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Embracing Learning through Stretch Assignments: A Guide to Success

Stretch Assignments, Upskilling, Leadership Development

Industries now evolve 5 times faster than 5 years ago. With unrelenting change, adaptability is essential. McKinsey ( 2019) finds leaders exposed to 5+ functions and 3+ countries become 69% more change-ready. Harvard Business Review (2020) analysis shows broad experiences expand perspectives to envision transformation. Further studies show experiential learning opportunities directly enable greater agility—employees with wider skillsets adjust up to 40% quicker to disruptions.

This blog explores how "stretch assignments" and experiential learning are not just beneficial but essential for thriving in such a fast-paced environment. We delve into the intricacies of implementing successful stretch assignments and how they can be a key to not only surviving but excelling in today's ever-changing work world.

Stretch assignments are developmental projects that push people beyond their comfort zones. By tackling unfamiliar responsibilities, employees expand their skill sets and perspectives.

Stretch assignments are impactful for several reasons. They provide real-world practice, enhance problem-solving abilities, build resilience, boost engagement, and promote leadership skills. With continuous feedback and learning, employees progress in their careers and become better equipped to drive innovation.

9 key experiences that you should consider as stretch assignments:

  • Operational Delivery: Leading a project to enhance the efficiency of a critical production process.

  • Unfamiliar Environment: Taking a short-term role in a different department or geographical location.

  • People Management: Managing a cross-functional team on a high-profile project.

  • Global Remit: Overseeing a project with team members from multiple international offices.

  • Change Management: Leading an initiative to implement a new organisational structure.

  • Growth: Developing and executing a plan to enter a new market.

  • Start-up: Launching a new product line or service from scratch.

  • Turnaround: Revitalizing a struggling business unit or product.

  • Special Project: Managing a corporate social responsibility project with high visibility.

If you want to learn more about these key experiences, download our 9 Key Experiences to Develop Future-ready Leaders Handbook. Click here to download

The effectiveness of 'learning by doing' through stretch assignments critically depends on addressing 4 specific elements essential for success. This comprehensive guide explores these four elements, offering insights and practical strategies to maximise the benefits of learning through stretch assignments.

Element 1: Overcoming Organisational Resistance to Experiential Learning

One significant obstacle in implementing stretch assignments is overcoming organisational resistance to experiential learning. This resistance often stems from a lack of understanding of the practical benefits of 'learning by doing,' apprehension about the outcomes, or a preference for more traditional, structured learning methods such as classroom-based or e-learning modules. Overcoming resistance to stretch assignments requires a proactive and positive approach that emphasises educating and showcasing their tangible advantages, which can be achieved through securing management buy-in, effective internal communication of successes, and positioning HR as a facilitator of experiential learning opportunities:

  • Management Buy-In: Securing the active endorsement and support of top management for stretch assignments is essential. When leaders share their personal experiences with stretch assignments, they highlight their value in personal and organisational growth, effectively linking development with success.

  • Effective Internal Communication: Consistent communication about the successes and benefits of stretch assignments is critical. Showcasing stories of employee growth and their contributions to organisational objectives can help create a positive outlook towards experiential learning.

  • HR's Role in Facilitating Experiential Learning: The Human Resources department should be at the forefront of creating and implementing frameworks for experiential learning opportunities. Organising focus groups with senior leaders to discuss and share their experiences with major projects and stretch assignments not only reinforces the value of experiential learning but also serves as a powerful reminder of its effectiveness to the leadership team.

Element 2: Securing the Right Stretch Role

In the second element of our exploration into stretch assignments, we focus on the critical factors of ensuring that the stretch role that has been selected for an employee is right. This involves careful consideration of several key criteria, including aligning the role with both the individual's career path and the organisation's objectives, determining the optimal level of challenge to encourage growth without overwhelming, and clearly defining role objectives and expectations. By paying close attention to these factors, we can significantly enhance the effectiveness and impact of stretch assignments in employee development. It’s important to set employees up for success.

