Balancing Risk: A Conversation with General Stanley McChrystal

As recent world events clearly demonstrate, risk is an inherent, and at times unwelcome, part of life. Yet, without taking thoughtful, calculated risks, there can be no reward. Retired Four-Star General Stanley McChrystal knows this well.

On March 15 at 12 p.m. CT, General McChrystal will join Cresset for a virtual event on how to navigate risk in all areas of life. He will share the strategies outlined in his new book, “Risk: A User’s Guide,” on how to effectively anticipate, analyze, and act in situations where there is a likely possibility that things won’t go as planned. Specifically, General McChrystal will explain how to build and strengthen your “risk immune system” through the 10 dimensions of control that can be used to respond to risk.

Below, General McChrystal provides a preview into his thinking around risk and what he will share on March 15:

General, risk has obviously been a huge part of your personal and professional life. How do you find balance between what is acceptable risk and what is simply foolish?

Risk, for better or for worse, is a constant variable in our lives. Whether you’re a soldier or a CEO, we all share a fear that we won’t be able to navigate uncertainty with any level of control. I would argue that there is no one level of “acceptable” risk – rather, we have to understand how to assess risk for ourselves. Risk is a product of probability and consequence. It is safest to take risks where either the consequence would not be especially weighty, or when that heavy consequence has a sufficiently low probability of coming to pass. Making a good decision requires us to evaluate our own tolerance for risk and make an informed decision about how to proceed. You may choose to proceed with caution, you may choose to dive into risk (with the proper preparation). In either case, know thyself and make the decision mindfully.

In your new book, “Risk: A User’s Guide,” you explore strategies for anticipating, identifying, analyzing, and acting upon the possibility that things won’t go as planned. Can you share examples of how that works?

Of course. We’ve been living through an enormous risk simulation for the past two years! The Covid-19 pandemic is a great example of how we can either rise to the occasion when risk comes our way, or how we can falter.

First, what did we get wrong? We failed to be proactive. In 2019, the Department of Health and Human Services (HHS) convened a series of exercises called Crimson Contagion. The exercise’s findings were conclusive: the nation was woefully underprepared. However, we took no action, and when Covid reached our nation, we failed to create a unified response within the government, various industries, and even our own neighborhoods. Despite access to the miracle of the speedily developed vaccine, we still are fighting the pandemic in our schools, our home, and our workplaces. When we fail to understand the nature of the risk we are facing, we cannot develop a successful response.

However, it can be done! In Boston, Mayor Marty Walsh watched as New York City’s outbreak reached a fever pitch. Given his experience in a crisis (including the snowstorms that shut down the city in prior winters), he knew that he had to build a coalition before the virus overtook the city. With a level of streamlined, interconnected communication, his “crisis response forum” built both a prevention and response effort into the city’s infrastructure. The results speak for themselves, and the city remains a terrific example of how to recognize a risk in advance and build a team to respond. That’s leadership.

More specifically, you write about 10 dimensions of control that people can use to respond to risk. What are some of those dimensions?

Well, leadership binds together the risk immune system – which, as you mention, is comprised of 10 dimensions of control that help us navigate risk. Those dimensions are communication, narrative, structure, technology, diversity, bias, action, timing, and adaptability; all fueled by leadership.

One that I love to discuss with my clients and colleagues is adaptability. When we face uncertainty, it is easy to try to rely on the existing structures and rules to find some comfort. However, the best leaders and organizations are able to adapt those existing practices and use their experiences to chart a new path.

I also think it’s critical to think about timing. If you take the right course of action at the wrong time, it can have unintended consequences. This means that when facing risk, we must work together to meet the moment, rather than delaying until the risk has subsided.

Diversity matters, too – and not just in the way that we have come to use “diversity” as a buzzword. When we fail to bring in new perspectives, our organizations can inadvertently fall into groupthink. Prioritizing a diversity of perspectives is a key to helping an organization respond to risk – with more views on how to tackle risk, you are more likely to find a version that works best for you and your team.

Planning for and responding to risk and threats can be exhausting. What is your advice for avoiding burnout and harboring a world view that is rooted in cynicism and pessimism?

You’re right, it’s easy to feel exhausted by the constant uncertainty we face each day. However, this is why leadership is more important than ever. Good leaders don’t take on the entire burden of risk themselves – they empower their team and their trusted colleagues to share the burden together. While the leader does take on the responsibility of decision-making, the strongest and most resilient organizations are ones where every individual has a voice and shared interest in carrying a portion of the risk themselves. Preparation and encouragement breed success, and when you aren’t in a cycle managing risk alone, you can find energy in rising to a challenge, rather than the challenge wearing you down.

Register for Cresset’s event on March 15 to hear more from General McChrystal.

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About Cresset

Cresset is an independent, award-winning multi-family office and private investment firm with more than $45 billion in assets under management (as of 04/01/2024). Cresset serves the unique needs of entrepreneurs, CEO founders, wealth creators, executives, and partners, as well as high-net-worth and multi-generational families. Our goal is to deliver a new paradigm for wealth management, giving you time to pursue what matters to you most.

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