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Embracing Learning through Stretch Assignments: A Guide to Success

Updated: Aug 7

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.

Experiential development is the key to new supercharged leadership qualities: Read here

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:

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.

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.

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'.

Download your free copy now 

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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Stretch Assignments 101: Maximize Opportunities for Growth With Thoughtful, Guided Supervision

Challenging workers with new assignments and responsibilities is good for both the employee and the employer. But it requires a well-considered process.

stretch assignment questions

Stretch assignments are well understood to enhance individuals’ skills and experience. But how is it done right — without the career version of a pulled muscle?

The vice president of life sciences at Iterative Health , Laura Mantell, shared her methods and techniques for doing this safely and effectively. It starts with training the individual to give them technical proficiency as well as to give them self-confidence. She also advises assigning the employee a project area and client with whom that person is familiar. 

Provide close supervision and plenty of support at the beginning of the stretch assignment, tapering back as the trainee scores more points in the win column, said Mantell. And always offer support, even in the latter stages.

  Built In Boston spoke with Mantell to discover how Iterative Health is able to attract some of the best talent because of this culture and approach to growing its people.  

Image of Laura Mantell

Iterative Health uses AI to transform gastroenterology treatment and improve patient outcomes.

Please share an example of when you extended a stretch assignment to a direct report. What was the assignment, and how did you know the individual was ready to take it on?

Recently, a member of my team had an opportunity to take on more of an active role in managing an important client relationship, which was a critical relationship for the business. This team member had spent several months getting to know more junior members of the client company and established a strong rapport with them, making him a trusted partner. The team member's diligence, thoughtfulness and high-quality work product clearly demonstrated that he was ready for more of a challenge. He met it head on, becoming a well-regarded partner across the client's organization, which led to continued success and growth today.

It was important to me that my teammate felt set up to succeed and grow individually.”

How do you ensure that team members are not overburdened by stretch assignments and are supported throughout its completion? 

In the previous example, it was important to me that my teammate felt supported throughout this stretch opportunity and that he was set up to succeed and grow individually. As a result, I worked closely with him — giving him space to run and manage the client with increasing independence and space while also providing feedback, answering questions, reviewing materials, etc. In this way, my team member was positioned to grow as a result of this opportunity, while also being able to learn from the team and those around them in the process.

How can managers make sure that they take a thoughtful approach to stretch assignments so that they lead to growth — and not stress — for their assignees?

In my experience, the best way for managers to stretch their employees without causing undue stress is to spend and invest significant time and training upfront, ensuring and building confidence that the team member can continue to grow with increasing independence. When done well I've seen team members be able to grow faster and with more autonomy as they feel well prepped and trusted by their team. 

I also believe that building trust is critical to this process. There needs to be a strong level of trust between manager and teammate so that the teammate feels that the manager has their back. Also, the manager knows the teammate can handle opportunities independently and doesn't feel the need to micromanage.

Responses have been edited for length and clarity. Images provided by Shutterstock and Iterative Health

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Stretch Assignments: What Are They and Is Your Employee Ready For One?

Picture of Michelle Bennett

Stretch assignments are a cornerstone of a strong employee development plan. A statement that is backed by a number of research studies. In one conducted by the Harvard Business Review of 823 executives, it was found that 71% of respondents said stretch assignments had the biggest impact on unleashing their potential. In another, this one conducted by Korn Ferry, stretch assignments were named the most valuable developmental experience, ahead of things like mentoring, classroom training, 360-degree assessments, and even exposure to senior leaders.

An intentional and strategic stretch assignment can go a long way in accelerating an employee’s development or supporting the trajectory of their career at your organization, though their success relies heavily on the one assigning the task - their leader.

In the following article, you will learn more about what stretch assignments are, what they are not, how to tell when an employee is ready for one, and more. Let’s begin.

What are Stretch Assignments?

While there are countless ways to define a stretch assignment, the following definition from BeLeaderly perfectly sums it up for the purposes of this article: “Stretch assignments are temporary, internal learning gigs that simultaneously offer an employee a chance to develop new skills while helping the organization solve a real business problem.”

Most commonly, stretch assignments are implemented to prepare an employee for an upcoming promotion, engage a high-performing employee, encourage skill development, or evaluate an employee’s level of interest or aptitude for another role.

As the name implies, stretch assignments mean they “stretch” or challenge an employee to think and act outside their comfort zone or day-to-day job. But what exactly makes a stretch assignment challenging ?

  • It presents employees with an unfamiliar challenge
  • It challenges an employee to create change
  • It gives an employee a high level of responsibility
  • It challenges an employee to work cross-functionally

At this point, it is important to define what stretch assignments are not. Stretch assignments are not a chance for you to hand off work you do not want to do. They should also not be what Korn Ferry calls “glass-cliff projects.” According to them, “stretch assignments and glass-cliff projects both involve some risk and often include crisis situations, but one is about building your skills and the other is about proving your worth, despite your many successes. One is encouraging; the other is an affront.”

Are you struggling to decide what to delegate and whom to delegate to? If so,  this guide will help!

4 Signs Your Employee Is Ready For a Stretch Assignment

Of course, there is a fine line between “stretching” or challenging an employee and overwhelming them. To help you distinguish if an employee is ready for and can handle a stretch assignment or not, here are a few key things to consider: 

  • Their Track Record An employee who is ready for a stretch assignment and can handle it will not only have a history of successful projects and good performance, but will have a track record of asking for help when they need it, respecting boundaries, proactively seeking learning opportunities, and taking accountability for their actions (whether good or bad). These behaviors show a level of discretion that is imperative to the success of a stretch assignment, where an employee is outside of their comfort zone.
  • Their Engagement According to Gallup , “engaged employees are highly involved in and enthusiastic about their work and workplace. They are psychological ‘owners,’ drive high performance and innovation, and move the organization forward.” Whereas, “actively disengaged employees aren't just unhappy at work - they are resentful that their needs aren't being met and are acting out their unhappiness. Every day, these workers potentially undermine what their engaged coworkers accomplish.” Fortunately, stretch assignments are an ideal chance to further engage already engaged employees and those bordering on disengaged. You should be quite certain that the individual you will give the assignment to will see it as a positive opportunity and be willing to do their best work, not just because they have to, but because they want to.

An employee who has been given a stretch assignment is going to need your support more so than they would for their everyday job. Therefore, before you give a stretch assignment, be sure you have the availability and capacity to proactively support your employee from start to finish. 

  • Your Relationship Given the nature of stretch assignments, there is always a risk of failure and for some employees, failure is hard to handle even if it is a valuable learning experience. That is why it is so important to have a relationship built on trust before delegating a stretch assignment. Your employee needs to feel comfortable sharing their challenges and questions without fear of judgment, or else they might try to “go at it alone,” which is ultimately where people get themselves into trouble.

