The Five C’s of Cultivating Courage for Stretch Roles

Contributed by CEO Coach Henna Inam

Do you have the courage to ask for and take on high-profile roles that will really stretch and prepare you for the big leadership positions? Facebook COO Sheryl Sandberg has said “Leadership belongs to those who take it.” Will you make the decision to take it?

Imagine a scenario where you’re being asked to move to a new country where you don’t speak the language. You’re being promoted to a general manager position, one you’ve never been in before. You’ll have P&L responsibility, and will manage functions you’ve never worked in. You have about 10 times the people responsibility you’ve ever handled in your career. You’ll be working for someone you’ve barely met before. It’s a crisis situation that requires a turn-around. And oh, your boss’s boss tells you that the company’s CEO is watching closely. “You’ll do great. Have fun” he says. Would you take it?

I did.

Recent Catalyst research among high potential men and women suggests that 70% of leadership growth happens on the job. Yet women get less access to the “hot jobs,” stretch assignments with high visibility, P&L responsibility, and international work experience they need to develop. In many situations women are perceived to be less willing to take the risky stretch assignments, so they are not even considered for these roles. How do we change this perception? Read on for five steps to cultivate courage.

While organizations work on removing the glass ceiling on these stretch jobs, each of us as women leaders have work to do as well. Our work is to understand our strengths, our priorities, unique motivators, and bust through the “glass ceiling” in our heads. We want to cultivate the courage to powerfully ask for and grow through the stretch roles that are right for us. As hierarchies flatten, we need to think strategically about the unique path we want to carve out for ourselves in the “career lattice.”

In my 20-year corporate career, I had many stretch assignments. In some I was hugely successful, in others not so much. In both cases, I learned a lot, probably more from the failures. Here’s what I learned about preparing for and taking on these roles.

Five C’s of Cultivating Courage

1. Clarity. First step in courage is to get clear on what we want – not a specific position, but the sets of experiences that will help us to learn, contribute, and grow toward roles we aspire for. Here are some useful questions I asked myself as I navigated my career:

  • What motivates and drives me?
  • What kind of roles would I best thrive in and succeed?
  • What kind of learning experiences do I need to get into these roles?
  • What are my unique work and life integration requirements and priorities right now?
  • What restrictions do I have?

These questions helped me get clear about where I would best thrive and contribute. I knew that career was a major priority for me and also that I was motivated by a broad set of challenges to learn from. I wanted to be able to see and influence all aspects of a business (not just one functional aspect). With that clarity, I sought out experiences working in cross-functional areas, running P&Ls. Each person has unique motivators. For long-term career success, it’s important to understand ourselves first. Here are some resources to grow in self-awareness.

2. Confidence. Clarity and confidence work hand in hand and feed each other. When we start with clarity on who we are and what motivates us, and we seek situations where we can thrive, it naturally breeds confidence. I work often with my executive coaching clients as well as in workshops to help leaders articulate their unique “Authentic Brand: YOU.” This process helps them become more confident by getting clear on their motivators, their strengths, their sense of purpose. In my “Cultivating Courage” workshop, we work on leadership practices that help us navigate fear of failure and also become more resilient. Here is a video to help you think about your personal brand.

3. Communication. Once we’re clear on the right general direction of our career, it’s time to make sure we communicate this powerfully to bosses, mentors, sponsors, HR, etc. Our clarity helps our supporters help us. As we communicate it’s important to stay focused on learning experiences rather than specific positions. Our sponsors have much greater visibility of opportunities that are available, and we want more opportunities presented to us than less. For example, I shared my aspiration to run businesses and P&Ls consistently in all career discussions. It led to my getting cross functional assignments across Finance, Marketing and Sales. I could have never predicted the specific opportunity I spoke about above. Here is a resource to think about how you market your personal brand.

4. Connections. Our sponsoring relationships are the make-or-break in our ability to get stretch assignments and succeed in them. I was lucky to have some great sponsors throughout my career. Most of them were bosses or in my hierarchy. The biggest lesson I learned is that when you have a sponsor who “has your back,” you are more confident in taking risks.

In the example above, I was asked to take on a general manager role in Mexico. While I didn’t know my boss, I did know my boss’s boss and his boss. I knew they “had my back.” In another stretch assignment I took on, my boss (and initial sponsor) left the organization after 8 months. Not wanting to undermine my new boss, I made the mistake of not connecting with sponsors who were three levels up in the organization, thinking I could handle it. When you feel like you have to “prove yourself” to a new boss while undertaking a significant business challenge, it diverts your energy and focus, not to mention your confidence. That was a good lesson for me. Here are some resources on how to attract sponsors.

5. Calculated Risk. Determine which stretches are risky and which are not. Here are some useful questions I asked myself and others:

  • How does this contribute to the sets of experiences I have identified as important?
  • What does success look like? What critical skill sets are required for the role and what strengths do I bring?
  • Who are my sponsors and what is my support system (resources, network, etc.)?

As I understood my personal brand, for the assignment in Mexico I knew which “stretches” were risky and which were not. For example, I knew that I thrived in global environments (I grew up living in three different countries and learned three new languages from the age of 11 to 19). I knew that the turnaround issues that the market was dealing with were issues where I had functional expertise. The assignment offered great challenges in driving a turnaround and managing a complete P&L (including a manufacturing plant and R&D). I knew I had strong sponsors supporting me.

No one is willing to give us guarantees of success, but we can take the steps above give us the courage we need. Importantly, I listened to my heart and intuition. In my “look see” trip, I fell in love with the opportunity to contribute to restoring the confidence of an organization that had a proud heritage but had recently lost its way.

I hope you use this framework to think about navigating the “lattice” and taking on the right stretch roles that fit for you. Anais Nin said: “Life shrinks or expands in proportion to one’s courage.” The place to start is by knowing ourselves. I would welcome connecting with you for that purpose.

Henna Inam is CEO of Transformational Leadership Inc., a company focused on helping women achieve their potential to be transformational leaders. A former C-Suite executive with Fortune 500 companies, her passion is to help leaders be successful, deeply engaged, and create organizations that drive breakthroughs in innovation, growth and engagement. Connect @hennainam. Subscribe to her blog at