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Asking for a friend(*) - when it comes to buying, implementing and integrating enterprise IT solutions like Website + Membership + LMS + payments + etc, etc. how do you convince (non-IT) senior leadership that it’s not just a case of buying a bunch of stuff off the shelf (/cloud) and clicking a few buttons (like they can with if their iPad doesn’t do what they want) when that’s really what they believe and aren’t just pushing back a little for more detail? This in an organisation that has little IT expertise in-house.

Got any effective analogies, arguments or ideas you can share?

(*No, really! I’ve been fairly lucky with leaderships and boards who are willing to listen but this person is being really stubborn about everything being easy.)

2 Spice ups
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My boss is kind of a gear head so I typically use automotive mechanical analogies. Engine tolerances and torque specs (solution hardware and software requirements), interconnected components engineered to work together (unlike many disparate components of a complex software solution), cause and effect of pushing on a pedal and how systems in the car respond physically, etc.

I try to figure out what they’re passionate about and break down the complexities and compare them to IT. Sometimes it works. Sometimes the person has spent their entire life throwing money at problems and has no understanding of how complex stuff really is. Thankfully I haven’t had to deal with the latter. I have had to learn aspects of employment law to provide an accurate analogy to an attorney though, heh.

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The reason their iPad is so quick and easy to work with is because the teams at Apple, and whichever ISP the user is connecting to, have already gone through the time consuming processes on their respective ends, in order to set up what your friend is trying to achieve for their business.

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This is another example of why IT really should involve itself in understanding the business and not just holing up in the server room acting all grumpy and muttering things like “stupid users…” Analogies and examples will differ depending on the situation.

The most effective way is to take their area of expertise – whether it’s accounting or labor or the specific function of that part of the assembly line – and frame it in exactly the same way as they’re expecting technology to work.

For example, to an accounting manager:

So what you just asked for and how you asked it would be like if I was an auditor and told you “I need the amount that left the business.” That doesn’t help, right? You don’t know what amount, or when. And maybe even knowing WHY the auditor is asking will help you get the right numbers, because if I’m looking for cash expenditures from Q2, then I don’t care about inventory spoilage this fiscal year, right? So that’s why I need to know what you’re looking to do, what you want to accomplish, who’s going to be involved, and so on.

I can’t just build you a vehicle without knowing whether you’re looking for a performance car or a heavy-duty truck. And whether you want it in red or purple or silver.

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Or just simplify it for the accounting manager – “I can buy QuickBooks off the shelf for under $200. Why do I need an Accounting Department?”

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Thing is, the person asking the questions here is the CEO and there is no IT team, hiding in a server room or otherwise. There is an existing partner company who provide the membership system and website but they’re not, now the organisation has grown, providing such a great service as they did early on. So, the person I’ve been talking to, who understands how the organisation works and broadly what it needs wants to look at getting a new system (and is aware how complex a process that can be) but the CEO is having none of it and firmly believes you can just buy Dynamics and a bunch of add-ons from the app store and have it all up and running by a week on Thursday.

I’ll take back the various suggestions about trying to personalise the response to the person and see if there’s an analogy that could work for/on them!

Thanks all for the comments so far.