2 Major Things to Be Aware of With Stretch Assignments

  • Stretch Assignments Should Not Impede An Employee’s Day-to-Day Job As a leader, you need to closely monitor the progress of a stretch assignment, the well-being of your employee, and the health of their day-to-day roles and responsibilities. If your employee is suddenly working an exorbitant amount or is showing signs of burnout , then you need to be prepared to step in. While the stretch assignment is important, it should not put your employee's core roles and responsibilities , not to mention their wellbeing, at risk. If this becomes an issue, use it as a learning opportunity to help the employee identify their signs of burnout and set boundaries .
  • Stretch Assignments Need to be Fairly Distributed The unfortunate reality is stretch assignments are not always fairly distributed and accessible to all employees. This was highlighted in a study from BeLeaderly , which found that “women are less likely than men to receive challenging stretch assignments.” The report noted that “when stretch assignments are unclear, unadvertised, and unevenly offered, it makes women hesitate even more to pursue them. On the other hand, taking an open, equitable approach to stretch opportunities can create a thriving internal gig economy - one that’s accessible to all. This not only helps employees advance in the short term, but it can also set the course for diversifying, and therefore strengthening, your leadership ranks in the long term.” So, how can you ensure the distribution of stretch assignments is fair? According to a report by Catalyst , they recommend leaders link the distribution of stretch assignments to performance reviews, review the allocation of stretch assignments to ensure equitable distribution among women and equity-seeking groups, as well as consider providing new hires with a stretch assignment or assigning new hires to a team working on a stretch assignment. 

Employees who are given a stretch assignment will require more support, guidance, and encouragement than an average employee. Though the effort is well worth it as stretch assignments contribute to employee engagement, morale, satisfaction, productivity, and success, which in turn contributes to your success as their leader. It’s a win-win!

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4 Stretch Assignment Examples for Upskilling Your Workforce

Jocelyn Ho

There’s a reason why doctors and fitness experts encourage regular stretching. Doing so improves your performance, increases your range of motion, and builds flexibility. 

Likewise, employees can improve their performance and expand their skills when they stretch their abilities in the workplace. 

This can be done by taking on stretch assignments: projects or tasks that are beyond their current skill set or expertise. Stretch assignments play a critical role in upskilling programs by strengthening employees’ career prospects, enhancing performance in the workplace, and extending an individual’s range of knowledge.

Here are several types of stretch assignments you can assign employees to help them upskill for career development and internal mobility :

  • Teaching a class or developing a course
  • Leading or working on a cross-functional project
  • Coaching or mentoring a teammate 

Sound interesting? Next we'll jump into more detail on each type of stretch assignment and what kinds of skills they help employees develop.

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1. Ask subject-matter experts to teach peers

The protégé effect states that the best way for a person to learn is to teach. Therefore, empowering your internal subject matter experts to teach a class or create a course allows them to refresh existing knowledge and learn new skills in the process.

These employees learn how to better communicate their thoughts clearly and precisely, so colleagues who are taking the course can pick up the material quickly. This type of exercise also requires subject-matter experts to use their imagination and creativity to work out how to best deliver the content in an engaging and effective manner.

Take for example, a senior graphic designer who is creating a beginner Photoshop course for her organization. Even though she knows how to navigate the software like the back of her hand, she will still need to learn how to explain design concepts in a manner that non-designers can easily and quickly pick up.

To encourage more frequent peer training in your organization, consider investing in an LMS with an authoring tool that enables anyone to create internal courses in minutes. The most flexible employee training programs enable users to create and participate in both employer and employee-led learning remotely and asynchronously. 

Google, for example, has a formal employee-to-employee training system called “G2G” (Googler-to-Googler), in which employees volunteer to teach and train their peers. They can create a course on any topic that they’re interested and experienced in, which has covered topics as diverse as coding, cooking, and ballroom dancing.

This initiative has also created tangible benefits for volunteer teachers, such as improved performance and new hard and soft skills. A Google engineer even taught his co-workers how to fly airplanes , and in the process, he largely improved his skill and confidence in public speaking and presentation.

2. Assign employees to work on cross-functional projects

Although online learning and remote work give employees greater autonomy on how they learn and work, they can also be isolating . One way to offset this is to have your employees upskill and challenge themselves by participating in or leading cross-functional projects within your organization. For example, you could have an employee in product management work with the marketing and customer success teams on a new product launch. 

When employees collaborate with other teams or departments, they can share their expertise and learn from fellow colleagues, while expanding their own knowledge and skills. This could mean gaining tactical skills and discovering helpful new tools, but also developing communication and interpersonal skills, emotional intelligence, and teamwork. This transfer of knowledge and expertise also allows team members to exchange ideas and share different perspectives, which can help stimulate creative thinking and problem-solving.

3. Have experienced employees coach junior team members

Becoming an effective leader isn’t as easy as just reading a book or taking a course. It requires hands-on experience acquired through interpersonal interactions in the workplace. Help your employees gain this experience with an internal program teaching them how to coach their peers .

In the workplace, a coach is a person involved in the instruction, direction, or training of an individual or team to help them grow and develop their skills. A leadership coaching survey showed that 72% of companies offer some type of leadership coaching to improve the leadership skills of their employees. This type of stretch assignment is well-suited for employees who want to guide others in reaching specific goals, and to develop leadership skills like emotional intelligence, empathy, and self-awareness. 

There are two ways to support your employees with a coaching program:

  • One-on-one coaching : This occurs when a more knowledgeable or skilled employee works with a more junior team member in the same field to guide them on their professional development. This method allows the coach to follow their trainee’s work and habits to determine how they can help improve their performance. For example, in a design agency, a lead designer can coach a junior designer and help them plan and strategize their work.
  • Peer-to-peer coaching : This is a more informal method where two or more employees with similar levels of experience and seniority work together to help each reach their goals. It can be as simple as connecting to ask questions, review work, provide feedback, or help someone join a new project or team. For example, assigning onboarding buddies to new hires helps the latter acclimate to the company and their role–and gives the former an opportunity to take on more responsibility and engage with their work in a new way. 

4. Increase workplace engagement with a mentoring culture

Research from Gallup found that a whopping 60% of workers are emotionally detached at work. Giving your employees rewarding opportunities to become mentors can increase their engagement and satisfaction in the workplace. A study from the Harvard Business Review revealed that employees who served as mentors “described their job as more meaningful than those who did not mentor.” And mentors also experienced lower levels of anxiety than their non-mentoring counterparts.

Like coaching, mentoring is a relationship in which employees learn from someone else’s experience. Coaching is more performance-driven and often designed to help trainees reach milestones and achieve specific goals. On the other hand, mentoring is more focused on passing a mentor’s knowledge onto the mentee, rather than following direct instructions.

For example, desired outcomes of a mentor-mentee relationship are often: helping an individual realize their potential, accelerating their development, or supporting them in furthering their career. A mentor looks at their mentee’s holistic improvement, rather than specific skills that can be learned through practice. 

Mentorship also enables mentors to transform their individual knowledge into institutional knowledge . And this process of sharing their skills and ideas with others helps them improve their interpersonal and communication skills.

To make your mentorship program a greater success, pair mentors with mentees who have different experiences, knowledge, and skill sets. This encourages mentors to get outside their comfort zone and challenges them to think or see things differently. As part of its four-step mentorship program , Disney Media & Entertainment Distribution matches mentees with mentors who work in different locations. This approach creates more opportunities for interesting conversations and fresh perspectives because employees can interact with team members they wouldn’t normally encounter in their day-to-day work.

"Stretch" your employees to strengthen your organization

It’s easier for employees to excel at stretch assignments in a collaborative learning environment. A collaborative learning culture ensures that your employees are regularly sharing knowledge and building new skills, whether through peer-learning opportunities or mentorship and coaching programs.

Investing in a comprehensive learning platform like 360Learning allows employees to declare their learning needs in real-time–enabling L&D teams and SMEs to create courses that address the most immediate skills gaps within your organization.

Want to read about more upskilling strategies to develop a highly skilled, engaged, and loyal workforce that’s ready to take on new challenges and propel your business to greater heights? Explore more articles on the topic below, or book a personalized demo of 360Learning here .

