Feeling Overwhelmed? Here's How to Prioritize Strategic Initiatives

How to Prioritize Strategic Initiatives — When Everything Is a Priority

Three Steps to Prioritize Your Biggest Strategic Initiatives

To make this process as efficient as possible, I’ve designed a process to help us quickly narrow down our options and focus our deep-dive only on the most relevant & promising candidates.

Step 1: Prep Your Data

---

Garbage In, Garbage Out. The quality of our decision is only as good as the quality of our inputs.

a) Narrow the List. Filter just for the problems that map onto your top niche/audience target and top organizational goal.

Why filter on your org’s top goals? (eg: acquisition, retention, monetization, margin)

When you build without a clear primary goal, you risk wasting time on features that look good but solve the wrong problem.

Filter every idea through your top organizational priority. If retention is your primary goal, you build a streak counter, for instance, that keeps users coming back. If acquisition is your goal, you build a social sharing feature that brings new users in. Each choice creates different value and has different impact on your organization’s goal.

Of course, some features can further multiple goals. But clarify the primary one that matters most to you. This ensures your work stays aligned with what matters most.

 

Primary Org Goal	Feature Example	Strategic Outcome
Acquisition	Social Sharing Function	Brings new users through viral sharing loops
Retention	Daily Streak Counter	Keeps existing users engaged by incentivizing streaks
Monetization	Advanced Timer	Drives subscription upgrades
Margin	AI-Powered Search Bar	Lowers support costs by deflecting user questions

What to do if this isn’t possible

Have your top sponsor — or the teammate with the deepest internal context — scan the full list and use their judgment to pick the most important subset.

b) Convert to problem statements. Include the concrete consequences if not solved.

Here are three critical benefits of starting with the problem. The riskiest decision a team can make is to fall in love with a solution before they’ve fallen in love with the problem.

• Risk Reduction. If you skip this step, you risk building a shaky foundation that can’t be fixed later (most projects never get a do-over).

• Creativity. Zeroing in on the core issue and its root causes lets you come up with more creative, affordable solutions, instead of just running with the first idea that pops up.

• Trust. When you show you truly get your customer’s challenges from the start, you earn their trust right away—and become a partner, not just another vendor with a canned fix.

For more on this see “Why Your First Move Might Be Your Biggest Mistake.”

Problem statement examples.

Less Productive

“Project managers need to put their task list in their calendar.”

This statement is disguised as a problem but is actually a solution. It's already decided that "integrating a task list with a calendar" is the answer. It neither explores the user's actual frustration in their workflow, which could potentially be solved in many better ways, nor does it clarify the consequence if not solved to help the reader empathize with why this matters.

More Productive

“As a project manager, I get frustrated when I have to manually copy tasks onto my calendar, which is not just time-consuming but also leads me to drop the ball and lose sales if I forget critical tasks.”

This good example is powerful because it doesn't presume a solution. The team could now brainstorm multiple potential solutions: a one-click sync button, an intelligent assistant that suggests calendar blocks, a completely new type of integrated view, etc. It opens up creative possibilities by focusing on the real user problem.

c) Assign an “Empowered Scorer.” This person drafts initial scores and aligns the stakeholder team, keeping detailed records.

What about a live workshop?

A live workshop is a common way to build consensus, and it can be great for open-ended brainstorming. However, for the specific task of scoring, it has two major drawbacks:

1. It favors opinions over evidence. In a live meeting, the loudest or most senior voice can often dominate, and decisions can be made based on pressure rather than a thoughtful review of the data.

2. It is highly inefficient. It requires blocking many hours of synchronous time from your entire team, making it a slow and expensive way to work through a detailed rubric.

For these reasons, we strongly recommend the async ”Empowered Scorer” model. It ensures feedback is thoughtful, evidence-based, and documented, leading to a faster, smarter, and more defensible decision.

Step 2: Scan for Core Value

---

Value measures how important each problem is to solve. Influence measures how much support we have to actually fix it. Together, these scores show us which problems are worth tackling right now.

a) Value: Cost of Not Solving the Problem

The Core Question: Is this a problem people desperately need solved?

Rubric (Hit Toggle)

 

✔️

To make scoring easier, we use a simple checklist.

• For each "Yes," the problem gets +1.

• Each criteria can get up to 5 total points.

• Please adjust the points or penalties in a way that makes most sense to you.

