People often ask me, “What question are you asked most frequently?” Aside from, “Are you related to the Bob Ballard that found the Titanic?” that one question keeps resurfacing regardless of the technology and platform. It has a few forms, but they all translate back to one concept, “What should I do first, and then what is next?”

There are many ways I could answer this question. I could give you a list of quick wins in Azure but George has already done that post (found here.) I could walk you through the Cloud Maturity Model which literally is an application designed to figure out where you are in your cloud maturity and offer up what many other customers do next. However, these are both focused on a technology specific answer. “Customers that have deployed ASR do this next… If you have deployed OneDrive than a Groups/Teams deployment is usually next…” This is an excellent tactical way to go about things; and exactly what our job is here on the Cloud Strategist Team. For this blog, I would like to take things up a few levels and provide some thoughts that can be applied regardless of technology.

The first thing to consider when deploying a technology platform is to determine what you really need to have in place foundationally. I know this seems obvious, but sometimes we make assumptions that are not actually required. Nearly 90% of Office 365 deployments start with email as the first workload, and while there are tons of reasons to have your mail in the cloud, one could argue from an end user’s perspective, this is the least interesting of all the workloads. Not in terms of importance, but in terms of the transformation.

This leads me to the next point to consider. Obviously, IT has an agenda and expectations that are needed from any platform change, aging infrastructure, missing compliance elements, failing applications are just a few of the drivers to any upgrade, and especially a move to the cloud. If the transformation is going to happen over a period of time, I encourage my customers to balance the IT goals with giving end users something to sink their teeth in to. As I often say, “It’s a lot easier to keep writing checks when you can SEE the fruits of the labor.”

The best example of a mistake on this front begins with a customer making a huge investment in an IT transformation a few years back. They were thinking like good engineers and decided to focus on the foundation of all enterprise IT environments: Identity and Communications. They kicked off with a 9-month AD consolidation and a yearlong upgrade to VOIP. They were 21 months into a transformation, and the only noticeable difference to the end users was their phones changed from beige to black- and they didn’t know how to use them anymore. Of course, there are numerous benefits to getting your AD consolidated and upgrading your outdated telephony infrastructure, but not many of them are visible to your end-users; some of whom are writing the checks to fund your projects.

“So how do you fix this? You need to meet my IT objectives, don’t you?” The answer is of course you do, but can you sprinkle in a few business wins into your IT agenda.

“If I am moving my infrastructure to Azure, what applications bring visible benefit to your Business users? Can I move those up in the priority queue? Can I give the legal team OneDrive or Teams to help their collaboration challenges even though I am focused on a mail migration to save my failing email infrastructure?”

One final thought around prioritization. When taking on a significant transformation project we also tend to categorize the difficulty of the steps, and then do them in order. If we are nervous, we do the easy stuff first and then move up the ladder. If we are eager beavers, we take down the biggest trees first – often times with outside consulting help. I propose this is actually only one of the elements of the decision criteria.

In this graph, you will see that it is the intersection of Value to Difficulty that should be the prioritization engine here.

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