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All Articles Leadership Management 4 questions to ensure successful stretch assignments

4 questions to ensure successful stretch assignments

How do you stretch employees without burning them out? Read on for a guide on hitting this careful balance.

By Julie Winkle Giulioni 03/11/21

Think about the most profound professional development you’ve experienced in your career. Where were you? What were you doing? What did you learn? And what was it about that set of circumstances that made the learning so effective, productive or both?

I’ll bet it had something to do with a significant challenge that compelled you to draw upon your yet-to-be-discovered resourcefulness to address an issue or solve a problem. I know that was the case for me.

Years ago, I was charged with leading a team that would develop the first new product for a company that had been formed when three competitors merged. This was an environment of disparate corporate cultures, incompatible processes, political maneuvering and a longstanding history of grudges. I needed to figure out how to bring the factions together, foster the collaboration required to create a new model that all former operating units would salute, and get the troops to rally behind a new product and the new company.

To say it was a challenge is an understatement — and I still have the scars as reminders.

Despite the pain of it all – becoming very unpopular very quickly, the angry stakeholders, the late nights, the “one step forward, two steps back” progress — it remains to this day one of the most intense periods of growth I’ve ever experienced. The product was ultimately launched and is still in use 20 years later. Although proud of my team and our work, as soon as it was complete, I promptly resigned. It took so much out of me, and I needed time to recover before bouncing back.

Stretch assignments like this and other on-the-job challenges are among the most powerful and cost-effective tools a leader has to offer in role development. But in crafting such experiences, leaders frequently fail to consider the important step of calibration – figuring out how far to stretch the rubber band (that is, the employee’s capacity) to generate the intended growth but not so far that it eventually snaps (as in my case).

Clearly, when it comes to challenge as a development strategy, one size doesn’t fit all. This is especially true today, as people may already be pushed to their personal limits trying to work from home , care for and educate children, navigate vaccine websites and more. Finding what’s right for each individual has never been more important — or challenging.

Leaders who consistently strike that Goldilocks-like “just right” level of stretch with their employees tend to approach challenge-based development with discipline and intention. And you can, too, by considering these four questions.

What is the developmental purpose of the stretch assignment?

The great news about stretch assignments is that they serve double duty: Real work gets done, and somebody has the chance to grow in the process. Unfortunately, too frequently, the work is in the foreground and development stays way in the background.

Avoid this by deliberately determining the purpose or growth goal the employee will be working toward during the assignment. Will they be working on enhancing their negotiation skills? Learning more about the broader organization? Managing complexity? Without a clear purpose, it’s just more work. But when you and the employee can describe and agree upon the specific growth focus, that makes for electrifying development.

What is the current level of skill, motivation, and resilience of the employee?

Understanding the starting point is essential for determining the best way to move toward a desired future state. Too frequently, that stretch assignment’s rubber band snaps back or breaks because the distance is too great between where the employee is and what’s expected.

So, jointly assess the current skill set. Evaluate just how motivated the employee is – both to achieve the business and growth outcomes. And take a clear-eyed view of the level of   resilience the employee is able to bring to the situation right now. In many ways, this represents the emotional stretchiness available to the individual at any given time.

And since resilience is fluid and in flux due to changing life conditions, it’s important to check your assumptions and factor an understanding of this into the stretch assignment, as well.

What experiences might offer the appropriate (but not excessive) level of challenge needed to grow?

With a clear understanding of the developmental purpose and where the individual is starting from, you can collaborate to calibrate just how much stretch will be optimal and what kinds of experiences and activities will make it possible.

Options might include:

  • Raising the bar with a focus on elevating the volume, velocity or accuracy of the work employees currently do.
  • Adding complexity to current tasks or role.
  • Increasing the employee’s level of responsibility (which could look like larger teams, bigger budgets, etc.).
  • Finding a new context for the employee’s existing skills.
  • Imposing limitations or constraints. Author Whitney Johnson advocates for challenging others to grow by introducing constraints related to time, money, expertise and buy-in.
  • Elevating the stakes and level of visibility to elevate the pressure and challenge.
  • Challenging others to create something new — a new product, service, process, etc.
  • Inviting the employee to step into the unknown by taking on ambiguous, ill-defined or completely unknowable projects or initiatives.

What resources will the employee need to ensure that the stretch delivers its desired developmental outcomes?

Taking on a challenge demands emotional resources on the part of the employee. But it may also demand resources from the organization. Failing to offer what’s needed to produce the business results will nearly always compromise the learning results. So, determine what’s necessary for success. Budget? Staff? Time?

And remember that in many cases, it’s the priceless element of support from you, the leader. Your support acts as an insurance policy that the rubber band won’t snap or break because you are monitoring the process, offering guidance, addressing obstacles and suggesting adjustments.

These questions offer a framework for considering and crafting challenges that facilitate the development people need. These challenges propel people beyond their preconceived sense of capability, establish the psychological safety required for optimal learning and improve the probability of success.

As for me, my overly stretched development challenge turns out to have been a tremendous gift. I learned more in a shorter period of time than I thought possible about influence, change management and the psychology of M&A. The intensity of the experience forged some of my most cherished business relationships. It was the impetus for leaving corporate life and forming my own business. And it gave me new insights into how a supported stretch can offer the growth people want without suffering the snap-back of a burnout or, worse, resignation.

Looking for additional leadership ideas and resources? Because supporting employee engagement and performance this year demands a clear-eyed look at last year, download our complimentary e-toolkit,  Hot Mess? Dumpster Fire? Train Wreck? You Still Have to Conduct Year-End Reviews . In it, you’ll find a novel way to get employees to prepare, a roadmap to a productive conversation, the must-ask questions, pitfalls, tips for handling it remotely, and even strategies for addressing the dreaded money question.

Julie Winkle Giulioni works with organizations worldwide to improve performance through leadership and learning. Named one of Inc. Magazine’s top 100 leadership speakers, Giulioni is the co-author of the Amazon and Washington Post bestseller “ Help Them Grow or Watch Them Go: Career Conversations Organizations Need and Employees Want ,” You can learn more about her speaking, training and blog at JulieWinkleGiulioni.com .

If you enjoyed this article, sign up for SmartBrief’s free e-mail on leadership and management, among SmartBrief’s more than 200 industry-focused newsletters .

HR Mavericks

Stretch Assignment

Brandi M Fannell, Ph.D.

What Are Stretch Assignments?

Why are stretch assignments beneficial.

  • Catalyzes growth. These dynamic projects or tasks are designed to propel employees out of their comfort zones and catapult them into the realm of professional growth. By taking on unfamiliar responsibilities, employees are exposed to fresh challenges and opportunities to develop new skills and knowledge. It's like strapping a rocket to their career trajectory.
  • Supercharges engagement and motivation. We all know that engaged employees are the heart and soul of any thriving organization. Stretch assignments inject a much-needed dose of excitement and purpose into the work lives of your employees. By entrusting them with challenging projects, you're sending a clear message: We believe in you. Their commitment, initiative, and creativity skyrocket, resulting in a turbocharged organization firing on all cylinders.
  • Builds confidence and resilience. Stretch assignments give employees the perfect training ground for building confidence and resilience. As they conquer challenges and complete demanding projects, their sense of accomplishment skyrockets, boosting confidence levels and fueling a can-do attitude. Plus, the resilience developed through stretch assignments equips employees to navigate change and uncertainty with ease, making them valuable assets to your organization.

