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The Strategic Side Gig

By Ken Banta and Orlan Boston

The Strategic Side Gig

Photo credit: Sandra Navarro

Ken Banta is founder and principal of The Vanguard Network, which convenes C-Suite discussions around high-performance leadership, and advises top executives on leadership.

Orlan Boston is a partner in the Ernst & Young LLP Global Health Sciences practice. He has spent the past two decades serving in a variety of senior leadership roles in business, media, public service, nonprofits, and philanthropy as a senior partner at EY and Deloitte, entrepreneur, venture capital investor, film producer, author, presidential appointee, philanthropist, and member of several boards.


Amit Paley spent the first seven years of his career as a reporter for the Washington Post. While he put in long hours and did stints in war zones in the Middle East, 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—another demanding job. But 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 and financial challenges of such groups and inspired him to get more involved in McKinsey’s nonprofit work. This virtuous cycle 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.

What Is External Engagement?

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, especially to the C-suite, 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 stretch role, you should give it all your attention to make sure you excel and position yourself for the next step. 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—and even your career.

Why? Now more than ever, engagement in strategic side gigs is a requirement for executives. The pace of change and disruption 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—and help their organizations thrive—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 and networking events 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 public, private, or nonprofit boards; teaching, fellowships, publishing, or film production; public or civic service at the federal, state, or municipal level; advising or investing in start-ups; leadership roles in professional associations and clubs; and speaking at or organizing idea forums, festivals, and conferences. 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 today and going forward. All but one said that organizations also benefit when employees have such experiences. More than 100 told us that they have even considered people’s external activities when assessing their fit in succession planning.

To learn how leaders find the right opportunities and what they gain from them, we conducted in-depth interviews with private- and public-sector leaders of varying ages and career stages who exemplified that philosophy. In this article we’ve distilled their lessons.

How Can You Make It Happen?

Finding the time.

One of the biggest constraints executives face is an already packed schedule. Given all your professional and personal demands, it might seem impossible to add anything to your plate. But it’s been our shared experience that you can find the time if you make it a priority (though it may mean giving up some nights and weekends). You can, for instance, block off one or more hours a week on your calendar for these activities. Inviting your friends, spouse, or family members—people you want to spend time with anyway—to join you in them can be an enriching win-win. If you can also involve a small group of like-minded professionals or perhaps younger staff who share your interests, it will help keep you committed and give you people with whom to compare notes. And if you get buy-in from your boss, he or she might allow you to devote office hours to your outside passion.

How much time should you spend on these “extracurricular” activities? Our survey respondents said 10% to 20%, but the amount needn’t be consistent every day, week, or month. Often you can space out your commitments to external projects. The balance can and should shift to as low as 2% when your work and home lives are extremely busy, or as high as 30% when they’re not. 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.

Kara Medoff Barnett is the executive director of the American Ballet Theatre and the mother of three girls, ages 10, eight, and four. But she’s also involved in the American Theater Wing, which keeps her connected to a different kind of performance art, and she just completed a five-year stint as a term member on the Council on Foreign Relations, which helps her better understand the issues facing her organization’s dancers, who come from some 15 countries. “I put a lot of thought into what I can and can’t handle outside my full-time day job and active family life,” she explains. That includes saying not just “no” but also “not now” to many groups and being very deliberate about her schedule by, for example, always reserving Friday nights for time with her husband and kids. “The key is being present in the room you are in,” she says. “When you’re in work mode, be all-in. When you’re home with your kids, put your phone away so that you can read bedtime stories without checking email. And as for the other activities, participate in the ones that spark your intellectual curiosity. Meet people you wouldn’t encounter in your current industry or workplace. Open your aperture.”

The late David Stern, a lawyer who became the commissioner of the National Basketball Association, served on various boards throughout his career and agreed that it was important to fit those meaningful outside commitments into an already hectic schedule. He noted that his own early exposure to different people and problem-solving approaches equipped him to negotiate a groundbreaking collective bargaining agreement between the NBA’s players and owners in 2011. “No matter how busy you are, you should be learning,” he explained to us. “That was something I always pushed myself on by asking: ‘What did I do to stretch myself today?’ I think there is a lot to be learned outside the office.”

Identifying roles.

How can you find the right opportunities—ones that create the kind of virtuous cycle we described earlier? First, spread the word within your organization and to your trusted contacts that you’re looking for outside activities relevant to your job or the skills needed in it. Explore your passions and see if groups connected to them have any open positions that would give you a chance to learn and develop. Seek out friends and colleagues who already have meaningful volunteer jobs and offer to help them. Get your name, interests, and expertise out there through public speaking, social media, and publishing so that people start presenting possibilities to you.

