What could go wrong? Conducting pre-mortems on your work relationships

Katie Cerar
May 3, 2018 · 5 min read

Both the products we build and how we build them are important. Great teams put time not just into building, but into finding risk in their projects and solving for it.

We know our working relationships are important to the success of any project. Studies from places like Google show that performance is best predicted not by the smarts of the people on the team, but by the way they work together.

So why do we have so many well used tools to mitigate product risk, but so few to mitigate relationship risks?

Well for one, humans are way harder to understand than code. If you’re looking for one tool to add to your toolbox for relationship building, I’d like to nominate the pre-mortem.

The Pre-Mortem

Teams use pre-mortems to help them find ways their project could go wrong and then try to prevent it. Pre-mortems also make sure that all voices are heard before a project goes forward —making them a great tool to combat group think.

In a pre-mortem, the team brainstorms ways the project could fail in the future, and then work backwards to understand how to prevent those potential futures. It’s a way to help teams make sure they’ve considered all sources of potential risk.

I’ve been using pre-mortems to establish better work relationships faster.

Some leaders already do this all the time, but it’s worth labelling and calling out as a specific tool to think about and use.

The Relationship Pre-Mortem

I work at Shopify Plus as part of what we call a “trifecta”. I represent Product Management, and have a counterpart UX Lead and Engineering Lead. Together, the three of us are responsible for the success of the teams in our area and the products we build.

Until a few months ago, we hadn’t yet hired a UX Lead for my trifecta. The Eng Lead and I were more of a duo. And we’d been working together for over a year so were in a good groove. Then we hired a kickass UX Lead.

Through an informal conversation, we talked through all the ways we could fail. Generally I’m an optimist, so it’s not my first inclination to talk about failure. But that experience taught me that talking about failure can help foster success.

Follow these steps (formally, or just in spirit) to conduct a pre-mortem on your own relationships.

Step 0: Know your relationship goals first
You wouldn’t start a project pre-mortem without knowing what your project was. So, don’t start this conversation until you all have some idea of why and how you might be working together.

Start the pre-mortem by reminding each other and agreeing on your goals.

For my trifecta, we talked about goals and how we thought we might work together.

Step 1: Ask yourselves “in what ways can this relationship fail”?
Talk about ways in which you might fail. Brainstorm ways your relationships could fall apart in short and long term.

In my trifecta, we identified a few key ways we could fail:

  • The Eng Lead and I could cut out our new UX Lead from over-the-shoulder conversations
  • We could struggle to keep all three people on the same page
  • We could end up in unhealthy two-against-one dynamics
  • We could have potential conflict or unclear responsibilities between myself (a UX-leaning PM) and the UX Lead (a PM-leaning UXer)

Step 2: Work backwards to identify symptoms and preemptive solutions
For each failure, identify behaviours that would show you’re heading on that path. Then, talk about ways to prevent them.

We decided to:

  • Move desks so that the three of us sat in cramped quarters but couldn’t cut each other out of conversations
  • Agree the UX Lead should tell us if he felt we were leaving him out of conversations
  • Schedule a recurring weekly sync for the three of us to talk about projects but also share how we’re feeling
  • Create a slack channel for the three of us to share ideas
  • Watch for two-against-one dynamics
  • Clarify PM and UX role, and look for places we may be able to help each other rather than feel like we’re stepping on toes

Step 3: Check back in
Put in place your strategies and see what happens. Circle back regularly to check in — are we seeing these symptoms? Are there new potential ways we’re failing? Have our behaviours changed for the better?

Having had this conversation, I felt confident later talking about how we were doing . We all agreed on potential ways we could fail so were confident in calling out symptoms when we saw them.

Why do this?

Pre-mortems are great for projects because they help us head off potential mistakes, and they create a place where it’s safe to talk about failure. The same thing happens when we apply them to relationships.

We can throw out the expectations. No relationship is perfect at first. By starting with discussing the ways we could fail, we shatter any preconceived notions of immediate perfection. We make it safe to talk about our flaws and failures, present and future.

We can start with vulnerability. An honest discussion of failure means being open about fears and shortcomings. Once you’ve been vulnerable once, it becomes easier and easier to continue to be open and honest.

We have concrete behaviours to look for and call out. It’s simpler to point out something to correct. We’ve all agreed already, so the conversation is much easier.

But most of all, we’ll build intentional relationships. Rather than hoping relationships will go well, let’s intentionally design the way we work with each other.

You should conduct relationship pre-mortems because your relationships are important.

I work as a Product Manager at Shopify Plus in Waterloo, Ontario. If you want to learn more about working in Product at Shopify (spoiler: I fucking love it) then please reach out on Linkedin. Or, browse our current openings to see if there’s a good fit for your next move!

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Katie Cerar

Written by

Senior Product Manager, automation @ Shopify Plus. Great hobbies like lifting heavy things, cat wrangling, and coffee drinking. Recovering UX Designer.

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