Why Prioritization Matters More Than Ever
Harry’s own experiences at companies like Rackspace, DreamWorks, and a pioneering wine e-commerce startup (the first to use an online shopping cart!) revealed a universal problem: even high-powered teams struggle with putting the right items at the front of the line. As he learned, having a consistent approach (or “operating model”) can help you deliberately tackle what’s urgent, essential, or even aspirational without drifting into reaction mode.
The Wake-Up Call: “Everything Got Thrown Up in the Air”
Harry recalled a pivotal moment at Rackspace. After spending months aligning a thousand-person product organization behind a cloud initiative, he discovered during a leadership conference that his boss was let go. In an instant, priorities once carefully arranged were back up in the air. That experience reinforced a lesson:
“Your priorities are your inputs to your plans and decisions. If you understand what they’re supposed to be, you’re in a much stronger position to develop better plans or make more intentional decisions.” — Harry Max
With that shake-up, Harry realized how critical it was to document and practice prioritization. Without a shared approach, even an accomplished team can be left scrambling.
“D-E-G-A-P”—A Five-Step Methodology
A major highlight of the interview was Harry’s D-E-G-A-P framework, shorthand for Decide, Engage, Gather, Arrange, and Prioritize. Far too often, teams conflate prioritization with a single step: “sort items and pick the top ones.” But Harry explains it’s far more nuanced.
Decide: Confirm why you’re prioritizing and who needs to be part of the conversation.
Engage: Talk to stakeholders, gather context, and secure buy-in for a common approach.
Gather: Compile all potential priorities (the “items”) and their important details.
Arrange: Organize those items (e.g., remove duplicates, clarify confusion).
Prioritize: Only after thorough alignment do you start ranking items as must-haves vs. nice-to-haves.
By following these steps, teams avoid the “quick fix” trap of letting a single matrix or scoring tool blindly dictate decisions. That matrix is just a sense-making tool, not the ultimate decision-maker.
Saying “No” to Say a Bigger “Yes”
One of the sticking points around prioritization is how it sometimes feels painful—particularly when we must say no to seemingly good ideas. But Harry suggests reframing that discomfort: if you never say no, you risk “death by a thousand paper cuts.” Each time you accept low-priority items, you drain resources from the most important, game-changing efforts.
Healthy Ways to Practice “No”
Reframe: When you say no to a small request, you’re saying a bigger “yes” to your most important goals.
Negotiate: Instead of a flat “no,” try “Yes, and here’s the risk if we add this in now.”
Align with the Vision: Remind teammates, stakeholders, or leaders how a no keeps everyone laser-focused on top-priority outcomes.
Practical Tips for Building Your Prioritization Muscles:
- The Morning Boot Routine: Harry shared a simple morning ritual for personal prioritization he calls the “Morning Boot Routine,” which starts by asking: What am I avoiding today? Tackle that item first, even if it’s just for 20 or 30 minutes. This technique helps you gain momentum and reduce the mental burden of avoidance.
- Check Your Operating Model: Whether it’s Agile, EOS (Entrepreneurial Operating System), or something else, consistency is king.
- Maintain Judgment: Even the best frameworks are just tools. Ultimately, your team’s wisdom and context decide what matters most.
- Small Wins Count: Celebrating minor successes fosters a culture of proactive rather than reactive decision-making
Want More? Grab the Book.
If you’re hungry to learn more, Harry’s book, Managing Priorities, dives deep into the step-by-step process and includes frameworks, real-life stories, and practical exercises. You can find it at Rosenfeld Media or on Amazon.
Continuing the Conversation
Here at Peak Priorities, we specialize in helping leaders and teams gain clarity so they can align around what truly moves the needle. Drawing on decades of experience in UX, product, and organizational strategy, we coach you to:
- Develop robust, flexible prioritization methods
- Strengthen decision-making through frameworks and facilitation
- Create alignment so your personal and professional goals are congruent
Ready to take the first step?
- Visit peakpriorities.com (we’ll be adding fresh resources and insights regularly).
- Connect with Harry on LinkedIn for ongoing thoughts on leadership, innovation, and of course, managing priorities.
Remember, prioritization is not about cramming everything in. It’s about making space for what truly matters—so that you and your team can thrive in a rapidly shifting world.
Thanks for reading and listening. Here’s to making better decisions, faster—and with far less stress!