On the Relationship between Leadership, Improvisation, and Trust

What can the recent financial trading experience of Sam Bankman-Fried, (a) a 30 year old MIT graduate, with a net worth of $16 billion USD, (b) hailed as a crypto-genius, (c) accused of improperly using billions of dollars of customer funds to prop up his trading firm, and (d) who displayed a cavalier-attitude to his own decision-making: “I’m improvising,” teach us about the relationship between leadership, improvisation, and trust?

Within the world of entertainment we encounter improvisation through what is generally accepted as “improv-comedy.” The game here is that improv-performers receive any statement from the audience with an attitude of “YES, AND...” - “You are from Shah Alam...” (Yes...And) or “Tom Hanks as Colonel Tom Parker...” (Yes...And...). With each statement that is offered, both the performers and the audience are left with a condition of not knowing. The audience does not know what performers will do with statements offered. And neither do the performers. First, performers do not know what statements will be offered. Second, in accepting such statements (YES), performers do not know where they will take any offered statement. It (AND) is “made-up” as the performer speaks. Responses are not scripted. Improv, then, can be viewed as a script with no pre-scribed script. The performer simply goes with the flow of his or her immediate thoughts. The genius and success of “improv-comedy” is not only in what performers do with statements offered (process), but also on the audience’s laughter (result).

Within the context of leadership, what is note-worthy is that the nature of “improv-comedy” is such that it brings us to the world of uncertainty and unpredictability (Let’s call it NK – Not Knowing). If we accept this, then I suggest that the relationship between leadership and improvisation is akin to the relationship between leadership and NK. In the same way that improvisation is a coming together of the familiar and the unfamiliar, leadership is also about paying attention and responding to the unfamiliar (for example, COVID-19) amid all we have come to accept as familiar.

In the financial world, Bankman-Fried chose to improvise trading with an unfamiliar crypto-currency, which is also labeled as “digital gold” bitcoin. This was his “YES.” At the same time, he is also accused of stealing user-funds for his own private interests. This is his alleged AND. So, what can we learn from both his YES and his AND within the context of the question raised in the opening paragraph.

The language of “alleged” and “accused” bring us to an all-too-familiar legal realm - at least in the United (Divided?) States of America. Legal prosecutors and defenders are now charged with the burden of proof: is he guilty or innocent? Legal options in a case like this, are such that it limits us to think in terms of either-or (either innocent or guilty; either right or wrong). It precludes us from thinking (and offering) third, fourth, or fifth possibilities and/or options or choices. It precludes us, for example, from thinking that what is fundamentally at stake, in this case, is trust, or more appropriately, a brokenness of trust. As an investor, will you trust someone like Bankman-Fried with your hard earned money in the future?
Bringing the matter to the law-courts has also created another element of distrust. Many news outlets and the Assistant U.S. Attorney Nicolas Roos, for example, described the bail imposed on Bankman-Fried as “the largest ever” pretrial bond of $250 million USD. In reality, Bankman-Fried paid nothing. Nada. Zero. Instead, his parents promised to pledge their Palo Alto, California, home, rumoured to be worth $4 million as a collateral. The legal courts released Bankman-Fried from custody on something called a personal recognisance bond. It simply involves Bankman-Fried and his parents’ promise to pay the court $250 million if he fails to show up for trial at the appointed time. This has created a new problem. It is well described by a question raised by Colin Desk: “Who could have imagined that the Bahamas would have stricter bail laws for financial fraud than the United States?” Now, the integrity of the “bail-system” within the American legal-system, is raised as a problem. In the context of improv-comedy, perhaps this is indeed laughable! The point to remember is this: familiar solutions to what appears to be familiar problems creates new problems.

Stepping outside of this particular case study, but staying within the context of not knowing, what other responses increase trust?