Let's delve into these critical success factors in more detail.

Firstly, Strategic Alignment: It is crucial to select stretch roles that align with the employee's career trajectory while contributing significantly to the organisation's objectives. This approach ensures the unlocking of potential with precision. When both individual and organisational goals are aligned to the stretch role, both the individual and the organisation are going to care more about making the assignment a success. 

Secondly, Optimal Challenge Level: The role should present an appropriate level of challenge, promoting autonomy and decision-making in employees. This balance fosters innovation and growth while ensuring the role remains achievable and the employee is not overstretched.

To determine if a role offers the right level of stretch, consider these aspects:

Employee’s Reaction and Confidence Level:

Observe the employee's initial reaction to the assignment. Signs of excessive anxiety or doubt may suggest the role is too challenging. In contrast, if they seem too comfortable or unchallenged, the role may not be challenging enough. The ideal stretch induces cautious optimism and an eagerness to embrace the challenge.

Past Performance and Learning Curve: Evaluate the employee’s historical performance and adaptability in similar contexts. If they have consistently managed slightly challenging tasks well, a more demanding assignment could be appropriate. On the other hand, if they have struggled with moderate challenges before, a more modest assignment would be advisable. The role should encourage them to utilise and expand upon their existing skills and knowledge.

Time and Effort Estimation: Assess the required time and effort for the assignment relative to the employee's current workload and abilities. A suitably challenging assignment should necessitate a substantial, yet manageable, increase in effort and time beyond their usual responsibilities. If the role demands an inordinate amount of time or effort well beyond the scope of their current position, it may be excessively challenging.

The final factor in securing the right role is Role Clarity: It is essential to clearly define the objectives and expectations of the stretch role. Regular check-ins and documented goals are vital for maintaining alignment and clarity, particularly in roles that are new or involve novel challenges. For those in the earlier stages of their career, roles with well-defined parameters often prove more successful as stretch assignments.

Element 3: Preparing the Employee for the Stretch Role

This third section is focused on providing employees with the essential preparation and support they need to successfully navigate and thrive in their stretch roles. The right preparation and support are crucial in ensuring the employee is not only ready but also set up for success in their stretch role. 

First, start with a skills assessment. Conducting a skills assessment is vital because it helps to identify the specific competencies an employee currently possesses and the areas where they may need further development. This assessment ensures that the employee is placed in a stretch role that is challenging yet achievable, aligning with their existing skills and potential for growth. By understanding their strengths and weaknesses, the assignment can be tailored to maximise learning and minimise the risk of failure, making the experience both developmental and beneficial for the individual and the organisation.

For high-stretch roles, it pays off to assess additional aspects to ensure the role is both safe and developmental. This can be done through a semi-structured interview. 

Additional aspects to assess include:

  • Assess the candidate's ability to adapt to new situations and learn quickly from experiences

  • Consider their level of emotional intelligence, including self-awareness, empathy, and ability to handle interpersonal relationships judiciously and empathetically

  • Gauge their tolerance for ambiguity and change and their resilience in the face of challenges

  • Review their past performances, especially in challenging situations, to predict future potential and development areas

  • Understand their career goals and motivation to ensure alignment with the objectives of the stretch assignment

Secondly, providing comprehensive and balanced support with realistic goals is crucial in the preparation for a stretch role. This involves offering robust mentorship and guidance to help employees navigate new challenges they might encounter. Furthermore, it's important to set achievable, clearly defined goals that are in alignment with the employee's capabilities and the objectives of the stretch role.

Regular and constructive feedback is essential to aid in their development and to adjust goals as necessary. Encouraging a work-life balance is also key, especially considering the extra effort and time that a stretch role might require; this can be supported through flexible working conditions. Additionally, ensuring that employees have access to the necessary resources and training to develop skills and address knowledge gaps identified in the assessment is vital for their success and growth in the new role.

Finally, creating a safe-to-fail environment: Cultivate a culture where failure is viewed as a stepping stone to learning. Emotional support and recognition of efforts, irrespective of outcomes, are essential. Not every stretch project goes as well as expected, sometimes not through the fault of the employee but because the role has changed. 