 

Evidence Checklist	Definition	Definition
High Impact (Cost): Does this problem have a high and concrete cost in terms of wasted time, money, or resources?	+1: Yes, there is a clear, large, and quantifiable dollar, time, or mission/program cost.	+0: The cost is minimal or hard to define.
High Impact (Breadth): Does this problem affect a large number of people in their workflow?	+1: Yes, it affects a whole department or multiple teams.	+0: It only affects a small group or is an edge case.
High Unmet Need: Have users explicitly stated this is a top-three pain point in their workflow for which they have no good existing solution (unique problem for them)?	+1: Yes, we have direct quotes from our audience stating this is a top 3 pain point.	+0: It's an issue, but not a top-of-mind one for users.
Active Workarounds: Is the team already trying to solve this problem with inefficient, manual workarounds they’re dissatisfied with?	+1: Yes, they're constantly building and reworking their own spreadsheets, checklists, or other "duct tape" solutions to cope.	+0: No, the current workaround (or lack thereof) is stable and sufficient.
Urgent & Rigid Deadline: Is there a fixed, non‑negotiable deadline or event that makes solving this urgent right now? (eg: burning platform, legal threat, contract, etc)	+1: Yes, there is an urgent, fixed deadline with a major impact if missed.	+0: No, it’s internally driven without any major consequences if missed.

Examples

• High-Scoring Example: ("Manually compiling weekly compliance reports"): Scores a 5/5.
It's a high-cost problem for the entire compliance team (Breadth), the Chief Compliance Officer has called it a top priority (Unmet Need), they use complex, error-prone spreadsheets (Active Workarounds), and a new regulatory audit is scheduled (Burning Platform).

• Low-Scoring Example ("Updating internal team contact information"): Scores a 1/5.
While it affects many people (Breadth), the cost of the problem is low, no one has requested a better solution, and there is no urgent deadline.

b) Influence: Political Support

The Core Question: Will solving this be supported, or will it be sabotaged?

Rubric (Hit Toggle)

---

Evidence Checklist	Definition	Definition
Active Champion: Is there any influential leader or individual contributor who is actively and passionately trying to solve this problem?	+1: Yes, there is an internal leader actively advocating to solve this problem.	+0: There is no clear, influential champion.
Executive-Level Sponsor: Is the primary champion a senior executive whose support carries significant weight?	+1: Yes, the champion has significant decision-making authority or influence (e.g., senior VP or executive level).	+0: The champion is a manager or individual contributor.
Strategic Alignment: Does this use case directly support a currently funded, high-priority public initiative?	+1: Yes, it clearly addresses a persistent challenge for a top-three and active strategic priority.	+0: The alignment is weak or non-existent.
Unique Approach: Does solving it offer a unique or innovative approach that enhances our leadership position?	+1: Yes, it offers a unique angle that no one or very others are doing.	+0: No, this approach is a standard "keeping the lights on" task.
Low Political Risk: Does this use case avoid threatening the turf, budget, or pride of any other powerful stakeholders or have any hidden political dependencies?	+1: Yes, it's a "win-win" or an internal efficiency tool and so it is also politically self-contained.	+0: No, it will likely create political conflict and requires another team’s buy-in.

Examples

• High-Scoring Example ("Manually compiling weekly compliance reports"): Scores a 5/5.
The CCO is an active, senior champion, it aligns with the "audit readiness" goal, and it's an internal tool with low political risk.

• Low-Scoring Example ("Updating internal team contact information"): Scores a 1/5.
While strategically aligned, it has no single champion and actively threatens the turf of every department, making it politically toxic.

 

💡

Think of these criteria as a living framework.

As we work together and learn, we’ll keep checking: Are these the right signals? What should we update for next time? That way, the framework just gets smarter and more useful with every project.

 

Step 3: Tie-Break based on Feasibility

---

Take your top scoring problems and put each solution through two final tests. First, do you have a clear pathway to actually pull this off and make a real difference? Second, what’s your evidence quality that this will work? These scores will help you pick your top priorities.

c) Pathway: Ease of Execution

The Core Question: Can we deliver a simple, elegant, and high-quality win for this problem?

Rubric (Hit Toggle)

 

💡

Tip: Partner With Your Implementation Lead

• If you’re unsure about any of these scores, ask your engineering lead or the expert on that part for more details. If the solution does not score well, don’t throw it away immediately. Brainstorm together to find better solutions to the problem you’ve prioritized — ones that boost value and reduce cost and risk.

• Please adjust the points or penalties in a way that makes most sense to you.

