Build Your Own Red Team

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At some point or another, I’d imagine virtually all of us have answered some form of the “money is no object” question. Essentially this: If you didn’t have to worry about money at all, what would you do?

My standard reply is to open some form of bookstore and coffee shop.

There would be no WiFi, and we’d stack the whole place with good old-fashioned physical books. If we want to get really specific, I’d name it “Penny University,” a callback to English coffeehouses in the 17th and 18th century. Oh, and we’d have monthly discussions where we call in experts to debate both sides of a “hot topic” (education, politics, poverty, future of work, etc).

I’ve thought about this a lot!

As much as I love this idea though, I’m probably not going to open a bookstore. The whole thing just feels so risky, especially as we talk about a worldwide pandemic (setting aside the ebook vs. physical book discussion).

Imagine my shock and delight when I read about Ryan Holiday’s new bookstore outside of Austin, Texas—The Painted Porch. He wrote a piece for the Texas Monthly aptly titled “Opening a Small-Town Bookstore During the Pandemic Was the Craziest Thing We Ever Did.

Sounds accurate.

The whole experience was fascinating, but one piece stuck out, what I would equate to a version of red teaming:

Whenever I’m considering an idea I’m excited about, I like to ask friends to talk me out of it.

Red Teaming in a Nutshell

If you’re not familiar, red teaming is a concept used in many circles including military, government, and cybersecurity. It can even be expanded to high profile decision making scenarios.

The concept originated from wargaming scenarios. The “home” team is typically the blue team whereas the red team represents the enemy.

Regardless of context, the entire purpose of red teaming is to continuously challenge plans, concepts, and strategies to reveal holes and lack of preparation. If we can put ourselves in the enemies shoes and approach our strategy from their perspective, we can shore up shortcomings and gaps before they become a problem.

For high profile decisions, red teams can be purposefully built from members of the group. Their entire role is to play “devil’s advocate” and poke holes in your thinking.

When done properly, red teaming makes your plans and processes that much more successful.

Now, let’s get back to books.

Talk Me Out of It

Opening a physical bookstore is a risk no doubt, or as Ryan would say, “the craziest thing we ever did.” I appreciated the tactic of asking friends to talk him out of it.

When done properly, great friends can poke holes in your plan and help you think of downsides you won’t anticipate.

In late 2019, I was cautioned with plenty of pessimistic scenarios and potential difficulties. It’ll take longer than you think. It will cost more than you think. It will be more work than you think.

All of this was correct. 

“Opening a Small-Town Bookstore During the Pandemic Was the Craziest Thing We Ever Did”

This is tricky because while it might be valuable to think through all of the downsides, it’s not what we want to hear.

We’re pumped about the idea. We want support. We’re sharing the idea within our circle of friends because we want them to be excited. At that moment, we’re not exactly looking for someone to share the hundred ways our idea could go sideways.

Build Your Own Red Team

It’s tough to dismiss the value of red teaming your ideas, but since our feelings and emotions get in the mix, it can be a tricky concept to execute well.

So, what do we do?

Surround yourself with people that can disagree with you.

We’re naturally attracted to friends that think and act like we do. But, everyone in our friend group thinks the same way, it’s nearly impossible to critique ideas. Purposefully seek out people that share a different perspective and appreciate friends and colleagues that can present alternative views.

Respond with “thank you”.

In What Got You Here Won’t Get You There, Marshall Goldsmith talks about 20 habits preventing leaders from being more successful. Habit #5: Starting with “No,” “But,” or “However.”

We all want to be right. Our naturally tendency is to be combative when someone tells us we’re wrong. We shutdown and go into defensive mode. We miss an opportunity to learn.

The value in red teaming comes from listening to alternate perspectives. The proper response is to listen intently and reply with “Thank you.” Defaulting into combative mode is a surefire way to prevent any critical feedback from flowing your way in the future.

Consider that they might be right.

We’ve built the team. We’ve replied with “thank you.” Now, the really hard part. We have to consider that they might be correct. The only way to capitalize on the value is to consider, “What would happen if they were right and I was wrong?”

From there, we can build contingencies, tweak our plans, or scrap the whole thing if appropriate.

Photo by Alfons Morales on Unsplash

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