Copperbox Leadership

Executives are the strategic thinkers, talent champions, and company visionaries…Or are they?

Leaders are always a work in progress. Ever unfinished. They’re in a constant state of ‘becoming.’ And that’s a good thing. The moment a leader thinks that they’ve arrived is a sure sign they’ve already started to fall behind.

Becoming a world-class executive is hard work. That was never made more clear to us than when we were running executives through leadership simulations at our prior firm. We’d create scenarios based on a fictitious company, throw difficult bosses, colleagues and complex business scenarios at them, and essentially see what happened next. We had a front-row seat to executive performance, gaining insights on what would normally take years to understand about a person. We watched how these leaders responded in real-time and recorded their skill levels on a range of leadership competencies using a carefully calibrated rating system. It was fascinating to be play-acting and evaluating these leaders at the same time. Like both watching and being in the movie. The only thing missing was the popcorn.

What did we learn putting these senior business leaders through their paces?

Through our observations of over 100 executives, we found that most of the leaders we assessed were average, a few were terrible, and fewer still were truly exceptional. The normal distribution (‘bell’) curve was well at work here just as it is in many aspects of human performance. While virtually all of these executives had achieved some level of success, patterns emerged around where they typically displayed strengths and where the gaps were. And the gaps, as we found, aren’t what you’d expect.

Senior leaders will unlikely improve their ability to think strategically

This may seem surprising to read, but notice we said senior leaders. We firmly believe in the growth mindset, made well-known by the seminal research of Stanford University psychologist Carol Dweck. People have the capacity to grow and improve. Strategic thinking is both an innate ability and a learned skill. While underlying strategic ability is difficult to assess, tools such as the Raven’s Advanced Progressive Matrices™ , can provide a glimpse into an executive’s strategic thinking ability. However, perceptions of which leaders are strategic within a company are usually just that – perceptions.

If strategic thinking is at least partially a learned skill, why can’t senior leaders close the strategic thinking gap? Improving strategic thinking requires much more than just reading an article (insert irony here). An executive must not only have a strong motivation to improve, but also enough of a runway (i.e. time left in a career) that will allow the executive to implement practices and gain experiences that could elevate their strategic thinking ability.

We saw that about two thirds of senior leaders (i.e. at the VP and up level) scored below average on their ability to think strategically, even though these leaders were at higher levels within their organizations. One would expect these individuals to be able to easily review the fictional business situations and confidently put together business plans that incorporated both short- and long-term strategic initiatives for their division. We realized this wasn’t the case. Instead of displaying a honed strategic mindset, we saw that the majority of these leaders still took a fairly tactical approach, and largely thought about their businesses through a narrow functional lens. While about a quarter created strategic plans for their divisions that would not only drive results forward in the short-term but also in the long-term, the majority did not and focused solely on those tactical steps that would lead to immediate change. When these leaders received requests for their division, most simply accepted or denied the requests and moved on. Only about a third demonstrated thinking around how they could tie requests together to develop more holistic solutions.

Depending on their level (e.g. director, vice president or C-level), executives ‘express’ or display leadership competencies differently. The concept of ‘court vision’ in basketball draws an interesting parallel to the competency of strategic thinking. In Seeing the court like the great ones, Tom Farrey, Executive Director of Sports and Society at the Aspen Institute and former ESPN writer, defines court vision as “the ability to anticipate what will happen next when bodies are in motion and split-second decisions must be made.” Much like the way leaders express competencies uniquely at different levels, a basketball player with strong court vision looks distinctly different at each level of the game (see Figure 1 below).

Figure 1 – Court Vision at Different Levels of Play

Graphic of court vision at different levels of play

The same is true for business leaders. What strategic mindset should look like as a front-line leader varies significantly compared to what it should look like for a mid-level or senior leader. A well-developed sense of court vision in basketball is like having a sharp strategic mindset for a corporate executive – it sets you apart from the rest. Despite some controversies during his playing career, Jason Kidd was known for his strong sense of court vision and this helped him become a phenomenal playmaker. Fellow former NBA player Steve Nash and WNBA players Sue Bird and Courtney Vandersloot have also been known for their exceptional court vision. As Tyler Costen of PGC Basketball puts it – “If you only look straight ahead, you’re just playing the game.” It’s a reasonable belief that all elite basketball players have good court vision. Much in the same way, you may think that all seasoned leaders have strong strategic mindsets. But as we’ve discovered through watching these leaders in action, many do not.


