The Overlooked Inner Life of the Systems Entrepreneur

From high-tech startups to Hollywood, changemakers once lauded for their individualism and innovation have been rightly ousted as their dark side has been revealed.

This welcome growing intolerance for abusive and abrasive leadership everywhere, from business and entertainment to sport, acknowledges that you can’t truly achieve good things by treating people badly.

When Uber CEO Travis Kalanick—who would later leave the company—announced earlier this year that he was taking a leave of absence for personal reasons and to make plans for the ride-share service’s future, he noted in a message that, “If we are going to work on Uber 2.0, I also need to work on Travis 2.0 to become the leader that this company needs and that you deserve.”

Extreme as high-profile leadership failures like Kalanick’s and others such as Harvey Weinstein may have been, they do spotlight an issue that I believe has yet to gain the attention it deserves among those involved in philanthropic work: the need to address fundamental issues in our own internal world before trying to fix the one around us.

And nowhere is this more crucial than in the area of systems change—the multiple, simultaneous top-down and bottom-up actions that need to be taken to really move the needle on an issue—and for the person or organization at the center of it, the systems entrepreneur.

Why Systems Entrepreneurs Must Know Themselves

I am not downplaying the importance of the systems entrepreneurs’ “external world”—their abilities, their experience, their knowledge, their reputation, their personality. All are critical in making systems change possible. If you are looking for a systems entrepreneur to work in systems change, you will want evidence of these competencies in the person or organization you choose.

But perhaps more than anyone else, the systems entrepreneur needs to also have at least begun to get a handle on their inner world if they are to help bring about the far-reaching change that is being sought. Only when they are aware of what makes them tick—what makes them the way they are and how they respond to pressure or criticism or conflict—will they be able to most effectively exercise their external skills. Without this awareness, they will simply not have what it takes to apply the leverage needed to keep moving the initiative forward.

Why do I say this?

Because of the unique environment they face. All leadership requires a level of people management, getting others to work together through inspiration, encouragement, negotiation, and compromise. But if the typical leader needs to do some degree-level self-assessment to be effective, those in systems change need to go to the PhD level.

This is because, in their world, the scope and scale of collaboration is significantly magnified. There are multiple stakeholders who may share a broad, overarching goal, but who likely also have overlapping—if not at times, competing—interests. With such a diverse community, any one group’s or person’s ability to direct or dictate is reduced, and their ability to negatively impact the initiative is enhanced.

Business often involves two parties looking for a win-win; systems change can mean multiple parties looking for a win-win-win-win. This level of complication exposes the systems entrepreneur to greater stress; there is likely always going to be someone who is less happy with their part in the bigger picture. If someone hasn’t recognized how they respond to and deal with others’ dissatisfaction, they may shy away from pursuing a better end result by defaulting to something that keeps everyone equally happy.

Because of the unique skill set they require. Working with a broad group of actors means being able to wear multiple hats well: ambassador, big-picture thinker, conductor, diplomat, negotiator, and more. You often deal with people who speak different verbal and vocational languages—from the West and the South, and from academic, business, government, and nonprofit backgrounds.

As such, the systems entrepreneur is likely to be stretched beyond what may be their natural strengths and talents, and when we find ourselves out of our depth, we can often become defensive. But that only impedes potential progress, so the systems entrepreneur needs to have invested time in recognizing where they may need to develop and practice new skills—or be willing to give way to those who have them.

Becoming more attuned to your inner world develops a sort of filter as you move in your outer world, enabling you to recognize where—because of your personal makeup—you may need to be careful to keep the end goal in mind. That could mean letting someone else take the credit for something you initiated, if it means getting the job done, or, having led the way in reaching a big decision, allowing someone else who is better positioned to oversee its implementation.

What Systems Entrepreneurs Need to Ask Themselves

Fundamentally, addressing your inner life means dealing with your ego. Many of us think of the word only in relation to arrogance, but in the original meaning, as a sense of identity, of who we are (and are not), it’s not a bad thing. We all develop and need an ego. Much of the first half of life is about exploring and defining this central part of us.

The trick is to come to a place where we are secure enough in our identity that we can then acknowledge and address the negative aspect of ego—being open to admitting when we feel threatened or insecure because someone disagrees with us or doesn’t like what we are proposing. No one can really ever leave his or her ego at the door; rather we need to teach it to come in, sit down, and be quiet.

