Defining the leaders who are defining the moment


We’re still at home doing our best coming to grips with the loss of life, lack of resources and uncertainty. And yet, we’re still here, recognizing what we can and cannot control.

Hopefully, if you read Part 1 of this series, you agree Work From Home (WFH) makes sense, your team has been inadvertently training for it for more than a decade, and you can put it in the “can control” bucket.

That major shift in how we do business is what leads me to the other thing you          “can control”…your leadership.

We’ve seen every kind of leader over the last month. Here are a few of the prevalent archetypes…

  • The Holiday Execs shut it all down and are enjoying time at home with their family waiting to get back to normal.
  • The Grinders holding on for dear life, trying to make it another week and unable to see beyond the day.
  • The Analysts, frozen in analysis paralysis, and the Fallen, curled up in the fetal position. Both segments are so afraid of making a misstep the best they can do is stand still or just fade away.
  • The White Knights with substantial resources using them in really powerful ways. You can argue about the trade-offs we make when we depend on billionaires to save us, but you can’t deny the incredible impact they’ve made donating their time, knowledge and money.

In this article I’d like to focus on a segment of leadership we have seen emerging into a truly inspirational group of people leading businesses… The Challenger Executive. 


The Foundation of Leadership – What Traits Matter?

Our organization, views leadership from the role of Chief of Staff. As an impartial third party and servant leader we see a side of executives few others do. For the purposes of understanding the emergence of the Challenger Executive, we will pair our heuristic analysis with a baseline of successful leadership.

One of the largest and most extensive studies on the subject is the CEO Genome project executed by the ghSMART organization. The study took place over 10-years with 14 researchers of varying specialties and amassed 17,000 C-Suite executive evaluations. Their focus was not what is perceived as making leaders successful. This study focuses on successful leaders and the common behaviors shared among them.

The study identified Boards of Directors and others responsible for hiring CEOs tend to gravitate toward traits and behaviors that don’t correlate with high performing CEOs. In other words, the charismatic extrovert with flawless previous experience and an Ivy League degree are not the variables to look for. Like those incredible soon-to-be NFL players entering the draft over the next few days, we have to look at the data, but also evaluate the intangibles. The researchers behind the CEO Genome study summarized it in four deceivingly simple behaviors in a Harvard Business Review Article, What Sets Successful CEOs Apart.


Deciding with Speed & Conviction 

“Legends about CEOs who always seem to know exactly how to steer their companies to wild success seem to abound in business. But we discovered that high-performing CEOs do not necessarily stand out for making great decisions all the time; rather, they stand out for being more decisive. They make decisions earlier, faster, and with greater conviction. They do so consistently—even amid ambiguity, with incomplete information, and in unfamiliar domains. In our data, people who were described as “decisive” were 12 times more likely to be high-performing CEOs.”


“Good CEOs realize that a wrong decision may be better than no decision at all.” – ghSMART


Proxxy clients recognize every moment matters and giving an executive the headspace to make focused analyses and decisions is a top priority for a Chief of Staff. The ripple effect of stagnation is felt throughout the entire organization. In the midst of the COVID-19 crisis the Challenger Executive’s request is the distillation of data as quickly as possible so they can act and course correct if necessary when data changes. The other part of decision making we have seen that correlates with the study is the Challenger Executive’s need for a “kitchen cabinet” or “trusted adviser who can be counted on for unvarnished opinions and sound judgment.”

Consider This… Get your processes in order to improve both speed and accuracy. Organizations with good business processes were able to submit for government support much faster and were in line before the unprepared. “Among the CEOs studied who were fired over issues related to decision making, only one-third lost their jobs because they’d made bad calls; the rest were ousted for being indecisive.”


Engaging for Impact 

“Once CEOs set a clear course for the business, they must get buy-in among their employees and other stakeholders. We found that strong performers balance keen insight into their stakeholders’ priorities with an unrelenting focus on delivering business results. They start by developing an astute understanding of their stakeholders’ needs and motivations, and then get people on board by driving for performance and aligning them around the goal of value creation. In our data, CEOs who deftly engaged stakeholders with this results orientation were 75% more successful in the role.”


“CEOs who excel at bringing others along plan and execute disciplined communications and influencing strategies.” – ghSMART


In this period of crisis, we have seen the Challenger Executive do this exceptionally well. They know every word they say is scrutinized, but they don’t run from it. They first make the necessary decisions to ensure the organization can achieve their vision, but then they relate it to each stakeholder. They have a strong Emotional Quotient (EQ) and care about their staff so the Challenger Executive can make each stakeholder feel they are a part of the process and play a necessary role.

However, as the study showed, “leaders who are good at engagement give everyone a voice but not a vote. They listen and solicit views but do not default to consensus-driven decision making.”

