🧠 Strategic Judgment

← back to all Learning Tracks

Developing Strategic Thinking

Building the mental models needed to identify high-leverage opportunities and solve the right problems.

The UX Altitude Shift: How to unite tactical craft skills with strategic business impact.
How to Turn Critical Thinking Into Your Strongest Design Skill: Moving beyond obvious solutions to find what truly matters.
How a UX team lost $2M by listening to users: Learning the hard way that user feedback isn’t always the right strategic direction.
Solving the Wrong Problem Perfectly: A case study on why strategic research must precede any solutioning.
UX Design Darwinism: Adapt or Fade: Why your current expertise can become a liability if your thinking doesn’t evolve.

Learning to speak the language of leadership (risk, ROI, and growth) to align design with company goals.

Risk is the Real Language of Leadership: Why leaders prioritize risk mitigation over “delightful” experiences.
You Sound Like You’re Selling Cupcakes, Not Solving Business Problems: How “user-centered” language can actually shut down executive interest.
The Only UX Skill That AI Can’t Replace in 2026: Identifying the core human judgment that remains valuable despite automation.
The AI Strategy Narrative That’s Getting UXers Promoted Right Now: Moving beyond the hype to talk about AI in terms of business strategy.
The Most Expensive Work UX Does (That Nobody Notices): The hidden value in decoding and refining vague business requests.

Using systematic tools to prioritize work, measure success, and prove value to the organization.

The HEART, PIE, and RICE of UX success: Three foundational frameworks for measuring and proving UX impact.
The Year I Worked Harder Than Ever… But My Level Stayed the Same: A personal framework for ensuring effort translates into measurable growth.
Leadership Launchpad: A 90-day action plan and toolkit for transitioning into strategic leadership.
3 strength-finding exercises for stuck UXers: A systematic approach to identifying where your unique strategic value lies.
Authenticity in Leadership (The CRED approach): A framework for building leadership credibility through consistency and expertise.

Ensuring your insights shape company direction by documenting the “why” and not just the “what.”

The “Political Intelligence” Playbook: How to document and present research so it actually changes the roadmap.
How to Frame Research as a Team Win (Not a Delay): Positioning research as a strategic accelerator rather than a bottleneck.
Reframing UX impact: From numbers to narratives: Moving from dry metrics to strategic stories that stick with stakeholders.
Fix the Pain Before Adding the Sparkle: How to document and advocate for fixing critical issues before adding new features.

Making difficult calls, managing stakeholder friction, and navigating conflicting priorities.

The Art of the Strategic “No”: How to reject bad ideas without damaging stakeholder relationships.
How to Guide Your CEO’s Enthusiasm for “Shiny New Features”: Redirecting impulsive leadership energy into meaningful product evolution.
The Designer Who Made a CEO Cry (And Got Promoted for It): Using professional friction and honesty to build deep trust.
When Stakeholders Know Just Enough UX to Be Dangerous: Guiding leaders from surface-level buzzwords to sound strategic decisions.
Why your input keeps getting ignored (and the 2-minute fix): Recognizing “influence windows” to exercise judgment when it counts most.
Mistaking Strategic Fluency for Strategic Power: (Silent Career Killer #32) Why knowing strategy isn’t the same as having the power to execute it.
Full access to all learning tracks materials is available to paid subscribers. Upgrade to paid and start learning!