resource was actually more secure than the company itself. This discovery reversed the audit recommendation.
However, compliance may be another matter. Cloud is far enough removed from traditional hosting to create new compliance problems. For example, a private cloud may be moving data to geographies that are prohibited by law.
Promoting your project
You should start promoting your project early, to ensure that you can get an adequate budget. Promoting your project means building line managers’ demand for your project by informing them about cloud technology and the benefit of cloud-based solutions.
Promotion requires the ability to understand line managers’ requirements and attitudes, and to talk to the managers in a way they will understand. Usually the quickest way to do all that — especially if you don’t have much experience in promotion — is to ask the vendor for help. Most vendors will provide some help, because they recognize that by so doing they are protecting their own income.
A common mistake
No one can know everything. Don’t make the common mistake of overestimating your knowledge of cloud technology or cloud-based solutions. The success of your project may depend on a conservative estimate of how much you know at the time the planning begins — in spite of other peoples’ assumptions that you already know everything about cloud.
The best way to avoid overestimating your knowledge is to make sure that you have someone on the planning team who has already been successful in building a cloud. Remember, in spite of having completed many years of medical training, a general practitioner will call in a specialist when one is needed. You should, too. Bring in someone who has the specialized experience and knowledge, and rely on them.
Set realistic expectations
If you set realistic expectations, you will have a much higher probability of success. Cooperate with the line organization. Jointly and carefully define the requirements, set the budget, and put in place the milestones. If you can all agree on the desired outcome and deadlines, you’ll be in good shape to begin building.
And remember a wise old rule of business and of human relationships in general: Under-promise and over-deliver. Don’t over-promise and get the customer excited and then fail to deliver all you promised. It’s better to somewhat under-promise and risk making the customer a little unhappy at the front end of the project, and then exceed the expectations and make him ecstatic.
But ideally, make the expectations reasonable and meet them. Create and maintain trust.
Reduce the drama
The more drama you experience, the worse the project will go. The project is supposed to be a productive and peaceful partnership of line managers and IT managers — not two organizations competing for the favors of the CEO. Because IT is participating in the partnership to provide a service to line managers (the customers), IT’s happiness depends on the customers’ happiness.
If line managers are happy with the work you’re doing, they won’t be tempted to work around you or displace you. And if someone outside criticizes your work, line managers will defend you.
Recognize two things about the partnership: (1) line managers have the money; (2) if you’re giving them a service they can’t live without, they will value you. And as long as they value you, you have nothing to worry about.
A cloud implementation can be complex and challenging. But IT has learned, and is still learning, how to use better planning methods to smooth implementation and ensure that the final product meets the needs of everyone involved — including IT. Good planning pays for itself many times over.
About the Enderle Group
The Enderle Group delivers customized advisory services to businesses based on their unique needs. Those services include business operations review, assessment and guidance, market and competitive evaluation and recommendations, customer and vendor insight and market strategy, marketing and product introduction counseling, and new hardware and software testing and review. For more information, visit www.enderlegroup.com.

Rob Enderle, President and Principal Analyst, Enderle Group
Rob Enderle is one of the most influential technology pundits in the world. As president and principal analyst of the Enderle Group, he provides regional and global companies with guidance in how to create credible dialogue with the market, target customer needs, create new business opportunities, anticipate technology changes, select vendors and products, and practice zero-dollar marketing. He expanded his IT industry analysis skills at Dataquest, Giga Information Group, and Forrester Research. Rob can be contacted at renderle@enderlegroup.com.
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