The CIO has a Problem, and AI isn’t Helping

The vast majority of organizations report substantial difficulty matching IT output with strategic and operational business demand in 2025. This is a problem.  To make matters even worse, the growing demand from the business to charge forward with AI-related initiatives is putting even more pressure on the CIO and their IT departments.

If you’re the CIO or in IT, I am “preaching to the choir”.  Every single client I have worked with in the last several years is having difficulty getting their IT departments to keep up with the business demands. In a 2025 market study, 67% of technology companies failed to hit their product roadmaps due to resource constraints and project overload.  Staffing is difficult, hiring takes time, and it is even difficult to find skilled consultants to fill the gap.  Factor in tighter budgets and the stress level in IT departments continues to escalate.

Several years ago, it seemed like one of the characteristics of high-performing CIOs was their ability to “sell” better technology solutions that would help the business.  While that remains as a critical skill set for CIOs, it is becoming increasingly important for CIOs to help manage the inflow of project requests from the business. 

Technology vendors are culpable in this problem as well.  How many IT leaders walk into the office each day only to find out that some business leader has gone and “signed up” for some new software-based technology or service and then demands that IT support the new platform and integrate it into their other operations?  I call this “BusinessWeek Syndrome”.  You know the drill…a business leader is on a plane, usually on their way to or from a conference, and finds a copy of BusinessWeek in the seatback pocket, reads an article or an advertisement, comes back to the office, and signs up for another technology solution. 

The technology vendors make it perilously easy to sign up and get started using their software…no need to run it past IT first. It is becoming more common for mid-sized companies to suddenly realize their IT department is trying to manage dozens, if not more than 100 business-important technology solutions.

IT leadership is increasingly finding itself in the delicate, if not uncomfortable position of balancing customer service with project enforcement.  Throttle down on project intake and tick off the business.  Let the business inundate your department with new technology and run the risk of missing critical deadlines. Worst case scenario is when IT gets so overwhelmed, they slip up on maintaining the core IT operations needed to “keep the lights on” and to maintain security.

All this begs the question, what is the solution? I’ve had the opportunity to “roam the halls” of over 300 businesses over the last 30+ years and I have seen countless methods to try to address this fundamental challenge.  Certainly, some handle the challenge much better than others.  Here are a few factors I have seen from those companies and leaders who have managed it most effectively.

The most important indicator of how well a company will manage the balance of project intake with project enforcement is how prominent a role the CIO plays on the executive team.  If the CIO is NOT on the most senior executive leadership team, all bets are off. The role of technology in every organization is becoming so vitally important that if the CIO does not have a seat at the executive table, it is clear the CEO or the Board are behind the times and do not value technology. 

The more successful CIOs today have a broader business background, and their role affords them a lighthouse perspective of many key initiatives going on in the organization.  This perspective is vital in helping to spot overlapping initiatives or even opposing initiatives. They may be better equipped to spot opportunities where one initiative can be leveraged in other areas to maximize investments. Finally, they can spot potential surges in technology demands and influence that demand before crucial decisions are made by the business. One would think that should be what is already happening, but far too many department leaders are acquiring technology absent from the counsel from the CIO or their team.

Another indicator of how well an organization balances project intake with project enforcement is whether or not they use a process for evaluating project requests. Not just any process.  A process that evaluates how well the proposed initiative is aligned with stated technology and corporate objectives. As I have helped companies craft data strategies over the years, I developed a tool to help this process called a Strategy Matrix.  It is a key component of the Analytics TO WIN^® method being used by numerous organizations around the world.

The strategy matrix first aligns the current corporate objectives to specific data management and analytics (DMA) strategic objectives.  Common DMA strategic objectives include improving data quality or establishing a central, trusted repository of curated data sets. We then evaluate potential data-related initiatives against the DMA strategic objectives and establish a score.  For a data-related project to “make the cut”, it needs to show clear support of both the DMA strategic objectives and the overall corporate objectives.  In other words, executing the proposed project is more likely to help the organization achieve its designated corporate objectives.

