Imagine Failure to Succeed
Simply Identifying Risk Is Not Enough
We had a solid plan.
Everyone was bought in.
We even talked through some risks.
And yet...
We didn't get the results we wanted.
That’s the problem with most planning.
We assume success, then sprinkle in some light risk management.
What we rarely do is assume failure—and ask what contributed to it before it happens.
Why We Skip the Hard Part
We usually wait until the end to reflect.
It makes sense. We assume success and the plan looks solid.
And let's be honest, no one likes the "Negative Nelly"
(apologies to Nelly, who I personally know to be quite positive).
We tell ourselves we're resilient.
We'll adjust as needed.
Grit will get us through.
But if that's true, why do many business initiatives still fail?
Is it the people?
Or have the people not set themselves up for success?
Let's dig deeper.
After Action Review (aka the Post-Mortem)
Back in the 1970s, the US Army began using a process known as the After Action Review (AAR) to reflect on what happened during a mission, why it happened and how to improve next time.
The process was designed to not just identify "failures" but also identify areas for improvement in future missions (even in successful areas).
Harvard Business Review explored the concept in a piece, "Learning in the Thick of It".
The article highlights how AARs can be a helpful tool when used consistently and rigorously and not just as a check box at the end.
And, in fact, you've probably experienced the business equivalent of an AAR: the post-mortem. While not exactly the same as an AAR, the spirit of a post-mortem is the same.
Team members gather.
We ask simple questions like "what went wrong", "how do we prevent those problems in the future" and "how can we improve".
And while we may not always run the perfect post-mortem, the core issue is this:
By the time we convene a post-mortem, the costs are sunk.
Identifying Risks isn't Enough to Avoid Failure
What if we take the time to truly foresee the challenges beforehand.
No one has a crystal ball (well, I don't).
And predicting the future might feel like a fool's errand.
But that's not what we're doing here.
We're not predicting; rather, we are considering what failure would look like.
It's important to note that is not the same as identifying risks.
Most teams indeed work to identify risks during planning.
For example, let's assume our goal is to launch a new feature in Q3 to drive upsell revenue.
We may identify risks such as:
We may miss our development deadlines.
We could get low adoption from customers.
Marketing may not have enough time to build awareness.
And we acknowledge these risks.
Yet, we still assume success.
The risks don't quite feel real. Words like "may" and "could" keep us comfortably optimistic.
We assume our existing processes will get us through.
As a result, the risks aren't prioritized.
They are merely potential road bumps on the road to success.
Imagine Failure
Instead of identifying risks, truly imagine what failure can look like for the initiative.
Seriously.
Stop reading for a moment and think about the difference between a risk and failure.
Here's the difference:
A risk may not happen.
A failure already has.
Do you feel the difference.
Did your heart rate tick up when considering failure - just a bit?
The Pre-Mortem
Gary Klein, a renowned psychologist, coined the phrase pre-mortem to capture this exact difference.
Instead of waiting until something goes wrong, a pre-mortem asks us to image failure has already taken place.
Then we work backward to figure out what caused it.
Let's go back to the Q3 feature launch.
If we imagined the launch failed, what would we say happened?
Instead of going through standard lists of risks, we need to imagine - we need to believe - this initiative has failed.
What led to our failure?
Can we think beyond risks?
By imaging failure, can we see more clearly what contributed to the failure?
Perhaps we'd come up with a list such as:
We assumed customers wanted the product but never validated demand.
We tried to include too much, and the scope ballooned.
Sales didn't fully understand the value proposition, so they didn't push it.
We set the launch date based upon board pressure, not reality.
In each case, we're challenging an underlying assumption, going beyond just listing what could happen. We're challenging whether we were addressing true customer demand, whether we can deliver in the time allotted, and we're challenging whether we’re properly communicating to all necessary parties.
Pre-mortems do something a list of risks can't:
They force us to visualize failure.
They force us to dig deeper for the contributing factors.
That mental shift creates urgency and leads to more specific, more honest action plans.
Key Takeaways (TL;DR)
Post-mortems are useful—but they come too late. By the time we reflect, the outcome is set, and the cost is already paid. And while most teams talk about risks during planning, that rarely changes the outcome. We stay optimistic, note a few “maybes,” and move forward assuming things will work out.
A pre-mortem forces a different mindset. It assumes failure has already happened, then asks what caused it. That subtle shift changes everything. We stop listing vague possibilities and start confronting real assumptions. We get more specific. More honest. More prepared.
When failure feels real, the urgency becomes real too. And that leads to better action, not just better planning.
Try This
Before your next initiative kicks off, ask the team one uncomfortable question:
“Let’s assume this fails. What caused it?”
Then listen.
Because clarity doesn’t come from confidence.
It comes from asking the question no one wants to ask, while there’s still time to do something about it.
If you want to know more, Gary Klein’s original HBR discussion is worth a read.
Before you go
If you've ever tried this or have any stories to share, I'd love to hear them. Drop a comment.
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Royal Dutch Shell was the only oil company in the 1960's to do "scenario planning" for risks of oil production in the Middle East.
When the oil fields were nationalized, Shell was the only company that came out out. They had not done a pre-mortem on that exact scenario, but since they had envisioned failure already, they acted much quicker than the other oil companies.
It is ironic that when you ask people in advance to visualize failure, they all know what could go wrong.
Crazy not to ask.