Types of Stretch Assignments

The skill-building extravaganza, the cross-functional adventure, the project of epic proportions, the innovation challenge, the client-facing expedition, how to implement stretch assignments in the workplace, step 1: align assignments with development goals, step 2: provide support and resources, step 3: set clear objectives and expectations, step 4: recognize and celebrate achievements, challenges associated with stretch assignments, challenge 1: the comfort zone conundrum.

  • Understand the employee's perspective. Recognize that employees may be hesitant to take on stretch assignments due to various reasons such as fear of failure, lack of confidence, or concerns about work-life balance. Take the time to listen and understand their concerns before addressing them.
  • Communicate the value . Clearly explain how the assignment can enhance their skill or broaden their experience and highlight the positive impact it can have on their career trajectory.
  • Provide support and resources. Assure employees that they will receive the necessary support, guidance, and resources to succeed in the stretch assignment. Offer training, mentorship, and coaching to help them build the skills and confidence required for the task. Reassure them that you are invested in their success.
  • Set realistic expectations .Ensure that employees understand the expectations and scope of the stretch assignment. Clearly define the goals, deliverables, and timelines involved. Break down the assignment into manageable steps and provide a roadmap for success. This will help alleviate concerns and make the assignment less daunting.

Challenge 2: Time and Resource Crunch

Challenge 3: skills gaps, challenge 4: balancing act, challenge 5: ensuring equity, evaluation and reflection, assess progress and outcomes, support reflection, refine and improve.

Brandi M Fannell, Ph.D.

Brandi M Fannell, Ph.D.

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Berger Leadership Blog

How to structure effective stretch assignments.

Dan Berger

You can set high expectations and work to motivate your team the right way, but an important component of that is ensuring the projects and responsibilities you develop to push your employees are developed in ways that set them up for success.

Leadership guru Julie Winkle Giulioni has a recent piece on stretch assignments. These assignments are intended to push employees past their comfort zone, but not so far that it breaks them. While each person will have varying tolerance levels for the discomfort and be motivated in different ways, she outlines four questions for leaders to consider in order to develop successful stretch assignments :

  • What is the developmental purpose of the stretch assignment? One of my recent blogs covered the power of purpose . Understanding the "why" behind a stretch assignment is important. But you can't just detail how this assignment will benefit the company. Leaders must demonstrate how the skills and knowledge gained from completing it will be good for the employee long term. Work with the employee to identify their professional goals and connect those to the task at hand.
  • What is the current level of skill, motivation, and resilience of the employee? It's important to understand the starting point. Think about your fitness goals – if you want to run a marathon by the end of the year, but you haven't worked out in weeks, you can't expect yourself to be able to run all 26 miles on Day 1. If you try, you'll likely become discouraged and give up on your goal. The same is true for stretch assignments. Recognize the gap in an employee's current skillset and where they want to be, as well as their resilience when facing obstacles .
  • What experiences might offer the appropriate (but not excessive) level of challenge needed to grow? Establish checkpoints during the assignment that demonstrate growth. As the employee hits certain points, identify areas that can be enhanced to keep progressing. Giulioni offers options like adding complexity to a current task, increasing the level of responsibility, imposing new constraints, and challenging them to take on developing a new product or a project that has a sense of uncertainty.
  • What resources will the employee need to ensure that the stretch delivers its desired developmental outcomes? There is an emotional toll of facing challenges, in addition to the organizational cost. Be ready to be a sounding board and offer your employee the guidance and encouragement needed to overcome obstacles. Leaders must also be willing to invest the resources – whether it's a new budget item, additional staff, or reconfiguring current responsibilities so they have time to devote to the stretch assignment.

Pushing your team and organization to new heights requires intentional effort to ensure it is done constructively and not to the detriment of your people. Considering these questions as you encourage growth and development will help you be successful in doing so.

Follow me on Twitter ( @BDanBerger )

About the Author

B. dan berger, president and ceo, nafcu.

Dan Berger

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Stretch Assignments that Develop Strategic, Interpersonal, and Personal Skills

stretch assignment questions

Given that most development occurs through experience (McCall, Lombardo, & Morrison, 1988), stretch assignments can provide a great vehicle for driving employee learning and/or leadership development. Stretch assignments are essentially short-term projects or assignments that provide unique and challenging experiences for the purpose of developing employee/leader skills and abilities. Although the use of on-the-job development is clearly on the rise, it is often applied without consideration of the necessary planning and support mechanisms.

The first thing to keep in mind if you’re thinking about leveraging stretch assignments for developmental purposes is the common-sense notion that different stretch assignments develop different abilities (e.g., public speaking skills cannot be developed through writing policy statements or crunching numbers). Because of this, it is important to first identify the specific skill(s) to be developed. Once you have a list of skills, the next step is to identify the available assignments that provide relevant exposure. This article will help you with this first critical stage of using stretch assignments – that is, thinking about competencies and identifying assignments. Below is a list of stretch assignments that have been shown to develop competence in the following three areas: strategic skills, interpersonal skills, or personal effectiveness.

If you would like to share this list, check out our reference guide which contains the same information in a PDF format.

Strategic Skills

These assignments will help develop competencies related to expanding one’s awareness of organizational functions and strategy ( e.g., coping with ambiguous situations, gaining a strategic perspective, influencing others, working with customers, problem solving )

  • Spend 3 days with clients and report back (presentation or written report)
  • Conduct a customer-needs analysis
  • Write a policy statement
  • Interview external stakeholders about their opinions of the organization
  • Analyze and compare a competitor’s product or service
  • Put together a presentation for a senior employee (i.e., supervisor or manager)
  • Evaluate a training program
  • Join a cross-functional team
  • Join work on a project that has been unsuccessful
  • Put together a task-force to solve a tough problem
  • Monitor a new product or service through its entire life cycle

Interpersonal Skills

These will help develop competencies that increase one’s effectiveness to work with and manage other employees or teams ( e.g., communication, listening, managing conflict, managing relationships, teamwork, negotiation, trust, approachability, delegation, leadership )

  • Lead a team meeting
  • Become a mentor to a new employee
  • Train a new employee in a particular skill
  • Represent team concerns to supervisor
  • Join a team that’s dealing with conflict
  • Negotiate a new customer contract
  • Take responsibility in resolving a team conflict
  • Troubleshoot a performance issue
  • Become a campus recruiter
  • Interview customers and report back
  • Work with a peer on a developmental opportunity
  • Delegate 2 tasks to a peer and ask him/her to delegate 2 to you

Personal Effectiveness

These are oriented around competencies most closely related to your performance and personal development ( e.g., organizing, planning, intellectual acumen, creativity, composure, time management, work/life balance, decision quality, customer service )

  • Help launch a new product or service
  • Re-launch a product or service that previously failed
  • Learn a new tool, process, or approach and give a presentation on it
  • Work with someone from another department on a tough issue
  • Handle a difficult negotiation with an internal or external client
  • Take on a project that others have failed in
  • Write a press release
  • Teach a seminar on an unfamiliar topic
  • Create a customer satisfaction survey
  • Take on a task that you do not like to do
  • Take on an employee’s tasks who is on vacation
  • Conduct interviews with employees on their work/life balance experience & present findings

Note: This list is informed by research presented in Lombardo & Eichinger’s (1989) book entitled “Eighty-eight assignments for development in place,” and Yost & Plunkett’s (2009) book entitled “Real time leadership development.” I highly recommend both books as resources for any organization that currently applies stretch assignments or plans to in the future.

