I’ve sat through more IT planning cycles than I care to count. They rarely go badly in a dramatic way – they just move painfully slowly and produce outcomes that don’t quite make sense. The culprit is almost always the same: no agreed framework for comparing initiatives. Every leader defends their own projects, nobody challenges a peer, and the final ranking ends up as a polite compromise rather than a strategic decision. The initiatives that needed a hard conversation never got one.

The fix is a prioritization methodology – a structured, agreed way of answering ‘which of these should we do first, and why?’ At its best, it is the most practical answer to how to align IT investments with business goals in a way everyone can stand behind. Done badly, it creates a false sense of rigor while the same instincts play out underneath. Here are six approaches I’ve seen work, when to reach for each, and where each breaks down.

Financial Return: When the numbers can speak for themselves

If your organization has solid financial data on most initiatives – NPV, ROI, payback period – this is a compelling starting point.

Where it falls down is with a mixed portfolio: the Financial Index will rank the short-term, quantifiable stuff to the top every time, and your strategic bets quietly drop off the list.

Watch out: A financially rational portfolio isn’t always strategically smart. Pair with a Strategic Alignment Index as a secondary check.

Weighted Shortest Project First (WSPF): When speed of delivery is the constraint

WSPF is my go-to for large, diverse portfolios. The idea is elegant: rank by Cost of Delay divided by Project Size, where Cost of Delay captures Business Value, Time Criticality, and Risk Reduction. The result rewards high-value, low-effort initiatives and stops big projects from perpetually crowding out smaller, faster wins.

WSPF gives you a common language across departments – Finance, operations, HR all describe value differently, and WSPF forces a consistent conversation. It is the purest expression of value-based planning: every initiative ranked by the cost of not doing it, not by who asked for it. 

Watch out: WSPF only works if scoring is calibrated consistently across teams. Governance around score definitions is non-negotiable.

Strategic Alignment Index (SAI): When OKRs are the north star

The SAI is for organizations where strategy is well-defined and the obligation is to stay true to it. You define strategic themes, assign weights, and score each initiative on its contribution. The portfolio that emerges is the one most aligned to where the organization said it was going.

I find this particularly powerful in transformation programs, where the temptation to fund quick wins at the expense of the strategic agenda is constant. It’s also the right tool when leadership has made public commitments to the board or investors about strategic direction.

Watch out: The SAI is only as good as the OKRs it’s built on. Vague themes mean every initiative can be made to look aligned. And if OKRs change dramatically year to year, next year’s plan may be built on outdated themes. A beautifully aligned portfolio can still be economically disastrous – pair with a financial lens.

Multi-Criteria Decision Analysis (MCDA): When no single metric captures what matters

MCDA admits upfront that investment decisions are multi-dimensional. You define your own criteria – financial return, strategic alignment, innovation, compliance, technical debt – weight them, and score each initiative against the full set.

It works best with IT steering committees that already informally evaluate across several dimensions – MCDA makes that thought process explicit and defensible.

Watch out: Weight-setting is political. Without strong governance, weights shift to reflect whoever is most persuasive – defeating the purpose. Also watch for criteria creep: add enough dimensions and the model becomes too complex for anyone to trust.

RICE: The product team’s tool – with caveats for IT

RICE – Reach, Impact, Confidence, Effort – comes from product management and works well for feature backlogs where user impact can be estimated with precision. I’ve also seen it adapted for IT organizations with a strong product orientation.

Though Effort estimation at early stages is unreliable – underestimated effort inflates the score misleadingly.

Watch out: Without mature estimation practices, Reach and Impact tend to be optimistic and Effort understated. The scores look rigorous but aren’t.

Simple Ranking: A starting point, not a destination

Sometimes the most valuable thing is to sort the portfolio by a few meaningful fields and get alignment on the result – no weighted scores, no formulas, just a transparent rule. I’ve seen it work for smaller portfolios and as a tiebreaker within more complex methodologies.

But it has no mechanism for nuance: when someone asks ‘why did A rank above B?’, the best answer is ‘the sort order’ – which isn’t always enough.

Watch out: Most organizations outgrow this quickly. Treat it as a starting point, not a destination.

So which one should you use?

The question I’d start with: what conversation do you most need to have? Economic return – reach for the Financial Index. Staying true to strategy – the SAI. Delivery efficiency across a large portfolio – WSPF.

Most mature organizations use a primary methodology and a secondary one – the primary drives the ranking, the secondary catches what the primary can’t see. The common thread is a commitment to value-based planning: investment decisions made on explicit, comparable criteria rather than instinct or advocacy.

The methodology doesn’t make the decision. It makes the conversation faster, more focused, and harder to game. That’s what good prioritization actually looks like.

Whatever you choose, hold onto one principle: the score is an input, not a verdict. I’ve seen organizations follow their scores mechanically and fund a portfolio nobody believed in. The best ones use the scores to have better conversations – and then make the call. The methodology is the mechanism. The real goal is always the same: how to align IT investments with business goals clearly enough that every stakeholder can see it, challenge it, and ultimately trust it.

 

Method

Best Suited For

Key Caveat

Watch For

Financial Index

ROI-driven orgs with hard dollar data on most initiatives

Crowds out strategic long-term bets with no near-term ROI

Double-counting if paired with WSPF Business Value

WSPF

Orgs optimizing flow and time-to-market across many initiatives

Breaks down if scoring isn’t calibrated consistently across teams

Confidence score gaming across departments

Strategic Alignment Index

Orgs with defined OKRs and long-term strategic commitments

Vague OKRs produce vague – and gameable – scores

High SAI scores with no financial grounding

MCDA

Multi-stakeholder orgs with genuinely diverse decision criteria

Weight-setting is political without strong governance

Criteria creep inflating complexity over time

Simple / Nested Sort

Early-stage orgs starting their prioritization journey

Fully subjective – hard to defend at scale

Becomes ungovernable as the portfolio grows

RICE

Product and engineering teams managing feature backlogs

Effort estimates are unreliable at early project stages

Scope inflation in Reach and Impact estimates

How is your organization approaching IT planning?