 

Evidence Checklist	Definition	Definition
Goal Achievement: Is the proposed V1 solution likely to have a high, "wow-worthy" impact on the user's workflow or goals?	+2: Yes, it will be a dramatic and immediately obvious improvement.	+0: No, the improvement is minor or incremental.
Low Adoption Friction: Can a new user quickly get to the core value with only a few simple steps and little setup or training?	+1: Yes, it is a "plug-and-play" solution that gets them value immediately.	-1: No, it requires a lengthy onboarding, complex setup, or a significant change in user behavior.
Lightweight: Can the V1 solution be built with minimal, contained engineering effort?	+1: Yes, it can be built in a short, predictable timeframe (e.g., a few weeks, one sprint).	-2: No, it requires a large amount of new code, multiple integrations, or a lengthy build that can span multiple months.
Certainty: Does this problem have a clear technical solution, play to our team’s proven skills, and avoid outside roadblocks such as access to data or people?	+1: Yes, the solution is clear, proven, and based on tech we know well, with an easy path to the resources we need to build and test it	-3: The solution is likely to be complex “science project,” with challenges we haven’t faced before with possible access hurdles.

Examples

• High-Scoring Example ("Manually compiling weekly compliance reports"): Scores a 4/5.
It aligns with the team's strengths, is technically simple, and people are accessible. The only risk is a potential minor delay in data access from one system.

• Low-Scoring Example ("Updating internal team contact information"): Scores a 1/5.
It's a new area for the team, requires complex real-time data feeds they don't have access to, and has a major prerequisite of a brand new tool the team has never used and needs to get budget for.

d) Strength: Evidence Quality of Your Scores

The Core Question: How much of this is fact, and how much is a guess? This is a lens through which we view the other scores. A high-scoring but low-evidence idea is a risky bet.

Rubric (Hit Toggle)

---

Evidence Checklist	Definition	Definition
1. No Data: Is the core of this idea based on a gut feeling or an internal-only opinion? Get +1 if YES.	+1: Yes, it's an initial hypothesis.	+0: N/A
2. Secondary Data: Is the idea supported by research or the experiences of other organizations?	+1: Yes, we have market research or case studies.	+0: No, we have no external supporting data.
3. Verbal Interest: Have we spoken directly to our target users and confirmed this is a top pain point?	+1: Yes, we have direct quotes from recent interviews from our target customer.	+0: No, we are assuming this is a pain point.
4. Initial Testing: Have we seen users take a small but meaningful action that indicates they want this?	+1: Yes, we have an artifact from an initial test (e.g., prototype feedback).	+0: No, we only have their words, not their actions.
5. Repeated Action: Have we seen a large number of users repeatedly take the desired action?	+1: Yes, we have quantitative data showing repeated, desired behavior (e.g., pilot usage).	+0: No, we only have initial positive signals.

To use this to make better decisions, see this strategic decision-making framework.

 

Example

• Low Scoring ("Streamlining the Current Grant Writing Process"): Scores 1/5
This is a pure "gut feeling" idea with no secondary research, user interviews, or testing to support it. It is a high-risk, unvalidated guess.

• Medium Scoring ("Manually compiling weekly compliance reports"): Scores a 3/5.
We have a gut feeling it's a good idea (+1), we know other companies have done this (+1), and we have direct quotes from our compliance team saying they desperately need it (+1). However, we have not yet shown them a prototype.

• High Scoring (after validation via pre-selling or other approaches): Scores a 5/5.
You later took the compliance reports idea and validated it getting higher quality evidence from the rubric above. We have the initial idea (+1), market data (+1), user requests (+1), positive prototype feedback (+1), and data showing high daily use of the current dashboard (+1). We have extremely high confidence in this idea.
 
💡
If a promising idea scores low because of its evidence quality, don't discard it completely.
Instead, add it to your backlog. Use the rubric as your research plan to generate better evidence to support it.
For more on this suggestion, see this strategic decision-making framework.

When Not to Use This Framework for Prioritizing Strategic Initiatives

• You Have Perfect Data: In the rare case that you have a perfect, quantitative model (like a pure ROI calculation) that all stakeholders already trust, that simpler model may be sufficient.

• The Path is Obvious: If there is a true "burning platform" crisis (e.g., a system outage), the priority is clear. The time for strategic prioritization is after the immediate fire is out.

• The Decision is Low-Risk: If a decision is easily reversible or the cost of failure is very low, a simple "good enough" choice is better than a lengthy analysis.

FAQ on How to Prioritize Strategic Initiatives

What is a prioritization framework?

What are the most common prioritization methods?

What does VIPS ultimately help us achieve?

How do you balance competing priorities at work?

Why do you use a checklist over a scale?