How to Prioritize When Everything Seems Important: DEGAP and the Power of Slowing Down

In a recent podcast interview with host Caden Damiano, Harry—co-founder of Peak Priorities and author of Managing Priorities—dove into the messy business of making trade-offs and deciding what really matters. Whether you’re a product leader juggling roadmaps or an individual balancing personal ambitions, the principles he shared can help you steer clear of “urgent” chaos and aim for outcomes that actually move the needle.

Below are the conversation’s most compelling points, along with Harry’s DEGAP framework—a simple but powerful way to approach prioritization in any domain.

The Way of Product, Episode 120

1. Why Prioritization Feels So Tough

From startups to Fortune 500 giants, prioritization fails most often where there’s:

False Urgency: Everything’s marked “ASAP,” so people act before thinking.
Fragmented Ownership: Leaders say “That’s not my job” instead of claiming responsibility.
Fear of Missing Out: The panic that if we don’t do it all, we’ll fall behind.

When organizations or individuals try to do everything, they often lose sight of the few things that matter most.

“Even at big companies like Apple or Rackspace, they succeed by knowing what matters most—and what doesn’t.”
—Harry

2. Introducing DEGAP: Your 5-Step Prioritization Playbook

Harry’s book, Managing Priorities, unpacks DEGAP—a process for moving from a “current state” to a “desired state” without getting lost in the middle.

Decide
- Determine if slowing down to prioritize is worth the effort. (Spoiler: it usually is!)
- Recognize that humans are good at prioritizing simple tasks, but complex environments demand intentional thinking.
Engage
- Identify and involve stakeholders (including your “inner voices”—like the “inner CFO” who wants to save every dollar).
- Bring in the right people, early, for genuine alignment.
Gather
- Collect your “items” (potential priorities) and relevant data or metadata (e.g., cost, complexity, ROI).
- Think of these items as not yet priorities—they’re just candidates until you sort them.
Arrange
- Clarify, deduplicate, and structure your list in a way that makes comparison possible.
- Choose a technique: stack ranking, paired comparison, a 2×2 matrix, or even marketplace simulations (e.g., budgeting “monopoly money”).
Prioritize
- Run your chosen method to finalize which items top the list—and which can wait.
- Then, revisit earlier steps if something feels off or new info appears.

“DEGAP is method-agnostic. You can use a sorting technique, a visual framework—whatever fits your context best. The point is doing it intentionally.”
—Harry

3. Apply DEGAP Everywhere (Yes, Even Buying a Car!)

One of Harry’s hallmark observations is that prioritization transcends tasks, roadmaps, or frameworks. It can be as personal as selecting a car or as sweeping as rethinking corporate strategy.

Individuals: Harry suggests a “morning boot routine”—ask yourself what you’re avoiding, what has a high cost of delay, and which long-term goal needs your next step.
Teams: Embrace open dialogues about hidden tensions, shift away from a my-department-vs-yours mindset, and unify around a clear set of priorities.
Enterprises: Follow structured frameworks (OKRs, or your own pyramid of convictions) to tie top-level ambitions to day-to-day tasks.

4. “Prioritize Prioritization” for Real Impact

Harry notes many people conflate time management with prioritization. By stepping back and focusing on whichoutcomes truly matter, you’ll avoid spinning your wheels on tasks that don’t deliver lasting value. Oliver Burkman’s 4,000 Weeks is one resource Harry recommends to challenge the myth that “doing more, faster” is always the best goal.

Key Takeaway:
The best leaders “own” their results, build trust by clarifying trade-offs, and advocate for meaningful priorities—even under pressure to do it all.

Ready to Level Up Your Decision-Making?

Try DEGAP: Apply Decide–Engage–Gather–Arrange–Prioritize on a current project or personal dilemma.
Read Managing Priorities: Harry’s book provides more examples of how to use DEGAP at individual, team, and organizational levels.
Embrace Ownership: Whether it’s a potential feature or a tricky conversation you’re avoiding, remember that real growth happens when you prioritize and act.

For more insights from Harry or to explore how Peak Priorities can help your team clarify what matters most, reach out. Because when everything screams urgency, the real power lies in choosing the right things to do—and letting go of the rest.

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