Consider This…“CEOs who engage stakeholders do not invest their energy in being liked or protecting their teams from painful decisions. In fact, both those behaviors are commonly seen in lower-performing CEOs.”


Adapting Proactively  

There may not be a more valuable behavior in the wake of this “adapt or die” environment, but the study showed it matters all the time. “CEOs who excel at adapting are 6.7 times more likely to succeed.”

“Most CEOs know they have to divide their attention among short-, medium-, and long-term perspectives, but the adaptable CEOs spent significantly more of their time—as much as 50%—thinking about the long term. Other executives, by contrast, devoted an average of 30% of their time to long-term thinking. We believe a long-term focus helps because it makes CEOs more likely to pick up on early signals. Highly adaptable CEOs regularly plug into broad information flows: They scan wide networks and diverse sources of data, finding relevance in information that may at first seem unrelated to their businesses. As a result, they sense change earlier and make strategic moves to take advantage of it.”


Nearly 90% of the strong CEO candidates we reviewed scored high on dealing with setbacks. – ghSMART


This point underscores why we focused on decisive actions with our Proxxy clients in the early stage of this crisis. The sooner they could look forward the sooner they could formulate a strategy relevant to this new normal. Many of the leaders we work with had already constructed very forward-thinking concepts of what the future could look like. They found this to be an opportunity to advance some of those concepts.

Consider This… “CEOs who considered setbacks to be failures had 50% less chance of thriving.” If your decisions are wrong, they are learning opportunities.


Delivering Reliably 

“Mundane as it may sound, the ability to reliably produce results was possibly the most powerful of the four essential CEO behaviors. In our sample, CEO candidates who scored high on reliability were twice as likely to be picked for the role and 15 times more likely to succeed in it.”


A stunning 94% of the strong CEO candidates we analyzed scored high on consistently following through on their commitments. – ghSMART


The Challenger Executives, though making decisions with imperfect data and operating future forward, excelled in this area, as well. While many SMBs lack the structure and processes seen in Fortune 500 organizations, the study highlights business management systems like, “a cadence of meetings, dashboards of metrics, clear accountability, and multiple channels for monitoring performance and making rapid course corrections” as being a very important part of this behavior. This is the primary function of a Chief of Staff and the reason this partnership is so valuable to a Challenger Executive.

Consider This… If you would like some tips for how you can save yourself more time, check out this article from The Harvard Business Review, Productivity Skills to Help You Gain Time Back. After you read it, if you think it will take you more time to implement the suggestions than you will save in time, reach out and we will have a Chief of Staff implement them for you. You can calculate your ROI here.



Your Leadership Foundation 

So now you can see Challenger Executives aren’t a bunch of Joe Exotic’s from Tiger King. Yes, he had a big dream, but it came with a heaping dose of crazy and none of those key behaviors (good luck, Carole Baskin!).

Though the CEO Genome project was primarily focused on larger organizations, during this pandemic we have seen these behaviors resonate in SMB leadership, as well. What it reveals is that executives must be honest with themselves about their strengths and abilities. The Challenger Executive identifies where they can find others to bolster their weaknesses so they can focus where they excel.

Consider This… If you would like to take part in the CEO Genome study you can take the survey here. At Proxxy, as we help clients prioritize how we can help, we often introduce StrengthsFinder 2.0 or Clifton Strengths from Gallup. It is a quick and easy way to document your top five strengths.


The Challenger Executive Difference

The foundation of research from the CEO Genome project highlighted what the highest performing executives do and what we have seen in the Challenger Executives at Proxxy. That’s not the whole story though. There’s something special about this breed of leader being formed in the fires of this hundred-year crisis.

They are as defined by what they’re not, as by what they are. The Challenger Executive is not defined by the size of their company, their rank in their industry, their years in business, their title, where they’re from, or their degree – if they even have one. They recognize these are constraints others have forced on them, but when you focus on outcome over output those are no longer constraints. They are simply parts of your story.

What makes this audience stand out from the other leaders in industry is their view of the world. The Challenger Executive sees…


Worthy Challenges

Status quo, the way it’s always been done, hierarchy, the competitors…a crisis. These are all real issues a leader faces, but the Challenger Executive leans into them and welcomes them. Not to pick a fight, but to give way to a better world.

As an example, a software consulting firm, Headstorm, had always had an altruistic perspective, aligning their work with the U.N. Sustainable Development Goals, but during the crisis they doubled down. The organization had a specialty in Agricultural Technology and their CEO, Lawrence King, immediately recognized the food supply chain would be of the utmost importance during this crisis. Since then the organization has been working with leaders in the space to bring new solutions, frameworks, and concepts to make them more efficient and to strengthen AgTech for the future.


