Ok it’s a little dramatic as a heading, but stick with me here.

Last week I explored Fail Fast. Well this week we’re talking about Fail Big, and directors and senior leaders having the courage to ask the essential question.

If you have a bold and challenging strategy and vision, it won’t be a walk in the park to deliver it, so it is likely at some point you will face into a very tough question. I’m not talking about a slight pivot or iteration here. But a full on, do we need to stop, regroup and start over kind of question.

The question: At what point do we recognise that success is not a realistic outcome?

This question can apply at the technology project level or at the business strategy level. Neither are easy places to be. In an ideal situation (let’s face it, none of this is ideal if you’re facing this), when this question is asked it should be met with stunned and highly tense silence, that paves the way for a sober exploration of the options. But often this is not the reaction. Sometimes it is met with a dismissive response, sometimes anger, and sometimes the question is completely ignored. None of these reactions is unexpected, nor do they negate the criticality of the question.

In my experience the hardest part about this question, is not about the technical challenges that might exist and needing to understand them, but about getting above the fray and having the courage to ask the question at all. This makes it both an ideal and essential question for directors to consider.

There has been much research over many years that documents the high failure rates of large programs. A simple google search will land you at many well researched reports that show that this is a systemic issue – not limited to industry, geography or recency. The issues have a degree of commonality, yet projects continue to fail and the losses mount. For a significant portion of these projects, I guarantee that there are many situations where decision makers’ intuition was writhing in response to challenges. But the statistics on project and product failures suggest that irrespective of active intuition, this question was not asked or explored as early, as deeply or as often as it should have been. Where it is asked, it is often not taken seriously, or it is shut down fast by leaders who are not prepared to contemplate the possibility of failure.

Never underestimate the vested interests and emotions that surround strategic challenges like this. There is a lot at stake when big programs or strategies fail and starting over is the outcome. It takes greater courage, strength and determination to admit when something is doomed than it does to continue. But just because failure may be unthinkable, it is not impossible, and directors and senior leaders have a responsibility to face into the possibility of failure and have a robust debate about the options, which must include the option to stop and start over.

Exercising courage does not stop at asking the question. Courage is also required to create a safe place for exploring the question if someone else asks it, and to insist on the conversation when the question is dismissed. And asking the question on more than one occasion if the decision is made to stay on course, yet problems continue.

Having asked the question, a robust consideration of it should lead to defining the line in the sand: how much further should we continue down this path? It is critical that there is clarity on your line in the sand: what does it look like, and when do you know when you’re approaching it. These are serious, complex questions and unlikely to be answered in one conversation.

To finish up, I wanted to share with you two interesting articles that you might enjoy.

The first article from the Atlantic tells the story of how on the day the iPhone launched, Google immediately recognised that Apple had changed the game and they needed to start over.

The second article in the New Yorker, tells the story of the very different response from Blackberry, which was to dig in.

It would be fascinating to have been a fly in the wall in the boardrooms of each of these companies as they contemplated their responses.