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Part 3 - Human Element and Final Thoughts


Following on from the previous two articles which covered the ‘assessment’ and ‘execution’ phases of the project, the following article provides more practical advice for tackling the complexities and leadership hurdles that these projects typically face.


Know When to Hold ‘em - you need to pick and choose which hills you are willing to die on, the battles you choose not to fight are just as important as the battles you do, at times you may need to align with the company strategy, even in disagreement, whilst consistently leading by example.

It is Hard – systems migrations are energy sapping, time consuming, expensive, full of unexpected challenges and can take their toll both professionally and personally. Whilst you can do as much as possible to mitigate this (you are reading this, which is a good start), know that it will be a rough journey with multiple highs and lows.

This is where having a good team around you is paramount, having people you can trust and lean on when things get tough makes an enormous difference. I have been lucky enough to work with numerous high calibre and talented professionals over the years who have each played their part when times were tough, this ensures that there is not a single point of failure, and each can go through their rough patches knowing that other team members are there to keep the momentum going.


Expect the Unexpected - whether that be config, code, data or businesses processes that were implemented either a long time ago before anyone was around or unintentionally implemented without a formal change process. Know that it wasn’t anyone’s fault, it is rare to come across a scenario where an employee went to work each day just to make life harder for everyone else. For the most part, people are not being malicious when they implement these processes or deviate from the norm, they are generally just trying to get the job done as effectively as possible (according to their own measure of effectiveness).Use these experiences as learning exercises and if you have someone who likes to try and avert an agreed process on a repeat basis, bring them into the camp, make them part of the project team and let them see for themselves why guardrails and governance are important.


Go Easy on the CIO/CTO/IT Director/GM IT/IT Manager - it isn’t an exact science, for those that have worked in tech for a long time we can have a view on how long something will take and how much it may cost, but ultimately when dealing with complex systems migrations, it is impossible to predict all of the variables, people and business process challenges that will be encountered along the way. Ask if they have done everything in their power to manage the situation, if the answer is ‘yes’, trust them. If you don’t, then you have a much bigger problem on your hands. Create a supportive and open environment to ensure that they feel comfortable surfacing the issues as they occur. If you keep shooting the messenger, you will very quickly run out of messengers.



Don’t Forget the Service Recipients - whether that be the customer, your colleagues outside of tech or wherever they may reside, remember why you are doing what you are doing and keep them involved with regular feedback loops. Ultimately there should be a broader strategic plan that not everyone may be privy to, but ensure everyone knows as much as possible about the plan and gain buy in to the project.

Remember that this isn’t a popularity contest, the organisational objectives will almost always trump personal preferences. The key skill here is how you manage the messaging so that you are perceived to be managing the needs and wants of the individuals whilst always aligning to your ‘north star’ (see Part 1 of this series).


Stay on Top of the Detail – many projects start to go awry not because the team aren’t following the plan diligently or there is something wrong with the software, it is simply because market trends have shifted or the business has had to pivot in a particular area, it is times like this when the senior IT leader needs to be across as much detail as possible in all aspects of the project and the broader business strategy.

This can become particularly important when trying to win conquest customers or repositioning products and services to meet a particular demand, if the project team aren’t aware this is happening you will end up with numerous orphan processes managed off system.

Now I happen to think that Excel is one of the greatest software applications ever developed, you can run entire businesses off it should you so wish, but ‘off system’ solutions using tools such as Excel, whilst creative, do not offer the sustainability or innovation needed for long-term growth and effective risk management. Separate article on this topic at a later date.


Relationships – have I mentioned how important the people are… As the owner of the project your relationships with colleagues, team members, executives, third parties and whoever else is a key stakeholder in the project is one of the most critical areas you need to focus on and always manage. Collaboration is key when things go wrong, which they inevitably do with large and complex software implementations, and when they do, the ability to leverage from these relationships will be priceless.

Enjoy the ride...

This article was crafted exclusively by human expertise, without the use of artificial intelligence.

Part 2 - Execution and Management of Migration Projects


Following on from the previous article which covered the ‘assessment’ phase of the project, the following six tips are designed to assist with the execution and management of the project after approval has been received to proceed.


Project Management Methodology – the most simplistic way of looking at a project is as a series of tasks that need to be accomplished in a certain order, you can try using different techniques and ways to make this more efficient, but it mostly comes down to the basics:
    1. have a clear plan up front which is agreed by all key stakeholders. If the plan changes at any point, ensure all stakeholders are aware of this.
    2. communicate early and often – the good and the bad. Well defined steering committees and regular status reports are non-negotiable.
    3. plan your tasks carefully and be militant about maintaining an accurate and up to date plan.
    4. do not be afraid to adapt to changing circumstances, be open and honest when challenges arise and work through them as a collective to define an appropriate path forward.
    5. remember the triangle of balance – scope, time, budget. There is no silver bullet no matter how hard you try and find one.
    6. sometimes the right thing to do is to stop the project and re-evaluate. Hard decisions are hard for a reason and underlying problems don’t magically get better with time.

It is Not the Software’s Fault! – I have seen many good software products tarnished or given a poor reputation simply because they were not configured correctly or in line with the ‘to be’ business processes.Systems cannot answer back and as such they tend to be an easy thing to blame, but behind every piece of software are the people who develop, configure, and maintain it. Always remember this when something is not working the way you would have hoped.

