We were heading into an offsite in 2021 with only C-level execs. We were starting to think about planning and broader strategic initiatives. However, at the same time, we were in the midst of a broader debate about where we as a company were, whether we should build a bigger marketplace, whether we should build a flywheel, and also what the world would look like. We wanted to have some debate about these things and get to clarity.

You could also pre-mortem projects, when you're going to launch something. I like to think of this as a kind of scenario planning.

And pre-mortems can be useful at different levels of planning, at the highest level of strategy, but also at the individual initiative level or team level. So if I were looking at the growth team and, hey, your goal is to increase conversion by 15%. What if you were to pre-mortem that goal right now -- what would be the reasons why that that didn't happen?

You know, they could say, well, we need, we're short a designer. And it's like, oh, this is really important. Why don't we move a designer onto this? Or why don't we get you some freelance money to help unblock you faster so that as you're hiring for full time, you're not waiting around so that you don't burn half the quarter just trying to hire someone.

Or they might say, well, there's a dependency on this other team needing to build an API. And then you're like, oh, well, do they have a date? Let's not let these risks just sit there if you can do something about.

Be as specific as possible about these goals. In order to pre-mortem, there has to be a failure mode. You need to be specific so you can't say "eh, we kind of made it" afterwards.

We set up the pre-mortem like this - we have a financial goal. We need to get to this run rate. There are a bunch of things that could go wrong. Imagine we just fail miserably at hitting those goals, and what are all the reasons you could think of.

That's part of the reason we used the long timeframe - 2023+. And the metrics were double or triple what we were at the time, so it felt like it was really aspirational and in the future.

This was important to include and to enable. Sometimes it's easier to be skeptical than to be optimistic, so it's good to give people permission to be brutally honest.

I find it's helpful to give people categorizations (likely to happen, might happen, etc.) to get the gears turning.

But ultimately the trick isn't whether you'll get enough volume. It's about not going down a rabbit hole on things that likely won't happen. If someone starts going down that rabbit hole, you need to divert them away (and perhaps come up with a plan B), but you should try to avoid spinning.

Our goal was really to focus on show-stoppers or things with a high likelihood of happening. Discard the things we have no control over.

And then, by the end of this exercise, we wanted to be able to take this back to our big planning and see whether this exercise brought up any new initiatives that we should focus on.

Tom Willerer

When engaging in long-term goals planning at Opendoor, the exec team and I used this pre-mortem exercise to identify major sources of risk, in order to adjust or mitigate them.

Achieve our 2023+ customer growth, company financial, and company scaling goals

X% contribution margin: X% from core, X% from services

Scalable processes (financial, comms, people, etc) & hiring/retaining top talent

Imagine we fail miserably at hitting the above goals in 2023+ and write down every reason you can think of for why we failed, 

especially the kinds of things you ordinarily wouldn’t mention as potential problems, for fear of being impolite or too blunt

We can’t shy away from being brutally honest

. This is our time to air out all the potential issues.

After everyone has created their list, we will go around listing out one reason for potential failure until all reasons have been written down.

Pick the top-10 potential problems. Each person picks their top 10 potential problems. 

Here are some guidelines for how to do so

Focus on show-stoppers. The problems we focus on solving should be critical to our success.

Pick problems likely to happen. Let's not waste time solving problems that aren't likely to actually happen.

Discard problems we have no control over. there are some external factors that we have no control over, so lets not spin our wheels on them.

For our top-10 list, let’s create potential solutions for each one.

For ones that are imminent or we are currently facing, we should have a proactive solution.

For ones that are hypothetical, we should have a backup plan.


By the end of this exercise we should have a list of the top-10 potential issues that may hinder our 2022 goals as well as proactive solutions or backup plans for each

15 minutes for individuals to write down potential problems

15 minutes to create individual top-10 lists

15 minutes to align on a shared top-10 list

15 minutes to create an individual solution list

15 minutes to align on a shared solution list

Pre-mortem agenda for long-term goals planning at Opendoor

Pre Mortem Prep: Opendoor Exec Offsite

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