Why prioritisation feels painful (and how to fix it)

"Damn prioritisation!"

Is a phrase mumbled in product offices everywhere. You’re staring at a backlog of 14,000 items, sweating over a roadmap presentation, knowing that whatever you present will be challenged, or fighting battles over "quick wins" vs. "tech debt"…and it feels personal.

Büşra Coşkuner, product trainer, coach, educator, and speaker, suggests that we are directing our frustration at the wrong target: prioritisation is inherently difficult. It involves saying no, managing trade-offs, and dealing with uncertainty. That’s part of the job. But if prioritisation feels painful, you have a different problem.

When prioritisation becomes painful, the cause is rarely the wrong framework or a lack of spreadsheet skills: the pain is usually upstream. It traces back to missing strategic choices and goals too vague to guide real trade-offs. When leadership doesn’t make and hold those choices, teams need to compensate for missing focus with scoring models and spreadsheets that were never meant to carry that load.

Here is how to move from painful sorting to strategic execution.

“Good strategy works by focusing energy and resources on one or a very few pivotal objectives, whose accomplishment will lead to a cascade of favorable outcomes.” - Richard Rumelt

The first principles: it’s not just sorting

Most teams treat prioritisation as a single activity: taking a list of items and putting them in order (1, 2, 3...). They jump straight to sorting.

However, we need to look at the first principles. Prioritisation actually consists of three distinct activities, and "sorting" is only the final one

Categorisation

Before making decisions, organise items into buckets that answer a specific question, with each bucket given a clear label. These categories provide a shared frame of reference.

Filtering

This is the most critical and underused step. Focus by applying explicit criteria, and set aside the items that do not meet these criteria. This reduces the number of options that require attention, and make “not now” an acceptable outcome.

Sorting

Order items once the list has already been narrowed. This is typically where value is weighed against cost, often described as return on investment. For sorting to be effective, the definitions of both return and investment must be agreed upon in advance.

The four kinds of tools people reach for

When teams look for ways to prioritise, they usually end up choosing from a small set of recurring tool types with similar underlying mechanics. These frameworks rely on four concepts that support prioritisation in different ways:

Scoring systems

Estimate return against defined criteria. Items are assessed relative to those criteria and given scores that allow comparison.

2 x 2 matrices

Compare items relative to one another across two dimensions. Items are placed on a grid to reveal patterns and clusters rather than a precise order.

Ruling out

Remove items that do not meet agreed goals or criteria. By excluding options early, it limits the number of items that require deeper discussion or analysis.

Calculations

Uses estimation to explore expected business impact. This can range from rough reasoning to structured business cases. The result is greater visibility into potential outcomes.

All these tools try to support one of the core activities of categorising, filtering, or sorting, but most teams jump straight to sorting because it feels the most concrete.

Prioritisation as a decision-making cascade

Strategic prioritisation becomes more manageable when it is understood as a sequence of linked decisions. Instead of starting at the backlog, the cascade approach moves from long term direction down to near term execution, with each level constraining the next.

On paper, this cascade looks clean and linear. In practice, teams move up and down between levels as they learn. It is a signal that strategy and execution are in conversation rather than disconnected. This is why the cascade is not meant to be followed in one direction only.

Level one - Long term strategy

At the top of the cascade sit long term strategic choices.

This is where leadership decides which problem spaces matter, which groups to focus on, and which value propositions are worth pursuing over time. These decisions are difficult precisely because they exclude options: every strategic bet implies something that will not be worked on.

From the outside, this level can look deceptively simple, often reduced to a handful of statements on a slide. In reality, these choices are made under market uncertainty, internal constraints, and financial pressure. This explains why clarity at this level is hard to achieve and easy to underestimate.

For prioritisation to work downstream, these bets need to be explained in a way teams can use. It requires enough shared understanding to guide later decisions.

Level two - Mid term focus

Once long term direction exists, the next step is narrowing focus over a defined time horizon, often a year.

At this level, prioritisation is primarily about filtering. Business objectives are used to reduce the set of possible initiatives, themes, or outcomes. The specific tools matter less than the behaviour, as the goal is to limit how many things can be true at the same time so that execution does not turn into constant context switching.

Many organisations struggle here because options are kept open in the name of flexibility, and nothing is explicitly ruled out.

"If nothing is explicitly ruled out... the result is that everything stays important, and there is no clear decision.” - Büşra Coşkuner

Level three - Short term focus

On a quarterly level, initiatives are evaluated against near-term objectives (like OKRs). Here, we ask: Does this meaningfully move the needle on our specific goal? If an item doesn't pay into the strategy, it gets filtered out.

Treating prioritisation as a narrowing exercise rather than a compromise helps teams concentrate effort where it has the highest chance of creating visible progress.

Research and experimentation feed into the decision-making process by checking if your strategic choices actually hold up in the real world, allowing to refine assumptions based on evidence.

The confidence factor

Even after items have been filtered through strategy and goals, teams still face a problem. Many initiatives are described as high impact, and disagreement appears around which ones truly deserve attention.

This is where you must introduce confidence. Prioritisation is not just about Impact vs. Effort, it is about Impact vs. Confidence

  • High impact, high confidence: Plan to build it.
  • High impact, low confidence: Do not commit to the roadmap. Instead, prioritise learning. Run an experiment or a prototype to generate evidence.

By making confidence explicit, you shift the conversation from persuasion ("I think this is a good idea") to validation ("We need to verify this assumption").

Backlog prioritisation as the final narrowing

By the time work reaches the backlog, teams should not be facing an unfiltered list of ideas.

You should be looking at a categorised set of opportunities that have already passed through strategic direction, mid-term focus, short-term impact filtering, and confidence checks.

Sorting finally plays a role at this level: decide what to execute next based on capacity, timing, dependencies, risk, and context. There is no single "right" framework here: whether you use RICE, WSJF, or intuition, it works because the list is already strategically aligned.

"But my company strategy is unclear..."

This is the most common objection: what if leadership hasn’t defined the "bets"?

If the strategy is absent, look at the patterns in your organisation, interpret the implicit goals, create a provisional product strategy. Your own "bubble" of clarity, and explicitly communicate it to your stakeholders: "Based on X and Y, we are prioritising this goal, which means we are filtering out Z."

"This is your space to create the bubble... and then the explanation, how this connects to the company strategy." - Büşra Coşkuner

Make your assumptions defensible. It is better to prioritise against a provisional strategy than to prioritise against nothing at all.

Conclusion

Prioritisation is difficult, and it always will be. There is no technique that removes the difficulty of deciding what to work on next. However, you can remove the pain.

Effective prioritisation

  • Starts with explicit strategic choices, moving from long-term direction to near-term focus.
  • Filters work consistently against strategic goals, does not only rely on sorting
  • Moves up and down levels as learning emerges

Painful prioritisation

  • Happens when strategic focus is missing
  • Emerges when goals are unclear
  • Increases when strategic decisions change frequently or are not well communicated

Ultimately, strategic prioritisation is a "joint effort."

  • For Leaders: Your job is to make the "hardcore" choices that narrow the playing field so your teams aren't paralysed by infinite options.
  • For Product Teams: If the strategy is unclear, build your "strategic bubble," present options to your leadership, and say, "This is what we are prioritising, and here is why."

Start building the decision cascade to make the backlog a shared plan of action that everyone understands.

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