Backcasting and Premortem
Work backward from success and failure to plan the path
Backcasting and premortems are two complementary planning techniques that work backward from imagined futures rather than forward from the present. Backcasting starts with a positive outcome -- imagine you have achieved your goal, then work backward to identify the steps, decisions, and fortunate events that got you there. Premortems start with a negative outcome -- imagine you have failed to achieve your goal, then work backward to identify what went wrong.
Research shows that 'prospective hindsight' -- imagining that an event has already occurred -- increases the ability to correctly identify reasons for future outcomes by 30%. This is because backward planning recruits different cognitive processes than forward planning. When looking forward, we tend to over-plan for the present and under-plan for the future. When looking backward from an imagined outcome, we naturally consider a richer set of intermediate steps and potential obstacles.
The two techniques are complementary: backcasting reveals the positive space (what must go right), while the premortem reveals the negative space (what could go wrong). Together, they provide a more complete picture than either alone. The premortem is especially valuable because it creates permission to voice concerns that team-player culture typically suppresses, making it a natural implementation of organized skepticism.
- Looking backward from an imagined future is 30% more effective at identifying causal factors than looking forward.
- Backcasting reveals what must go right; premortems reveal what could go wrong.
- Positive visualization alone actually impedes goal achievement; mental contrasting improves it.
- Premortems create safe space for dissent by reframing criticism as productive contribution.
- The most complete planning combines both positive and negative future imagination.
- Define the goal clearlyState your goal in specific, measurable terms. Make it vivid enough that you can imagine a newspaper headline announcing its achievement. For example: 'Company X Has Doubled Its Market Share over the Past Three Years' or 'I Have Lost Twenty Pounds in Six Months.'Pro tipThe more specific and vivid the goal, the more productive both the backcasting and premortem will be.
- Backcast from successImagine you have achieved the goal. Now work backward: what were the key milestones along the way? What decisions did you make? What went well? What lucky breaks did you get? What resources did you acquire? This reveals the necessary steps and dependencies that forward planning might miss.Pro tipHave each team member independently backcast before sharing, then combine the perspectives for a richer picture.
- Conduct the premortemNow imagine the negative headline: 'We Failed to Reach Our Goal.' Work backward from this failure. What went wrong? What obstacles emerged? What decisions backfired? What did you fail to anticipate? The premortem gives permission for team members to voice concerns that optimism-driven planning would suppress.Pro tipFrame the premortem as a competition: who can identify the most creative and plausible failure scenarios? This makes dissent feel like team contribution rather than negativity.WarningDo not skip the premortem because the backcast felt sufficient. The negative space reveals different and equally important information.
- Synthesize into an action planCombine the insights from both exercises. The backcast tells you what to pursue; the premortem tells you what to guard against. Create a plan that includes both proactive steps (from backcasting) and contingency plans (from the premortem). Identify where Ulysses Contracts might be useful.Pro tipPay special attention to low-probability but high-impact scenarios from the premortem -- these are the ones most likely to be overlooked.
- Build in checkpoints and re-evaluationAs the plan unfolds, compare reality to your scenario maps. Use inflection points as opportunities to re-evaluate assumptions, update probabilities, and adjust the plan. This closes the feedback loop and improves future planning accuracy.Pro tipPrecommit to specific checkpoints rather than waiting until something goes wrong to re-evaluate.WarningDo not treat the plan as sacred. The purpose of planning is to prepare for reality, not to prove the plan was right.
Olmsted designed Central Park by starting from what it would look like decades in the future, when trees and landscaping had matured. Visitors in 1858 saw barren land, but Olmsted was working backward from a vision of the fully developed park.
The Allied invasion of Normandy involved extensive scenario planning for what could go wrong: bad weather, communication failures, paratroopers blown off course, currents interfering with beach landings, separated forces. All of these things did go wrong.
Duke drew on multiple sources for this framework. Backcasting was illustrated through Frederick Law Olmsted's design of Central Park, where he started from what the park would look like decades in the future and worked backward to determine what to plant and build. The premortem concept was popularized by decision scientist Gary Klein. Duke added the insight from Gabriele Oettingen's research showing that 'mental contrasting' -- imagining obstacles alongside goals -- consistently outperforms pure positive visualization, with studies showing dieters who only visualized success lost 24 pounds less than those who also imagined obstacles.