How to get the best outcomes in a complex project (without driving to Invercargill)

Invercargill is cold, even by New Zealand standards, with average temperatures of around 15°C.  It’s one of the southernmost towns in the World and is the gateway to Stewart Island, large areas of conservation land and marine reserves.  But, why am I starting this IT blog, talking about Invercargill?  I’ll get to that.

Consider how you’d feel if you inadvertently ended up in Invercargill when you actually needed to be in Auckland.   The World of IT has shifted over the last decade.  With more and more cloud-based SaaS solutions, technology implementations have become simpler.  Microsoft 365 is a great example of how previously complex technology has become commoditised and is now comparatively easy to deploy.  No longer do you need to hire a development team to code widgets and complicated page templates for a SharePoint Intranet.  Similarly, you no longer need a team of infrastructure engineers and Exchange specialists to deploy Exchange Online.   


Microsoft 365 is now a large platform of many integrated parts.  Often, decisions made in one part can have unforeseen consequences to the way another part will operate.  When seeking to deploy all what Microsoft 365 has to offer, even if taking a step-by-step approach over time, things like sequencing, information architecture, regulatory/legal obligations, governance and change management can typically present obstacles to success.  This is because the aggregation of all these components makes for a pretty complex situation.   


When faced with complexity, it’s natural to try and simplify things – breaking the complex situation down into its component parts.  We’ve all heard the phrase “don’t boil the ocean”, and that makes sense.  But, if your end goal is to have an ocean’s worth of water reach 100˚ c, you’re not going to make much progress by boiling a few kettles’ worth.  Rather, the first thing you should do is take a step back and make sure you fully understand the situation, your desired end-state, freedoms and constraints and stakeholder interests.  Just how much water is there in that ocean? 

Who do you need to talk to about the ships sailing by?  We need to recognise that in complex projects there are multiple ways to achieve the desired outcome, with often overlapping points of view, they’re unpredictable and ambiguous and it is difficult to repeat the results.  In the image above, we’ve broken down the famous da Vinci painting of the Mona Lisa into its high-level component parts.  It’s easy to recognise that painting these components will not lead to a very good replication of the actual painting. 

 Another useful analogy, that I often talk customers through, is to imagine that you’ve purchased a nice shiny vehicle.  This vehicle represents Microsoft 365 (or any another complex technology platform).  The first typical misstep is to confuse the vehicle with the destination.  Microsoft 365 can help to take your organisation on a journey, yes, but where you’re trying to get to (i.e., the business outcome you’re seeking) needs to be defined before you set off driving.  Many organisations have invested in expensive licences and, perhaps as an initial step, have migrated their on-premises Exchange Servers to Exchange Online and configured Azure AD Synchronisation. 

For our analogy’s sake, let’s say that this is the equivalent of putting fuel and oil into our vehicle; these are preparatory steps, but we’ve not gone anywhere yet.  At this stage, the CIO is looking carefully at the odometer and wondering why it hasn’t increased.  Pressure starts to build to demonstrate return on the investment.  At this stage, organisations will decide to start driving and will set off down the road.  Which road?  The one that looks the best from a first glance?  The road that everyone else seems to be going down?  Perhaps this initial leg would be a Microsoft Teams implementation or a SharePoint Intranet as these are easy, right?  To keep with our analogy, imagine that your vehicle is a coach (or a series of coaches) containing your organisation’s staff. 

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As I’m in New Zealand, let’s imagine that our organisation is in Wellington. 

We’ve decided, with no consideration for our ultimate destination, that we’re going to drive South. 

To get South of Wellington, in a coach at least, you have to take the Interislander ferry across to Picton. 

This is a very scenic journey that takes a few hours.  It’s quite expensive, but is truly breath-taking as the ferry slowly winds through the Marlborough Sounds. 

Once we get off to ferry in Picton, we decide to take the scenic route along the East coast towards Christchurch. 

Our passengers are thrilled at the journey and are having a great time taking in the scenery. 

We often hear that initial implementations of Microsoft Teams are like this.  Everyone is happy to have the new technology and quickly gets to work setting up new Teams.  But, if the organisation hasn’t thought about governance or information architecture, such deployments can often end up causing more harm than good.  Let’s continue with our analogy to illustrate the point.  If you continue driving South (well, Southwest) from Christchurch, you will eventually end up in Invercargill.  Whilst Invercargill is a great place, with lots of history, it’s got a small population and its economy is largely centred around primary industries, like farming, fishing and forestry.  I’m certainly not implying that Invercargill is not a nice place to end up.  The point is that, if you end up there, you had better be sure it’s where you want to be.  In our case, of course, we didn’t plan to go to Invercargill – it’s just where the journey took us. 


In our analogy, your organisation’s staff have now disembarked the coach and are stood at the side of the road scratching their heads.  Yes, they enjoyed the journey but are now unsure where you took them and what they’re meant to do here.  You look back on the experience thus far and start to consider the longer-term outcomes you were trying to achieve for your organisation. 

You realise you needed to be in a place with a bustling CBD, high-rise office blocks, with an international airport and high-tech industry – you needed to be in Auckland.  Not only are you not in Auckland, you’re actually further away from there than you were before you set off from Wellington. 

You’ve now got to convince the organisation to get back on the coach so you can retrace your steps back to Wellington.  That’s going to not only be expensive, it’s going to erode the goodwill of the organisation and make it a lot harder to convince them to restart the journey towards Auckland. 

We’re not saying that you should keep your vehicle parked up until you know all the ins and outs of every factor involved in the journey.  Rapid Circle’s expertise is being comfortable working with customers in the complex space.  We don’t try and break things out into component pieces and hope to replicate the Mona Lisa. 

We work with our customers to conceptualise complexity, synthesise the various factors, establish key principles and use hypotheses to test our thinking and come to the right conclusions.  We use tools such as Dialogue Mapping, Emergent Design Practice and then iterate to remove ambiguity.  We quickly help you establish the direction of travel, and high-level route options, so that even if the ultimate destination isn’t perfectly defined, you at least know you’re driving towards it.  This saves time, money and frustration.  Ultimately it helps you make the most from your investment and achieve the business outcomes your organisation is seeking.  We then act as your satellite navigation system – guiding you safely towards your destination and taking account of any roadblocks, new road layouts (cloud platforms are ever-changing) and can easily factor in the necessary service-station stops along the route. 



  1. Consider the longer-term objective you’re trying to achieve – where does your journey ultimately need to take you?  What does that place look like and how will your organisation operate differently when you get there? 
  2. Determine the internal and external constraints you have and challenge initial assumptions.  Consider how these might impact your journey.  Internal constraints might impose driver’s hours that limit the amount of progress you can make each day – this could be in relation to managing change fatigue by not doing too much, too soon.  External constraints might be speed limits – in Microsoft 365 these could be ingestion rate throttling for the migration of data. 
  3. Large technology platforms have many interconnected components.  Identify dependencies and interdependencies to ensure that early decisions don’t end up constraining your options later on.  You don’t want to end up taking a fork in the road that leads to a toll booth, and then find you don’t have the money to pay the toll.  Before you set off on your journey, consider the high-level route options and the main alternatives if you hit a roadblock. 


As a Client Technology Partner, I work with organisations to help establish the right mid to long-term strategies for successful technology and business outcomes.  Contact me today if I can help your organisation to achieve what’s next on your journey with the Microsoft cloud. 

Written by Ady Foot.

Client Technology Partner, based in Wellington, New Zealand.

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