Some clients have adapted the Strategy Matrix concept to other strategic concepts such as AI or CRM. Others have used it to manage their overall IT backlog to weed out extraneous projects that are a distraction or are unlikely to help achieve the overall corporate objectives.  My clients are well aware of my questioning phrase of “is the juice worth the squeeze”.

A critical advantage of using a method, including the Strategy Matrix, is that the method is what will bounce a proposed project from current consideration…not the CIO.  Therefore, the process is the “enemy”, not a person.  It is also possible to show the sponsor of the proposed project how their project “scored” respective to the other projects being evaluated or already underway.  This promotes transparency and reduces the likelihood of favoritism for one department or another. 

Some organizations utilize a Project Management Office (PMO) to manage the intake of new projects and some PMOs may also serve as the new project gatekeepers. As with most corporate functions, I have seen PMO’s succeed and fail. Some simply provide the project managers with overseeing larger projects and provide structure to help execute the projects and track progress. While this is a very helpful function, it does not mean the PMO is best served to evaluate the merits of a new project, particularly a technology project.  Some simply check to see if they have enough project management bandwidth to manage the proposed project, but are ill-equipped to know if the project will actually help achieve the corporate objectives. Successful PMOs often have deeper technical capabilities, may be part of the IT department, and follow an alignment process for evaluating potential projects.

The final indicator of how well an organization balances project intake with project enforcement is the way in which new projects are surfaced. As previously mentioned, if BusinessWeek Syndrome is rampant in the organization, you are not doing things right.  A best practice that is emerging is to utilize objective assessments to gain valuable insight into where there are weaknesses in the organization. If there are suspicions or complaints about a function or practice in the organization, consider taking an assessment to zero in on the core issues.

Assessment results themselves are not the final step.  A vendor solution and/or a consultant may be valuable in helping address the issue or missing capability through a project.  However, an assessment can help you better understand which vendor solutions or consultants may be a better fit to address your needs.  Most importantly, an assessment can help you better understand the scope of what needs to be addressed.  If you engage a consultant, having a clearer understanding of the potential scope will almost always save you time and fees.  The simple phrase is to only pay for what you need.

Consultants love helping you establish the scope of their work, and sometimes they may help you know what you don’t know, which is a benefit.  However, start with a tighter scope of work to establish the relationship and let it evolve from there, so you are in better control of the process. Determine if the consultant is a good partner to continue leveraging their insights. Vendors are especially prone to solution scope creep and love to create needs for capabilities their solution provides, in excess of what you originally requested.

The challenge with assessments is that most of them are offered by the consultants or vendors themselves. Most of them are “free” but will result in endless emails and calls from account reps and inside sales teams.  Other assessment providers only make their assessments available if you sign up for some large subscription package offering you access to a bunch of other white papers and thought leadership. So do your homework, as there are sources for assessments that don’t come with all the strings attached.  This very challenge was part of the genesis of a company called assessIT.io.  They have a small but growing portfolio of assessments that will give you proper insights into weaknesses, without the sales pressure from vendors or consultants. Their assessments are crafted and curated from consultants who have experience in the field associated with each assessment. 

As AI continues to churn up endless opportunities for new technology initiatives, consider the challenges the CIO is facing in determining which ones warrant investment. Seek out some assessments to match your issues with potential solutions and consider a method leveraging a tool like the Strategy Matrix to evaluate your potential projects.  The extra effort to evaluate these projects will pay dividends and keep your organization focused on meeting your objectives.

About the Author

Shawn Helwig is the CEO of assessIT.io and managing partner at Total View Analytics, a data strategy consultancy.  He created the Analytics TO WIN^® method to help organizations craft their data strategy and has established a worldwide network of delivery partners. He is also the host of the Drinks ‘n Data podcast and a frequent speaker at conferences and events.