Businessman with cloud computing and connectivity concept

You have just started a new position as a CIO. You are adjusting to the office, decide you like the view, ensure your pictures are optimally arranged, and stare at an inbox which is likely as empty as it will ever be from this point forward. You are still rehearsing the new names, staring at your organizational chart, and sorting through your mobile phone email setup. Before you lies a diverse field of opportunities within technology, talent, strategies, providers, consultants, services, and options on how to develop and execute your vision for IT. There is only one problem. Where do you start? Here are 10 questions you can ask which will quickly provide insight into the kind of challenges you are facing and give an idea of where to begin. Each of these questions will naturally yield many additional questions. By the end of this process, you will reflect back longingly to that nearly empty inbox.

 

1. How does the business perceive IT?
You do not need detailed a communications campaign or survey analytics to ask this question. Once you are introduced to leaders around the company, start by simply setting up some one-on-one discussions to get an idea of how they perceive IT. Has IT met their demands?  Is IT limiting or bottlenecking their opportunities? Is IT enabling the business to compete? You cannot necessarily take each of these answers at face value before completing the rest of this list. At times, customers in the business may feel completely content with IT, simply because they don’t know what is possible. They may feel some resentment because their projects were recently rejected for very valid reasons. Regardless of how the conversations vary, listen intently and get a sense for their overall view. If IT has any serious credibility issues, they must be addressed before you can effectively tackle any serious technology or IT organizational strategies.

 

2. Who within IT is currently interfacing with the business?
While you have the attention of your key stakeholders, ask them who they normally interface with from IT. How often does this occur? What kind of visibility do they have into IT performance or capabilities? Are they aware of what IT is doing in other parts of the business? Who do they call when they need help understanding the technology impact or opportunities on their upcoming projects? If they can’t answer these questions, you have some organizational and governance challenges. You may resolve some of this gap in your new role, but you cannot do it alone. Ensuring effective communication at varying levels, with specific roles for business relationships and communications, is critical to future success.

 

3. What are your IT leader’s top priorities?
Now that you have some perspective from the business, it is time to start looking inward to the IT team. A good place to start is by having your senior team deliver a brief presentation on their top priorities and challenges. The purpose is not to get a status update on current initiatives, although this is a side benefit. The purpose of this question is to help you learn about them as leaders. How they answer this question will tell you a great deal about their thought process, organization capabilities, and perceptions of IT delivery.Is there agreement? Do their priorities conflict? Are the biggest challenges with operational issues, project delivery, acquiring/retaining talent, budget constraints, etc.? How do their priorities match those of the business? Do they have a plan to tackle their priorities?

 

4. Where is an updated inventory of software and hardware in the environment?
Perhaps you felt an early issue would be big data, cloud strategy, of social media platforms.  Long before you can worry about how your team is handling details such as data taxonomy, it is often best to find out if they even know what is in the environment today. Obviously, you are not going to comb through this inventory personally. This is really a very simple IT maturity test. If an inventory with some reasonable level of accuracy is difficult to assemble, there is clearly some groundwork ahead. How many applications are in the environment? Who uses them? What are your hardware standards? Where are your assets at in their lifecycle? What are your top 10 most used business applications by cost? What impact will future projects have on the current environment? These critical questions will prove difficult to answer if you lack effective IT asset management. If you don’t know what you have, you cannot determine what you need. Perhaps the business has a challenge that you already have the capability to deliver.

 

5. How is your operating budget being allocated across ‘keep the lights on’, regulatory costs, innovation, or business improvement activity?
There is perhaps no better reflection of what has historically been important within IT than what the IT budget tells you. This is especially true if you can see how the budget has trended year-to-year in both size and percentage of allocation. Does IT differentiate opex between day-to-day operational activity, regulatory or security costs, innovation, or business improvement? If this does not occur, it is likely a challenge in itself. If a similar allocation exists, how are they trending within the categories? Are operational costs increasing or decreasing year-over-year? Is IT creating opportunities to spend more time on business improvement or innovation activity year-over-year?

 

6. Where is a list of open regulatory, audit, or security issues?

Most companies have multiple audit and regulatory standards to maintain. Whether the challenge is SOX, PCI, HIPAA, or others, there is likely an active program, driven outside of IT, to ensure a certain level of data security and integrity is in place.  Is there a record of external or self-audits for IT? Does anybody have accountability to track these efforts, responses, and remediation efforts? Are findings prioritized or considered in the annual budget process? Addressing IT security alone evolves every year and is growing particularly crucial in a world with more dependences on external IT offerings via the cloud or managed services. Does your IT group have visibility into IT security trends and services? What security issues have occurred within environment? How did IT respond in terms of organization, processes, and tools? How do these responses factor into vendor management?

7. Where is a list of current projects by status, budget, impact area, funding source, and benefit expectation?
This is another simple maturity test. This question carries a number of implications which will help drive your priorities. Is there accountability for project delivery? Is there any indication that projects may be at risk? This often ties back to IT credibility. If IT is doing a poor job of tracking and governing project execution, this is often demonstrated in an inability to spend the annual budget allocation. IT may often go back and ask for a similar, or higher, amount of capital for the following year, without ever demonstrating the ability to deliver on previous efforts. While a full PMO may, or may not, be necessary, some level of project tracking and reporting process is critical to ensure project accountability.

 

8. How are IT projects selected for funding?
It is more important to deliver the right service than to deliver the wrong service well.  Understanding how technology projects are funded by the business, within IT, or even when buried within operational activity, is a key insight into your new organizations. Does the loudest voice get more budget? Is there a quantitative selection process in place? Are there clear value propositions analyzed against the proposed costs and risks?  Does business strategy factor into project selection? How early do you have visibility into the pipeline? Your influence into improving this process may be your greatest IT transformation tool. Picking the right projects based on clear metrics and executing them well is key to maturing IT into a business partner.

 

9. Is the current IT organizational structure designed to handle rapid change while maintaining effective delivery?
IT organizations have transformed significantly over recent the years. IT previously focused on technical siloes in many large IT organizations. Today, organizations are increasingly aligning to business service delivery processes. These type of organizations help ensure focus across strategy, solutions design, project execution, and governance activity as they relate to each distinct IT offering. If you are still organized along technical silos, it may be time to evaluate opportunities available through new operating models.

 

10. How accessible is critical knowledge?
Knowledge management within organizations is more than a fad driven by document management systems and corporate social platform tools. One of the most critical roles facing IT today is enabling the business to effectively transition new generations of workers without losing deep business, functional, and technical insight gained over many years. The information must be easy to access, and readily available via mobility platforms 24×7.  This requires a transformation to how people search, find, and utilize business and IT information. If you ask for details of IT or business processes, and get referred to file shares or document binders, you have certainly found a high-priority area to begin impacting your new organization successfully.