Going Forward…

Going forward, keep in mind that this is only a single piece in effective use of stretch assignments for developmental purposes. There are a number of mechanisms that are critical for actually translating experience into learning and development. Employees who will be given stretch assignments need the active support ant participation of their supervisor before, during, and after:

  • Before – to meet with the employee and discuss what skills to develop, then chose a stretch assignment and identify learning goals
  • During – to give immediate feedback, support and encouragement, and provide access to resources (e.g., time to participate in assignments, introductions to other people who can provide guidance)
  • After – to reflect and debrief on what was learned during the assignment and how that can be applied to their current job or future development

Happy Development!

– Scontrino-Powell

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How to Use Stretch Assignments to Support Social Good

by Mark Horoszowski

stretch assignment questions

A proven way to get ahead in your career is to take on stretch assignments. These projects can develop your skills and confidence, as well as prove to leaders that you can succeed at the next level. Many companies go to great lengths to create these assignments for employees as part of a retention and development strategy, and for good reason – if employees can’t find stretch opportunities, they leave. In fact, the number one reason people leave their jobs is because they lack a career path, according to recent  research . This fact is especially relevant for Millennials, who often value meaning in their careers and are actively looking for the opportunity to become leaders .

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4 ways to execute a stretch assignment like a rock star.

  • In fact, a well-executed stretch assignment can propel your career to new heights.
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Want to uncover a bigger, bolder vision for your career than you can imagine today? Try taking on a stretch assignment. That’s exactly what Tara Jaye Frank did.

In 2014, when Frank was Vice President of Consumer Platforms at Hallmark Cards, her manager asked her to take on a stretch assignment in addition to her line management role.

It was to serve as an advocate for the company to think differently in its approach to multicultural consumers. “We explored the many different models companies were using to reach multicultural consumers,” recalls Frank. “One of those models included a Multicultural Center of Excellence, and when I shared it with my boss, she asked me to write a proposal for what it could look like, and how it could enhance Hallmark’s efforts.”

Excited by the proposal and its potential, Frank created a charter with short- and long-term goals to embed multicultural insights across the entire enterprise and translate those insights into opportunities. What started out as a side project ultimately led Frank to envision, establish and lead the center in a new role as Vice President of Multicultural Strategy for Hallmark North America.

A stretch assignment requires you to step outside of your day-to-day responsibilities and take on a challenging new task, project or role. You’ll develop new networks, knowledge and skill sets. These are often very visible roles, so the stakes can be high. In fact, a well-executed stretch assignment can propel your career to new heights.

Today, Frank is President and CEO of P3T Group, Inc., a company that helps organizations turn employee potential into greater performance. I interviewed Frank for a recent webinar and asked her to share some keys to success for executing a stretch assignment like a rock star.

1. Bring A Beginner’s Mind-set

“My favorite advice to anyone starting a stretch assignment is to allow yourself to be new at it,” says Frank. “When we're asked to do something new, many of us want everyone to believe we know exactly what we're doing,” she says. So when we have questions or we're unsure about how something works or whom to call, we keep it to ourselves. We just try to figure it out.” Whatever you do, don’t try to go it alone, advises Frank, or you’ll deny yourself a rich learning experience. “Starting something new is the perfect opportunity to ask all the questions that you have, which leads me to the next tip.”

2. Be Inquisitive

“Be as curious as you can possibly be,” says Frank, who recommends speaking to a wide cross-section of those involved. Ask management why they felt it was important for you to devote time to this issue and what a successful execution of this assignment looks like to them. Also, speak with colleagues and stakeholders on the project to identify shared goals and challenges you may encounter. “And seek contacts beyond the specific assignment you've been given,” says Frank. For instance, you can also speak to people who have done this type of work before. “Being curious will only make you smarter and give you a much better perspective on what you're trying to achieve,” she says.

3. Over-Deliver

Don’t lose sight of the opportunity that’s been entrusted to you. “Many people don't get stretch assignments or, at least, highly visible ones,” notes Frank. If you are selected for a special assignment, it means someone took a risk on your behalf and put his or her reputation on the line to advocate for you. This person, along with your organization, is invested in your success and will be watching to see how you perform. “When someone gives you the opportunity to stretch, don't just hit the status quo,” says Frank. “Give it your absolute all.”

4. Utilize The Springboard

Stretch assignments can become important stepping stones on the way to your next big career milestone, so it helps to be clear on what you hope to gain from an assignment. Whether it is to develop new technical or leadership skills, strengthen relationships with colleagues and influencers, raise your profile or assure your organization you’re ready for your next role, keep your personal goal firmly in mind as you execute on the assignment.

“I always look at stretch assignments as springboard opportunities,” encourages Frank. “Use this moment to your fullest advantage. You can go on to do bigger and better things, meet more people, broaden your network and expand your knowledge base. Take this opportunity and do amazing things with it.”

Jo Miller

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30 HR Stretch Assignments That Can Enhance Your Growth, Development & Promotability

Plus a one-page cheat sheet you can use!

stretch assignment questions

by Alan Collins

Want to take your career to the next level with your current employer?

Taking on a stretch assignment in your current role may be your ticket.

A stretch assignment is simply a project or task you take on that falls outside your typical duties and requires you to step outside your comfort zone and learn new skills.

There are lots of benefits of tackling one of these assignments:

  • It can accelerate your growth and development without changing jobs.
  • It can infuse more joy, excitement or challenge into your current role.
  • It sends the message that you’re ready for more responsibility.
  • It prepares you for future leadership or promotional opportunities.
  • It potentially provides visibility to higher ups who can open doors for you.

If nothing else, a stretch assignment can add bullets to beef up your resume and prepare for an HR future outside of your organization.

Need some specific examples?

Check out this one-page cheat sheet.

CLICK HERE To DOWNLOAD this “CHEAT SHEET.”

To squeeze the most juice out of this one-pager:     

(a) Use it as a reminder of the types of assignments you may want to pursue.  

(b) Keep it handy on your all devices (phone, laptop, tablet) to access quickly for future reference.

(c) Forward it to HR colleagues who might welcome having this information to aid in their career advancement efforts.

(d) Use it any way you want!

Here’s a case study to illustrate.

Gabrielle Lewis-Smith was frustrated.

As a senior HR manager with one of the largest hospitals in Chicago, she didn’t feel she was moving fast enough in her career.

She loved the organization, didn’t want to leave, but was clueless about what to do.

However, a career-defining moment arrived when she was suddenly thrust into a highly visible leadership role.

When a colleague of hers resigned in the middle of planning the annual organization-wide talent review process, involving 225 leaders in 45 departments, Gabrielle received an unexpected visit from her manager.

“My boss came to me sweating, in a breathless panic,” she recounts.

“And he said, ‘Gabrielle, I need your help. You’ve been doing a great job. I know you’re swamped, but I need you to step up, lead and facilitate this whole thing. Can you do it?’”

In that moment, she felt terrified and out of her comfort zone, having never led something this big and visible to the senior management team.

But, she also had the self-awareness to realize, “This might be my opportunity. Someone sees more leadership potential in me than frankly I see in myself. And trusts me to do this.”

So, with her boss’ 100% assurance that he’d support her all the way, she agreed to bail him out.

And, the experiences and exposure she gained from this “stretch assignment” changed everything.

“It was a turning point in my HR career, and changed forever how I saw myself as a leader. In the end, this project helped me bond with my boss and showcase skills he didn’t know I had.