Here are our top quick tips for creating a ‘safe to fail environment’ 

  • Have leaders publicly discuss their own early failures and career detours. Vulnerability from the top makes it psychologically safer.

  • Separate performance reviews from assignment-based development initiatives. Ensure stretch projects are evaluated independently from day-to-day job effectiveness.

  • Set explicit expectations that stretch initiatives likely only have a 60% probability of fully realizing the original intent. Frame them as learning journeys.

  • Build slack time into participant schedules - roughly 20% - for reflection and application of learning during experimental projects.

  • Establish formal mentorship check-ins for talent in stretch roles to discuss learnings separate from line managers.

  • Publicly celebrate examples of teams pivoting ambitious initiatives due to external variables rather than viewing them as failures.

Element 4: Recognising and Advancing Career through Stretch Assignments

The recognition of the efforts and learning gained from stretch assignments is vital in ensuring they are seen as valuable experiences. And so is the need to continue an employee’s development journey after the completion of the stretch assignment. 

Continuing an employee's development following a stretch assignment is crucial for several reasons. 

First, it maintains employee engagement by acknowledging and rewarding the extra effort and risks undertaken during the assignment. This recognition helps employees see the tangible benefits of their hard work.

Secondly, ongoing development is key to retaining talent. Without meaningful opportunities for further growth or new challenges post-assignment, employees, particularly those with high potential, might feel undervalued and consider leaving the organisation. This could lead to a loss of critical talent.

Furthermore, it's important for other employees and line managers in the organisation to see the value of taking developmental risks. When they observe that personal and professional growth leads to positive outcomes, it encourages a culture of development and risk-taking for the greater good of the organisation.

Finally, post-assignment development helps in leveraging the investment made in an employee's growth during the stretch assignment. Stretch assignments inherently involve risks, including the possibility of personal or organisational setbacks. However, when employees successfully navigate these challenges, they emerge with enhanced skills and experience. Effectively utilizing these new competencies not only benefits the individual but also contributes significantly to the organisation's growth and success.

At the end of a stretch assignment, it is vital, as a first step, to update the employee’s personal development plan to address outstanding development areas and to capture future career aspirations. This must include inclusion in succession planning to understand and prepare for future roles and responsibilities. As a next step, consideration must be given to the person’s next role. There may not always be the right follow-on role available for an employee who has completed a stretch assignment, however, there are other ways to keep them learning and to harness their new skills and experiences. 

Three ways to continue the development journey in the absence of an immediately suitable role:

  1. Follow-Up Projects: Engage in subsequent projects that build on the skills and experiences gained. This can include cross-functional collaboration working on diverse projects to apply skills in different contexts.

  2. Mentorship or Coaching: Work with a mentor or coach to actively work on any remaining development areas to smooth the way to a new role or promotion.

  3. Networking: Actively facilitate networking with senior stakeholders to open doors to new roles and opportunities. This may include regular meetings with senior leaders or participation in senior leadership meetings. 


When effectively executed and supported, stretch assignments can serve as a catalyst for substantial growth, both for the individual and the organisation. The four essential elements to consider are embracing organisational change, selecting the appropriate stretch role, effectively preparing the employee, and acknowledging their efforts and the insights gained. This comprehensive approach maximises the benefits of learning through stretch assignments. It not only encourages personal development but also contributes to the overall success of the organisation, fostering an environment where continuous learning and adaptability are key.

Having explored the impactful nature of stretch assignments and the strategies for their successful implementation, it's vital to take the next step in advancing your leadership development. To deepen your understanding and enhance your capabilities, we encourage you to download our in-depth guide, '9 Key Experiences to Develop Future-Ready Leaders'.

Not sure which key experience to dive into? Let fate decide! Spin the roulette and embrace the challenge that lands your way. It's a fun, exciting, and somewhat mysterious way to discover what your career might be missing.


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