The Problem Statement

Google Gemini Prompt

When technology organizations are troubled and the business customers don't believe that they are getting value from the information technology organization, then what is wrong?

Google Gemini Response

When an IT organization is out of sync with its business partners, the issue usually isn't just a "technical" problem; it's a credibility and alignment gap. The business views IT as a "black box" where money goes in and complexity comes out, rather than a value driver.

The Root Causes: Why the Friction Exists

If customers don't see value, the problem typically falls into one of these three categories:

  1. Mismatch of Priorities: IT is focused on "keeping the lights on" or technical debt, while the business wants growth and innovation.

  2. The "Order Taker" Mentality: IT waits for instructions instead of bringing strategic ideas to the table. This leads to the business feeling like IT is a bottleneck rather than a partner.

  3. Lack of Transparency: When IT doesn't speak the language of the business (ROI, speed-to-market, customer experience), the business defaults to measuring IT only by its cost

Discussion

Today, every business is a technology business. Cars and trucks have more computer chips than a server, which is why a chip shortage affects vehicle supply chains. Most businesses rely heavily on online transactions. In the Quarterly Retail E-Commerce Sales Report (March 10, 2026), the US Census Bureau of the Department of Commerce announced that the estimate of U.S. retail e-commerce sales for the fourth quarter of 2025, adjusted for seasonal variation, but not for price changes, was $316.1 billion, an increase of 1.7 percent (±0.5%) from the third quarter of 2025 and an all time high. Skilled workers that deliver plumbing, landscaping, electrical work, and HVAC all have tablets to manage their work orders and accept payment. Almost every food venue uses a digital menu, promotes online, and has an electronic point of sale (POS) system. Technology does not just serve the business, technology IS the business. The importance of technology extends to government services. Every agency is also a technology agency. Whether the mission is public safety, health and human services, transportation, financial, educational, or cultural (like museums), all agencies rely heavily on technology and can’t complete their missions without it. Our citizens, that are used to fully participating in a digital economy, expect a baseline digital experience from their government. When technology fails to deliver and innovate, service falters and citizens are not served the way that they expect. The people (leaders, staff, and customers) are not happy.

The Gemini response is correct. When the technology organization customers, whether clients or lines of business, are unhappy with the technology organization, then there are fundamental problems. Though technology may contribute to the problem, it is rarely the root cause. The root cause is a misalignment and lack of relationship between the customer and the provider; a credibility and alignment gap. The customers don’t perceive the technology organization as working for them. There isn’t trust in the motivations of the technology organization and there isn’t trust in the technology organization’s ability to execute and deliver to meet their business commitments.

Infographic illustrating the technology supply chain and its impact on sales, transportation, manufacturing, and public safety, highlighting the gap between technology organizations and their customers.

One of my turnaround project successes was on a program with the US Army. As the systems integrator (SI), we were responsible for the data center and delivery of a critical workforce development application. The application served over two million soldiers and the contract was valued at roughly $30M/year over a multi-year term. My company was in the third year of the contract, and our Army customers were not happy. On paper, we were meeting all program requirements and scoring almost perfect contract performance scores as we met the letter of the contract. However, behind the scenes we weren’t delivering real business value. The program metrics did not reflect the reality that the program was failing. The program requirements that had been set years ago through a lengthy government procurement process were not relevant to today’s needs and our processes to adapt (and the leaders running the project) were overly rigid. Every adjustment or change incurred a price increase and the customer felt like the relationship had become purely transactional. We had to reset and restart the relationship to create a more aligned and mutually beneficial working relationship. I was part of the reset where fresh leadership could realign with our customer without any emotional baggage and get a fresh start.

When a team or organization is troubled and failing, then everyone knows it. You can feel it in the air and see it in the interactions of the staff with the customer and with each other. You see a lack of direct eye contact, hear few laughs, and people overly focused on their screens and not each other. When teams are remote, you see it in the lack of engagement on virtual meetings with few speakers and blank screens as people turn off their cameras. Participants are present but not engaged. There are silos within silos with people and teams striving to be individually successful within an overly unsuccessful project. It’s the sports team with a losing record where individual players are trying to stand out, juice their statistics and position themselves for a trade to a better team. They have already given up on their current team. One project team that I was brought in to save was so beaten up that team members flinched if you raised your voice and always spoke in a passive voice. It was sad to see a group of professionals so mentally and emotionally beaten down.

The people in a troubled and/or failing organization do not always realize the situation that they are in. This can often be the case when an organization is a monopoly, and the staff have no competition (like a government service or function). Because the customers don’t have a choice, there is less of a competitive drive to understand the environment and marketplace. Sometimes the staff are so focused on the day-to-day operations, that they don’t realize the danger that they are in of becoming obsolete and less relevant. It’s too easy to dismiss business and customer complaints instead of hearing the feedback and call to action. When the business or customers don’t feel served, then “shadow IT” or unapproved IT, flourishes and they try to find ways around the technology organization. Shadow IT is a symptom of failed enterprise technology.

When you have a troubled and/or failing project or organization, the most important thing is to recognize that you have a troubled and/or failing project or organization. Once you recognize and define the problem, then you can do something about it. If you are in denial and pretending that everything is fine, then you won’t put in the transformation work to get to a better place. That was the problem on the Army program where the project leadership assumed that their high contract performance scores indicated that they were being successful when the opposite was the case and they were about to lose their next option year. Transformation is hard and takes a lot of focus, energy, and funding. If you aren’t committed to the transformation then you will just play along, do the least to get by, and the opportunity to transform the organization will be delayed or even lost.

