Two Lessons Learnt in Pursuit of Constructive Challenge

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


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:

  • Sit next to them (the party on the receiving end of the challenge). Both physically in the room and metaphorically (frame your speech as if you are working together not in opposition).
  • Listen. And be seen to listen. Summarise their premise, assumptions and conclusions back. Build and show empathy – that you see things from their viewpoint.
  • Understand the psychology at play. Powerful forces are likely to be in play here: ego, identity and beliefs are all likely to be bound up in someone’s ideas and the work they have produced. If you can understand this, you might stand a chance of avoiding triggering a sense that you are criticising their identity or deeply-held beliefs while challenging the work (this is hard though, and it might not be possible, especially without knowing the individuals well).
  • Understand the incentives at play. We are deeply wired to respond to incentives whether consciously or not. Fear, status are extremely powerful drivers but often hard to spot in others. So always think – who has the incentive to preserve vs change the status quo, who is looking to maintain their existing status in the hierarchy and who is looking/needs to increase their standing. Who is fearful of what.
  • Understand the personalities at play. Even if you don’t know people well, a basic knowledge of the classic personality types can be hugely enlightening in understanding where people are coming from and how best to approach them. Alignment can never be taken for granted as we are all “wired” so differently.
  • Think about body language. No leg crossing, arm crossing, or jaw setting. Hands visible and palm up on the table, get rid of that laptop sitting like a defensive wall on the table infront of you.
  • Avoid using jargon in discussions . Jargon often signals in/out membership of the “in the know” group which may alienate and not go down well.
  • Aim for curiosity. “Help me understand what I’m not seeing here”
  • Aim for humility – really convince yourself that you genuinely might be wrong, and open your thinking to other perspectives. Frame your language as such.
  • Depersonalise. Don’t frame in terms of “your idea”, “my idea”
  • Separate beliefs, assumptions and implementation. If you want to challenge and speak up and say that you would have arrived at a different answer, be prepared to think through whether this arose from a difference in underlying beliefs, a difference in assumptions in designing the solution, or an implementation detail of how the solution was done. Knowing which of these “levels” the conversation is at is really helpful to lay out to frame the debate.
  • Look to facilitators. To make this work, you do need to be able to “hold the tension” around the meeting room table a little. Not just have one side either cave or say “let me take it away” and then move on. Ideally the discussion swirls around a little coming at the point from different sides giving both sides time to state and explore their viewpoint. This tends to be only possible with a good facilitator (or chair) who can manage the discussion and balance up the tension.
  • Use humour well. Inject a little humour and levity if at all possible – can lighten the mood and diffuse any potential confrontational atmosphere which can keep things moving along. I’ve seen this done really well by certain board chairs at just the right moment (not detracting from the seriousness of the debate, but a well judged comment can lighten tone and relax people).

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.

  • Build relationships. Spend time, eat dinner, drink, play games, socialise. These things matter and you really need all parties to be on a solid relationship footing for this to work, which is why it is so rare in business. Ray Dalio calls this “getting in sync”.
Source: Ray Dalio Principles
  • Lower the stakes. You need to get away from the idea of the big bang trustee board meeting where 3 months of work and ideas come flooding out to praise, criticsim and (hopefully) challenge in front of everyone sat round the big boardroom table. It just won’t work.
  • Disrupt your working model. To do this break the process up with more frequent, and earlier meetings of the key parties while ideas are still in formation. This will create a better environment. We can learn a lot from the tech industry here who tend to employ much more dynamic collaboration techniques compared to the standard quarterly board meeting.
  • Take roles. In some of these earlier working meetings assign particular roles such as red team/devil’s advocate. I have even seen particular meetings framed solely around receiving challenge to ideas early on in the process. If this is expected upfront, and people are accustomed to it will be less threatening and a bit of humour may even develop around it.
  • Work through from first principles learn to love the whiteboard. Often the 100-page slide deck packed with data is a bit of a defense barrier against criticism and perceived attack. Early on in a process you should be able to work through different ideas from first principles on a whiteboard to solidify the key arguments and logic and expose them for discussion. At the end of it you should probably be able to summarise any proposal on a maximum of two sides of A4 (which is what Jef Bezos famously insists on at Amazon meetings).

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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