“Take baby steps,” advises Mehmood Khan, the former chief scientific officer of global research and development at PepsiCo and now the CEO of Life Biosciences. Khan has served on multiple advisory boards, including one that allowed him, when in his thirties, to help craft public health policy. “You can do a lot on your own time, such as helping nonprofits in the community where you live,” he says. “Look for these opportunities. Every experience can be a value-add.”

Senior executives considered people’s external activities in succession planning.

After this period of exploration and experimentation, you’ll want to be highly selective about the roles you commit to seriously. “It’s incredibly important when you engage in activities outside work that you do it for sincere reasons and not just as a way to self-promote or to rub shoulders with potential professional connections,” says Kathryn Wylde, the president and CEO of the Partnership for New York City, which runs the David Rockefeller Fellows Program (in which Orlan participated).

Paley agrees: “If you’re spending your free time on something that you’re not passionate about or that doesn’t give you energy, it’s a missed opportunity both for you and for anyone who might otherwise benefit from your insights.”

Ensure, too, that you’re picking a role in which you can really make a worthwhile contribution. Ken Mehlman, who was formerly in politics but is now the global head of public affairs and cohead of global impact at the investment firm KKR, currently holds board positions at Mount Sinai Hospital of New York, Franklin & Marshall College, Teach for America, and Sponsors for Educational Opportunity. He notes, “I have always tried to find institutions to get involved in where I can make a measurable difference.”

Justifying your commitment.

When you take on a strategic side gig, it’s often wise to ask for permission (or sometimes forgiveness) 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. (More on this below.) “Challenge your organization in an appropriate manner,” advises Khan. “Have a clear story about how the activity benefits your company and your development, and its alignment with company values. Make a case for why it’s synergistic.”

You can even talk to your boss about making external engagements one of your annual objectives or aligning your outside passion with the interests of your employer. For example, in Orlan’s roles as an EY executive and a board member for the Trevor Project, he helped create a formal strategic relationship between the two, which allowed the nonprofit to tap into EY resources and staff.

Earlier in Medoff Barnett’s career, when she was the managing director of Lincoln Center International and her girls were even younger than they are now, she was selected for an Aspen Institute fellowship that required her to spend four weeks away from home over a two-year period. Despite being a young mother with a huge job, she knew it would be “a transformational personal and professional growth experience,” so she negotiated with her bosses, employees, and husband—what she describes as “an incredible team back at home”—to make it happen.

If your employer balks at letting you devote time to an outside cause even after you’ve made the case that it will add value to you and the company, that’s a red flag. As Khan says, “If the organization you work for doesn’t understand the value in engaging on the outside, it’s at risk of becoming obsolete. Why would you want to be part of that?”

What Are the Long-Term Benefits?

Recharging your energy.

Keith Krach, a serial entrepreneur, a cofounder of Ariba, and the former CEO and chairman of DocuSign, who was recently appointed 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 (including those of Angie’s List and Opportunity International) and helped create a leadership-training program for Purdue University’s Sigma Chi fraternity, for which he still serves as a mentor. “Every time I take a week to go facilitate the program for these kids, my batteries are recharged,” he says. “I get inspired. It makes me think thoughts I never would have had otherwise. It broadens my scope of empathy and understanding. As my mom always told me, the best way to learn is through OPE: other people’s experiences.”

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 and its causes. 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 and join other networks, 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 the Japanese prefabricated housing industry and how a different society was responding to homelessness. “It redirected my thinking in ways that still reverberate,” she says.

David Pyott, the former chairman and CEO of Allergan, served on multiple boards outside the pharmaceutical industry during his career and encouraged his subordinates to do the same. “You realize how different the world looks from the other side,” he explains. He says the extra roles he took on helped him meet more potential commercial partners, better identify trends, and understand prospective markets for products such as Botox.

All this adds up to a more well-rounded leadership mindset. As Mehlman notes, “Lateral thinking beats linear thinking every day of the week. What’s critical these days is to bring a different perspective and apply it to whatever you’re doing. And you can’t do that if all your attention and focus is limited to the four walls of your organization.”


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. “As the business world becomes more complex, it’s increasingly difficult to find solutions in a single field or discipline,” Khan concludes. “To develop as a leader, you need to leave your comfort zone. That’s how personal growth occurs.”


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