At its core, systems change hinges on building trust with different actors across different sectors all in the service of a bigger goal than any of us. That occurs when the systems entrepreneur is self-aware enough to keep out of the way while leading others to find the way ahead together.

It’s about learning how we can often impede others and ourselves if we do not understand ourselves as we need to. And when we know how to manage our own ego, we’re better placed to deal with other peoples’ egos.

Here are some of the questions I have asked that have helped me as I have tried to cultivate my own inner life, so that I can be better equipped as a systems entrepreneur.

What drives me? We all are wired differently in what feeds our sense of achievement, value, or worth. Trying to gain clarity on what motivates me has made me more alert to how, if I’m not careful, I’m prone to being swayed—as much when my goals are being supported as when they may appear to be thwarted.

One way to look at this whole area is to spend some time thinking back over your greatest successes—and failures. What contributed to those outcomes, and how do you feel about all of that?

This kind of awareness can have concrete results. One time, we were facing a difficult situation with a client over a difference of opinion regarding a project. I felt that the facts clearly pointed in our favor, but I also knew that being challenged as we were pushed a button in me somewhere. We talked through what we wanted from the discussion as a team, and when we’d agreed on a plan I then took a step away from its implementation. I knew that I needed to let someone else lead the Geneva Global response, while I held back. In due course, the situation was resolved, as we’d hoped, which I attribute, in part, to having recused myself from the hands-on process.

By taking myself out of the equation because I knew the discussion might trigger something in me, possibly leading me to say something that wouldn’t be helpful, we were able to agree on steps that could be part of bringing about real systems change.

What am I missing? For the most part, our deficiencies aren’t that obvious to us, otherwise we would try to fix them. Typically, we are more attuned to our strengths, in part, because we tend to naturally move in them and they more often bring the reward of a sense of satisfaction.

So uncovering blind spots can take some work. Journaling may help; it forces you to slow down and express what you’re thinking and feeling in a way that can help things sink in. It’s as though you get to ask yourself hard questions without letting yourself change the subject.

Even more helpful can be asking others for their opinions. An outside coach or mentor might be a good sounding board. Three-sixty reviews can be enormously revealing, if you are really open to hearing what others have to say. There are plenty of books and even apps that can help develop this kind of reflective mindfulness.

What do I need? Succeeding as a systems entrepreneur requires a unique mix of internal qualities. You must have a passion for, and commitment to, the issue you want to impact, while at the same time be able to hold it lightly and recognize that true collaboration means that progress may be slow.

You need a high level of EQ, or “emotional intelligence,”—being able to read others and their needs and drives, and knowing how to bring different participants with different perspectives together. You need to have a strong curiosity, and genuinely want to know why and how people think the way they do, rather than automatically dismissing their viewpoint because it’s different from the way you think. It is also important to be patient, flexible, and able to develop and foster strong interpersonal relationships. Humor is a key tool in cultivating cooperation, especially in stressful conditions.

Waking Up to the Importance of Wellbeing

Developing this kind of strong inner life is not only beneficial to the individuals involved in systems change, it can help organizations, too. Just as individuals have personalities, so do groups of people. An organization tends to reflect its leadership, for good or ill. If he or she is arrogant or aggressive, chances are the culture of the organization will be as well. For example, just as you can tell much about someone by how they greet you, you can learn a lot about an organization from how well the receptionist is treated and treats you.

It’s true that the need for leaders to first lead themselves well if they are to really succeed has long been acknowledged. Stephen Covey and others have spoken to the way a leader’s identity, humility, and integrity are the building blocks on which successful businesses and organizations are built.

Yet while this critical aspect of the importance of a leader’s inner world has been broadly embraced in the business, nonprofit, and academic worlds, it has yet to be widely acknowledged where those three intersect—in the world of systems change thinking.

Encouragingly, there are signs of it being embraced. I am glad to see others beginning to talk about this important need. Not long ago, the World Economic Forum website featured an article titled, “The inner path to becoming a systems entrepreneur.”

Meanwhile, under the banner “Wellbeing inspires Welldoing,” The Wellbeing Project offers an 18-month program of retreats, study, and personal mentoring focused on “cultivating a culture of personal and inner wellbeing in the field of social change.”

The growing recognition that a systems change approach is needed to really make a difference in some of the big issues facing the world today is one of the most exciting trends I have observed in my more than a quarter-century in international development.

But I believe that the potential for unprecedented progress that is offered in approaching intractable challenges by viewing them through this new lens will only be fully realized if we address the inner life of the systems entrepreneurs who are at the center of the systems change effort.