Why You Should Take on More Stretch Assignments

Author: Jahna Berry

When you think about what success will look like for you in your career, what do you imagine? Maybe it’s landing a role at the company of your dreams. Or maybe it’s finally getting a job that will help you transition into a new industry.

Whatever comes to mind when you think about potential career wins, there’s a good chance “taking on a stretch assignment” wasn’t on your list. It’s time to change that.

A stretch assignment is a project you take on in your role that requires skills or knowledge beyond your current level of development. The reason such projects can be so positive for your career growth is that they offer a great opportunity for you to learn new things, meet new people, and shine in a new arena.

This is also the exact reason why they can feel so scary. It can be terrifying to take on a project you’re not totally equipped for or unsure if you can execute perfectly. But if you’re willing to take the risk, and you do it well, taking on a stretch assignment can be the very thing that helps you move forward in your career.

Of course, the stakes are higher if you, like me, are queer, Black, a woman, or have other overlapping identities and work in an industry where you are a first or one of the few. Botching an unfamiliar task is one of the most common fears I’ve heard during my decade as a mentor and coach to rising leaders of color and queer managers. Considerable research shows that women, people of color, and members of the queer community are punished more heavily when they make mistakes. This is true at every level of experience, from CEOs to students. Those of us who share these identities know that a job setback or loss may be harder to recover from. It’s no wonder we feel pressure to perform perfectly.

While systemic biases are real—and it’s ultimately on leaders, lawmakers, voters, and industry watchdogs to tackle them—we are not powerless. Based on my own career and experience mentoring others, I can tell you that, despite the initial fear, taking on a stretch assignment is usually worth it. Many of the promotions I’ve had can be traced back to saying yes to these opportunities. Handling unfamiliar work is a skill that you can learn and refine.

Here’s how to tackle your next stretch assignment and use the opportunity to reach your career goals.

Recognize and Shift Your Negative Self-Talk

When you’re starting a stretch project, it might be hard to not focus on everything that could go wrong. You may fear people will find out you don’t know what you’re doing. This is especially true for those of us who have overlapping identities or work in environments rife with microaggressions.

If you already feel pressure to perform perfectly, in a dark moment you may experience thoughts like “I don’t belong here,” “I can’t do this,” or “I’ll mess this up.” A key part of your success will depend on your ability to turn down the volume of the imposter in your head.

Earlier in my career, I had the opportunity to lead the daily morning news meeting at a media outlet where I worked. My job was to steer news coverage, making sure everyone’s voice was heard, asking smart questions, and keeping the dozen or so attendees engaged and productive. Until that point in my career, I had most often seen men or white women play this high-profile role. It was rarely, if ever, owned by a woman of color. The first few weeks I led the meeting, my stomach was in knots every morning.

Today, I recognize that my initial unease was a natural feeling. I was the only Black editor in the newsroom. This was often a theme in my career: I’ve been the only Black intern, Black editor, Black manager, and so on.

A good way to shift your mindset is journaling. This strategy has worked for many of the leaders I coach. When you’re feeling overwhelmed by self-doubt, pause and take some time to reflect. Write down all of the times that you tried something new and figured it out. It could be a skill you acquired at work that makes you proud, like public speaking, copywriting, or data analysis. It could also be something you learned outside of work, like a new language or how to make friends and build community in a new city.

Don’t just jot down what you learned. Describe in detail any setbacks you faced, any fears you felt along the way, and how you overcame them. Reminding yourself of these wins will help you build confidence and give your mind the evidence it needs to prove that you’re capable of taking on challenges.

Even now, as a chief operating officer, I sometimes use this practice in the face of new or challenging tasks that shake my confidence. Looking back at my journal entries helps me remember I can trust myself to eventually figure things out.

Get Clarity

When taking on a stretch project, odds are you won’t be given all of the information you need up front to be successful. That’s the nature of stepping onto a new team or raising your hand for an assignment that’s never been done. This lack of clarity can be especially difficult for those with overlapping identities.

Emerging BIPOC, female, and/or queer leaders working in predominantly white, male, heteronormative spaces are operating in environments that were not created with them in mind. This means you often have less access to stakeholders at the highest level of your organization than your white counterparts. You might also be less likely to have senior colleagues guiding and supporting you.

If this is your situation, you may sometimes find yourself late to pick up on nonverbal cues or jargon that your peers know well—simply because you have not been in the room. For instance, you may not initially know that a C-level executive always twirls her pen when she wants you to wrap up a presentation. Or you may not know that people are sharing key information in Slack channels you haven’t been invited to. This guarding of knowledge can sometimes extend to the projects you take on, including stretch projects, which are more challenging by nature.

