The Right Leadership
Google Gemini Prompt
As the Chief Executive Officer of a large organization, I have a troubled and underperforming information technology organization that is not meeting business expectations. How important is it that I have the right Chief Information Officer and what kind of CIO do I need?
Google Gemini Response
Being the CEO of a company with a failing IT department is like trying to win a race while your engine is misfiring and the steering wheel is loose. In 2026, technology isn't just a "support function"—it is the nervous system of your business.
To answer your first question: Having the right CIO is mission-critical. A "troubled" IT organization usually suffers from a lack of alignment, poor culture, or technical debt, all of which require a specific type of leadership to fix.
Why the CIO is Your Most Critical Hire
If IT is underperforming, you aren't just losing money on hardware; you are losing agility, security, and competitive advantage. The right CIO doesn't just "fix the Wi-Fi"—they bridge the gap between your strategic vision and the technical execution required to achieve it.
The Cost of the "Wrong" CIO
The Order Taker: They say "yes" to every business request without a roadmap, leading to a bloated, unmanageable tech stack.
The Infrastructure Recluse: They focus entirely on servers and security but don't understand how the company actually makes money.
The Shadow IT Catalyst: When IT is slow or "troubled," business units start buying their own software, creating massive security risks and fragmented data.
The Profile You Need: The "Transformational CIO"
Since your organization is currently underperforming, you don't need a "maintainer." You need a Turnaround Specialist or a Digital Strategist.
1. The "Translator" Capability
You need someone who can sit in a board meeting and discuss EBITDA, customer churn, and market share without mentioning "latency" or "microservices" unless specifically asked. They must translate business pain into technical solutions.
2. The Cultural Architect
Troubled IT departments are often demoralized. You need a leader who can:
Stop the "blame game" between IT and the rest of the business.
Implement Agile or DevOps mindsets to speed up delivery.
Attract top-tier talent to a previously toxic or stagnant environment.
3. The "Pragmatic Modernizer"
A large organization likely has "technical debt" (old, slow systems). You need a CIO who knows when to refactor (fix), when to replace (buy new), and when to retire (shut down) systems to maximize ROI.
Discussion
In sports, if a player is not performing, then you replace the player. If the team is not performing, then you replace the coach. In my 30 years of experience working with technology leaders from Directors to CIOs, I have generally found two types of IT Leaders: Maintain and Operate (M&O) Leaders and Transformational Leaders. M&O Leaders are steady, incrementally improve, and great for IT organizations that are generally working well and meeting business commitments. They are good at maintaining the steady state and optimizing the As-Is but not so good at transforming. M&O Leaders are often well-respected by their peers and have long term trusted relationships. Transformational Leaders are the leaders that are brought in when there are severe organizational performance problems and a transformation is necessary to address those performance deficiencies.
The Gemini response was on target and recognized the importance and mission criticality of an organization having a high performing IT organization. As previously discussed, every business is a now a technology business and if IT is not performing, then it becomes a drag on the entire organization. When IT is not performing, then a Transformational Leader, like a Turnaround Specialist or Digital Strategist, is needed to realign, refocus, and modernize the IT organization. The work of the Transformational Leader will be to heal the relationship between the technology organization and the business organizations, rebuild the culture of the technology organization, and modernize the people, processes, technology, and finances. The hard work of fixing a troubled organization starts with getting the right Transformational Leader.
Once the need for a Transformational Leader is established, the next step is getting such a leader for the role. The Transformational Leader will need to bring capability and credibility in strategic planning, relationship building, technology acumen, and business management. The IT organization of today operates like a business and financial performance is as important as server performance. The Transformational Leader should be skilled at leveraging cost takeout in one part of the technology portfolio to generate funds to invest in more critical areas. A system to continuously reprioritize and refocus on the highest value opportunities at any given time will need to be created.
There was a troubled project that I was asked to salvage for the State of Florida. My firm had been hired to modernize a legacy application and the project was valued at roughly $43M. The project was severely behind schedule and over budget. Two prior Project Executives had been asked to leave the project. Interestingly, both prior Project Execs had been named Bob so I was the third Bob to be assigned to lead the project. When I arrived on scene, the tension between the project team and the client was extremely tense and salty. The client was threatening our firm with liquidated damages (which were contractually their right). As the new “Bob,” my job was to reset the relationship and realign and restructure the project team (with some reasonable additional investment from my firm) such that we could deliver a working product to the customer and salvage our reputation in the marketplace. The state, local, and higher education (known as SLED) market is very connected and a large project failure would be bad for both my firm and for the State of Florida. Nobody wants to be a juicy story in the news.
As the new Transformational Leader, the client gave me a bit of grace to do my work to realign the project team and get back on track. Being new was extremely helpful as I could view the situation from multiple perspectives without the baggage of prior misunderstandings. With a great deal of teamwork, we were able to turnaround the project. I was able to listen and hear the prioritized requirements from the client such that we focused on the highest impact features. I heard my team and brought in critical skills and capabilities that were missing that helped accelerate delivery. I heard my leadership and helped them understand that some key investment this quarter would yield a more profitable project in later quarters and save the downstream revenue. With some reengineered processes, we were able to smoothly deliver features on plan and deploy to production without errors. When I left the project two and half years later, the project was in much better shape, and the team had won additional follow-on work.
Though being new and external helped me at the State of Florida, a strong internal Transformational Leader can still be successful given the right conditions. I recall working on a workforce development project for the State of Pennsylvania. My firm was a subcontractor to the firm that was delivering an ERP project (SAP R/3) for the entire state. My project manager was struggling to handle the complexity of the multimillion dollar workforce development project and the client was getting frustrated with the lack of organization and slow pace of delivery. There seemed more excuses than results and the project manager was asked to be replaced. I stepped in to replace him. Being already on the project, I could see the lack of metrics, unbalanced team workloads, and lack of modern technology to accelerate the work. As a team, we restructured and realigned the project. We applied more metrics to visibly show progress and identify deficiencies and bottlenecks early where they could be addressed before becoming critical situations. As an internal Transformational Leader, existing insight into the As-Is helped me skip the assessment phase and transform to the To-Be state a lot more quickly.
The difference between the State of Florida and State of Pennsylvania projects was the size of the troubled organization’s blast radius. The Florida team was viewed as failing as a whole, so they needed a full makeover. An internal Transformational Leader from the existing team would not have been credible, accepted, or given a chance. Whereas the Pennsylvania situation was viewed as a leadership problem and the overall team was still viewed as capable and salvageable, so an internal candidate could be potentially trusted to succeed. As potential candidates are considered, make sure that they have proven and demonstrable experiences in all the required capabilities and experience transforming progressively more challenging organizations. Once the Transformational Leader is identified and engaged, then the real work begins!