Stretch projects are a path to learning, growing and competing through your whole life and career. Still, they aren't exactly labeled as "Pass" "So-So" or "Promotion-Worthy". So how do you tell which ones are a good fit and which ones might just blow up in your face?


1. Your sponsor believes in you.


Fear of failure and self-doubt can wrap stretch projects in an unattractive light. But Kirsten Rhodes, San Francisco Managing Principal for Deloitte LLP points out it's actually a big compliment when someone recommends that you take on a stretch project. Even if you're scared and don't think you have the skills, personality or experience to handle it, the person who recommends the project to you has the faith that you do. So take the time to relish that, and then focus on dealing with your inner critic properly. Be inquisitive and thoughtful about bringing colleagues, as well.

"Tell yourself that this is a unique opportunity and that you can make it on your own," Rhodes says. "Make sure you're prepared to be open to new challenges, and have the grit to say, 'I'm going to knock this one out of the park! Even if I make a mistake or two, I'll bounce back, and I'll add value to the organization and to myself.'"

So looking at this from a slightly different angle, if your executive sponsor for the project doesn't really seem to be enthusiastic for you, then be open to the possibility that maybe they have reservations for a reason. It's important to know if you really have a gap to correct or if the sponsor has some other issue to deal with that's manifesting as contempt. And even if it's clear the sponsor is emotionally supportive, you need to know what the sponsor actually can give you in terms of logistics, time and other resources.

"It's always a good idea to have an upfront conversation with your executive sponsor who has made the ask of you as a way of clarifying specifically how they will support you throughout the assignment. By doing this, you maximize your chance of success--with a combination of their backing and your own commitment to knock it out of the park."


2. You have an entire network of people who can be there for you.


"My mom always said that it takes a village to raise kids, and it takes a village at work to feel supported and to be sponsored for opportunities," says Rhodes. "I've needed to create a village of friends, family, mentors and sponsors to help support me during my stretch assignments--keeping me grounded, making sure I don't lose my confidence and celebrate successes. It's up to each person to decide how much and what kind of support they need from their organization and their family and friends."

3. You have access to specific, critical tools within your overall support framework.


Erica Mackey, co-founder and CEO of in-home childcare franchise MyVillage, uses a quarterly Objectives and Key Results (OKR) framework to make more stretch goals achievable.

"Using the OKR (Objectives & Key Results) framework has been incredibly helpful in achieving [our customer expansion] goal, because it highlights distractions and helps to keep us laser focused. We've actually surpassed our stretch target, and in fact doubled in size every quarter for the past year. We recently broke our state's record for closing the largest seed raise ever, $6 million, and now have a team of 20. As a distributed [remote] team, we have found that our OKR process lets us drive the ship, instead of being dragged behind it." 


4. You wholeheartedly believe in what the project is meant to accomplish.


Dr. Nancy Nekvasil, professor of biology at Saint Mary's College, was asked unexpectedly take on the role of interim president of the South Bend, Indiana college.

 "Often, we don't know why opportunities are put in front of us," says Nekvasil, "but if you believe in the mission, it isn't hard to say yes and stretch yourself. When I was asked to take on the role of president of Saint Mary's College, I was preparing to take a year-long sabbatical following serving as provost, a role I had assumed after many years of teaching. However, since I firmly believe in our goal of providing a high-quality education for women, the choice was easy."


5. You have a gnawing sense that, while you don't have ideal experience, you should.


This feeling connects to a clear sense of where you want to go and how you want to develop yourself over the long haul.

"The projects I said yes to were in areas that I had no experience in, but wanted to," says management consultant, trainer, coach and author Christie Lindor. "[And] I felt like they had the right leadership support to see them through."

When to hand the stretch project to somebody else


Taking stretch projects can ensure you don't miss career opportunities. But if there's another dream goal in the way, or if you encounter a life challenge, then you've got a perfectly legitimate, ethical reason for declining.

"I was a caregiver role for my ailing mother at one point and turned down what I considered a dream opportunity," Lindor explains. "To this day, I've never regretted turning it down. Another time, I was writing my first book and decided to dedicate my free time to that instead of the project."

Rhodes similarly accepts that there are life curveballs that can make "no" the best choice.

"There may be prohibitive reasons, e.g., a family or health situation or timing that does not support the assignment, and that's OK, too."

But in general, Rhodes says, saying yes is usually a good choice, not only because you avoid missing opportunities, but also because you develop in a holistic way you might not anticipate.

"Growing your capacity for additional responsibilities can make you stronger in your existing responsibilities, increase your credibility in the workplace and even your sense of empathy for colleagues. [So] I no longer talk about 'balance', but [rather] focus on 'integration' and intertwining your life in a way that works for you."

So choose wisely, but choose often. The clearer your personal priorities are for you, the easier it will be to sort through the options and take paths you're happy with.