The Culmination of a Long Career in Silicon Valley
Early in the podcast, Jorge asked Harry about his background. Harry’s journey includes founding startups, serving in product and design executive roles at companies like Apple, DreamWorks, Hewlett-Packard, and Rackspace, and coaching diverse teams from nimble startups to large enterprises. Through these experiences, Harry saw an unmet need: while everyone agrees prioritization is vital, no one had comprehensively tackled how to do it at scale.
His response was to write Managing Priorities. The book debunks the notion that prioritization is just about personal productivity or time management; Harry wants readers to recognize it’s a holistic practice—one that holds teams and entire organizations together when uncertainty strikes.
The DEGAP Process Model
One of Harry’s key contributions is the DEGAP model, which outlines five sequential phases for making better decisions:
- Decide
Determine if you have the time and resources to slow down and prioritize deliberately. Sometimes you must move quickly—but more often, slowing down to go fast later pays off.
- Engage
Identify and involve your stakeholders, whether they’re colleagues, external partners, or that “inner CFO” who wants to keep costs down. Engaging people upfront makes them more willing to align with the final plan.
- Gather
Collect the options, requirements, and supporting data. This step can involve everything from user research to stakeholder interviews—whatever you need to see the full slate of possibilities.
- Arrange
Sort, categorize, and de-duplicate what you’ve gathered. A metaphor Harry likes is the chef’s “mise en place”: everything in its right place before you begin the real “cooking.”
- Prioritize
Only after clarifying your data and goals do you actually rank what matters most. At scale, this might involve frameworks or visual aids (like Harry’s “prioritization pyramid”) to help teams see trade-offs clearly.
“The final act is prioritizing,” says Harry. “But first, you have to decide, engage, gather, and arrange.”
Lessons from Virtual Vineyards and Rackspace
Harry’s deep experience in Silicon Valley revealed how misaligned priorities can derail even the most promising ventures. He recounts his time at Virtual Vineyards (later Wine.com), one of the earliest secure e-commerce sites, launched before Amazon. Its original founders envisioned a template for specialty retail online—but diverging goals eventually led to conflict and missed opportunities. Had there been a clear process for aligning around shared priorities, the company’s path might have been different.
A later story from Rackspace finds Harry relying on his prioritization frameworks to keep a 1,000-person organization from unraveling after a sudden leadership change. By mapping out what still mattered, what might change, and how the team would move forward, Harry helped restore calm and clarity—a tangible example of how prioritization can stabilize a high-pressure environment.
Leadership Is Not a Title—It’s a Choice
A recurring theme in Harry’s conversation with Jorge was that leadership doesn’t depend on your position in the hierarchy. Anyone can choose to be a leader in their own life by:
- Listening Effectively: Understanding what people fear, where they’re confused, and what goals they’re aiming for.
- Making Things Visible: Whether it’s a prioritization spreadsheet or a mental model, laying out the information so others can see why certain items rise to the top.
- Creating a Safe Space: Teams rally around leaders who help them understand what they’re working toward and why it matters.
“Are we going to show up as leaders for ourselves, our teams, our families, our organizations?” Harry asks. “It’s about setting the conditions for others to succeed.”
Your Next Steps
If you’re stuck in a situation where the sky seems to be falling, Harry suggests focusing on the next best step rather than waiting for “perfect” alignment. Try these tips:
- Map Out Possibilities: Identify the “anchors” holding you back, the “rocks” you need to avoid, and the “propellers” that drive you forward.
- Zoom In and Zoom Out: Align daily tasks with broader goals. Even if you don’t have final clarity on the big picture, consistent, incremental progress calms anxiety and keeps teams cohesive.
- Embrace Process over Panic: Use frameworks like DEGAP to slow down, gather information, and set actionable priorities—one move at a time.
Where to Learn More
- Get the Book: Managing Priorities: How to Create Better Plans and Make Smarter Decisions is available through Rosenfeld Media
- Stay Connected: Visit peakpriorities.com to learn more about Harry’s coaching and consulting work.
- Follow Jorge Arango: Check out The Informed Life podcast for more conversations about organizing information and making sense of complexity.
Final Takeaway
The heart of Harry’s message is that prioritization creates coherence—it’s the glue that holds high-performing teams (and entire organizations) together in uncertain times. By deciding to lead (regardless of title) and applying structured frameworks like DEGAP, you can realign around what matters most, keep your “satellites” on course, and confidently guide yourself and others toward a shared vision.