4 Questions to Ensure Successful Stretch Assignments

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 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 burnout or, worse, resignation.

Employee engagement will be key in the months to come – to retain the employees you have and to build an employment brand that will attract top talent. And career development is a primary driver to make both happen. If you’re looking for actionable strategies for growing and retaining employees, download our latest complimentary e-guide, Looking to Improve Engagement? Look No Further than Career Development.

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Julie Winkle Giulioni
Julie Winkle Giulionihttps://www.juliewinklegiulioni.com/
Julie Winkle Giulioni is a guardian of growth, defender of development, and promoter of potential in today’s workplace. She’s the author of  Promotions Are So Yesterday: Redefine Career Development. Help Employees Thrive and co-author of the international bestseller, Help Them Grow or Watch Them Go: Career Conversations Organizations Need and Employees Want. Named one of Inc. Magazine’s Top 100 speakers, Julie offers memorable and actionable live and virtual keynotes and presentations worldwide. Julie is a regular columnist for Training Industry Magazine, SmartBrief, and contributes her thought leadership around career development and workplace trends to The Economist and other publications. You can keep up with Julie through her blogLinkedIn and Twitter.


  1. So true, Aldo… and it’s so nice to get to chat with you here. I agree… and I might include older generations in this characterization as well. As I talk with people of various ages in the workplace, I consistently hear a plea for more opportunities for growth. Stretch assignments are a cost-effective way to scale development while also accomplishing real work that needs to get done. It’s a win-win the benefits the individual and the organization!

  2. The new generations are very demanding and ambitious, they love to have the opportunity to train and evolve, even on a professional level.
    New workers believe it is important to work in a company that demonstrates that it enhances the skills and training paths of its talents by promoting dedicated courses. Tackling challenges should therefore be in their DNA.
    Stretch assignment challenges employees, putting them in uncomfortable situations to learn how to grow. It is the tool that requires a worker to leap beyond his comfort zone and, in the process, acquire new skills.