Handling Uncertainty with a Chief of Staff

Photo by Jannes Glas on Unsplash

If there is one thing that we can agree on from the past 12 months, it is that the world is way less certain than we previously imagined. From the COVID-19 crisis, to societal strife, and more recently the climate disasters in Texas, our frame for what is ‘normal’ has shifted. Then we think of the advances in technology, geopolitical squabbles, and other macro trends, it is becoming increasingly clear that we may never go back to ‘business as usual.’

The only thing normal about the future is uncertainty.

Author Nassim Nicholas Taleb is famous for writing about thriving in an uncertain world. He discusses concepts like randomness, black swans, and having skin in the game, but as we ponder an uncertain future, his concept called ‘antifragility’ is worth revisiting in detail.

Most English speakers are well aware of the term ‘fragile.’ For the sake of simplicity, let’s define it as things that are easily broken. However, what most do not realize is, prior to Taleb, there was no opposite term for fragile. After some thought, many believe the word robust meets the mark; but robust means hard to break. The opposite of fragile is not hard to break, but that which becomes stronger in the wake of volatility. Rather than robust, things that get stronger when exposed to destructive force are antifragile.

We all know that uncertainty makes planning difficult.

While building robust systems are a worthy goal, even the most robust systems will eventually reach a breaking point.

Building an Antifragile Organization

To truly thrive in an uncertain future the best leaders have shifted focus to building antifragile organizations.

This is easier said than done and most who try end up failing.

Those who have succeeded have a few things in common. They spend a lot of time trying to see the present clearly. They distill their businesses to a few factors that are critical. They simplify their strategies and operations as much as possible.

Above all else they create space to think.

Does that sound bizarre? Time to think?

For many, it does.

Most executives are barely above water. They move from one crisis to another, one Zoom call to the next, with little to no time to think about bigger picture things like mission, vision, and strategy. Many can barely see the road ahead, let alone navigate to a future destination.

In stable times, frenetic energy and grit can be enough to survive, and with luck some even thrive. But to navigate this age of uncertainty, thinking time is the most precious resource and valuable weapon that an executive can have.

Cultivating Space

But how does one cultivate this space? We can’t allow the tasks we are juggling to hit the floor, that’s simply not an option. We all need to keep the lights on. While carving out extra time, becoming more disciplined, or focusing on better habits are all worthwhile endeavors, we all know how challenging that can be.

Sometimes additional resources are needed to solve a problem, and many of the best executives do this by having a trusted Chief of Staff.

Over the last few years, there has been a growing awareness across the business world of the benefit of a Chief of Staff. This is not a new concept. In politics, the Chief of Staff is commonly thought of as the center of power and the critical point of leverage for Heads of State. If it worked for George Washington (see Alexander Hamilton) or Franklin D. Roosevelt (see William Leahy) why shouldn’t it be worth considering?

So, what does a Chief of Staff do exactly? Better yet, what doesn’t a Chief of Staff do?

A Chief of Staff is not an executive assistant. It is not a project manager. It is not a task master or calendar manager. While some of these things could fall into the purview of a Chief of Staff, it is important to make these distinctions. At its core the Chief of Staff role is about providing leverage.

This can work in a few ways.

First, a Chief of Staff helps amplify an executive’s strengths. This means taking things off of an executive’s plate. Everyone possesses strengths and weaknesses, and a substantial body of research highlights that doing things we are good at leads to more enjoyment, fulfillment, and overall better outcomes in work. A Chief of Staff provides the luxury of offloading things that kill energy, so the most critical things can be prioritized.

But it’s not all about lightening the load for the executive.

A Chief of Staff can also be a force-multiplier to helping an executive get the most important work done. This means being a thought partner to help set strategy, make decisions, and generally run the organization better. This means aligning people, operating cadences, and technology, so that it supports an organization’s goals.

Lessons from the Best

Many of the greatest leaders in business have leveraged Chief of Staff like resources in the past. Take Amazon founder Jeff Bezos for example. When Amazon was dealing with the fallout of the dot.com bust, Bezos hired an Amazon manager to serve as his ‘brain double’ or ‘shadow.’ That man, Andy Jassy, provided tremendous leverage and was a thought partner in helping make the key decisions that helped propel Amazon to where it is today. One of those decisions led to one of the most transformational initiatives at Amazon: AWS. Just recently when Bezos announced that he was stepping down as CEO of Amazon, who did he name CEO? Andy Jassy.

What about Mark Zuckerberg, the founder of Facebook? Looking back, it is easy to forget Facebook’s humble start. When Zuckerberg founded the company, he was still a teenager. While he was a talented technologist and had the ability to recruit well, he lacked general business sense and struggled to figure out a repeatable business model. Understanding this challenge, who did he turn to? Sheryl Sandberg. Sandberg had pioneered the ad word product at Google and was an expert in monetizing attention. While Sandberg was given the title of COO, the same principles regarding the benefit of having a Chief of Staff held true. Sandberg allowed Zuckerberg to focus on his strengths and mitigated his weaknesses. The result? Facebook has built an ad product that rivals Google and is one of the most influential companies in the world.

We know… you’re probably nodding along.

But you might be wondering, do I actually need a Chief of Staff? Is my organization big enough? Is there enough complexity? Are things really that bad?

In normal times these are all fair questions.

Thinking Time

But in an uncertain future, one that will present an array of both challenges and opportunities, the best executives and leaders must prioritize time to think. It is the only way to design an antifragile organization. Organizations whose executives do not spend this critical time to think, risk breaking under uncertainty.

The obvious next question is should you hire a full time Chief of Staff or work with a partner to contract the service? While we believe hiring a full time Chief of Staff is often the right move, finding the right person can be time consuming. With the challenges of working remotely present, getting a permanent team member up to speed is even more challenging.

That’s where an outsourced Chief of Staff option can make sense.

Working with a partner organization like Slalom will help you quickly get a highly capable Chief of Staff in place and allow you to test if it is the right model for you. At the same time, it also buys time to find and hire the right permanent person.

As executives, we need to be better prepared to deal with an uncertain future. This means taking the time to design an antifragile organization and amplifying our strengths.

A good step to making this happen is hiring a Chief of Staff.

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