The most productive way to develop as a leader

Everybody loves self-improvement. We want to get smarter, network better, be connected, balance our lives, and so on. That’s why we’re such avid consumers of ‘top 10’ lists of things to do to be a more effective, productive, promotable, mindful — you name it — leader. We read all the lists, but we have trouble sticking to the ‘easy steps’ because while we all want the benefits of change, we rarely ever want to do the hard work of change.

But what if we didn’t think of self-improvement as work? What if we thought of it as play — specifically, as playing with our sense of self?

Let’s say an executive we’ll call John lacks empathy in his dealings with people. For example, he’s overly blunt when he gives feedback to others and he’s not a very good listener. Thanks to a recent promotion, he needs to be less of a task-master and more people-oriented. He wants to improve on the leadership skills he’s been told are vital for his future success but, unfortunately, they are alien to him. What can he do?

John has two options. He can work on himself, committing to do everything in his power to change his leadership style from model A to model B. Or he can play with his self-concept by ‘flirting’ with a diverse array of styles and approaches and withholding allegiance to a favored result until he is better informed. The difference between these two approaches is both nuanced and instructive for anyone striving to transform how they lead.

Let’s first imagine John working on himself. The adjectives that come to mind include diligent, serious, thorough, methodical, reasonable, and disciplined. The notion of ‘work’ evokes diligence, efficiency, and duty — focusing on what you should do, especially as others see it, as opposed to what you want to do. I imagine John making a systematic assessment of his strengths and weaknesses, collecting feedback on areas for improvement, setting concrete SMART goals, devising a timetable and strategies for achieving them, possibly engaging a coach psychologist to dig deeper into the root causes of his poor people skills, monitoring his progress, and so on. With a clear end in mind, he proceeds in a logical, step-by-step manner, striving for progress. There is one right answer. Success or failure is the outcome. We judge ourselves.

Now, let’s imagine John being playful with his sense of self. What adjectives come to mind now? The words lively, good-humored, spirited, irreverent, divergent, amused, and full of fun and life now spring to mind. The notion of ‘play’ evokes an element of fantasy and potential — the ‘possible self’, as Stanford psychologist Hazel Markus calls the cacophony of images we all have in our heads for who we might become. I imagine John saying, ‘I have no idea what to do, but let’s just try something and see where this leads me’. If it doesn’t work, he’s free to pivot to something completely different because he isn’t invested in his initial approach. Trial and error takes time, but getting to finish line first isn’t the objective, enjoyment is. Many different and desirable versions of our future self are possible. Learning, not performance is the outcome. We suspend judgement.

Whatever activity you’re engaged in, when you are in ‘work’ mode, you are purposeful: you set goals and objectives, are mindful of your time, and seek efficient resolution. You’re not going to deviate from the straight and narrow. It’s all very serious and not whole lot of fun. Worse, each episode becomes a performance, a test in which you either fail or succeed.

In contrast, no matter what you’re up to, when you’re in ‘play’ mode, your primary drivers are enjoyment and discovery instead of goals and objectives. You’re curious. You lose track of time. You meander. The normal rules of ‘real life’ don’t apply, so you’re free to be inconsistent — you welcome deviation and detour. That’s why play increases the likelihood that you will discover things you might have never thought to look for at the outset.

Much research shows how play fosters creativity and innovation. I’ve found that the same benefits apply when you are playful with your self-concept. Playing with your own notion of yourself is akin to flirting with future possibilities. Like in all forms of play, the journey becomes more important than a pre-set destination. So, we stop evaluating today’s self against an unattainable, heroic, or one-size-fits all ideal of leadership that doesn’t really exist. We also stop trying to will ourselves to ‘commit’ to becoming something we are not even sure we want to be — what Markus calls the ‘feared self’, which is composed of images of negative role models, for example, a former boss who we worry we’ll come to resemble if we stray too far from our base of technical expertise. And, we shift direction, from complying with what other people want us to be to becoming more self-authoring. As a result, when you play, you’re more creative and more open to what you might learn about yourself.

The problem is we don’t often get — or give ourselves — permission to play with our sense of self. As organizational sociologist James March noted in his celebrated elegy to playfulness, The Technology of Foolishness, the very experiences children seek out in play are the ones organizations are designed to avoid: disequilibrium, novelty, and surprise. We equate playfulness with the perpetual dilettante, who dabbles in a great variety of possibilities, never committing to any. We find inconstancy distasteful, so we foreclose on options that seem too far off from today’s ‘authentic self’, without ever giving them a try. This stifles the discontinuous growth that only comes when we surprise ourselves.

Paradoxically, my research finds that often the most productive way to develop as a leader is the most seemingly inefficient. It involves adopting a stance of what I call ‘committed flirtation’, fully embracing new possibilities as if they were plausible and desirable, but limiting our commitment to being that person to the ‘play mode’. I’ve found that committed flirtation frees people like John to do three things that will help him become a better leader:

In ‘pretend’ play, it’s OK to borrow liberally from different sources. A playful attitude would free John from being ‘himself’ as he is today. Play allows him to try out behaviors he has seen in more successful bosses and peers, perhaps stealing different elements of style from each to form his own pastiche, as opposed to clinging to a straight-jacketing sense of authenticity.

Playfulness changes your mind-set from a performance focus to a learning orientation. One of the biggest reasons we don’t stretch beyond our current selves is that we are afraid to suffer a hit to our performance. A playful posture might help John feel less defensive about his old identity — after all, he’s not forever giving up his ‘secret sauce’ and fountain of past success, he’s just practicing his bad swing.

Play generates variety not consistency. By suspending the cardinal rule of unswerving, reliable behavior, it allows our ‘shadow’, as Carl Jung called the unexpressed facets of our nature, fuller expression. John might, for example, sign up for some new projects and extracurricular activities, each a setting in which he’s free to rehearse behaviors that deviate from what people have come to expect of him. He’s not being mercurial; he’s just experimenting.

Psychoanalyst Adam Phillips once said, “People tend to flirt only with serious things — madness, disaster, other people.” Flirting with yourself is a serious endeavor because who we might become is not knowable or predictable at the outset. That’s why it’s as inherently dangerous as it is necessary for growth.