Optimism = Self Assurance

There’s no executive that welcomes challenges like we are facing today, but this class of leader recognizes good can come from bad. That’s not to say they are unaware, unrealistic or naive. They know the latest statistics and the odds against them, but they have a self-assurance telling them they can find a way. People with self-assurance and an optimistic view believe in their abilities and know they will be able to deliver when they’re needed.


Opportunities To Inspire

The Challenger Executive has a vision for their organization, as many leaders do, but their’s creates excitement. It is palatable and contagious. They can be humble, honest, thought provoking and even confrontational, but they do it in a way that leaves you prepared to walk through a wall for them. In the early stages of the quarantine we saw outreach from Challenger Executives that inspired their organizations and all of us at the same time.

A poignant example of knowing your mission, but acknowledging change is illustrated in a piece written by Religion of Sport, a collective of storytellers founded by Tom Brady, Michael Strahan and Gotham Chopra. Done in the early days of the quarantine, The Other Side of Now, is a voice that resonates.

“There is no returning to a pre-pandemic world – but we also have faith that the world tomorrow will exist. It’s up to us what that world will look like.” Their CEO, Ameeth Sankaran, said those aren’t just words, because it’s driving the organization forward by experimenting with new channels and formats, capturing content differently and redefining their storytelling with their networks, brands and athletes.


Think Different, Operate Different

Steve Jobs celebrated those who “Think Different.” This manifesto made words like “innovation,” “creativity,” “design-think,” and “entrepreneurial” commonplace in boardrooms as executives tried to introduce “different” to their companies. Consultants offered an inoculation in the form of projects and workshops, but it didn’t stick unless there was a leader willing to truly invest in “different.” Challenger Executives are now using this to hire, manage, invest, and run their businesses in a constant state of progress.

Michael Rubin is a guy that would probably be considered a White Knight, but he’s a Challenger Executive showing what happens when you think differently in your efforts to help. The founder of Fanatics could have simply written a check to those in need, but instead he introduced a challenge that looks as if it will become the equivalent of a “billionaire’s #icebucketchallenge.” It’s called the All In Challenge (#allinchallenge) and he’s challenging other high net worth individuals, musicians, actors, sports teams, etc., to create a package and raffle it. The packages are now letting other Challenger Executives like Mark Cuban, Ellen DeGeneres and Kevin Hart show their creativity, too. At this time it has already raised nearly $17MM to feed those in need.


Embrace Irrationality

I remember a time when we would all say, “It makes no sense for us to create a three year plan. It’s all changing too fast and it will be irrelevant in a year.” Everyone shrugged their shoulders and settled back into their quarterly programs and forgot about dreaming of what could be. Then came Amazon…and Netflix…and Uber…and AirBnB…and Tesla…and the Coronvirus. They are aggressive, game changing, rapidly growing, thought to be impossible, and they demand you rethink everything or they will put you down. I don’t want to suggest these tech juggernauts are viruses, but this is no time to stare at quarterly plans. We have to think irrational and act agile.

The author of Embracing Irrationality, Ben Gaddis, has penned what I believe should be required reading for the Challenger Executive. This book can help you create a blueprint for deciding what success can look like, but it’s balanced against a realistic approach for what you will do tomorrow. It’s all based on three simple steps – 1. See the world devoid of constraints, 2. Have an irrational vision, 3. Make one-degree decisions. While Proxxy introduces business management strategies to all our clients, we focus on this approach for the Challenger Executives.


Look Up, Look Forward


I’m pleased to say our Proxxy clients took the necessary measures to ensure company viability and they were able to reach a stable state quickly. They licked their wounds and settled into a state of resolution. They are done worrying, feeling bad, and wondering what is next. This change in our world and in business is fueling them to leverage every one of their Challenger Executive traits.

What about you? Now you have seen things from the Chief of Staff’s seat. Do you see Challenger Executives around you? Are you a Challenger Executive? If so, you can put your remote staff (Part 1) and your Leadership (Part 2) in the “can control” bucket.

The next thing you can control are what you do after reading this…

  • If you are having trouble achieving stability, transferring your business to remote or managing remotely, don’t hesitate to reach out. We are happy to provide counsel during this time at no charge. We just want to help SMB leaders.
  • If you have reached stability and you would like to know what other Challenger Executives are doing today, tomorrow and the day after, please follow me and I’ll share that with you in Part 3 of this series, The Challenger Executive: Part 3 / Welcome to Recovery.
  • If YOU are a Challenger Executive, please direct message me and lets talk. I would love to include you in the third installment of this series and in turn help other SMB leaders.
  • And if you are interested in having a Chief of Staff behind the scenes or working with you and your team you can evaluate the value it would bring you here.
  • One way or another, let’s get connected!


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