when leaders stumble

by Andrew Simon

When leaders stumble

It seems to me, that leaders stumble more than we like.

Misjudgements, bad calls, harsh words, poor timing, lack of oversight all seem to be common failings amongst many leaders as they grapple with the complexities, difficulties and pressures that come with the demanding role of leadership.

Indeed as I look and reflect on at my own failings as a leader, it’s a bit like looking at the boat of Earnest Hemingway’s old fisherman man, in his Pulitzer Prize winning book of 1952 The old man and the sea, who had a sail for his small boat which looked like the ‘flag of permanent defeat’- a collection of flourbags patched together into what resembled a sail!

It’s quickly worth noting however that there is a difference of course between good leaders who stumble and just bad leadership. Harvard Business School Professor Barbara Kellerman talks about two general kinds of bad leadership. One kind, as meaning ineffective and the other as being unethical. But this is not what I mean by stumbling.

Good leaders who stumble make mistakes that perhaps any other person is typically prone to. The crucial difference however, is that the leader’s error may cast a very long shadow over the organisation and sometimes even beyond.

Leaders therefore are under enormous pressure to not stumble. Yet, they inevitably do.

It could be said that failure and stumbling appear in many cases to be the hallmarks of successful leadership. This paradox is not an attempt to justify stumbling or a recommendation to fail deliberately or to claim some sort of causal relationship. Rather it’s an observation that suggests that when we learn and recover well from failure and from our stumbling, that this often can lead to great insight, transformation and better leadership. Failure can lead to success if handled well.

This transformation of failure into leadership progress is perhaps contingent on several factors:

  1. Courageous followers, peers, colleagues and loved ones who can name and call it when leaders stumble and fail and when they cause hurt.
  2. A humble openness on the part of the leader to face and admit to error.
  3. The ability of the leader to say sorry unreservedly when hurt is caused.
  4. The willingness to reflect on and identify in precise ways what went wrong and to see new meaning and insight.
  5. The courage to face one’s limitations and self-doubt and the disappointment that comes from the realisation of error and hurt caused but to also realistically acknowledge one’s strengths.
  6. The determination and presence to re-focus and move forward with the lessons of failure providing clear signposts and the encouragement of loyal friends providing sustenance.

These and other factors are not to do with just being skillful. Rather, they seem to me, to do with character, the character of the leader and indeed, of those who are led. And “character is not the absence of flaws, but the manner in which we face them”.

This is perhaps the essence of the old fisherman in Hemmingway’s book: that despite defeat and failure, lying exhausted and alone on the beach, the old man picked up his patchwork sail and stood up.


Hemmingway, Earnest (1952) The old man and the sea. Scribner. New York.
Kellerman, Barbara (2004) Bad Leadership. Harvard Business School Press. Boston.
Strom, Mark (2014) Lead with Wisdom. Wiley. Milton, Qld.

This article is dedicated to my courageous colleagues and staff at Yellow Edge who keep me honest and to my loved ones who help me stand up.

Andrew is Chief Executive of Yellow Edge a company focused on inspiring individuals, teams and organisations to greater levels of performance.