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The Truth About the Creative Executive Leap
Your Design Career Is Now Measured in P&L, Not Prototypes. (Master the Shift)

Photo by Ian Schneider on Unsplash
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⏱️ Today, in 5 Minutes or Less
As an aspiring creative leader, you've likely dreamt of the Chief Design Officer title. It’s the ultimate validation of your craft, talent, and leadership. But let’s pull back the curtain on this rarefied air.
What happens when your career success is no longer measured by pixel-perfect UI or user delight, but by seven-figure budgets, quarterly financial results, and boardroom influence?
The journey from a design manager to an executive design leader is a radical metamorphosis. As a former Chief Design Officer, it takes you away from the practice of your craft and away from managing directly to a place that relies on projecting your value and having an impact through influence.
🔎 Did You Know
The Executive Reality: Lonely, Intense, and Life-Changing
Being an executive is often lonely. You trade time with your teams for countless meetings with leaders who speak the language of finance, operations, and market share, expecting you to speak it too. You pore over spreadsheets, endlessly recruit, present to "scary dudes," and are in a constant state of context-switching. If you let it, your time is no longer your own.
Yet, this is a rare, privileged position where the financial rewards can offer life-changing generational wealth. When your compensation breaches the seven-figure threshold, the stakes—and the pressures—become immense. You're in the "shark tank," where complacency is a death sentence, and your perceived value is a battleground.
The question is: Are you ready to trade your designer's heart for an executive's mindset?
🧠 The Mindset Shift: Designer vs. Executive
Creative behavior and portfolio skills alone may not be enough to sustain long-term success at this level. The executive arena demands an additional investment in financial education and the ability to communicate the value of your organization’s output to the business bottom line.
Business leaders focus on the verbal, analytical, and orderly (left-brain thinking), measuring worth by collecting hard skills in financial strategy and quantitative analysis. As a designer, you live in the broader world of creation and process flow (right-brain thinking).
To thrive, you must seamlessly merge these two worlds. Here is a look at the fundamental shift in focus required to make that leap:
Attribute | Design Manager | Creative Leader/Executive |
Scope of Impact | A feature set, a single product, or a specific user journey. | Entire portfolio of products, major organizational function, or long-term company strategy. |
Autonomy | Works under direction of a director/VP; focuses on how to achieve defined goals. | Defines the goals; operates with minimal direction provided by the CEO/Board. |
Expertise | Deep expertise in design craft (UX/UI, research); solving technical challenges within their domain. | Expertise in organizational and business architecture; solving complex resource, political, and systemic challenges. |
Manages | Manages individual contributors; focuses on skill development and team output quality. | Manages managers (Directors/VPs); focuses on succession planning and defining the entire department's culture and structure. |
Collaborators | Collaborates with Product and Engineering peers to ship features; influence is limited to the product trio. | Collaborates with the C-Suite (CFO, COO, CEO) to drive business outcomes; influence affects enterprise-wide capital allocation. |
Problem Scope | Tackles defined problems (e.g., how to improve checkout conversion by 5%). | Tackles highly ambiguous, unstructured problems (e.g., how to secure the company's competitive advantage in 3 years). |
Time Horizon | Weekly sprints, quarterly roadmaps, and immediate project delivery. | Multi-year strategic planning, organizational design, and long-term market positioning (3-5 years). |
Accountable For | Accountable for quality, usability, and on-time delivery of team's features and failure means feature delays or bad user experience. | Accountable for the ROI of the entire design function and decisions that carry significant financial or market risk. |
🕵🏼 The Research Backs It Up
This distinction between design management and executive leadership isn't just theory—it's backed by research into successful C-suite transitions:
Shift from Functional Expertise to Strategic Acumen:
A study published in the Academy of Management Executive emphasizes that the transition to executive roles requires leaders to shift from a focus on deep functional knowledge (like design) to a greater emphasis on strategic vision, resource allocation, and organizational architecture. The skills that made you a great design manager (mastery of craft) become secondary to your ability to communicate financial and strategic value to the CEO.
The Need for "Organizational Savvy"
Research by Marshall Goldsmith highlights the "What Got You Here Won't Get You There" principle. Moving to the executive level demands Organizational Savvy—the political intelligence, interpersonal influence, and financial literacy necessary to operate effectively at the top. This replaces the emphasis on individual or team output, which defines a successful design manager.viding the experience and visibility required to fast-track your journey to the top.
Landing the top design leadership role is an achievement, but sustaining it requires a proactive, multifaceted approach.

Opening the first edition of my new book Leading by Design
In my recently published book, Leading by Design: The Insider's Playbook for Tech Leadership, I delve deep into the essential strategies for surviving and thriving in this executive design seat. We explore how to demonstrate your impact rapidly, build unshakeable relationships, and amplify your sphere of influence.
Are you ready to design your career transition from manager to executive with intention?
That's it for this week!
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With ❤️ from Sally

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