Playing Chess

Would you sit across from an opponent to win a chess match with the same set of strategies that you employ while playing a less-complex game like checkers?

Probably not. Similarly, leaders, who strive to find “wins” for their teams, should not bring only one approach to the table to solve complex leadership challenges without first ascertaining which “game” their team is playing.

Executive leaders encounter challenges that demand their attention and resolution daily. Given the nature of virtual/hybrid workplaces and the developing technologies that are altering standard operating systems for many global teams, some of these challenges may be unfamiliar and overwhelming.

In order to ensure company growth, it is amid this ever-evolving workplace culture that leaders need to identify the nature of each organizational challenge to best address it. Misdiagnosis can lead to wasted resources, ineffective strategies, and prolonged periods of stagnation. There is less margin for error and more room for burnout than ever before.

Before developing their problem-solving approach, leaders should always take a step back and ask themselves: “Am I playing checkers or chess? Which strategy matches the complexity of this challenge?”

According to the adaptive leadership framework methodology developed by Ron Heifetz and Marty Linsky of Harvard University, leadership challenges come in two distinct forms: technical and adaptive. Technical challenges lend themselves to solutions grounded in expertise and known methodologies. Adaptive challenges, on the other hand, present a more elusive landscape, characterized by volatility, complexity, and ambiguity.

Understanding the fundamental differences between these two types of challenges is essential to charting a course toward effective problem-solving and team and organizational growth.

The Dichotomy of Leadership Challenges

The father of the adaptive leadership framework Ron Heifetz emphasized that understanding the nuances between technical and adaptive challenges shouldn’t be taken lightly. He stated the health of teams relies on leaders’ abilities to differentiate between obstacles and adapt solutions accordingly.

“The most common failure that I’ve seen in leadership over many years is this diagnostic failure of people in high positions of authority who have failed to lead because they’ve ended up treating adaptive challenges as if they were technical. They throw technical fixes at the problem. The problem persists and then, over time, people get disappointed that you haven’t really solved the problem.”
-Ron Heifetz

So what are the definitions of technical and adaptive problems? Let’s delve deeper.

Technical Challenges Explained

Picture a straightforward problem with a clear solution similar to a simple game of checkers. Technical challenges are those that can be tackled with existing knowledge, skills, and procedures. Technical challenges are concrete and well-defined, often requiring an application of expertise or a known process to solve. For instance, changing a performance management process is a technical problem with a defined solution

Adaptive Challenges Explained

Unlike technical challenges, adaptive challenges are more complex and elusive, similar to the game of chess with its more agile game-play process. Adaptive challenges involve shifts in deeply ingrained organizational cultures.

Adaptive solutions usually require leaders and teams to engage in agile learning and discover new:

  • Mindsets, attitudes, and transforming beliefs
  • Creative approaches to different ways of working
  • Team-development perspectives and intentions
  • Relationship-building internally and externally
  • Methods to measure and share success

A common adaptive challenge clients request Churchill’s support with is to develop a feedback culture. The lack of a feedback culture is an adaptive challenge that manifests in ineffective feedback loops between managers and employees, as well as among peers. The consequence is employee attrition due to a lack of developmental feedback, alongside diminished innovation stemming from a culture that discourages idea sharing, honest feedback and difficult conversations.

Organizations who seek us out aspire to cultivate a feedback culture tailored to their teams’ needs. However, achieving this goal requires transforming mindsets, expectations, behaviors, values, and even redefining success metrics. The complexity of this challenge lies in effecting sustainable and impactful change across various dimensions.

In a nutshell, adaptive challenges demand a willingness to explore uncharted territories with flexible “system thinking” that push leaders and teams out of their comfort zones.

Identifying & Overcoming the Challenge at Hand

Here are four key indicators to help discern between technical and adaptive challenges:

1. Clarity of Solution: Technical challenges often come with a clearer solution or a known set of steps to follow. In contrast, adaptive challenges lack a straightforward answer and may require experimentation and learning through trial and error.

