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Two Lessons Learnt in Pursuit of Constructive Challenge

Reading Time: 7 minutes

“Your commercials suck… The iPad is revolutionizing the world, and we need something big. You’ve given me small sh*t.”

Ouch.

That’s what Steve Jobs reportedly told the creative head of TBWA/ Media Arts in the run up to the IPad launch. Challenge? Yes. Constructive? Probably not.

Two little words that are so easy to say aren’t they? As an adviser I’ve often been asked to provide Constructive Challenge, or been in situations where it is being encouraged. It’s an easy little phrase to say, but so hard to do well. It sort of conjures this ideal of a couple of insightful, wise, well chosen, firm but balanced remarks that challenge the status quo but leave everyone feeling better and wiser. Is that how it tends to work in practice?! I have certainly been challenged un-constructively, and almost certaintly have done the same to others (sorry!) but I’ve also learnt a thing or two over the years about what it takes to really get this important skill right.

I know it when I see it, but I can’t define it exactly.

One thorny problem. We have become accustomed to know that constructive challenge is a good thing without the tools to put it into practice or the understanding of how difficult it actually is given we are more or less wired against it through ego. This leads to all sorts of problems not least of which is the fact that in many situations what people want isn’t really constructive challenge, they want the appearance of constructive challenge, so that they can feel good process was followed without having to actually change much. It’s important to try and recognise if you are in this situation, the first set of lessons below can still help.

“Never have your ego so close to your position that if your position falls, your ego goes with it.”

Sound advice from Colin Powell, but often un-heeded by overconfident people in positions of authority, which presents a big obstacle for those tasked with providing challenge to them.

What are my top lessons?

1. In the moment

Real genuine constructive challenge really rests on a lot of groundwork in advance to build trust and relationships, and find the right ways of working. So there are limits to what’s achievable if you are thrust straight into a situation where you’re being asked to provide it. But there are always things that are important to bear in mind in the moment, and some of these are also useful if you are being put into a constructive challenge situation tomorrow without any longer timeframe to lay the groundwork, try these tactics:

Bon Iger (Disney CEO) has some good advice:

Never start out negatively and never start out small. I’ve found that often people will focus on little details as a way of masking lack of clear, coherent big thoughts. If you start petty, you seem petty. And if the big picture is a mess the small things don’t matter anyway.

Bob Iger – Ride of a Lifetime

But really, the fact of the matter is that true constructive challenge is months or years in the making and you can’t expect to just turn up cold and get there straight away. More likely you’ll end up watering down your thoughts or hedging language to the point where it isn’t clear what you are saying, or resorting to passive aggresivity.

2. The Real Deal

True constructive challenge rests on two words: psychological safety. This is the shared belief and understanding that no-one will be punished, criticised or marginalised through challenges to the status quo. The problem is that your standard quarterly trustee meeting is not set up to really be psychologically safe – the stakes are just too high after months of work in the office, hundreds of pages of analysis and papers. There is often just too much ego and identity bound up into the proposals to avoid the perception that challenge to the ideas amounts to existential criticism to the individual and their competence or identity . And the more people are involved in the conversation, the harder it is to bring up uncomfortable truths. So we need to get radical with some suggestions here, and a lot of groundwork is needed.

Source: Ray Dalio Principles

Ray Dalio has popularised a lot of the ideas around “thoughtful disagreement” – which is closely related to constructive challenge in his book Principles and his further writing. I particularly found a podcast discussion between Reid Hoffman and Ray interesting and helpful on this point.

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