In today’s rapidly evolving business landscape, where artificial intelligence (AI) advances are both a boon and a bane, the role of design and design thinking has never been more crucial. AI advancement is often labeled as a “wicked problem”—a complex issue with no clear solution, constantly evolving, and intertwined with other challenges. However, through the lens of design thinking, businesses can effectively navigate these turbulent waters, especially concerning workforce management.

What Defines “Wicked Problems”? 

“Wicked problems” are a unique class of issues that are difficult, if not impossible, to solve due to their complexity and interconnectedness. Coined by design theorists Horst Rittel and Melvin Webber in 1973, wicked problems have several defining characteristics:

  1. No Definitive Solution – Wicked problems don’t have a clear, final solution. Any solution is only a temporary fix.
  2. Uniqueness – Each wicked problem is unique, and the approach to solving it must be customized.
  3. Interconnected Issues – Solutions often impact other problems, creating a web of interdependencies.
  4. Dynamic Nature – The problem evolves over time, and so must the solutions.
  5. Unclear Problem Definition – The problem itself can be difficult to define, making it challenging to address.

AI’s impact on the workforce is a quintessential wicked problem, involving technology, economics, ethics, and human behavior, all intertwined in a continuously shifting landscape.

Understanding Design Thinking 

Design thinking is a human-centered, iterative approach to problem-solving that emphasizes understanding the user, challenging assumptions, redefining problems, and creating innovative solutions to prototype and test. It’s scientific and disciplined yet inherently creative and collaborative. This methodology is particularly adept at tackling wicked problems due to its adaptability and focus on empathy.


The Workforce Challenge in the Age of AI 

The workforce landscape is shifting dramatically as AI and automation become more prevalent. Companies are grappling with how to acquire, manage, and retain talent across various categories—from full-time employees to gig workers and everything in between. The traditional roles and skills are evolving, necessitating a move toward skills-based organizations. Here’s how design thinking can play a pivotal role in this transformation.


Framing the Problem 

The first step in design thinking is empathy. For businesses, this means deeply understanding the concerns, aspirations, and challenges of their workforce. By conducting interviews, surveys, and ethnographic studies, companies can gain insights into employee experiences, motivations, and pain points. This human-centric approach ensures that solutions are grounded in reality, not just in theory.


Building Empathy 

Empathy is the cornerstone of design thinking. It enables companies to see the world through their employees’ eyes, fostering a culture of understanding and respect. When businesses take the time to listen and empathize, they can uncover unmet needs and latent desires, which are critical for developing effective workforce strategies.


Ideation and Prototyping Talent Acquisition 

Once the problem is framed, the ideation phase begins. Here, creativity is unleashed, and a multitude of ideas are generated. This phase is collaborative, often involving cross-functional teams to ensure diverse perspectives. Prototyping these ideas allows for quick testing and iteration, enabling companies to refine solutions before full-scale implementation.


Applying Design Thinking to Workforce Challenges


  1. Talent Acquisition Talent Management

   – Problem: Finding the right talent with the necessary skills in a competitive market.

   – Design Thinking Approach: Use empathy to understand the candidate’s journey, from job search to application and onboarding. Ideate ways to make the process more seamless and engaging, such as AI-driven personalized job recommendations and virtual reality (VR) onboarding experiences.


  1. Talent Management 

   – Problem: Managing a diverse workforce, including remote workers, gig workers, and full-time employees.

   – Design Thinking Approach: Map out the employee journey and identify pain points in communication, collaboration, and career development. Prototype solutions like AI-driven performance management tools and hybrid work environments that foster inclusivity and productivity.


  1. Skills Development Retention and Engagement

   – Problem: Upskilling and reskilling employees to meet the demands of an AI-driven economy.

   – Design Thinking Approach: Collaborate with employees to co-create personalized learning paths. Test solutions like AI-powered adaptive learning platforms and mentorship programs to ensure they meet the needs of different learning styles and career goals.


  1. Retention and Engagement Moving Toward Skills-Based Organizations

   – Problem: Keeping employees motivated and reducing turnover.

   – Design Thinking Approach: Engage with employees to understand what drives their satisfaction and loyalty. Prototype initiatives like flexible work arrangements, mental health support, and recognition programs that are continuously refined based on employee feedback.


Moving Toward Skills-Based Organizations

As AI reshapes the workforce, the emphasis is shifting from roles to skills. Skills-based organizations focus on the capabilities employees bring to the table, rather than their job titles. Design thinking can facilitate this transition by helping companies identify the skills needed for future success and creating pathways for employees to develop these skills.

Through iterative processes and continuous feedback, companies can build a more agile, resilient workforce. This approach ensures that businesses are not just reacting to changes but proactively shaping their futures in an AI-driven world.



Design thinking offers a powerful framework for addressing the complex, multifaceted challenges of workforce management in the age of AI. By fostering empathy, encouraging collaboration, and embracing a scientific yet creative approach, businesses can navigate the wicked problems of today’s workforce landscape. Ultimately, design thinking empowers companies to not only solve problems but to innovate and thrive in an ever-changing environment. As we move toward skills-based organizations, the principles of design thinking will be instrumental in driving sustainable success and creating a more adaptive and resilient workforce.



Authored By:

 Mark Condon

Co-Founder & Managing Partner, QuantumWork Advisory

An Australian based in the US for the last six years and previously in Singapore for eight years, Mark is a pioneer in the talent and workforce sector, with over 20 years global experience with both start-ups and multinationals.

Mark’s specialties include advising clients on Talent Strategy, Workforce Service Design, Technology and Transformation. Mark’s advisory projects bring a disciplined, data-driven approach interwoven with user-centric frameworks based on design thinking principles.

Dedicated to life-long learning, Mark has completed an MBA, degrees in Psychology and HR, and executive education with MIT, HBS, and IDEO.