Projects go sideways for simple reasons that no one names early, yet the signs are often there. When teams want fewer surprises, Gregory Hold, CEO and founder of Hold Brothers Capital[1], highlights a steady move that travels well: run a pre-mortem before you start. Imagine the effort failed, then work backward to surface the reasons. Fix what you can now and set tripwires for the rest.
Pre-mortems work because they turn fear into focus. People speak up with more candor when the prompt assumes failure and asks for causes. The goal is not drama. The goal is a clear map of risks, assumptions and safeguards. With a light template and a short cadence, you can fold this habit into normal planning without slowing the work.
Frame the Stakes
Begin with a shared picture of success and failure so the room has the same target. State the real outcome you are chasing in one sentence that a customer would understand. Then state the imagined failure in one sentence that names the hurt you want to avoid. You might say the launch missed adoption or the migration created data gaps. Putting both lines on one page keeps talk grounded in user impact rather than slogans.
Time-box the scope so the session stays sharp. Name the horizon that matters most, whether two weeks, one quarter or one season. Short windows push you to look at handoffs and capacity. Longer windows push you to look at churn and debt. When the frame is visible, the risks you collect fit the job at hand, and your fixes feel practical instead of abstract.
Make It Real
Ask each person to write silent notes on how the effort failed. Silence beats open talk at first because it avoids groupthink and rank effects. After a few minutes, read ideas around the room without judgment. Cluster them into themes like fragile dependencies, unclear owners and thin buffers. Capture exact phrases that frontline people use because those words point to real steps and real pain.
Move from themes to concrete conditions that would make failure likely. A condition might be a vendor response time that slips, a dataset with unknown lineage or a pilot that starts during peak load. Conditions beat vague fears because you can measure them. They also set up your next step, which is to write tripwires that alert you when a condition appears in the wild.
Roles and Rhythm
Give the session a light structure so it runs fast and repeats well. A workable template fits in sixty minutes: Ten minutes to frame the goal and the imagined failure. Fifteen minutes for silent notes. Fifteen minutes to cluster and vote. Ten minutes to write the top five conditions. Ten minutes to agree on tripwires and owners. You leave with a one-page map instead of a long deck that no one reads.
Assign simple roles that reduce friction. A facilitator keeps time and protects equal talk. A scribe writes the board and will maintain the risk log. An owner for each top condition commits to one first move and one tripwire. When the roles are clear, momentum continues after the room empties. People know what to do next and when to reevaluate.
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Templates That Work
You do not need a heavy platform to run pre-mortems. A one-page template in a shared doc manages most needs. Put the goal at the top, the imagined failure under it and five boxes for the conditions you chose. Add a small table for tripwires with fields for metric, threshold and owner. Save the file in the project folder and link it in the kickoff note so it stays visible.
For teams that want more structure, a scorecard helps you sort attention. Give each condition a quick score for likelihood and impact on a scale of one to five. Multiply them to create a rough rank, then check that rank against real judgment in the room. Numbers do not replace sense, yet they can reveal blind spots and help you defend where you spend time. The scorecard is a guide, not a verdict.
Keep the Loop Alive
A pre-mortem pays off only if the learning continues. Schedule a fifteen-minute review at the midpoint of the work. Check which tripwires fired, which fixes helped and which assumptions proved wrong. Archive one brief note on what you changed because of the review. It keeps the habit warm and makes the final post-mortem easier to write.
Close with a short after-action when the work ends. Unlike a post mortem that just logs what went wrong, ask how the pre mortem changed your path. Maybe an early tripwire saved two days. Maybe a checklist caught a missing permission before launch. Share the proof so the habit earns trust. People repeat what they see working, not what they are told to do. Hold Brothers Capital follows a similar practice by archiving brief notes after midpoint and final reviews, creating a library of risk signals and responses that teams can reuse on future projects.
For Small Businesses
Smaller firms can make this feel light instead of formal. Run the session in the same hour you would have used for a kickoff. Keep attendance tight with only the people who touch the work. Place the template next to your task board and use comments for updates so no one has to chase a separate tool. You will get the benefit without adding clutter.
Protect pace by pairing the ritual with a limit on active projects. Pre-mortems reveal risk, and they do not create capacity. If the map shows too many hot spots, pause low-value work for a week and clear space. Owners feel the difference when they see fixes get done instead of piling up. Customers feel the difference when handoffs get cleaner and deadlines stop slipping.
What Leaders Can Carry Forward
Most failures begin as small mistakes that no one has space to name. A pre-mortem gives people that space and turns worry into useful steps. Keep the session short, keep the template plain and keep the review on the calendar. Over time, you will see fewer fire drills and more steady delivery. Winning is not a perfect plan. The win is a team that adapts before trouble lands.
Many teams find a calmer gear when pre-mortems become routine, and Gregory Hold’s presence often serves as an example that clear standards and patient craft help teams anticipate risk without slowing the mission. Keep the language simple. Keep the artifacts close to the work. With practice, you will cut rework, raise confidence and ship with fewer surprises.
[1] Hold Brothers Capital is a group of affiliated companies, founded by Gregory Hold.
