The Challenge of Enterprise IT Initiatives, Part 3 – The Readiness Quandary

“The man who goes alone can start today; but he who travels with another must wait till that other is ready.”

-         Henry David Thoreau

The Oxford Dictionary defines the word ready as “in a suitable state for an activity, action, or situation; fully prepared.” The last part mentioning “fully prepared” is important. In this article we will explore a few key aspects of being ready for an enterprise IT initiative by examining what it means to be “fully prepared”.  For an enterprise initiative, consider customer or business readiness, environment readiness and finally technical readiness. Putting these in the context of your key objective(s) will help you get “fully prepared” to implement your initiative.

As a digital transformation consultant, listening to the customer is critical to understanding the level of effort required to be “fully prepared”. First, this is a unicorn for our industry. In many cases, we have to settle for “mostly prepared” since the financial impact begins once you start logging hours against a cost center. This can be a challenge. The key is doing the diligence and walking through a readiness assessment to identify the obvious roadblocks or challenges that will cause the initiative to begin down a troubled path. Many of the efforts I am involved in now have a component of the sales cycle that includes a readiness assessment. The diligence required can vary by initiative, but they center around the following key items:

·        Defining the Customer

·        Identifying the scope of initiative impact

·        Alignment of target dates

Who is the customer? Are you an IT organization with internal customers or end users? Is this a back-office IT initiative that only impacts the IT organization? By identifying the recipient of the initiative, you define or validate the scope of impact. Once you have identified or validated the customer(s), validate how this initiative fits into their roadmap (or program). Is this the first of several customer initiatives? Is there another customer initiative that may be executing in parallel that requires coordination? Being aware of the customer landscape or roadmap is important especially if you can only be “mostly prepared” at the start. Now you identify the audience to validate your target dates. This is different from the project schedule planning that may occur during the planning phase of the effort. This is aligning the key target dates to the roadmap or landscape. In many cases, you may uncover unknown customer dependencies. The outcome of this exercise should always be communication. The more awareness of your initiative, the better for your readiness and a “more” prepared start. Finally, the result of this first exercise is the start of your risk or issue register. All items not ready should be captured, assessed and a mitigation plan communicated whenever possible.

The environment is a nebulous concept. To put context around this for readiness, environment is not the technical environment (we will delve into technical readiness soon). This does include considering the customer environment. Does this new initiative change “how” the customer or end user works? This is a huge driver for enterprise initiatives and can help you put some perspective on your readiness journey – not just for starting but for the completing the effort. Do you have adequate customer team members that understand the current environment to consult with the initiative delivery team? Are there organizational changes that need to be considered? Are there political considerations that need to be managed? For understanding the readiness for your initiative to start, you must understand if there are any external influences that need to be identified. Completing this part of the assessment can identify program-level risks and issues.

Since this series is about IT initiatives, the technical readiness is the most obvious component of any assessment. This will also vary by initiative. Because it is obvious, it is often the area we are most likely to miss something. You must consider the environment or “ecosystem” thoroughly. It may seem elementary to validate all the technical assumptions, cost of ownership, support structure (skill sets), security and architectural impact, but this is where we can miss a key item that can impact the delivery by affecting resources, time or cost. Consider what the IT landscape will look like once the initiative is complete. This is especially critical if the technology support is outsourced or a 3rd—party vendor is involved. Remember IT initiatives are the toughest to manage and the easiest to mismanage!

Are you ready for your enterprise initiative? Taking the time to understand if your customer is ready helps you with managing expectations. Identifying the environment your initiative will be delivered helps you identify your stakeholders and audience. Completing a self-examination of the IT organization and technical readiness helps you identify team members and those individuals or groups that need to be consulted in addition to the delivery team. The familiar theme is completeness and communication. Even if you can only be “mostly ready”, do the diligence with a readiness assessment to launch your initiative on a path that starts well. Where it goes from there is all about execution.

NEXT: Staffing, Transition and Closure