There are many ways to gain credibility and show you’re ready to move to the next level. One of them is to take on a “stretch assignment” that gets you out of your comfort zone.

It could be an additional project or a new job. It could be something you ask for or that you’re asked to do. Sometimes they’re nearly impossible assignments that no one else wants to do.

One senior executive – let’s call her Shelly – built her entire career on taking on those seemingly impossible jobs and making a success of them.

At first, as one of very few women at a major oil company, Shelly found herself watching from the sidelines while others got the plum jobs. She had plenty of talent and drive but her “keep working harder” strategy was keeping her stuck right where she was.

Shelly decided she needed to take some career risk if she really wanted to advance. She volunteered to take on a seemingly impossible job that no one else wanted to touch. Within 18 months she turned the department from a cash drain into a high performing unit delivering their first profit in a while.

She took on other stretch assignments and soon became seen as an expert in turnarounds and gained a high profile, which led to her being recognized for her abilities and discussed for more opportunities to advance.

Shelly’s story is one of success because she was savvy about choosing her stretch assignments – ones where she saw that taking a different approach could turn things around for the business.

Stretch assignments come with huge opportunities to gain credibility but they come with a great amount of risk, which leads to the question…

When is it worth putting your reputation on the line to take on a stretch assignment?

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Whether you’re being asked to take on the stretch assignment or putting yourself forward for one, there are three questions to ask yourself before deciding.

  1. Is it important to the organization?
  2. Is it right for me?
  3. Can I stack the odds in my favor?

Is it important to the organization?

The purpose of taking on a stretch role or project is to take you further on the path to your goal, whether that’s to establish your credibility in a new area or advance to the C-suite. So you owe it to yourself to figure out whether the job or task is worth doing in the first place.

If you’ve done all the heroics to make the project or opportunity happen, will the organization see it as valuable? Is the outcome going to make a meaningful impact?

When I was asked to transfer to London to start a new business, it was a huge stretch opportunity for me. Not only would I be building a business for the first time, I was also going to have to move my husband and three young children to a new country thousands of miles away from friends and family. There was a lot at stake personally and professionally and it had to be worth it.

So I asked how big a market opportunity this was and how it fit into the overall division’s strategy. The division head’s answer gave me comfort that this was a significant opportunity. Done well, this would be highly visible to the rest of the firm.

And when he set up conversations with top management, I knew this was an assignment worth taking on. Of course, I also talked to a few trusted mentors and colleagues to get their views to counterbalance the sales pitch from senior management.

But determining that the stretch assignment is meaningful in the eyes of the organization is only the first part of the equation. Equally important is the second question.

Is it right for me?

When you’re leaning into the things you do best, you’re more likely to succeed and enjoy the process. So make sure the stretch assignment allows you to use your best strengths and skills.

The reason this is so important is that what seems nearly impossible for one person can be a completely doable challenge for another.

For example, I’m comfortable handling what my colleagues would consider difficult conversations but put a legal document in front of me and I get lost in all the clauses.

Sometimes you get asked to take something on because you're convenient. Maybe you're about to outgrow your role or your area of work is dwindling. So you're the most easily moved team member and you get asked even though you may not be the perfect person for the role.

We each have our unique abilities and the more we can use them the simpler and more possible a stretch assignment can be.

So back to my example, I asked why they had chosen me for the stretch assignment and what was expected. As my division head described the role and what success looked like, I realized that I would get to use what I consider to be my “super strengths”: The ability to bring disparate groups together to collaborate on a common goal, and to do that through influencing rather than having direct authority. It would also leverage my credibility with the investment banking division, which is where I started my career.

What started out as a daunting assignment started sounding achievable and maybe even fun.

Which brings us to the third question.

Can I stack the odds in my favor?

Before saying yes to the stretch assignment, look for ways to reduce the risk. That means thinking about what could tip the scales in favor of success.

Is there additional staffing support you need so you’re not constantly redoubling your efforts and risking burnout? Do you have a powerful sponsor who is standing by to help you pave the way forward and help you trouble shoot?

Or maybe you have a mentor or others in your network who have done a similar kind of project or role and can give you advice along the way. And it might be as simple as being able to meet the key people involved before starting.

You owe it to yourself to set yourself up for greater chances of success. So whatever you can think of ahead of time, go and do it or ask for it. Because once you’ve said yes, people tend to move on to their next concern and expect you to just get on with it.

Career Mastery has been a game-changer for me. Wonderful, actionable advice that helps me be better than the day before.”

Carol Vincent

But what if you’ve been asked to take on a stretch assignment and you have no choice?

If your organization is the kind where saying no to your boss means the death of your career, then double down on negotiating for the resources you need, including staffing, introductions, a coach, weekly catch ups with your sponsoring manager.

In my case, I had said no to my stretch assignment, citing my husband’s job and having three children under the age of 8. But they persisted and in the end I got assurances that if I didn’t like it after the first year, I could transfer back to my old job in New York.

Just don’t take on a hopeless case

If others are turning down the opportunity, find out why. While it could just be a bad fit for their strengths and skills, it could also be because it’s a genuinely unachievable goal.

Sometimes it’s due to the lack of dedicated resources, in which case you can negotiate for those resources before saying yes. Other times it’s the politics involved in which case you’d have to be convinced that there’s a way to navigate those politics.

You might still want to take on the role, but at least you’ll be doing it with your eyes wide open because you’ve done the investigating.

Choose your stretch assignments well

Taking on stretch assignments is an important part of a successful career. Not only do they give you an opportunity to build your credibility, skills and reputation as a next level leader, they also give you visibility with a broader set of stakeholders and decision-makers.

But not every opportunity is created equal so you have to choose well.

When you’re faced with deciding whether to go for a stretch assignment or not, remember to ask yourself these three questions first.

  • Is it important to the organization? Before you go through the heroics of making the assignment a success, make sure it’s going to be seen as meaningful and valuable.
  • Is it right for me? When you get to use your special strengths, it can turn the “near impossible” into something achievable and even fun.
  • Can I stack the odds in my favor? Negotiate for what you need in advance and tap into all your resources to set yourself up for the greatest chance of success.

Have you ever taken on a stretch assignment? How did it turn out and what other advice would you share to help others?

Leave a comment – I’d love to hear from you.