I recently facilitated a strategy day for a large not-for-profit, which ended in a strange way.
Everyone was happy with where we landed; we’d narrowed down nine good options to the four great options that would be taken further.
Then the lead executive stopped proceedings, and said:

“It’s great that we’re aligned and happy, but there’s also value in the ‘No’ voice. Can we each go around and talk about what our ‘No’ would be?”

Eventually, everyone shared their reservations.
Nothing major, a collection of things that needed to be named; questions over how much time was allocated for testing, budget concerns, implementation details, and some scepticism over feasibility.
Afterwards, we recapped the positives and next steps, yet there was no lingering negativity. Instead, we were all happier for having discussed the negatives.

This is a great idea, with the power to identify disasters before they occur, and the chance to ensure all ideas get put forward - even if they’re uncomfortable.

It’s also the domain of jerks, who see this as grounds to be a complete ass in the name of “helping”.
It turns out, criticism is like fire – when harnessed, it is a wonderful tool, but if control is lost it can ruin everything.

Devil’s Advocates and Black Hats
Playing Devil’s Advocate is intriguing, a mixture of creativity and analysis.
Unfortunately, as Seth Godin said: “The Devil doesn’t need more advocates”

Most organisations are designed to resist change.
It’s so hard to try new things, or improve something that is still working.
So when some smartass comes in claiming to “Just want to play Devil’s Advocate”, it’s usually code for “I’m going to publicly dump all over your idea”
What we really need is more people committed to improving ideas.

Edward De Bono coined the term Black Hat Thinking, but in the context of a much wider variety of Thinking Hats.
Sadly, most people who enjoy the Black Hat don’t then want to try a more optimistic perspective.
The Black Hat isn’t about being hyper-critical.
It’s useful alongside the other viewpoints, all of which are geared towards making something work.

Ante Mortem
This is the subtle distinction with an Ante Mortem – predicting the cause of death ahead of time. By identifying what could knock over an idea, we discover areas that can be strengthened to increase our chances of survival.

That’s the incentive – the short term gloom of negativity, in exchange for a healthier, resilient idea.
For example, we may use sensitivity testing on the financials to highlight the weakest points.
e.g. “If we lose just two large customers, our whole operation falls over”
or “A 5% increase in costs destroys our margins”

That information is only useful if we then begin planning a way to increase our retention rates, or find creative ways to lock in our costs.

Gathering Objections
One interesting element is the way this executive proactively sought out objections.
This is clever for two reasons: the idea side, and the human side.

Firstly, this benefits the idea.
If there’s a fatal flaw, the safest and cheapest place to discover it is in a boardroom, rather than through a painful and costly failure.
Side note: It’s why I’m bewildered by people who say these strategy meetings are too expensive – building a doomed business will cost 50x more – both in terms of dollars and reputation.

Secondly, this respects the people in the room.
Make no mistake, an objection that doesn’t get aired is still an objection, and will bubble up at some point.
Worse still, the objection will be raised when you’re not in the room.
Silence is not consensus.

Patrick Lencioni has a great solution for this – everyone is given a safe opportunity to raise their concerns, and the leader takes them all on board.
A careful decision is made, and then every single person commits to the vision.
This prevents pouting, sulking and team members undermining the new project.

Same Team
The vital ingredient here is trust.
Trust reminds the person giving the feedback that they’re helping by saying something unpopular, and that they won’t be blamed for speaking the truth.
Trust reminds the person receiving the feedback that they’re not being judged as a person, that their job is safe, and that the speaker is on their team.

Let’s see if you agree: Think about a time you were horrified by negative feedback.
Was there an atmosphere of trust?

My guess is there wasn’t, because when trust is high, we don’t register the criticism as an emotional attack, and it’s not particularly memorable.
Many of my projects and pitches have been improved by my colleagues, who identify weaknesses and discuss solutions.

Instead of this being adversarial, it’s collaborative.
We’re not staring each other down, we’re standing shoulder to shoulder, both of us looking at the problem.
Trust reminds us that we’re not under attack, that we are safe to be vulnerable, and that temporary discomfort will allow for a much better result in the long run.

Expensive Yes’s
It’s tempting to forge on with an idea because we’ve already committed so much time, energy and money. It’s also tempting because of the embarrassment that may occur.

This is why it’s so hard for investors to cut their losses on a losing trade.
We hate to tell ourselves that we made an error, so we convince ourselves that we can claw it back.
If you saw someone talking like this at a casino, you’d say they had a gambling problem.
But for some reason, in a boardroom it’s seen as being “Prudent”.

Saying “Yes” is expensive - in terms of dollars, attention and opportunity costs.
Every Yes needs to be defended by a hundred No’s, so we want to be damn sure that this is worth pursuing.
When we look at it like that, the cost of cutting a loss is a relative bargain.

Try it yourself – create a safe environment for your team to be honest in their assessments.
Since they’re already thinking about the “No’s”, you may as well put them to good use, strengthening your ideas and creating an inclusive, constructive culture.

For more on this subject, you’ll enjoy Essentialism by Greg McKeown and The Advantage by Patrick Lencioni.