Most senior leaders lack a well-defined talent POV

How many leaders you’ve worked with were truly passionate about talent development? They are likely ahead of the talent game as many executives don’t bring that passion for growing the people they lead. Even those that have a heart for developing their team members typically only do so at the individual level, instead of thinking of talent as a system, how talent flows throughout the organization to optimize employee engagement and company performance. Or it’s exactly the opposite – leaders take a systems view of talent, yet fail to personally take the time to invest in developing their team and the leaders below them.

Developing oneself is difficult enough. By the time you reach a mid-level leadership role, you’ve largely taken advantage of all the low hanging development opportunities available to you. What’s left is all the hard stuff, the leadership skills that take a concerted effort to even slightly move the needle on. Becoming a better leader is hard work. When leaders must also focus on developing their people on top of that, it becomes overwhelming and frequently gets pushed to the side for what they consider more pressing priorities.

We have found that many leaders fail to position challenging development opportunities as precisely that – opportunities. Instead of going into development conversations energized to afford their people opportunities to grow, they view challenging projects and working with difficult people as tough sells and position these stretch assignments as “have to’s” instead of “get to’s.” They prefer to put talent development on HR’s plate or leave their employees to navigate their development on their own. In Building a Game-Changing Talent Strategy, a team of researchers from MIT Sloan, Harvard Business School and Accenture make a convincing case for active talent management – “Game-changing leaders not only excel at articulating the vital importance of talent management but also are heavily engaged in their companies’ actual practices.”

We saw this ring true during our time running executive simulations. Very few leaders were able to develop a talent plan that was fully fleshed out and looked at talent on both an individual and systems level. About two-thirds of the leaders we assessed only had a handful of ideas for how to develop their people and either took one view or the other as opposed to incorporating both. About half of leaders felt that talent development was a true priority in their fictitious organization. Meanwhile, the other half considered talent as an issue to be addressed once other priorities were taken care of, and therefore, pushed it out. About a third saw the importance of being directly involved in championing these efforts and were able to articulate the impact that talent had on business results, while the others primarily felt it was up to HR to push these initiatives forward. With most of the executives scoring as average or just below average on developing talent, it became abundantly clear that very few leaders had a strong talent POV and were able to communicate that as part of a cohesive plan.

We recently spoke to a very talented HR director whose company has just brought on a new CHRO. This director was excited to be working for and with his new boss, as she has widely been reputed to be a “CHRO Maker.” She is committed to developing the leaders under her, and a number have gone on to be successful CHROs themselves at other companies. Smart, high caliber professionals gravitate towards these types of leaders, who are committed to talent development and understand what that uniquely means for each person and for the organization.

Let’s head back onto the court. As a coach, it’s easy to focus on just developing your one or two best players. You turn to these players when the stakes are highest, so a natural tendency would be to focus all your time and energy on making them better. What if, instead, you thought of your team’s development through a bigger picture lens? What could your people achieve collectively if you developed your team in its entirety – helping individuals build their capability and improving how well they all work together? Michael Jordan couldn’t have won three-straight NBA championships (’96-’98) without Scottie Pippen and Dennis Rodman. But players such as Steve Kerr, a Bull’s shooting guard during that three-season run, who has the highest career three-point percentage (45.4%) in NBA history, played a quieter but critical role on those championship teams. Truly great leaders see the talent they have in front of them and understand the need to focus on their key players, their role players and the team as a whole.

Figure 2 – Regulation size NBA court dimensions

NBA Court regulation diagram


Few senior leaders are clear about how to align their teams with their company’s vision and mission.

