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How to use your Black Hat for good

I'm a critical thinker. I'm a coder with a background in maths - I excell at taking ideas and problems apart. The blessing of this is that I understand systems I work with intimately, perhaps even better than others. The curse is that some-times my deep-analysis mode presents like "pointing out all the problems"; a nay-sayer; a devils-advocate.

If you relate to any of things, welcome, I'm writing this for you - you have a Black Hat. I'm writing this because having a Black Hat is a super-power, and if you've got one you're probably deploying it sub-optimally. Here are a couple of easy tweaks to get the most out of it.

Know when to use it (and keep your friends!)

In the context of collaboration, I'm fantastic at reviewing, seeing vulnerabilities, and threats. Historically, I've also generated a lot of pushback for quashing fledgling ideas, or 'always seeing the negative'.

Looking at de Bono's thinking hats, has been a real help for me. There are six of them, each representing a different style - or mode - of thinking, de Bono proposed was that a lot of tension in a groups emerges from different people being in different modes. (In computer security, there are also 'hats', try the post-script for a mapping between the colors)

For example in a visioning session, I deploy the Black Hat (critical thinking), because it's a strength of mine. Meanwhile others in the team are wearing the Green Hat (generative, exploratory thinking). The combination feels bad, because most people know that things being suggested aren't perfect - that's not the point of the exercise at this point - but I'm doing the opposite of creating, I'm bringing nothing to the table, I'm just cracking the things other things are bringing open.

The problem is that I'm just leaning on my strengths - this is a common and lazy habit of Black Hats. If you notice yourself being called a devils advocate, you've probably fallen into this trap. Generally people don't like devils advocates and if you persist you're in for a bad time.

This doesn't mean you can't use your hat, just know when to use it - check in with your group about what 'mode' we're wanting to be in. If we're doing exploring, lets agree to be Green Hat, and then agree when we're ready to shift to stress testing the new ideas all at once (with our Black hats).

How to be think critically AND generatively

This is what I'm most excited about. It's the realisation that you can use you Black Hat to spot threats or weaknesses, and then put on a Yellow Hat. If the Black Hat is the destructive critical thinking, the Yellow hat is the future-facing critical thinking about our values. (This might not have been de Bono's intention, but bear with me.)

For example, I'm currently teaching a group of coders at Dev Academy. There's this dynamic emerging where 3 of my students are excellent at asking questions. I noticed I was feeling annoyed, and my Black Hat says "These students are dominating the air-space, to the exclusion of the quieter students, and to the exclusion of the women in the group". It goes on "There are gender and societal dynamics at play here, I wonder in what ways I could be contributing to this?". The solution that comes from this hats thinking is "You need to tell them to stop asking questions and tell them we're making the gender gap worse".

While this is kinda the desired outcome and there is truth in it, it lacks compassion, and sure as hell isn't going to be received well.

By pivoting into my Yellow Hat, I'm able to ask the critical question "In what ways is falling short of the desired values I want us to be living?" Which leads to the subtle shift in focus "What are the values I want to be living here?"

The answer is easy and I kind of already knew it but it was tangled up in my Black Hat deficit thinking. Clearly resolving "I want everyone to be practicing confident question asking, so they can be well equiped for their career." meant resolving the situation was a piece of cake. I invited the confident 3 to a conversation, told them the value I wanted to realise, and invited them to help me.

TL;DR - applying critical thinking to underlying values (as well as the problem) will help you see and communicate more clearly.

The difference between this solution and the Black Hat-only one is that it has baked into it the aspirational end state. If others don't agree with that aspiration, that's a fricken fantastic thing to talk about - you're going to skip out a bunch of painful mis-alignment.


Most of this learning was possible because of the incredibly supportive and nourishing atmosphere the Enspiral network is growing. Particular families I've had the priveldge of learning with / alongside are Loomio, Dev Academy, LifeHack, EXP, Root Systems.


p.s. mapping for Security Hat

de Bono Security
Black Black - cracker, approaches offensively, is
           | interested in poking holes

---------------|-------------------------------------------------- White + ? | White - employee, follows ‘the rules’, approaches | defensively, is interested in stopping holes ---------------|-------------------------------------------------- Black + Yellow | Grey - ‘the best defense is a good offense’, | the White Hat informed by a Black Hatness