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- #070: Pre-Mortem Analysis
#070: Pre-Mortem Analysis
See the future and win more deals
Read time: 2 minutes
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Do you ever wish you could see the future before a you lose a big deal? Wouldn’t you want to know exaclty why you lost the deal so you could stop it from happening?
That’s exactly what the “pre-mortem analysis” is designed to do. By looking ahead and imagining that you already lost the deal, you can diagnose potential problems and fix them before they happen.
By waiting to do a “post-mortem analysis”, the deal has already been lost and there’s no way of saving it.
In today’s newsletter, we’ll walk you through a step-by-step method to use the power of a pre-mortem analysis and start winning more deals right away.
Why a Pre-Mortem Matters
If it’s not clear already why it’s better to do a pre vs post-mortem, here you go.
Proactive vs Reactive Problem-Solving: By anticipating failure scenarios, you build robust strategies that address issues before they become deal-breakers.
Better Team Alignment: When everyone is on the same page about potential threats, you can rally around solutions more effectively.
Faster Decision-Making: Pinpointing weaknesses early prevents future bottlenecks and accelerates your deal cycles.
3-Step Pre-Mortem Process You Can Implement Today

You can do this exercise by yourself but it can be very helpful to do in a group setting. You may have blindspots for the deal that your team can help you identify.
Envision Failure
Fast forward 3 months and imagine you already lost the deal. What went wrong?
Key Questions
Did I understand the customer's pain points and priorities?
Were there misaligned expectations or unmet needs?
Do we know why they needed to do this project?
Were we aligned to a business initiative or just a project?
Did competitors outperform us in any area?
Identify Root Causes
What are the actual reasons those things went wrong? These are the hard questions you and your team need to ask. If you don’t ask the hard questions, you won’t get the real root cause.
Key Questions
Did I engage the right decision-makers early enough?
Were there gaps in our offering compared to competitors?
Did I misread the customer’s priorities or timeline?
Was there a business case put in place?
Did I build multiple 1:1 relationships with the buying committee
Did I go deep enough in discovery to know the business problems and initiatives? Turn technical problems into business problems.
Do we know when they actually need to get the results your product or service delivers and why?
Were we actually working a qualified opportunity to begin with or were they just getting quotes from us to check the box before going with a different vendor?
Do you know ALL the decision criteria for how they plan to make the decision? Are your differentiators a part of that?
Preventative Strategies
For each root cause gap that you’ve identified, stack rank them base on impact and importance. Then create specific actions and plans for you and your team to take to ensure they are resolved.
Example Actions
Reach out to the executive directly with a highly relevant message referencing the business initiatives your project is aligned to and the insights you’ve learned from your conversations.
Ask for 3 introductions to other people who care about the outcome of this decision. If you don’t get them, research who they might be and reach out directly.
If you don’t know the business initiative for why they need to buy your product or service, then you need to get on a call and figure it out by doing deeper discovery.
Get a list of decision criteria and then rig it in our favor. Highlight your differentiators.
Write a buisness case with a clear ROI both in terms of rational outcomes but also emotional outcomes.
Now What?
Block 30 Minutes: Schedule a short meeting or brainstorming session today or this week or do it on your next team call.
Set the Stage: Clearly explain the pre-mortem concept to participants so they understand the goal is to proactively uncover issues, not criticize current efforts.
Document It: Capture all ideas in a shared doc
Execute: Assign actionable next steps and start implementing
Review Progress: Review each strategy to ensure it is completed and keep yourself accountable.


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