10 Reasons Why Strategic IT Management Initiatives Fail

By Dennis Drogseth

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While the current global economy is in a state of confusion and recession, the need to take bold moves in managing IT and improving IT processes is more relevant than ever. “Business as usual” and simply cutting back across the board in high technology investments can often lead to competitive disadvantages and actually create costs; especially if initiatives to improve process efficiencies get stymied, or frozen at awkward half-way points.

On the other hand, it’s clearly counter-intuitive to make investments when anxiety and uncertainty argue otherwise. This is all the more true, since so many strategic initiatives end in disappointment. In this column I lay out some fundamental issues that touch most strategic initiatives—not with an eye to discouraging you but, in fact, with the hope that by singling out these common issues, you will be more prepared to move forward.

According to feedback gleaned through EMA’s IT consulting, 75% of strategic IT management initiatives fail (failure is defined as not meeting initial expectations in terms of time or budget to deliver expected value). Yet years of IT consulting have revealed that strategic IT initiatives share many of the same pain points. The dominant problems are so consistent, in fact, that they offer CIOs a useful checklist of “What to Avoid,” or, conversely, what to do proactively to help promote success. So, without further ado …  

The Top Ten List

Insufficiently detailed requirements — This may be pretty self evident, but the rush to get started on a tactical basis often overpowers better intentions. Take a little more time and make adequate, detailed plans. Sometimes you, as executives, can be part of the problem if there is a rush in terms of time to value that turns out to be inappropriate, or worse naïve. I am going to mention another corollary to this, which is the need to have a good core strategic team to begin with that includes the right mix of skill groups. For most strategic initiatives, this means a combination of skills ranging from process expertise, communications expertise, and a commitment to iterative dialog, a mix of appropriate architectural skills, and someone tuned to the details of the core technologies/products at hand.

Insufficient attention to process — While almost everyone recognizes the need to pay attention to best practices, such as ITIL, in a very large number of strategic initiatives, process education is dealt with in an ad-hoc manner; often after the initial planning is done. On the other hand, problems can arise when a religious approach is taken and ITIL, for instance, is treated as more gospel than departure point. The right approach combines proactive education with a realistic willingness to assimilate existing processes. This includes learning and documenting “best practices” from the various groups within your organization.

Executive support — Just in case you didn’t realize it, you’re all important in the success of strategic initiatives. The lack of firm commitment from executives can seriously disrupt strategic initiatives. This is especially true when one executive leaves and a new one comes on board. Our rule of thumb is that you, as executives, will need to see documented results no less frequently than every six-month. This can put constraints on project planning, but it can and should be achievable with the right detailed approach.

Inadequate or waffling budgets — This is probably not a popular thing to mention in the Winter of 2008/09, but inadequate or waffling budgets can produce rather than cure inefficiencies and ultimately create unnecessary costs as project objectives aren’t met, or projects are redirected. Some strategic initiatives are primarily enabling and, as such, should move to a core budget model versus a project model as soon as possible.

Staff buy-in — Getting the staff on board isn’t all your job as the executive. It should really fall to your core team. But you need to be there to support the effort and make clear that it’s your priority, as well. You also need to invest sufficiently in a core team that understands the need and has your perspective on the initiative. Ultimately, the goal is to enlist the staff as active and enthusiastic participants versus just consumers. To do this, talk to them regularly and make sure they feel like you've heard and understand their concerns.

Resistance to change — This is, needless to say, one of the chief obstacles that you and your core team will encounter when promoting almost any strategic initiative. We're pretty sure you've heard these before: "Show me this isn’t a boondoggle.” Or, “We live in the moment. We are very operations-oriented.” Or, “We are tactical, action-oriented people, and this initiative too strategic.” Explaining tangible near-term benefits, realizing them and then promoting them is of course the best answer to these natural born skeptics.

Managing expectations — Once you get some level of enthusiasm, managing expectations is critical. For instance, many stakeholders may cross the barrier from resistance to enthusiasm, but fail to pull their share of the load. They become the ultimate, spoiled consumers. And by the way, among the “expectations” to be managed by the core team, their's are likely to be at the top.

Lack of follow through — Too often there is a “hot topic of the month.” The media and many industry analysts make a good living promoting what’s in fashion; often maxing out longer-term directions on the maturity curve prematurely. (In case you’re wondering, strategic objectives like CMDB systems, service catalogs linked through modeling to active operational automation, and effective end-to-end service management aren’t going to “mature” and go on “maintenance” in the foreseeable future.) You should expect these initiatives to evolve and grow in value for many years to come.

Lack of integration and Lack of automation — I’m going to wrap up with two technology-centric failure points. Not only are more effective levels of management integration and automation benefits from many strategic initiatives, most strategic initiatives also depend on integration and automation to succeed in their own rights. Strategic initiatives that rely too much on manual actions quickly become elephants weighing down rather than enabling progress. In fact you can sometimes gauge your readiness to move on to the next phases by assessing how prepared your organization is to “integrate” and “automate” in support of better ways of working to support the initiative at hand.


Dennis Drogseth is vice president of Boulder, Colo.-based Enterprise Management Associates (www.enterprisemanagement.com), an industry research firm focused on IT management. Dennis can reached at ddrogseth@enterprisemanagement.com