Episode 33 — Prioritize IT initiatives using value, risk, and constraints leaders understand (Task 21)

In this episode, we take a problem that shows up in almost every organization, even when people are talented and trying hard: there are always more ideas than time, money, and attention. New learners often imagine that a strategic plan automatically tells everyone what to do first, but in real governance work, prioritization is the bridge between intention and action. If you cannot decide which initiatives go first and which ones wait, you end up with a crowded calendar of half-finished efforts, frustrated teams, and leaders who feel like results never match the promises. Prioritizing I T initiatives is not about finding a perfect answer that everyone loves, because that usually does not exist. It is about making tradeoffs in a way that is clear, explainable, and aligned with what the organization actually cares about. The key to doing this well is using a language leaders understand, which usually means focusing on value, risk, and constraints rather than technical excitement or internal preferences.

Before we continue, a quick note: this audio course is a companion to our course companion books. The first book is about the exam and provides detailed information on how to pass it best. The second book is a Kindle-only eBook that contains 1,000 flashcards that can be used on your mobile device or Kindle. Check them both out at Cyber Author dot me, in the Bare Metal Study Guides Series.

To start, it helps to define what an initiative is, because people use the word loosely. An initiative can be a project, a program, an upgrade, a new platform, a major process change, or even a policy effort that requires investment and coordination. What they all share is that they compete for limited resources and they create change that can either help or harm the organization. Prioritization is the process of comparing these initiatives and deciding an order, a pace, and sometimes a decision to not do something at all. Beginners sometimes think prioritization is just ranking, but it is more like designing a portfolio, where you want a mix of outcomes and you want to avoid taking on too much at once. A good governance mindset is that priorities should be stable enough to guide teams, but flexible enough to adjust when the environment changes. The reason we emphasize value, risk, and constraints is that these are the dimensions leaders already use when they allocate budget and accept tradeoffs.

Value is the first dimension, but value can mean different things depending on context, so it needs to be described in concrete terms. Value might be increased revenue, reduced costs, improved customer experience, faster delivery, better reliability, or stronger compliance posture. In governance, value should be connected to business outcomes, not to technical improvements for their own sake, even when those improvements are real. For example, replacing an old system might feel valuable to the technology team because it is hard to maintain, but leaders will understand it better if it is framed as reducing downtime, reducing operational risk, and enabling new capabilities. Value also includes opportunity value, which is the benefit of unlocking future options, like building a shared platform that makes later initiatives cheaper and faster. Beginners sometimes focus only on direct value, like a feature that users see, but indirect value is often what makes an initiative strategically important. The key is translating value into outcomes leaders can recognize and measure.

Risk is the second dimension, and it is not only about cybersecurity incidents, even though that is part of it. Risk includes anything that could harm the organization or prevent it from achieving its goals, such as operational failures, compliance penalties, reputational damage, vendor dependency, data loss, and major outages. Leaders tend to understand risk when it is described as likelihood and impact, even if those are estimated rather than precise. A common mistake is to describe risk only in technical language, like vulnerabilities and patches, because leaders may not see how that connects to the business. A better approach is to connect technical risk to business consequences, like account takeover leading to fraud losses, or outdated systems leading to downtime that disrupts revenue. Risk also includes delivery risk, which is the chance that an initiative will fail to deliver on time or within budget because it is too complex or poorly defined. A project with high promised value but high delivery risk might need to be broken into smaller steps, or it might be postponed until prerequisites are ready. When prioritization includes risk, the organization avoids choosing initiatives that look exciting but could create painful surprises.

Constraints are the third dimension, and they are often the reason good ideas cannot happen immediately. Constraints include budget limits, staffing limits, skill gaps, vendor lead times, contractual obligations, regulatory deadlines, and technical dependencies. Constraints can also include organizational capacity for change, meaning how much disruption people can absorb without losing productivity or morale. Beginners sometimes think constraints are excuses, but in governance they are realities that must be managed honestly. If a plan ignores constraints, it becomes a fantasy that burns trust when it fails. Leaders understand constraints because they live with constraints every day, and they often appreciate when governance teams can explain what is truly limiting and what can be changed. For example, if the constraint is a lack of certain skills, an initiative might still be possible if the organization can source expertise, simplify scope, or invest in capability building. If the constraint is time due to a regulatory deadline, that can push an initiative higher even if other projects have more long-term value.

When you combine value, risk, and constraints, you get a framework for prioritization that is understandable and defensible. A useful way to think about it is that value explains why you want to do something, risk explains what could go wrong if you do it or if you do not, and constraints explain what is realistically possible now. This is different from prioritizing based on who shouts the loudest or which team has the most influence, even though those pressures are common. Good governance makes prioritization visible and repeatable, so decisions feel consistent rather than political. For beginners, it helps to imagine a leader asking three questions: What do we get, what do we avoid, and what does it take. If you can answer those clearly for each initiative, leaders can compare them without needing to understand every technical detail. That comparison also reduces conflict because it focuses discussion on shared goals rather than personal preferences.