“I also got great feedback from the higher ups on my role in planning and facilitating many of the reviews.

“And, in the months that followed, I started getting calls and all kinds of opportunities opened themselves up to me, both within… and outside of the hospital.

“My boss promoted me to HR director eight months later.”

So, how do you obtain a stretch assignment?  

Here’s what not to do…

Don’t sit on your butt, waiting to be asked.

stretch assignment questions

Instead, take charge! 

Get proactive and seek out projects that would add value to the organization, but can’t get done because of insufficient resources, money or time. 

Or you might also dig into areas within HR or the larger organization where you’ve noticed problems, inefficiencies or dysfunction.

Or it also be as straightforward as raising your hand and volunteering to tackle a project no one else wants to do.

In any event, once you’ve identified an issue or project you’d like to take on, talk to your boss, offer your help and get the ball rolling.

Finally, here’s how to maximize the experience. 0

0 #1:  Stretch in the right direction .

Make certain that your stretch aligns with your current job accountabilities and/or your future career goals.

#2:  Take time to plan your stretch.

Stretch assignments can be time intensive and energy consuming. Make sure what you’ve selected inspires and excites you.

#3:  Where possible, include others.

Engaging others will offer you new leadership opportunities by allowing you to delegate tasks and coordinate assignments with colleagues.

Teaming up with peers, or possibly a mentor, can also cause the endeavor to seem less daunting.

 #4:  Seek guidance. 

Stretch assignments take you out of your comfort zone which means you are not expected to have all the answers. So do don’t be afraid to ask questions, request direction and ask for assistance when you need it.

#5:  Cross organizational boundaries.

Stretch assignment are often most effective when they include working with individuals from another area of your organization.

Such assignments can give you insights that can build your total business perspective and insight.

#6:  Market what you accomplish.

Even if you knocked the project out of the park, it won’t mean much if no one knows what you’ve accomplished.

In your pre-deal negotiation, request that your stretch assignment be marketed internally.

For example, ask that it serve as a best practice story and be shared through appropriate HR or company channels, whether it’s via an internal newsletter, social network, webinar or even in a brown-bag information session.

All this helps you publicize and maximize the value you gain from the experience.

Have you taken on a stretch assignment recently?

Now may be the perfect time to tackle one.

If you’re like Gabrielle, it may be exactly the kind career-defining move you need to launch your career forward.

Got comments, thoughts and additional insights?

Post them in the comments below by clicking HERE.

stretch assignment questions

Then check out: STAY INSPIRED IN HR: 21 Positive Reminders To Keep You Motivated, Encouraged, Confident & Committed To Success in Human Resources.   Get more details here.

stretch assignment questions

About the author: Alan Collins is Founder of Success in HR, Inc. and the author of a variety of best selling books for HR professionals.  He was formerly Vice President – Human Resources at PepsiCo where he led HR initiatives for their Quaker Oats, Gatorade and Tropicana businesses.

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Use Stretch Assignments to Get a Raise, a Promotion and Anything Else You Want at Work

stretch assignments

Want to uncover a bigger, bolder vision for your career than you can imagine today? Try taking on a stretch assignment — a project that can’t be completed using your current expertise.

A stretch opportunity could be a temporary assignment or project that you oversee for a few weeks or a few months. Or it could be taking on a new, permanent role that increases your scope.

Examples of stretch assignments include:

  • Delivering a presentation to a VIP client
  • Structuring and communicating a rollout for a key change
  • Leading the implementation of new tools to replace manual processes
  • Convening or serving on a task force created to solve a difficult problem
  • Relaunching an internal initiative that previously failed
  • Performing data analysis to find business efficiencies
  • Turning around a failing product or launching a new product

When you take on such an assignment, you’ll be compelled to develop new technical, business or leadership skills. As you engage in the process, you’ll build relationships with new stakeholders, and increase your visibility and your chances of earning a promotion or raise.

stretch assignments

Why Stretch Opportunities Can Be Career-making

“There’s now towering evidence to confirm the career-transforming power of stretch roles and stretch assignments,” says Jo Miller, CEO of Be Leaderly , a firm dedicated to helping organizations develop a pipeline of qualified and engaged emerging women leaders.

According to McKinsey & Company, people who get advice from managers about how to advance — and who then land stretch assignments — are more likely to to receive raises . Similar research from Korn Ferry names stretch or rotational assignments as the most valuable experiences for career development , ahead of action learning, mentoring, relationships, 360-degree assessments, exposure to more senior leaders and formal classroom training.

Unfortunately, despite the fact that stretch assignments provide so many benefits to individuals’ careers, men and women are not on a level playing field when it comes to those opportunities.

Women More Likely to Feel Unsure About Whether They’re Ready

Recently, Be Leaderly conducted a study on workers’ attitudes and experiences around stretch assignments . They found that both men and women have similar ambitions: both genders are equally interested in being promoted into director or vice president positions and ultimately advancing into C-suite roles.

stretch assignment questions

Yet, most women don’t feel their employers make it easy to gauge if they are ready for a promotion, while most men think their employers help them to know whether they are prepared to advance.

stretch assignment questions

Additionally, when women assess how ready they are for a new job, they are less likely than men to overestimate or “round up” their skills, and more likely to underestimate or “round down” what they know or can do.

What might account for these differences between male and female professionals?

Selena Rezvani — VP of Research at Be Leaderly and co-author of this report — suggests that “women may be more sensitive than men to social cues signaling readiness to advance. [So] when stretch opportunities are unclear, unadvertised and unevenly offered, it makes women hesitate even more to pursue them.”

[click_to_tweet tweet=”Most women don’t feel their employers make it easy to gauge if they are ready for a promotion, while most men think their employers help them to know whether they are prepared to advance.” quote=”Most women don’t feel their employers make it easy to gauge if they are ready for a promotion, while most men think their employers help them to know whether they are prepared to advance.”]

How Men Versus Women Evaluate Stretch Opportunities

For both genders, the top criteria for deciding whether to take a stretch assignment are having the influence to create a positive outcome, and getting an assignment that aligns with their career goals. Yet, men are 3.5 times more likely than women to cite pay as an important factor in evaluating the appeal of a new assignment, job or level!

9 Ways to Make the Most Out of Stretch Opportunities

How can you make the most of stretch opportunities at your organization, knowing that your organization might not advertise these assignments or provide clear clues as to how ready you are? Below are some key tips from some experts in the leadership development space, including the authors of Be Leaderly’s report on stretch assignments and others.

1. Chart Your course

If you understand your passions, innate strengths and the direction you want to take your career, it will be much easier to identify the stretches that make sense for you. What types of work do you naturally feel passionate about or gravitate toward? Look beyond your immediate role and identify those unmet needs in your organization that you have an interest in solving. Once you have ideas, find evidence to support why they would be helpful. Discuss your proposal with management and share why you’re excited about the part you could play.

2. Gather Your Own Data to Assess Your Readiness

Be proactive in assessing your own readiness to advance. Seek out clear, frequent feedback on your work — both formal and informal — that is tied to business outcomes. For example, send a survey to those who work with you and ask them for their perspective for your strengths and how you show up at work. Include questions to help you understand how others see you, such as “What three to five words would you use to describe me?,” “What’s a success or a big win I had in the last six months?” and “What one adjustment would you encourage me to make?.”

And here’s another important piece of advice from Selena: “If you’re a woman, aim to round up rather than round down your qualifications when deciding if you’ve got enough to go after a certain role or assignment.”