Within the context and reality of NK, we need to give ourselves and others the permission to say; “I don’t know.” Pretending to know or giving an air of knowing when one does not know, increases distrust and skepticism. It cannot, however, be denied, that senior officials in organisations, including those in higher education, are regarded as “experts,” and as such there is a higher propensity for others to lay the burden of having (all?) the answers on the shoulders of the experts. Acknowledging that “I do not know,” can in fact be freeing in two ways. First, it opens the door for others to be a part of the solution. Second, it distributes leadership across the organisation by enabling others to take responsibility for raising the questions that need to be asked and also for their suggested solutions. In so doing, blaming can be eliminated from the equation.
Our recent experience with the uncertainty and unpredictability of Covid-19, has also raised the challenge of rethinking familiar questions and solutions amid an unfamiliar event. It includes re-thinking outdated approaches like developing a 5-year strategic plan in the middle of a crisis and taking on the challenge of improvising new approaches by going with the flow of unfamiliar and ever-changing unpredictable events. I was personally surprised when I received a phone call requesting my assistance to facilitate a team of senior health officials through a 5-year strategic planning process in the middle of Covid-19. There was a long period of silence when I shared that such a process was simply not appropriate within this Covid-19 context of uncertainty and unpredictability.
Bringing others into the process of improvising rather than planning can be a mark of transparency and clarity. You are transparent about your intentions and clear that you are indeed improvising. In so doing, this could be an opportunity for giving everyone a sense of stability even when organisations and industries are being rocked. This mark of transparency and clarity, led Jonathan Nightingale, cofounder of a management training firm Raw Signal Group to admit: “Even if the world outside is really chaotic, I can understand what my job is if I can trust my colleagues, if I know what I am focused on.”
While trust is hard to define, we deeply know that trust is fundamental in any human relationship. Trust, however, is not blind. I trust you because you have demonstrated that you are worthy of trust and vice versa. In times of uncertainty and unpredictability, there is a greater need to trust that we are all in this together and that we are each attempting to do the “right” thing in ever changing times. Trust is the glue that holds us together. Trust will be our new guiding star. Betrayal of trust will only break us apart and it will lead to chaotic relationships in chaotic times.
Finally, I return to the very title of this short article. Notice, for example, that I use the language of “relationship.” Leadership, as it was displayed in James McGregor Burns’s volume on Leadership, is a relationship between those in positions of administrative authority and their constituents. Since the 1950s, however, one familiar understanding of leadership is captured under the term “influence.” In this vein, leadership is generally accepted as a process whereby an individual influences a group to achieve a common goal. The focus of this familiar definition is on the “individual” - the “leader.” It is a person or leader-centric definition of leadership. Today, in the face of seismic shifts in the structure of work, perhaps we need to re-think leadership from the perspective of relationships. In so doing, we need to be mindful of what Martin Buber notes in his book I and Thou, relationship is reciprocity, and any unilateral relationship, for example as A influencing B and/or C, only dilutes its meaning. It is to accept reciprocity and co-influencing as the new way of managing and leading. Unlike any one individual influencing others to achieve a common goal, leadership as a relationship organises itself around the notion of a collection of individuals connecting, interacting and co-influencing each other in their joint ventures. The quality of such a relationship is what is really at stake because it leads (or not) to conditions of trust.

How then can we re-organise ourselves in our chaotic, unpredictable and uncertain times?

First, we need to acknowledge that improvisation emerges as an option when we are faced with a new scenario. And, for a master family therapist like Salvador Minuchin, “each new scenario is an experiment in living – it requires improvisation, reading audience reactions, and experimenting once again.” In reality, there are variables beyond our comprehension. Recall, for example, our experience with the Covid-19 pandemic. Hence our need to improvise, deal with the unfamiliar in unfamiliar ways, and adapt. And each subsequent adaptation which cannot anticipate all variables, requires further experimentation and improvisation – and the beat goes on, and on, and on. You get the picture!

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Second, we need to be aware of the delicate balance between stability and change. Here’s the ‘thing’ - we change to keep things stable and at the same time stability without change is simply boring. Our world is constantly evolving – sometimes at a rate faster than we would like it to be. In a curious way, stability is an illusion – but a necessary illusion. Within this context we need to become familiar with the notion that our decisions cannot and must not be ‘final decisions.’

Third, I suggest that we learn to stop doing what we are doing – just for a moment. Give yourselves permission to take a step back and reflect on what you are doing. Begin with this question:

What am I doing, or what are we doing, that is getting us the results we are getting?

This question does not focus on what you or I are not doing. Instead, it is a question that focuses on what we are doing. It is to humbly accept that you and I are perfectly aligned for the results (good or bad) we are getting because of what we are doing.

Fourth, in this reflective space, give yourselves permission to laugh. This does not mean that your work is not serious. You are doing serious work. You are doing good work. At the same time, in dealing with the unfamiliar, we can expect things to go sideways. It is not the end of the world. Developing a sense of humour allows you (and I) to bring some levity not only in terms of our work but also in our relationship with our colleagues. So, resist taking yourself so seriously. Laugh with and not at each other, as you learn from all that may go sideways amid unpredictability and uncertainty.

Fifth, practice the art of listening. In listening, we learn to silence all that is familiar to us. It is not accidental that ‘silent’ and ‘listen’ are comprised of the same alphabets – mixed differently. In listening, we learn to silence the noise of familiarity. In listening, we open ourselves instead to hearing what is being asked of us in unfamiliar times - in times of chaos, unpredictability, and uncertainty. Have you been in a situation where you truly felt heard? Did such a feeling not lead you to trust the other more than you have before? Yes, that is the power of listening.

Finally, in times of uncertainty, fear and anxiety is high. People feel vulnerable. In times like this, be kind to each other believing, as the poet Khalil Gibran notes:,