2. Resistance to Change: Adaptive challenges typically encounter resistance from individuals or groups within the organization. This resistance stems from the discomfort associated with stepping outside familiar routines and embracing uncertainty. Technical challenges, on the other hand, tend to encounter less resistance, as they focus more on procedural changes versus mindset shifts.

3. Recurring Patterns: Technical challenges may recur due to specific circumstances, but adaptive challenges tend to manifest as recurring patterns or systemic issues deeply embedded within the organization’s culture.

4. Scope of Impact: While technical challenges may impact specific tasks or processes, adaptive challenges typically have a broader scope, affecting organizational culture, leadership dynamics, and stakeholder relationships.

However, knowledge is power. Once you know what type of obstacle you are facing, you can pivot your mindset, goals and methodology to empower yourself and your team. As the educator and originator of experimentalism philosophy, John Dewey, stated: “A problem well stated is a problem half solved.”

Churchill Leadership’s coaches enhance leaders’ understanding of challenge distinctions, enabling them to discern the nature of the obstacles that they encounter. Additionally, Churchill’s offerings aid leaders in exploring various approaches to plan effectively, execute, and evaluate success in addressing those challenges.

Churchill’s Adaptive Challenge Checklist

Adaptive challenges in the corporate workplace are commonplace, and it can be helpful to have a list of questions to help leaders and teams get clarity in order to move forward successfully and experience organizational growth.

We recommend you use these questions collaboratively to get all ideas on the table:

1. How should mindsets, attitudes, and beliefs shift to support the desired changes?

2. What current ways of working hinder progress, and what new approaches are necessary?

3. Where are there gaps in collaboration or isolation hindering progress?

4. Who are the key stakeholders that need to be engaged early and throughout the process?

5. How will creativity, experimentation, and agile learning be encouraged and empowered?

6. What metrics and strategies will ensure sustainable and effective change?


The Adaptive Challenge Checklist contains a more extensive set of questions that takes you step-by-step through the process of strategically overcoming workplace adaptive challenges. Remember, adaptability and resilience are key when facing adaptive challenges. This checklist is a guide to help leaders and teams navigate through uncertain seasons and situations and drive positive change in the corporate workplace.


Churchill Leadership Group Understands Leadership Challenges

In the dynamic workplace landscape, leadership challenges are inevitable. By discerning between technical and adaptive challenges and employing appropriate strategies to address them, leaders can steer their organizations toward sustainable growth and success.

Embracing the journey of adaptive change – even though it is often more complex – not only fosters resilience and agility, but also paves the way for innovation and continuous improvement. As leaders navigate the waters of uncertainty, it is their ability to adapt and evolve that will ultimately determine their success in charting a course toward a brighter future.

Unlock the full potential of your leaders and team by contacting us today to explore how our coaching and training solutions can help them handle all the challenges thrown their way. Whether your team requires support for technical or adaptive challenges, we are ready to partner with you and empower your organization’s growth.

Jayne Jenkins CEO Churchill Leadership Group, Inc.


Jayne Jenkins is the founder and CEO of Churchill Leadership Group. After 23 years as a seasoned Fortune 500 leadership veteran, working for AstraZeneca and Sanofi-Aventis, Jayne recognized the need to unleash untapped talent in the corporate world. Through her work in the US and Europe, Jayne observed many leaders and teams struggling to reach their full potential. Jayne’s years of corporate experience included building high-performance sales and operations teams, including an organization delivering annual revenue of $600 million.

In 2012, Jayne’s mission was to build a global coaching organization that could partner with corporate and government clients to maximize the talent they are already paying for! Today, Jayne is a certified Executive, Team, Strengths, and Conversational Intelligence® Coach. She proudly leads Churchill’s global team of over 400 coaches and SMEs in North and Latin America, Europe, The Middle East, and the Asia Pacific.

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