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The Strategic Side Gig

Amit Paley spent the first seven years of his career as a reporter for The Washington Post. While he put in long hours, he also made time to serve on the board of his alma mater’s newspaper, where he could help aspiring journalists and learn how nonprofits worked. After leaving the Post and attending business school, Paley joined McKinsey as a consultant. Again, he made it a priority to volunteer, this time staffing nighttime and weekend phone lines for the Trevor Project, an organization that works to prevent suicides among LGBTQ youth.

Eventually he joined its board (full disclosure: one of us also serves on it), which gave him exposure to the operational challenges of such groups and inspired him to get more involved in McKinsey’s nonprofit work. This eventually culminated in his being named CEO of the Trevor Project in 2017. “By investing my time outside work in things I was passionate about, I learned things that made me better at my job,” Paley explains. “Those experiences also prepared me for future leadership roles that I didn’t know I would have.”

That’s the power of strategically taking on extra jobs outside your organization.

Read also: How leadership anchors transformational attitudes in an organisation


A lot of managers and leaders focus obsessively on their current jobs and companies. Many believe they simply can’t be successful without that kind of single-mindedness. Of course, most people now realize that to advance in your career, you need diverse experiences and should explore opportunities in a variety of functions, industries and geographies. But the general thinking is that when you get a challenging role, you should give it all your attention to make sure you excel. That approach can pay off in the short term. However, in our combined work with thousands of executives as well as in our own experience, we’ve found that it can stymie your long-term development.

Why? Now more than ever, engagement in strategic side gigs is a requirement for executives. The pace of change is also making it difficult for corporate learning departments, management schools and executive education programs to keep their curricula relevant. As a result, leaders who want to rise need to find ways to expand their field of vision and build their knowledge, skills and connections even as they carry on their daily work.

This goes well beyond attending industry conferences or taking classes at night. We’re talking about meaningful engagement in outside activities that expose you to different people, information and cultures but are also in some way synergistic with both your personal interests and your current or future primary work. That can include membership on boards, teaching, publishing, public service, investing in startups and so on. Think of yourself as having a portfolio where your job is squarely in the middle, various outside activities surround and complement it, and you deploy what you’ve learned in each realm to the others.

When we surveyed 122 senior executives from a spectrum of industries, all agreed that outside engagements were critical to leadership success. To learn how leaders find the right opportunities and what they gain from them, we conducted interviews with leaders of varying career stages. In this article we’ve distilled their lessons.


— FINDING THE TIME: One of the biggest constraints executives face is an already packed schedule. But you can find the time if you make it a priority. You can, for instance, block off one or more hours a week on your calendar for these activities. Often you can space them out. In other words, you need to deliver in your job and for your family before you can take on additional responsibilities. But if things lighten up, seize the opportunity.

— IDENTIFYING ROLES: How can you find the right opportunities? First, spread the word within your organization and to your contacts that you’re looking for outside activities relevant to your job or skills. Explore your passions and see if groups connected to them have any open positions that would give you a chance to learn. Seek out friends and colleagues who already have volunteer jobs and offer to help them. Get your name out there through public speaking, social media and publishing so that people start presenting possibilities to you. After this period of exploration, you’ll want to be selective about the roles you commit to seriously.

— JUSTIFYING YOUR COMMITMENT: When you take on a strategic side gig, it’s often wise to ask for permission from your employer and family. The key is to show the relevance, including both personal benefits, such as increased engagement and energy, and organizational ones, such as a broader network.


— RECHARGING YOUR ENERGY: Keith Krach, the U.S. undersecretary of state for economic growth, energy and the environment, says that when you squeeze in time for outside activities, it can actually help you avoid burnout. “I’ve found that the busier you are, the more you can take on, and you definitely get better at your job,” he says. During his career, which began in General Motors’ engineering group, he has served on various nonprofit and corporate boards.

— BUILDING KNOWLEDGE, SKILLS AND CONFIDENCE: The best external engagement gives you something to bring back to your own organization. A great example comes from Rosanne Haggerty, the president and CEO of Community Solutions, an organization dedicated to ending homelessness. At age 30 she started her first nonprofit and, about that same time, applied to be on the board of trustees of her alma mater, Amherst College. Although it was daunting to take on the two commitments at once, she says, “the timing was perfect in that I received a remarkable education about what it meant to work with a board and what to pay attention to as I grew my own nonprofit. Serving on that board was like taking a master class in nonprofit leadership and long-term stewardship. Wherever you are on your career journey, anytime you can learn new skills, manage a complex project and even make some mistakes you can bounce back from, it will be extremely valuable.”

— DEVELOPING A BROADER PERSPECTIVE: When you do important work in other fields, you uncover areas of untapped opportunity for yourself and your organization. You can make connections that help you become a better innovator and manager. Ten years into her first nonprofit CEO role, Haggerty took time off to go to Tokyo on a fellowship and study how a different society was responding to homelessness. “It redirected my thinking in ways that still reverberate,” she says.

Finding the right engagement outside your day job isn’t always easy. But once you do it, it usually opens the door to many other opportunities. And it’s those experiences that will become your personal competitive advantage.

Ken Banta is the founder and principal of the Vanguard Group for Leadership. Orlan Boston is a partner in the Ernst and Young LLP Global Health Sciences practice.

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