Avoid Failure by Imagining It
Certainty blinds you.
You need confidence to lead, but your best idea might be a mistake.
Don’t learn from mistakes. In The Upside of Downside Thinking, Matthew Confer says it’s better to avoid failure by imagining it.
Instead of asking why something failed, ask why it might fail.
4 Ways to Avoid Failure
Matthew Confer offers a four-step framework called RISK.
#1. Recognize threats.
Get clear about your goal. Then ask:
- What are we overlooking?
- What assumptions could be wrong?
- Who sees a problem we haven’t discussed?
During meetings, invite teams to speak to each other, not you.
Invite quiet people to speak.
#2. Imagine disaster.
Pretend it’s six months from now. Your plan failed miserably.
Ask, “What went wrong?”
Don’t settle for generalities. Describe exactly how failure happened.
- What was the first sign of trouble?
- What did we ignore?
- What small problem became a big disaster?
- What did we assume would work but didn’t?
Work backward from failure.
#3. Solve vulnerabilities.
Don’t try to eliminate every risk. Focus on the two or three threats that matter most.
- What can we prevent?
- What can we minimize?
- What backup plan do we need?
Go beyond predicting failure to preventing it.
#4. Kickstart solutions.
Put insight into action.
Assign an owner, establish a deadline, and schedule a check-in.
A warning without action is just worry.
The Leadership Challenge
The person who challenges your plan might be the person who saves it. Thank them. Don’t punish them.
Optimism inspires action, but foresight prevents regret.
When might imagining failure help you avoid failure?
A Premortem: Reverse Positive Thinking for Success – Leadership Freak






Wow!! Great article! Leaders need to create an environment, culture, where this approach is the norm!!