You might think that leaders at the highest levels within organizations would be clear about what drives them, clear about what they see their ‘highest and best use’ to be, and clear about how they want to positively impact the people around them. However, we found that very few leaders can articulate their core purpose and how it connects to their company’s purpose, that is, their reason for existing. Yet the ability to communicate one’s core purpose is the first step in being able to align one’s team round the company’s vision, mission and values. If you are unclear about your purpose in the company, then how will you be able to get your team to understand theirs?

In The Aligned Organization, McKinsey stresses the importance of communicating the organization’s vision to employees to keep them motivated. The firm found that “when people understand and are excited about the direction their company is taking, the company’s earnings margin is twice as likely to be above the median.” Why then are so few leaders able to galvanize their people to move towards that bright future? Many executives still define leadership as their specific role – the responsibilities they have to fulfill and the targets they have to meet – because failing to do so means they will, to put it politely, get their asses fired. They frequently don’t take the time to ask themselves how what they do aligns with the company’s vision, let alone think about how this applies to their teams. This failure to “draw the red thread” between the value of people’s roles and the organization’s vision renders their people less effective and less motivated, which diminishes their ability to think more strategically in the future.

Of the leaders we assessed, about half communicated that requests sent in by fictitious direct reports aligned with the company’s vision and the direction the company wanted to move in. However, only about a quarter of them communicated what it was about these requests that aligned with this vision. The other three quarters failed to communicate the ‘why’ to their employees. We also observed that only about a third of these leaders were able to align their teams around shared issues and operational execution, and not many of them were able to do it consistently throughout the simulation. While half of the leaders seemed to have a fair understanding of the company’s vision and mission, very few seemed to have a clear idea of how to drive the vision and mission through their day-to-day work and that of their teams.

Let’s step back out onto the court one last time. Pro basketball players are all working towards making it to the postseason and winning the playoffs, but some of the best players and teams have already triumphed on the sport’s biggest stage. Their coaches understand that they need to paint a unique vision that motivates their team to get back to that spotlight. But how do those with a championship ring or two keep themselves and their teammates focused for the next season? What powers the team’s vision to get to the playoffs are individual motivations, goals, and aspirations – desired outcomes they have for themselves and those that they have for their team. By understanding the personal meaning-making of each player, the key role everyone plays, and supporting their teammates in the pursuit of well-aligned individual and shared goals, coaches and players alike can keep the team aspiring for that shared glory.

Figure 3 – Toronto Raptors 2019 NBA Championship Ring

Toronto Raptors 2019 NBA Championship Ring

Pro teams have clear performance benchmarks year after year – it starts with winning their division, making it to the postseason, and from there, attempting to win through the playoffs, before ultimately making it to the finals to secure their destiny as champions. The path for executive teams is harder to define. It’s more challenging to measure their performance when it isn’t as cut and dry as ‘wins’ and ‘losses.’ Without these clear success markers, it can be more difficult to keep these teams motivated, therefore that much more important for these corporate athletes and the ‘coaches’ that lead them to keep that personal and team connection to the vision clearly in sight.

Hundreds of hours spent assessing executives have shown us that the skills of strategic thinking, talent development, and aligning to company vision are often lacking in senior leaders, yet these are some of the skills most needed to drive organizational outcomes. As you assess your own career and what it takes to be a world-class business leader, consider what investment you will need to make in time and effort to develop a strong command of these indispensable leadership competencies. You know very well that the ‘playing season’ never ends, the competition will be fierce and your team needs you. So lace up and we’ll see you on the court.

Sue Bird with the Seattle Storm

Sue Bird (far right) winning one of her three WBNA championships with the Seattle Storm.

Becoming a world-class executive is hard work. So why don’t we see experienced business leaders focusing more on the skills that matter? We assessed over 100 senior executives and the results, as we found, aren’t what you’d expect. #businessleaders #leadership #basketball #strategicthinking

Wayland K. Lum is the Founder and Managing Director of Copperbox, an Austin-based leadership advisory and development firm focused on accelerating leadership wisdom for the modern leader. You can learn about Wayland’s work with leaders at, and connect with him at

Madison Laskarzewski is a Consultant at Copperbox, focused on creating custom leadership experiences, tools and thinking that advance and develop the modern leader. She also manages Copperbox’s social media and content marketing efforts.

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