Don Jones

Tech | Career | Musings

I’ve recently started forcing myself to play “Angel’s Advocate” in a number of conversations, and sometimes just with myself as a thought experiment. Here’s how it works:

Suppose someone in your organization suggests moving to Office 365 and off of your on-premises Exchange infrastructure. Now, someone else will often, in the conversation, say something like, “just playing Devil’s Advocate, but…” That’s a kind of weasel-word – the person is arguing against the move, usually by raising potential problems that seem insurmountable.

Play the other side – even just in your own head. Heck, forget reality – just take some contentious, difficult topic and ask: “What would have to happen to make that happen?” Be serious – no snarky replies allowed. You’re totally blue-sky, meaning you can come up with anything as a solution, but try to stick as close to reality and reason as possible. What if you really, really needed to engineer things so that whatever it was came to pass?

This can be hard.

What would it take for your organization to move to Office 365 for email?

I’ll give you an example of where playing “Angel’s Advocate” worked. The US department of defense got into conversations with Microsoft about O365, and ultimately did not decide that O365 wasn’t for them. What they found was that the tech worked fine, but there were concerns about who would control the data and where it would be stored – we’re talking sensitive stuff. “What’ll it take?” someone at Microsoft, I imagine, finally asked. “We’d need you to stand up a separate O365 in our own data centers.”

Blink, blink.

“That’d cost a lot.”

“We figure,” I imagine some general or someone saying. “But if we build a private DoD version of O365, we can resell it to other government agencies and DoD sub-agencies, and we can certify that it’ll meet their security requirements.”

Blink, blink.


And so that’s a project – I’ve no idea how far along it is, but it’s happening. Not because someone said why it wouldn’t work, but described how it could. And both sides wanted it enough to work through the problems – ultimately people/political ones, not technical ones – to make it happen.

What would it take for your organization to move to Office 365 for email?

I’m sure you can come up with reasons why you won’t or can’t – many organizations can. Turn those around. What would need to change in your organization to make it happen? Forget how likely that is – we’re just talking. Or take a different “impossible” topic, if you prefer. (By the way, if you’re already using Office 365, please pick a different topic – this one’s just on my mind today, so I picked it as an example.)

Get detailed. “Well, the CIO would need to die.” No, that’s not serious or detailed, unless you live in Las Vegas and own a shovel. Ahem. “The CIO would need to stop wanting to control our own Exchange infrastructure.” Ah, ok. What would that take? Drill down. What’re the actual problems? What would solve them?

You see, even if it never happens – even if you never have the discussion in real life – you’re moving your brain through an extremely important process of problem-solving. I find that if you regularly practice this skill – drilling down to the lowest possible level to identify a solution path – you become better at architecture. Better at troubleshooting. Better at buying a new car. Everything. Getting your brain into a detailed, analytical, problem-solving state really exercises the neurons. It forces you to operate at a very high cognitive level – analyzing, evaluating, and creating, the three top levels of Bloom’s Taxonomy.

You force yourself to truly understand the problem. The CIO’s continued existence isn’t the problem – it’s his attitude. What’s his attitude consist of? From where does it derive? What are the exact anti-arguments, and how could you develop a reasonable solution for them? Again, doesn’t matter if it happens or if you even discuss it – it’s a valuable brain exercise.

Never say “no.” Just describe “how.”

One thought on “Play the Angel’s Advocate

  1. FoxDeploy says:

    Reblogged this on and commented:
    In hindsight this attitude could have helped me to design better solutions for my clients. I’ll keep this in mind for the future.

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