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Sometimes life is simple. Sometimes it’s complicated. And sometimes it’s complex. While leadership is always needed, complex situations require it at the highest level. Mediocre leadership in such cases will result in failure. Regrettably, we are not always cognizant of the differences between these three types of situations, underestimate the challenges facing us and bring the wrong tools to resolve the problems or exploit the opportunities.

General Stanley McChrystal

General Stanley McChrystal, former commander of our forces in Afghanistan, in his recent book, Team of Teams: New Rules of Engagement For a Complex World (2015), argues that organizations need to recognize that the world is a complex environment and adjust their “game” to reflect this. He came to this realization while he was commanding the Joint Special Operations Task Force in Iraq (2003-08). Despite having the best trained soldiers in the world, and racking up quite a record of successful operations against Al Qaeda in Iraq (AQI), they weren’t making any real headway in changing the overall strategic situation his men were confronting. It was then that McChrystal and his team realized that they were functioning as if they were in a complicated environment, while in fact they were in a complex one. Only then did they begin to meet with strategic, not just tactical, success. (Unfortunately, much of that success has been reversed since U.S. forces have withdrawn from Iraq.)

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What is the difference? Complicated situations have multiple parts and often multiple steps that need to be followed. But they are interconnected in a relatively simple and predictable way. A pilot who follows a checklist to prepare his aircraft for takeoff is performing a complicated task. There might be many things to do but they ultimately can be reduced to a series of simple “A leads to B relationships” and A will always (unless there is a problem) lead to B, which will lead to C.

Complex things such as living organisms, ecosystems and stock markets “have a diverse array of connected elements that interact frequently. Because of this density of linkages, complex systems fluctuate extremely and exhibit unpredictability. In the case of weather, a small disturbance in one place can trigger a series of responses that build into unexpected and severe outcomes in another place because of the billions of tiny interactions that link the origin and the outcome” (p.56). According to this definition, the flight attendants on an aircraft work in a complex environment. Although they have their routines, they cannot predict what the actual tenor of the flight will be. A single upset passenger can create a disturbance that will impact everyone’s flight. It’s impossible to know at the outset.

It becomes evident that one who leads people by definition operates in a complex environment. He thus needs the appropriate skill set and the right personality to get everyone rowing in the same direction and to the right destination. The Torah’s description of Yehoshua’s appropriateness to succeed Moshe as leader in this week’s parsha attests to his ability to lead in a complex environment. This would prove to be a very valuable advantage when he led twelve different tribes in war, conquest and land division, all in an unpredictable environment. It’s hard to imagine a more complex context.

After hearing conclusively that he would not be leading Bnei Yisrael into the land of Canaan, Moshe immediately focuses on a succession plan. Referring to Hashem as the “G-d of spirits” (ruchot in Hebrew), Moshe implores Him to appoint a person capable of leading Bnei Yisrael so that they should not be like a flock of sheep without a shepherd (Bamidbar 27:16-17). Hashem responds that he should appoint Yehoshua, a man who has spirit, ruach in him. Rashi comments that the various uses of the word spirit to describe both G-d as well as Yehoshua point to a trait needed by a future leader. By referring to Hashem as the G-d of spirits, Moshe was explaining that since G-d created people with different spirits (i.e., personalities), He must appoint a person who is able to deal with each person on his or her own level and in his or her own way. G-d responds that Yehoshua is the perfect candidate, because he is a man of spirit and as such has a deep understanding of human nature and the ability to deal with each person according to his or her particular disposition.

The Or Hachaim Hakadosh (27:16) adds an interesting dimension to this discussion. The challenge in dealing with a variety of people is not just that their personalities are different. People make decisions based on their specific preferences, inclinations, and biases which will lead to even more pronounced and stark differences between them as time proceeds. In essence, the Or Hachaim is alerting us to the complexities involved in dealing with people.

What makes leadership extra challenging in such situations is that in addition to dealing with all sorts of people, who themselves develop in unpredictable ways, the leader must deal with them all at the same time, even as these people’s decisions impact the actions of others. Only a person with a truly deep spirit is capable of leading in such an environment. Hashem told Moshe that Yehoshua was that man and that this ability was necessary to lead Bnei Yisrael in the future.

To succeed in a complex environment a leader must be alert to even subtle changes in the situation he or she is dealing with that could result in major consequences. He must also have a thorough understanding of how people interact. He must then be flexible and adaptable since he can never know how things will play out. At most he can project possibilities to serve as guideposts. But the simple realization that they are guideposts and not train tracks can make all the difference in the world.

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Rabbi Dr. David Hertzberg is the principal of the Yeshivah of Flatbush Middle Division. He is also an adjunct assistant professor of History at Touro College. Comments can be emailed to him at [email protected].