Article you should read: ‘Play the Angel’s Advocate’ by Don Jones

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

For instance, if your CIO is afraid of change and says ‘no’ to critical updates to infrastructure, that should start you down the path to questioning why it is that he fears change.  Once you understand the reason, you can begin designing a product that would address all of his issues (for instance, maybe he feels but isn’t saying that your team has dropped the ball in testing things in the past, or perhaps he’s been burned elsewhere).  If a CIO doesn’t want to rock the boat, try to begin by pointing out previous successes that were game changing and examine how everyone felt about it at that time.

Everyone wants to be respected and looked to as an authority on the future of their industry; if you provide your client with clear cut reasons that he may want to take a choice of action, and then support him along the way, you may find you’re able to work your way past ‘No’.

Don Jones

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 

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