As the world becomes less certain, leaders must learn from the unpredictability, in order to sustain success. Coaching can role model this

By Lindsay Wittenberg


Our world seems to become more unpredictable with every passing day. Standing for, or up for, a value, an approach, a philosophy or an initiative is thus becoming increasingly complex. It looks to me harder for leaders to make well-founded, courageous judgments and decisions because the environment is becoming more complex, masked by simple or simplistic right-or-wrong messaging.

Yet our organisations, and we as individuals, succeed most sustainably when we learn consistently from complexity, when we see challenges in their systemic context, when we set our sights on our direction rather than our destination (see, for example, Berger and Johnson, 2015), when we value being wrong, when we let go of control and consistently try things out to create more learning.

That implies experimenting, which brings the risk of failing (and being seen to fail), being seen as vulnerable or not in control of the answer, not knowing, looking incompetent, stepping outside the tribe’s habitual practice or beliefs, being isolated or different, sacrificing relationships and safety, and the risk of a body blow to a career.

However, not experimenting can imply a worse risk: that of not innovating or not bringing in fresh or diverse thinking, and therefore not learning, which can threaten the survival of a project or even an organisation.

Leaders then, need courage to step into what’s risky, unknown or uncertain, unpredictable or unclear. It seems to me that as a coach I need to be a role model for that courage. I’ve been offering clients the kind of thinking that resources me to be courageous, and experimenting with its value for them.

Three sources of my courage have proven useful for clients: first, tuning in to my values – to what matters to me to the point of passionate indignation when it’s not there (integrity features prominently for me, as do behaving with humanity and compassion, acknowledging people as individual human beings, humility, taking responsibility and openness to learning). Being sufficiently exercised when my values are crossed gives me the courage to, for example, speak out.

Second, the discipline to examine my assumptions about the negative consequences I imagine might follow from a particular intervention: when – in the style of Nancy Kline ( – I contemplate a more liberating true assumption rather than the limiting one, the negative emotional charge seems to leak away, and the courage I need can appear of its own accord.

Third, contemplating how I would feel – and how at peace I would be with myself and those who matter to me – if I colluded and didn’t act on whatever it is I know, intuit or suspect is ‘wrong’, so I’m able to offer myself the freedom to act and be honest with myself and others.

So there’s courage that arises of its own accord because it’s deeply rooted in passionately held values, and courage that’s elicited in a more cognitive or rational way. I’ve learnt that both need carefully nurturing.



  • It’s harder for leaders to make courageous decisions in a more complex environment
  •  We succeed most sustainably when we learn from complexity and experiment
  • Experimenting carries risk – and leaders need courage to step into what’s risky
  • Three sources of courage can help: tuning in to values, examining assumptions and contemplating failing to act
  • Courage can arise of its own accord or can be elicited cognitively



  • J G Berger and K Johnson, Simple Habits for Complex Times: Powerful Practices for Leaders, Stanford University Press, 2015
  • Lindsay Wittenberg is director of Lindsay Wittenberg Ltd. She is an executive coach who specialises in authentic leadership, career development and
    cross-cultural coaching