The starting point for a troubled and/or failing team or organization is always people. The people on the team. The people in the business that depend on the technology team or organization. The customers who are or aren’t being served. The executives in all these areas that are frustrated with the lack of business value. People are not just a part of the organization - people are the organization. When we have a Level 5 troubled technology team or organization (on a troubled scale of 1 to 5), then we need radical change (aka transformation) to quickly and systematically rebuild. When the executive leadership teams start thinking about taking their entire technology team and replacing or outsourcing it to a vendor that can do a better job, then you know that things are pretty bad and the situation is critical.

When I interviewed for the IT Director (CIO) position at the Virginia Department of Transportation (VDOT), I knew that it was probably a troubled organization. VDOT is a remarkably high-performing organization that operates a roughly $9B budget to support transportation throughout the Commonwealth of Virginia. State organizations like VDOT typically promote from within when the divisions are in good shape. That they were strongly considering someone from industry (like me) who had never been an employee in a state organization was a strong indicator that they were looking for transformative change. As part of my interview, I asked this question to the Chief Deputy Commissioner (#2 at VDOT), “If the IT Division were a tree, do I need pruning shears or a chainsaw?” His answer, “Start with the pruning shears but if you need the chainsaw then I have got your back.” With strong executive leadership support, I had the support that I needed to lead the transformation of the VDOT IT Division. When presented with a new challenge to transform the Virginia IT Agency (VITA) which provided statewide IT services to the entire executive branch (including VDOT), I asked a similar question to the Governor’s Chief of Staff that was interviewing me, “If VITA were a tree, do I need pruning shears or a chainsaw?” As an agency customer of VITA, I knew that coming out of the pandemic, the VITA organization was in a rough spot and struggling. His answer, “No question, you need a can of gas to burn it to the ground and start over.” Sounds harsh? Sure, the sentiment from the Governor’s Chief of Staff was especially critical. However, when we are in a critical situation and addressing a challenged organization, then we need to know the true perspective of external stakeholders and executive leaders. If we can’t recognize and accept the problem, then we can’t fix it.

When I shared these perspectives to staff in the respective organizations, the reactions of the staff indicated the degree to which they were committed to improvement and transformation. Some embraced the feedback and empathetically acknowledged that leadership had a point. Those staff (Category 1) accepted the challenge, engaged their professional pride, and became some of the strongest champions of the turnaround. With focused guidance and supportive leadership, they improved to produce amazing results, individually improved professionally, and they advanced in their careers (many were promoted and some grew to become CIOs and executives in other agencies). Some (Category 2) reacted with denial or derision. Their perspective was that their excellent work was just misunderstood and unappreciated. With focused guidance and supportive leadership (and a lot of stubbornness), we were able to performance manage the Category 2 staff into reluctant change. Though some eventually became Category 1 staff (when they saw all the great work happening around them), many continued to view their legacy work as excellent and were resistant to change. The Category 2 staff that never accepted change ended up either transferring to less progressive agencies, retiring from the organization, or stayed in place doing the least necessary to preserve their employment. Interestingly, the majority of staff were Category 1 (roughly 75%) which fits my lifelong experiences that most staff are hardworking, professionally engaged, want to do a good job, and play for a winning team. Those Category 1 staff knew that though they were working hard and trying their best, that there were fundamental and structural problems holding them back and that the organization as a whole was not highly regarded and they wanted to do better. Everyone wants to be proud of the organization that they work for.

As tempting as it may be to burn a tree down and start over, it is not realistic. There is work that needs to done each and every day. We don’t have the luxury of stopping everything and take a couple of years to create a new organization. You have to replace the engines on the plane while the plane is flying. That forces us down a bimodal path. We have to continue to execute and deliver to get the work done. At the same time, we need to dedicate resources towards innovation and improvement. If we don’t do both, we will not improve and the organization will continue to struggle. Thankfully in both situations, we were able to transform both VDOT ITD and VITA without requiring an organizational termination, makeover and rebuild. Though all options were on the table, and I was grateful for the level of executive support provided, being able to reduce to save costs and shed non-performing practices, reuse the parts of the organization that were working at least moderately well, and recycle (aka transform) those functions that needed to be completely overhauled allowed us to deliver results far more quickly.

Throughout these efforts, maintaining strong relationships with business stakeholders, executive leaders, and team staff are critical. The stronger the relationships, the more that we can accomplish. And it is often the little things that seem inconsequential but turn out to be very important later. When you are in a government organization, there is often an annual budgetary process where funding is requested, budgeted, and appropriated. That process can take as long as a year so you are always working on your next year’s budget. Without budget, projects don’t get funded or completed. At the Virginia Department of Transportation (VDOT), there was a situation where a floor was being renovated which is a facilities project. What wasn’t included in the requirements to me was that they expected all the audio and video equipment to be renovated as part of the project. This was a reasonable request to the IT organization but it was never shared with me and I had not budgeted for it. We could have reused the old, obsolete equipment but that would have created a poor staff experience. I was within my rights to force the issue but at what cost? The affected business director view this situation as another example of the IT organization not delivering and would be reminded ever time they used a conference room with old equipment. What I did was to explain the situation and my dilemma. But then offered to pull some funding from some other efforts to get them most of what they needed this year and a commitment to include additional money in next year’s budget to complete the remainder. The affected business director thanked me for my transparency and creativity, and then surprised me by offering some of her own funding to fill in the gap. Together, we got all the work done and our relationship was forever strengthened. Sometimes the challenges become opportunities to show what can be done.

When I think about the many examples of successfully transformed projects, programs, and organizations, what I am proudest about are the people. We went from a low morale organization to a high morale organization. We went from a culture of caution to a culture of accomplishment. People started smiling more, complaining less, and working to deliver a LOT more technology products, services, and solutions. People want and like to be part of a winning team. The following chapters describe how its done.