At the start of your stretch project, seek to gain clarity around your manager’s expectations, important deadlines, specific goals you need to hit within those time frames, and any important stakeholders you need to keep in the loop along the way. Schedule some one-on-one time with your manager to thoroughly discuss these points. During your meeting, ask how you should communicate your progress, who needs updates by when, and what medium you should use to deliver information (in-person meetings, emails, quick Slack updates, and so forth). What decision points does your supervisor want to participate in? What team members, departments, or senior colleagues will the project impact? Most important, what does success look like?

For example, there may be a senior executive in another department who has unspoken or explicit authority over a part of your project. Once you know this, you can start to think strategically about their goals and anticipate the questions they may ask you as the project progresses. You can even plan to meet with them to learn more about their expectations.

With every milestone you hit, check in with your manager or stakeholders about the assignment’s original goals, as many projects tend to evolve over time.

Do a Listening Tour

You may initially feel hesitant or nervous to meet one-on-one with senior colleagues or executives. A listening tour is a good way to overcome that fear, build bridges with the different teams, and fast-track the knowledge you need to execute your stretch project.

At the start of the project, tell stakeholders and your manager that you plan to do a series of one-on-one meetings so you can get up to speed on the initiative. When you reach out, explain the project you’re leading and what information you want to learn from them. Keep it short. You can say something like “I’m reaching out because I’m spearheading X initiative. I’m talking to all of the key stakeholders to learn as much as I can. You and your team are experts on X, and I’d love to touch base so I can learn more about how X works, how your team works, and how we can best collaborate.”

Use your meeting to do three things: Communicate transparently that you are not an expert in the area yet; show a sincere interest in learning more; and give the people who are experts a chance to showcase what they know. Your goal isn’t to immediately become an expert; it’s to ask informed questions that will help you perform your role better. Try to ask similar questions in each meeting so that you can see patterns or other important information in your notes.

Here are a few questions that I like to ask during listening tours:

• How did you end up working here/on this project?

• What is your role and your team’s role on this project?

• What should we stop doing? What should we keep doing?

• What is harder than it needs to be?

• How did we end up doing XYZ process this way?

• What are some things you’re afraid I might get wrong?

• If you could wave a magic wand, what would you do?

• Who else should I talk to?

If the stakeholder shares their opinion but doesn’t elaborate, follow up with something like, “Wow, that’s an interesting observation. Why did you say that?” If they share a complex process that you find difficult to understand, explain that you’re having a hard to time digesting their point, and ask them to re-explain it as if they are talking to a relative who doesn’t work in the industry. This will help them communicate more clearly.

While asking follow-up questions may feel embarrassing—especially if you are an emerging leader and don’t want people to doubt your abilities—the most important thing is that you understand how the pieces of your project fit together. Think of these conversations as an exciting opportunity to learn something new and to excel at your assignment.

When the conversation is over, thank the other person, and ask, “If I come across something I don’t understand, may I reach out to you again?” People will appreciate your effort to educate yourself. No matter how senior they are, if this project and its success is important to them, they will want to support you and see you succeed.

Trust Your Gut

As you work your way through this exciting assignment, remember to cut yourself some slack along the way. Research shows that expertise is probably not what your new team or collaborators value the most. In Google’s internal research on managing, subject matter expertise ranked last on the list of top eight qualities that make a good manager. What mattered more? Excelling at the core task the manager was entrusted with—managing the team.

So, if you’ve been asked to project manage a big initiative, focus most of your energy on stewarding that project with excellence. (There’s probably a good chance you were chosen to steer a project on an unfamiliar topic because you are a strong project manager.)

A major component of leading with confidence is trusting your ability to figure things out. That might be hard at first, especially if you’re an emerging BIPOC, female, and/or queer leader—your personal sense of safety at work may come from avoiding criticism or constantly code switching. But remember, this project is an opportunity to hone new skills. Focus on learning how to sift through information, discern the most important details, and leverage your own expertise to make decisions.

And remember: Don’t let fear drive your decisions. Follow your intuition.

How do you distinguish the two? I tell my mentees to use an exercise called “I knew better,” adapted from the work of life coach Shirin Eskandani. Write down all of the times you had a hunch to do something, but against your better judgment you didn’t do it. In the end, if you found yourself saying “I knew better,” that initial hunch was your intuition.

When thinking back to that initial instinct, what did that inner knowing feel like in your body? Remember this, and the next time you have the intuition to do something, write it down. Note when you follow through and don’t follow through. The goal of this exercise is to use these moments as data points so you can learn what your gut instinct feels like when you’re stuck at a pivot point during your new project.

Taking on a project outside your area of expertise is a terrific way to grow as a leader. Like any opportunity, it will put you in a situation where you need to navigate discomfort. Take the risk and raise your hand for stretch assignments that catch your eye. It might take your career in a positive, unexpected direction.