3. Trust in What You Already Know and Bring It Forth

You may have a hard time “rounding up” your qualifications because you feel that you haven’t learned enough or don’t know enough to tackle a new challenge. Tara Mohr, author of Playing Big and career coach to emerging women leaders, identified this as an issue for many of her female coaching clients. She believes that the reason women and men feel this way is because our experience in schools have taught us to value external knowledge over our own lived experiences and judgment.

Tara, in her book, points that in many schools, the dominant activity is absorbing information from the outside — whether from a book, a teacher’s lecture or the internet — and then internalizing it.

In school, most assignments follow this pattern: 1) do the readings/research, 2) absorb the information, 3) apply it through writing a paper/report/making a presentation. The message is that the value we have to contribute on a topic comes from information absorbed from an external source — from teachers, homework reading and research.

When we carry this sort of conditioning into our professional lives, we are led to believe that we need another qualification, degree or certificate before we can tackle a stretch assignment. But to reach our full potential, we must start to value who we are as much as what we know.

“Playing big often requires assessing what we already know, trusting its value and bringing it forth. This is particularly true as women advance to senior levels in their careers, where they need to be the source of ideas and of thought leadership,” says Tara.

4. Identify your champions and talk to them about your career goals

In addition to your manager, there are others in your organization who could become champions for you and refer you opportunities you may not be aware of. This group includes your manager’s manager, more senior colleagues from groups/teams you work with and staff from your HR team. Build relationships with these people, make sure they know your work and what you aspire to do. When they have this knowledge, they’re likely to have you in mind when an opportunity opens up.

5. Make informed decisions and ask for what you need to be successful

Don’t agree to do the extra work without the extra pay. Remember, men are 3.5 times as likely than women to cite pay as an important factor in evaluating the appeal of a new assignment, job or level.

Gather the details on what the new opportunity entails, including compensation, recognition and career options that a stretch might lead to. “Don’t be afraid to ask, ‘If I do an excellent job on this project, what can I expect as a result?” says Jo and Selena in their report.

Also, make sure you negotiate for what you need — resources, authority and support — to be successful in the role.

6. Take a Project No One Wants

stretch assignments

Some projects are shiny, cool and trendy (e.g. working with a hip new client). But what about the riskier assignments no one else wants? When you raise your hand for the assignment that makes others nervous or uncomfortable, it demonstrates your confidence in your abilities and commitment to your organization. These projects can give you the opportunity to prove yourself as a problem-solver, change agent or emerging leader.

7. Focus on Learning as Much as the Outcome

Don’t be quick to judge the gaps in your knowledge when you take on a new role or project. Embrace your newcomer status and find joy in your learning process. Think of yourself as a student of the problem you’re solving.

8. Translate the experience and spotlight what you accomplish

Did your new assignment help you develop new technical skills? Did you learn a better way of working with a group? Document your learnings so others know what you have gained from an assignment. Identify at least three actions you can take in your current role based on what you learned.

9. Market what you accomplish

Even if you knocked the project out of the park, it won’t mean much if no one knows what you’ve accomplished. “In your pre-deal negotiation, request that your stretch assignment be marketed internally. For example, ask that it serve as a best practice story and be shared on appropriate company channels, whether it’s via an internal newsletter, social network, or even in a brown-bag information session,” suggests Jo and Selena.

Tell Us What You Think

Have you taken on a stretch assignment recently? We want to hear from you. Share your results in the comments or join the conversation on Twitter .

More articles

6 reasons women shouldn’t ‘act more like men’ at work, why the ‘lifestyle career’ is about more than work-life balance, how important is cost of living when considering relocation for a job, 4 things to remember while you’re chasing your dreams, for some employees, ‘mental health days’ aren’t vacation days, 3 ways to tell that your boss doesn’t want you to take vacation, salary raises: understanding cost of living vs. merit pay increases, how many americans have ‘good’ jobs.

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HCF and LCM - Problem Solving Full lesson including Stretch and Challenge and GCSE Questions

HCF and LCM - Problem Solving Full lesson including Stretch and Challenge and GCSE Questions

Subject: Mathematics

Age range: 11-14

Resource type: Lesson (complete)

O Hay's Shop

Last updated

28 August 2024

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stretch assignment questions

Lesson is designed to guide students through the concepts of Highest Common Factor (HCF) and Least Common Multiple (LCM) with a focus on problem-solving techniques. The lesson includes a step-by-step explanation of finding HCF and LCM, practical examples, and a variety of problem-solving questions, including GCSE-style questions for exam preparation… A worksheet accompanying the lesson provides additional practice with Stretch and Challenge questions, allowing students to apply what they’ve learned in a structured and rigorous way.

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Will Yankees Recall This Veteran Reliever to Help Boost Bullpen?

Pat ragazzo | 14 hours ago.

Oct 3, 2022; Arlington, Texas, USA; New York Yankees relief pitcher Scott Effross (59) delivers a pitch to the Texas Rangers during the ninth inning at Globe Life Field. The Yankees won 3-1. Mandatory Credit: Jim Cowsert-USA TODAY Sports

  • New York Yankees

Although the New York Yankees hold the best record in the American League at 78-56, bullpen remains a question mark as they gear up for the stretch run in September.

Luckily, they appear to have some internal options that are candidates to be recalled from Triple-A Scranton/Wilkes-Barre in the near future.

Among the possible names that could join the big-league roster in the coming weeks include the rehabbing Ian Hamilton, Scott Effross and Lou Trivino.

Hamilton, who is coming back from a lat strain, is a clear favorite to reclaim a spot in the Yankee bullpen once his rehab assignment finishes, which could be any day now.

But what about Effross?

“I don’t know if there’s anything holding him back at this point,” Yankees pitching coach Matt Blake told The Athletic's Chris Kirschner of Effross. “I think he’s thrown the ball really well lately. Earlier on, we wanted to make sure he was in a good spot physically. The (velocity) is getting back to where it was. He’s been bouncing back from outings. He’s taken the ball on quick turnarounds, back-to-backs and two-ups. I think we’re getting to a spot where we’re pretty comfortable with what he’s doing and I would imagine he will be back up here shortly.”

Effross has not appeared in the majors since 2022 after undergoing Tommy John surgery in October of that year. He then underwent back surgery this past February, which kept him out until June. The Yankees activated the righty from the 60-day IL on July 15 and optioned him to Triple-A Scranton/Wilkes Barre, where he has resided ever since.

The 30-year-old has turned things up in the minors as of late, and overall has posted a 3.46 ERA, a 1.08 WHIP, 24 strikeouts and one save across 26 innings.

However, manager Aaron Boone told reporters on Wednesday that it's "tough to carve out a spot" for Effross at the moment, but he is "knocking on the door."

Aaron Boone says it’s been “tough to carve out a spot” for Scott Effross, but the reliever is in a good spot down in AAA. “I think he’s been doing a pretty good job now for a couple weeks. His stuff is trending up. He’s knocking on the door.“ — Max Goodman (@MaxTGoodman) August 28, 2024

Although the path for Effross to make his major league return isn't fully clear at this point in time, the Yankees will need all the help they can get in their bullpen as they push for the AL East crown in the final month of the regular season. If he continues to find success in Triple-A, Effross could force his way onto the roster soon enough.

