The IT Leader’s Dilemma; When Everything Is a Priority
Last year I was in a leadership meeting with my VP and our business VP discussing our top priorities and a new initiative. The business VP insisted the new initiative was critical. When we looked at the IT roadmap, there were 20 top priorities, all marked urgent.
As the discussion progressed, we eventually arrived at the impossible question:
“Why can’t we do all of these in parallel?”
This question immediately creates tension in the room: Business leaders frustrated they cannot add another priority and IT frustrated at the complexity it would bring.
This question shows up in nearly every IT organization at some point. It’s not that anyone’s wrong, every initiative is important from someone’s perspective. However, when everyone’s initiative is added to the IT roadmap and everything becomes a priority, nothing truly is. The challenge isn’t lack of ambition or ideas. It’s lack of clarity about what creates the most value, and what should come first.
Why Everything Becomes a Priority
Here are a few common forces I’ve seen create this dynamic in IT organizations:
1. Strategic Ambiguity
In IT, you work with multiple business stakeholders, each with their own priority list. Leaders agree on the goals but not the tradeoffs. “Digital transformation,” “customer experience,” or “data-driven decisions” sound great in principle, but can mean different things to different teams. Without a shared definition, everyone pursues their own version of success.
2. The Capacity Illusion
The business often assumes that adding more people or tools means we can do more in parallel. But technology work doesn’t scale linearly, instead complexity compounds. Each new initiative adds dependencies, coordination, and risk.
3. A Reactive Culture
In many organizations, success is measured by responsiveness. The team that says “yes” fastest is seen as the most capable and may even be rewarded. Over time, IT becomes conditioned to accommodate every request, even when it dilutes focus and delivery.
4. Disconnected Metrics
Different functions measure success differently. Product teams want speed, finance wants efficiency, operations want stability. Without a unifying measure of business value, priorities compete instead of align.
When this happens, IT becomes a pressure valve for organizational misalignment. And eventually, even the best teams burn out trying to do too much.
The Cost of Over-Prioritization
When everything is a priority, it drives real cost and inflates IT budgets. It’s tempting to think that saying yes to everything accelerates progress. In reality, it does the opposite.
When everything is a priority:
- Delivery slows down because teams are spread too thin and constantly context-switching.
- Costs go up from duplicated efforts and half-finished initiatives.
- Trust erodes as IT misses deadlines trying to please everyone.
- Talent burns out because priorities shift weekly, they are constantly in firefighting mode and success feels out of reach.
The outcome is predictable: the roadmap fills up, but outcomes stall. Everyone’s busy, but few things move forward meaningfully. Dates are missed and budgets are blown.
A Framework for Focus
Getting out of this cycle requires structure — a way to separate what’s important from what’s merely urgent. Here’s a framework I’ve used with my teams and business partners to bring clarity and focus.
1. Anchor to Business Outcomes
Every initiative should clearly connect to a measurable business outcome: revenue growth, customer satisfaction, cost reduction, or risk mitigation. As I mentioned in a previous post, make sure to phrase it in business language so it is easy to understand. This way when two priorities conflict, the one tied to clearer business value wins.
2. Quantify Impact and Effort
Use a simple matrix or scoring model and iterate as you learn more. Estimate each initiative’s business impact and the effort required to deliver it. It doesn’t have to be perfect because the conversation itself creates alignment. The model we use today looks very different from the first 2x2. Our current model has five key characteristics that we measure each initiative against. Each characteristic is scored and the combined result gives us the assigned business value. We use this to accurately plot each initiative in our 2x2.
3. Expose Capacity Limits
Transparency is key. You have to make demand and capacity visible to make tradeoffs clear. Show leaders what can fit within your current capacity and what can’t. When executives see the whole picture, the conversation shifts from “why can’t you do it all?” to “what do we ‘the business’ want most?”
4. Decide Together
Prioritization shouldn’t be an IT decision in isolation. It’s a shared business responsibility, across stakeholders. When business and IT leaders make tradeoffs together, they share ownership of the outcome.
5. Communicate and Commit
Once priorities are set, communicate them broadly and consistently. Transparency prevents constant re-litigation and builds confidence across teams.
Using this basic framework and iterating to make it the right fit for our business and IT has allowed us to have the right conversations about what is most important to focus on.
The Leadership Mindset Shift
The hardest part of prioritization isn’t the process, it’s the mindset. Great IT leaders learn to say no without sounding defensive. They reframe it as:
“Here’s what we can do, why it matters most, and when we can address the rest.”
These leaders turn prioritization into a continuous, transparent conversation rather than a once-a-year exercise. They break the cycle of constant urgent drop-ins and shifting demands to help their team be more focused and impactful. They help their peers understand that tradeoffs are not a limitation of IT, but rather a natural part of strategic execution.
From Chaos to Clarity
The role of IT leadership isn’t to deliver everything. It’s to deliver what matters most, business value with focus and intent. Organizations that thrive aren’t the ones that say yes to everything, they are the ones that make hard choices early, align around business outcomes, and execute relentlessly.
When everything is a priority, nothing is.
When focus returns, momentum follows.
What about your organization?
How do you handle competing priorities and resource tradeoffs?
I’d love to hear your perspective — connect with me on LinkedIn or follow the discussion on Substack.