Brene Brown and Adam Grant have a new podcast called the Curiosity Shop. It's great. If you have to choose between reading whatever I'm about to say or listening to their podcast, I'd strongly recommend listening to their podcast lol. Not because what you're about to read is unimportant, but because their conversations are illustrative of the best ways of dealing with conflict in the workplace and in life.

I've loved both of their catalogues and have listened to almost any podcast I see that they're on, but had no idea how their specific relationship formed, and it's wild to me. They actually started off not HATING each other, but misunderstanding each other so fundamentally that they thought the other one hated THEM so that they had a contentious relationship. And then… a crazy thing happened… they talked through it and solved the misunderstanding. And even though they have very different ways of approaching problems, their philosophies are very similar which allows them to have a great rapport.

All of this to say, they are great. But that greatness pales in comparison to the actions that they not only preach but live in their own lives. The one I want to focus on is the idea of a pre-mortem.

In one of their pods, they actually do a pre-mortem for their own podcast venture, because in the end it's a business just like all the businesses that they work with.

I'd never specifically thought about pre-mortems (though apparently Adam has written about them and I've probably read those writings, and just didn't have it "hit" in the moment). I've thought a LOT about post-mortems. And Adam specifically addresses that exact way of thinking in the pod, saying plainly (I'm paraphrasing) that doing a post-mortem is the worst time to be reflective, because you've already made the mistake and there's not an opportunity to fix it. The right time, he proposes, to identify failures is before they've happened.

So this is where we get into the process of running a pre-mortem. And I realize, that the way he proposes is sounds very reasonable. We're all professionals, so in theory we're doing things within our area of expertise. So we should be able to see what is and isn't likely to happen based on different scenarios.

But I think this misses a fundamental aspect of being a human. Which is that some people really struggle to see the whole chess board.

That's not a problem or something that they should be shunned for, but it's just that people have different strengths and weaknesses. And the more I've worked in tech the more I've found that people's strengths rarely are in seeing the future for what it is.

People tend to live either in the overly optimistic or overly pessimistic ends of the spectrum. They see all the opportunities or all the pitfalls, but rarely do they see what's in the middle, the likely scenarios of what will happen.

And I think that Adam is trying to say that's fine, because the two will mix and create a nice little brew of realism through the process of a pre-mortem. And having never been rigorous about running pre-mortems, I'm more likely to believe that he's right than that he's wrong, even though it feels way too optimistic for my tastes lol.

That being said, I ran my first official "pre-mortem" this week, and found it to be… really cathartic and positive?

So before I get into the detail, what even IS a pre-mortem? Literally it's just a documenting of all the things that we've seen go wrong before that could go wrong here and what circumstances are allowing that to be a possibility that we could change up front? So there's an element of future casting, thinking about the things that are going to happen, mixed with trauma bonding, mixed with good old fashioned pessimism lol.

And when we tried it out this week, the first thing that happened when we started doing the pre-mortem was hilarious… because no one said anything. It was only 4 of us, and we're all friends, and we all treat each other with respect and care, and also are able to be open and honest with one another… but still we all were kinda like, huh, what COULD go wrong?

Then the flood gates opened.

It was a combination of things that we'd already experienced the pain of, and identification of areas where we just weren't as solid as we needed to be, and a surprising amount of things that didn't require anyone to intervene – we just needed to acknowledge that we needed to put more rigor into our process.

What I realized though as we were going through the process of putting all this on paper was that, yes this is all valuable for the project and will help us to do things the right way. But I honestly think that might not have been the biggest value we created. Because the thing I saw was that everyone felt seen and heard. It wasn't a bitch session, but it was for sure a therapy session.

The problem that often occurs in projects, and in life honestly, is that you get so focused on what you're dealing with, whether that's specific problems in a project, or a difficult situation with a family member, or whatever else is going on, that sometimes you forget that the people around you aren't in the same headspace you're in. They're dealing with their own sets of problems walking into any discussion you're having. And they're being influenced by them, just as you're being influenced by whatever is going on in your head.