A common misconception is that prioritization should be purely numeric, like giving each initiative a score and letting the highest score win. Scoring can help, but it can also create a false sense of precision, especially when the input estimates are uncertain. Leaders often prefer transparency over complexity, meaning they want to understand why something is prioritized, not just see a calculated number. A practical approach is to use structured judgment, where scoring is used to surface differences but final decisions are made with discussion and clear reasoning. Another issue with pure scoring is that it can ignore dependencies, such as a foundational initiative that enables several others. That foundational work might not score high on direct value, but it can have high strategic importance because it reduces future cost and complexity. Prioritization should also consider balance, such as not funding only growth projects while neglecting reliability and risk reduction. The goal is a portfolio that supports both performance today and resilience tomorrow.

It is also important to clarify the time horizon of value and risk because leaders think differently about near-term outcomes and long-term outcomes. Some initiatives produce quick wins, like improving a process to reduce errors, while others create long-term capability, like building a shared data foundation. Both can be valuable, but they should not be compared as if they operate on the same timeline. A short-term initiative might be prioritized if the organization needs immediate relief, but that does not mean long-term capability work should be ignored. Risk has a time horizon too, because some risks are immediate, like an exposed system, while others accumulate slowly, like technical debt that makes future change expensive. When prioritization includes time horizon, leaders can choose a plan that stabilizes urgent issues while still investing in strategic direction. For beginners, the simplest way to hear this is that priorities should reflect both urgency and importance, and those are not the same thing. A crisis can be urgent but not strategically important, while a foundational improvement can be important but not urgent until it becomes one.

Prioritization becomes more realistic when you separate effort from impact, because a high-impact initiative might be so large that it cannot be delivered quickly. Leaders often want big results, but governance needs to explain the tradeoff between speed and scope. One way to make this understandable is to talk about sequencing, where an initiative is delivered in stages that each provide some value while reducing risk. This also helps with constraints, because a smaller first stage might fit current capacity while building momentum and confidence. Another useful concept is the minimum viable outcome, which is the smallest set of results that meaningfully advances the goal. Even without discussing specific tools, you can explain that a major transformation might start with a core capability, then expand to additional areas once the approach is proven. Sequencing is not just project management; it is a governance decision because it determines which value arrives when and which risks are reduced first. Good prioritization often means choosing an order that makes later work easier, not just choosing the flashiest initiative.

Leaders also need prioritization to be communicated in a way that reduces surprise, because surprise is a major source of distrust. If an initiative is delayed, people want to know why, and if a new initiative suddenly jumps to the top, people want to know what changed. A value, risk, and constraints approach naturally supports this communication because it offers a consistent explanation. For example, a new regulatory requirement might increase risk, pushing a compliance initiative higher, or a sudden staffing change might increase constraints, delaying a complex project. When governance can explain these changes in plain language, leaders feel more confident even if they do not like every outcome. Beginners sometimes assume leaders only care about winning their own priorities, but many leaders care more about predictability and clarity than about getting every request approved. This is why prioritization frameworks matter: they create shared expectations and reduce the feeling that decisions are arbitrary.

Another key concept is that prioritization should include explicit tradeoffs, meaning when you choose one initiative, you are also choosing to delay or stop something else. Many organizations fail here by approving too many initiatives, which creates hidden overload. When everything is a priority, nothing is truly prioritized, and delivery slows down across the board. Governance should help leaders see capacity as a constraint that must be respected, because over-committing makes everyone lose. This is also where risk shows up again, because too many simultaneous initiatives increase delivery risk and operational disruption. For beginners, it can help to imagine trying to study for multiple exams at once; even if each exam matters, you still have to schedule focus, or you will underperform on all of them. An organization’s teams work the same way, and prioritization is how leadership chooses where focus goes. When tradeoffs are explicit, the organization can align resources, set expectations, and measure progress more honestly.

As a final teaching point, prioritization is not a one-time decision, because new information always emerges. Risks change, constraints change, and value assumptions can be confirmed or disproven as work begins. That does not mean priorities should constantly change, because constant change creates chaos, but it does mean there should be a disciplined cadence for revisiting priorities with updated facts. The most important thing is that the criteria remain stable and understandable, so changes are explained by changes in reality, not changes in politics. When governance prioritizes initiatives using value, risk, and constraints, leaders can make decisions that feel grounded and defensible, and teams can focus their effort where it matters most. For brand-new learners, the takeaway is that effective prioritization is less about perfect math and more about clear thinking, shared language, and honest tradeoffs that connect technology work to organizational outcomes. When done well, it is one of the clearest ways governance turns strategy into real progress.

Episode 33 — Prioritize IT initiatives using value, risk, and constraints leaders understand (Task 21)
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