Pat Ragazzo

PAT RAGAZZO

Pat Ragazzo is the reporter, publisher, site manager and executive editor for the Mets and Yankees websites on Sports Illustrated. Pat was selected as The Top Reporter & Publisher of the Year 2024 by the International Association of Top Professionals (IAOTP) for outstanding leadership, dedication, and commitment to the industry. He appears on several major TV Network stations including: NBC4, CBS2, FOX5, PIX11, SNY and NY1; and is frequently heard on ESPN New York FM 98.7 FM and WFAN Sports Radio 101.9 FM as a guest. Pat also serves as the Mets insider for the "Allow Me 2 Be Frank" podcast hosted by Frank "The Tank" Fleming of Barstool Sports. You can follow him on Twitter/X: @ragazzoreport.

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  2. Embracing Learning through Stretch Assignments: A Guide to Success

    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 ...

  3. How To Make a Stretch Assignment (Plus Template and Example)

    Following are the seven steps for designing a stretch assignment: 1. Analyze employee experiences. Before creating your stretch assignment, evaluate the candidate in comparison to your succession plan. Determine what skills, knowledge or experiences an employee could develop prior to taking on an advanced role at the company.

  4. What Is a Stretch Assignment? (With Benefits and Tips)

    A stretch assignment is a project that's beyond your current level of knowledge or skills. It gets its name from the idea that it allows employees to "stretch" themselves developmentally, enabling them to learn new abilities and grow professionally. Stretch assignments help you prove your adaptability to your management team, who may then ...

  5. Why You Should Take on More Stretch Assignments

    Why You Should Take on More Stretch Assignments. by. Jahna Berry. April 07, 2023. artpartner-images/Getty Images. Summary. Stretch projects require skills or knowledge beyond your current level of ...

  6. Stretch Assignments 101: Maximize Opportunities for Growth With

    Stretch Assignments 101: Maximize Opportunities for Growth With Thoughtful, Guided Supervision. Challenging workers with new assignments and responsibilities is good for both the employee and the employer. But it requires a well-considered process. ... answering questions, reviewing materials, etc. In this way, my team member was positioned to ...

  7. Stretch Assignments: What Are They and Is Your Employee Ready For One?

    Stretch assignments are a cornerstone of a strong employee development plan. A statement that is backed by a number of research studies. In one conducted by the Harvard Business Review of 823 executives, it was found that 71% of respondents said stretch assignments had the biggest impact on unleashing their potential. In another, this one conducted by Korn Ferry, stretch assignments were named ...

  8. 4 Stretch Assignment Examples for Upskilling Your Workforce

    Stretch assignments play a critical role in upskilling programs by strengthening employees' career prospects, enhancing performance in the workplace, ... It can be as simple as connecting to ask questions, review work, provide feedback, or help someone join a new project or team. For example, assigning onboarding buddies to new hires helps ...

  9. 4 questions to ensure successful stretch assignments

    Adding complexity to current tasks or role. Increasing the employee's level of responsibility (which could look like larger teams, bigger budgets, etc.). Finding a new context for the employee ...

  10. how to do a great job on a stretch assignment

    I just finished a 2.5 month stretch assignment and now I would like to send a follow up to the team that I worked with to get their feedback in these key areas: 1. Leadership 2. Communication 3. Engagement I would like to come up with 1-2 questions for each area and create an anonymous survey.

  11. Stretch Assignments: Going beyond regular assignments l Eddy

    Step 1: Align Assignments with Development Goals. Get to know your employees' aspirations and interests and design stretch assignments that align with their professional growth trajectory. This customized approach ensures the assignments are meaningful and truly impactful.

  12. Are You Being Pushed Outside Your Comfort Zone?

    We take your questions, look at the research, talk to the experts, and help you move forward. ALISON BEARD: Today we're talking about stretch goals with Jerry Colonna.

  13. How to structure effective stretch assignments

    These assignments are intended to push employees past their comfort zone, but not so far that it breaks them. While each person will have varying tolerance levels for the discomfort and be motivated in different ways, she outlines four questions for leaders to consider in order to develop successful stretch assignments:

  14. The Sneaky Way Your Boss Is Trying to Say "You're on the Promotion

    Kiner asserts: "A higher volume of work is not a stretch assignment, it's just more work!" To actually be a stretch assignment, it should enable you to grow in a new direction. Kiner explains: "The stretch should be interesting and challenging and include skills you want to learn or an opportunity to do something new. . .

  15. Stretch Assignments and Examples

    Given that most development occurs through experience (McCall, Lombardo, & Morrison, 1988), stretch assignments can provide a great vehicle for driving employee learning and/or leadership development. Stretch assignments are essentially short-term projects or assignments that provide unique and challenging experiences for the purpose of developing employee/leader skills and abilities.

  16. How to Use Stretch Assignments to Support Social Good

    How to Use Stretch Assignments to Support Social Good. Advance your career and give back at the same time. by. Mark Horoszowski. November 13, 2015. KENNETH ANDERSSON FOR HBR. Post. A proven way to ...

  17. 4 Rules For Accepting A Stretch Assignment

    Here are four rules for assessing whether an assignment is the right fit. Four Rules for Accepting a Stretch Assignment. Don't be afraid to take a risk. Stretch assignments come with tradeoffs ...

  18. 4 Ways To Execute A Stretch Assignment Like A Rock Star

    2. Be Inquisitive. "Be as curious as you can possibly be," says Frank, who recommends speaking to a wide cross-section of those involved. Ask management why they felt it was important for you ...

  19. 30 HR Stretch Assignments That Can Enhance Your Growth, Development

    Make certain that your stretch aligns with your current job accountabilities and/or your future career goals. #2: Take time to plan your stretch. Stretch assignments can be time intensive and energy consuming. Make sure what you've selected inspires and excites you. #3: Where possible, include others.

  20. 15 questions to ask before taking a stretch assignment

    15 questions to ask before saying yes to a stretch assignment We asked respondents how they decide if a potential stretch is a good fit. Here are some key themes that emerged, along with specific ...

  21. Use Stretch Assignments to Get Ahead at Work. Here's How.

    7. Focus on Learning as Much as the Outcome. Don't be quick to judge the gaps in your knowledge when you take on a new role or project. Embrace your newcomer status and find joy in your learning ...

  22. Stretch Assignments For Employees

    A stretch assignment is an extra project or task that's out of the ordinary that will build a skill or give employees visibility with important stakeholders. "Maybe there's something they need to learn or demonstrate that they've learned in order to be seen as more competent," says Mikaela Kiner, an executive career coach in Seattle ...

  23. HCF and LCM

    The lesson includes a step-by-step explanation of finding HCF and LCM, practical examples, and a variety of problem-solving questions, including GCSE-style questions for exam preparation… A worksheet accompanying the lesson provides additional practice with Stretch and Challenge questions, allowing students to apply what they've learned in ...

  24. San Francisco Giants Reinstate Young Star, Designate Veteran for Assignment

    - C Andrew Knapp designated for assignment. — SFGiants (@SFGiants) August 29, 2024 The second-year catcher was placed on the 10-day IL dating back to Aug. 19 with a right oblique strain.

  25. Detroit Tigers ready to get Casey Mize back from injured list Friday

    A four-start rehab assignment led to Mize's on-time return. He allowed four runs on 10 hits and four walks with 17 strikeouts across 13⅔ innings with Triple-A Toledo, registering a 2.63 ERA.

  26. Will Yankees Recall This Veteran Reliever to Help Boost Bullpen?

    Although the New York Yankees hold the best record in the American League at 78-56, bullpen remains a question mark as they gear up for the stretch run in September.. Luckily, they appear to have ...