Stepping outside of those problems to just hear one another for a minute is incredibly valuable. Not because of anything tangible in that moment, but also because when problems inevitably arise that you COULDN'T foresee, you all have a working relationship that can handle speaking up about problems. You can see each other and know that you'll be seen.

And since this whole venture was started to talk about empathy, this is the ultimate expression of it. By doing a pre-mortem yes you're guessing about the future and doing things that seem much more project based, but what you're really doing is seeing other people's perspectives and worries and prioritizing them!

What's funny is, I feel like I've been circling around the idea of a pre-mortem for at least a decade without ever landing on it correctly.

A friend and I used to joke when looking at any project we were working on that we had a super power that no one else seemed to have – we could see the future and every bad thing that was about to happen.

We'd use these conversations to vent but also to see what was coming and how we could better handle the inevitable horribleness that was coming our way. But we never formalized it or did anything with it.

Instead it became a burden of knowledge that we shouldered while everyone else seemed to naively run through the motions and hit the walls and pitfalls we saw coming weeks prior.

I'd always treated this burden of knowledge the way that I did in the beginning of this post… as a thing that some people could do and some people couldn't. I thought genuinely that it was a superpower. Hell, even as I write this I still kinda believe it. That's just the arrogance talking though.

Because the thing that was always missing wasn't the process element of bring things back to the team and making sure we addressed all the issues. That's a byproduct of what was missing, but it's not THE THING that was missing. The thing that was missing was the generosity of sharing the issues we saw coming with the people it would affect, AND hearing from them the things that they saw coming that we couldn't see.

It's really difficult to reframe that as generosity in my head. I'm not a yeller (anymore… if you were around me in my BofA days… my bad I'm better now lol). I'm not big on negativity. I try to create positivity and confidence through competence and kindness. So my framing tends to be "telling someone they're doing something wrong or poorly is mean". So sharing all my thoughts about everything that can go wrong FEELS like negativity in my gut.

But that's the thing about going on your gut – it's not coming from a place of empathy or kindness. It's just fight or flight all day in your gut. This scares me let's run. This makes me mad let's fight. This feels too hard let's run. This is moral to me let's fight.

When in reality, there's a lot of nuance. Yea, negativity feels cruel in my gut, but it's not cruel if you give someone feedback that allows them to get better and it's coming from a place of care. It's not kind to let someone keep doing something wrong and never give them advice on how to do it correctly. It's not kind to let someone flail when you can teach them how to swim.

Most of the times I had exponential growth as a person came from moments of deeply penetrating criticism.

Whether it was a teacher telling me that I needed to use my sardonic wit in my writing to make it more me (I had to look up what sardonic meant lol) or a boss telling me that I was mismanaging my time and not treating my client like a client the feedback always hurt in the moment. Mainly because I'm much more sensitive than I let on (probably not true but let me hold onto this fantasy about myself lol) but also because they didn't just give me things that weren't working – they gave me the tools to get better. And I did. In every case, which there are too many to detail, I was given constructive criticism, felt like shit for a day, then realized they were right and used the feedback to get better.

While there's value in the output of a pre-mortem, I find the process to be even more important because it ENABLES those types of interactions. You're creating the best feedback loops ever because you're creating space and safety for everyone to say what's really going on without fear of judgement.

And I guess that's what I really want to advocate. Creating space for more people. Another little tidbit from the podcast was that Brene asks the people furthest from power about their experiences before signing up to work with a new client. And that's just another sigh of what I'm talking about – if you haven't created space for the people furthest from power to voice their feelings then you haven't done all the work yet. You have more to do to enable your organization.

You should see that not as a failing that you have, but rather as an opportunity for you to get better.

You can't get better without recognizing the things that you're not doing perfectly, and I hate to break it to you, but if you're a human and you're reading this, you're not perfect.

As one of my Smith Barney colleagues used to say, until you're defined by the letters RIP you are a WIP. If you're not dead, you're a work in progress. And you gotta see that for yourself, and be open to the idea that you're not always right. Even when you feel it most deeply in your bones. You can still be wrong.

And that's a scary, but ultimately freeing realization.

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