How to use your Black Hat for good

I’m a critical thinker. I’m a coder with a background in maths — I excel 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 sometimes my deep-analysis means I present like the guy who “just points out all the problems”; a nay-sayer; a devils-advocate.

If you relate to any of these things, welcome. Having a Black Hat is a super-power, but 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.

a current cultural reference

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 from de Bono to Security colours.)

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 engaging by breaking other peoples ideas while bringing nothing new.

In that scenario, 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.

Ask the group whether they want Black Hat…

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 ideas together, with our Black hats.

How to think critically AND generatively

I’m most excited about the realisation that you can use you Black Hat to spot threats and weaknesses, and then switch in a Yellow Hat to shift into something more generative. 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. 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 Black hat thinking is, “Tell them to stop asking questions, and that 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 this falling short of ourdesired values?” 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. I resolved: “I want everyone to be practicing confident question asking, so they can be well equipped for their career.” It 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.

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 the aspirational end state. If others don’t agree with that aspiration (and that’s a fricken fantastic thing to talk about) you’re going to skip out a bunch of painful misalignment.

END

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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

Most of my learning is made possible by the incredible atmosphere of the Enspiral network. Particular families I’ve had the privileged of learning with / alongside are Loomio, Dev Academy, LifeHack, EXP, Root Systems.