Every business needs bug bounties

Hey everyone,

Picture your team in a room, the week before a big launch.

The product isn't ready. The systems are half-built. The data is wrong. And everyone around the table knows it.

But nobody is saying a word.

Groupthink is holding people back. And it can happen at a 10,000-person company just as easily as a 10-person company.

It happened at Target in 2013, and it’s why a $5.4 billion expansion into Canada went bankrupt two years later.

Here’s what happened, and how to fix it.

The disaster everyone saw coming

Target was launching 123 stores simultaneously in a market they’d never operated in (Canada). In the runup, they were hosting daily go-or-no-go phone calls. 

The problems weren’t hard to spot. Checkout registers couldn’t ring up products. Only 30% of the data in their IT system was accurate. (The US standard was 99%.) Distribution centers were overflowing while store shelves sat empty.

Everybody in those meetings knew. But nobody wanted to be the person to say they were making a huge mistake.

So they opened anyway.

Customers found bare shelves and prices 15% higher than the US equivalent, and walked straight out the door, into Walmart, and never looked back. 

Target even posted an apology video begging Canadians to give them another shot. They never did.

$5.4B and 20,000 jobs later, the experiment was over.

Three ways to hear what your team isn’t saying

The problem to solve is, groupthink doesn't feel like groupthink in the moment. 

It feels like being a team player. 

Either you don’t want to be the stick in the mud, or you assume leadership has more info than you. 

So here are 3 ways to fight it: 

“Dissent is tolerated” — sure, you can speak up and not get fired — is not the same as “dissent is rewarded.” 

Rewarded means someone who flags a real problem gets acknowledged for it, visibly, in front of the group. Software offers bug bounties. Why shouldn’t you?

Before any major launch or commitment, I ask someone I trust to actively argue against it. Not devil's advocate for sport, but actually building the case for why we shouldn't. 

It's uncomfortable, but it's caught real problems.

The goal is to stress-test your ideas internally before the market does.

The people closest to the problem usually know first. 

In Target’s case, store-level employees say the failure coming weeks before launch… but the signal got filtered out on the way up. 

So make a habit of talking directly to the people doing the work, not just the people managing them. A 20-minute conversation with someone on the front line will tell you things their manager’s weekly update never will.

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None of these are hard. But they all take intention. 

(If you want more suggestions, here’s my newsletter on how to pierce the fog of war in your business.)

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What does your team know that they're not telling you?

Thanks for reading!

Michael

P.S. Don’t forget to sign up for the AI lecture this coming Thursday! We’re holding lots of time for your questions.