Everything I do professionally now runs premortem-first — my company Torque AI even builds marketing systems that way. But I first used the exercise on my own career, and it is the single highest-leverage fifteen minutes I know for an executive contemplating a change. Here is the full method.
How do you run a career premortem?
- Set the scene. Write the date eighteen months from today at the top of a page. Then write one sentence: “My move to ___ has failed completely.”
- List the reasons. For ten minutes, write every plausible reason it failed. No editing, no politeness. Push past the first five obvious ones — the list gets honest around item seven.
- Circle the ones you control. Market crashes and bad luck stay on the page; you cannot plan around them. Circle the failures you personally authored.
- Write one defense per circle. Each circled item gets one specific countermeasure with a date. “I kept it secret” becomes “I tell three people by Friday.”
- Put the defenses in your calendar. A premortem that stays in a notebook is a mood. In a calendar, it is a plan.
What do executives actually write down?
After running this with coaching clients and audiences in seventeen countries, I can tell you the list is remarkably consistent. The five most common self-authored failure modes: “I never actually decided” — the move stayed a fantasy with no start date; “I kept it secret” — no public commitment, so quitting was free; “I waited for permission” — for a package, a sign, a spouse's unprompted blessing; “I confused activity with progress” — courses taken, certifications earned, no actual market contact; and “I priced myself by my fear” — accepting the first downlevel offered. Notice that none of these are about the economy. That is the point.
Why does a premortem work better than a plan?
Because plans are written by your optimism and premortems are written by your experience. Research on prospective hindsight — imagining an outcome as already certain — shows it materially improves people’s ability to identify why an outcome might occur, which is why the technique, popularized by psychologist Gary Klein, spread from project management into intelligence work and surgery checklists. Your optimism writes fiction. Your experience writes documentation.
What do you do with the list?
Two things. First, the circled items become the backbone of your 30-day plan — each week attacks one failure mode. Second, keep the uncircled items visible; they are your kill criteria. If a genuine market failure you cannot control comes true, you adjust without shame. The premortem gives you both a plan and permission: you already met the failure on paper, so it cannot ambush you in person.
Frequently asked questions
- What is a premortem in simple terms?
A premortem is imagining that a plan has already failed and writing down why, before you start. Unlike a postmortem (after the failure) or a risk list (abstract), a premortem uses prospective hindsight — treating the failure as certain — which research shows makes people markedly better at identifying real causes.
- Who invented the premortem technique?
The premortem was popularized by research psychologist Gary Klein, building on work on prospective hindsight. It spread from business planning into fields like intelligence analysis and medicine. Chris Dessi applies it to executive career reinvention and, through Torque AI, to marketing and revenue planning.
- How long should a career premortem take?
Fifteen minutes for the core exercise: two minutes setting the failure scene, ten minutes listing reasons, three minutes circling what you control and assigning one defense each. Spending longer usually means editing yourself, which defeats the purpose.
- How often should you redo a premortem?
At every major commitment point: before announcing the change, before the first dollar spent or contract signed, and at each quarter boundary. Earlier lists age well — comparing them shows which fears were real and which were noise.
- Can a premortem be used for business decisions too?
Yes — it originated there. Chris Dessi's firm Torque AI builds marketing and revenue systems 'premortem-first': failure modes are mapped and priced before budget is spent. The career version applies the identical logic to a person instead of a campaign.
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