Having people accountable and responsible for all aspects of the various business processes and functional areas will ensure a sense of ownership and pride in the outcomes being delivered, then there is less chance of it being ‘the software’s fault.’

'Surely' is a Slippery Slope to Circular Conversations – when any stakeholder or team member starts a sentence with ‘but surely’ know that common sense may be about to disappear out of the window and any pragmatic or practical debate will become very difficult, assumptions that are not shared by all parties are highly likely to be introduced at this time. In moments like this, knowing when not to speak is arguably one of the most valuable yet challenging disciplines in business.
Honesty and Transparency with Timelines – try and avoid having dates the steering committee are working towards and dates that are communicated to the team, it doesn’t engender confidence in the team and risks losing the trust of staff if they find out (which they inevitably do) that there were in fact two sets of dates in play.



Navigating the Perilous Pathways – maintain a risk register specific to the project, include the standard elements such as likelihood and consequence. Risk management may not be the most exhilarating aspect of a project, often being overlooked early on. However, it's crucial to exercise discipline in this area by keeping the risk register current and up to date - at a minimum, monthly, though fortnightly updates are ideal.This ensures all stakeholders are well informed about the project's associated risks. Additionally, adopting an approach of open and transparent communication in presenting these risks (as outlined in point 4) is essential for maintaining clarity and trust among all parties involved.


Mastering the Art of Transformation – change management is often an overlooked yet essential component of any successful project. Communication should not just be frequent but welcomed, especially if it is clear, tangible, and has a defined purpose. When crafting communications, prioritise addressing the recipient's perspective by answering the question, 'What does this mean for me?' Additionally, ensure the 'So what?' question is answered to clarify the objective of the information being presented. Embracing this approach ensures that every communication is meaningful and directly contributes to the project's success.

This article was crafted exclusively by human expertise, without the use of artificial intelligence.

Part 1 - Setting the Stage for Software Migration.


Given that software migrations in the fleet industry have become a rather common occurrence in recent times, I thought it might be timely to share a few of my learnings gathered over the years. The reputation for IT projects to ‘go wrong’ seems unlikely to abate anytime soon (Project Failure Rates), but there are many proactive practices and processes which can be implemented to avoid being on the wrong side of the statistics.

Having led or participated in many projects in this space, whether they be a multimillion-dollar initiative or a more modest endeavour, the same principles apply, I don’t profess to have gotten all this right during my time and continue to mature and evolve with each project, but I have learnt a great deal over my nearly 30-year long journey as a technology professional.

The following 6 tips are designed to assist in the assessment phase, ensuring a comprehensive understanding of the intricate nature of these projects.

Mastering Complexity - system migrations are inherently complex, particularly in the fleet sector; my experience has taught me that both internal and external stakeholders often severely underestimate this complexity. This underestimation pertains not just to the core fleet asset management platform but also to the adjacent systems underpinning operational and financial processes. To evaluate the complexity effectively, it is essential to consider the diverse range of products, services, processes, and datasets involved. Such an endeavour is challenging and should be approached with the necessary priority, focus and holistic mindset
People, Process, and Systems (not Systems, Process, and People) -
    1. People - before you venture down the path of commencing a migration exercise, whether that be onto a new platform or an existing one, choose your team wisely, I cannot even count the number of times we averted a crisis because we had someone on the team who stepped in and found a way out of it.  This is the time to bring the best people off the bench and into the team – tech and non tech, throw your best guns at this or at least have them standing by and ready to enter the fray should they be needed. Now is not the time for anyone to be precious about who is made available to work on the project. 
    2. Processes – having inefficient or sub-optimal processes in place will unlikely get better just because a new piece of software is being implemented, review your processes in advance and determine whether you will adopt the process dictated by the software or whether the software will be customised to meet the required process, the tail shouldn’t wag the dog here, if the objective of the project is to maximise process efficiency then understand how that will happen in advance of commencing, these things rarely happen by chance during the course of the project.  If the view is that we ‘hope’ everything will work out, ‘hope’ is not generally a winning strategy. Remember: If it is a core process that is a differentiator you want to be better than your competitors and be seen as leading edge.  If it is a supporting process, leverage industry best practices and standardise where possible. 
    3. Systems – whilst you are ensuring you have the right people in place and a strategy for your business processes, choose the right software and vendor to suit your business needs, this should be both tangible and intangible i.e. the software does what you want it to do (noting that sometimes near enough is good enough), and the provider(s) are in cultural alignment with your business.  Having a provider who has good software but a poor record of managing relationships does not bode well for success. 
Measure 3x - measure three times, cut once. Do your due diligence on every aspect of the provider and the project, I will provide a more detailed run through of how to do this in another article.  Suffice to say, and building on my previous point ‘it’s all about the people’, the choice of provider will make or break your project, especially at the pointy end when the pressure is on. The last 20% makes up 80% of the pressure in many of the projects I have been involved in.
Options are King – have a plan a, b, c and d – while leading your team down that one optimum path, always have multiple scenarios in your mind at each step of the journey, how and when you communicate these is up to you but expecting that the chosen path will always be the right one and shouldn’t require deviation is likely to end badly and cause unnecessary stress for you.


Optimum Outcome - define success early on. Depending on personal and professional agendas, objectives and key performance indicators, all stakeholders on the project will have their own definition of success, it may be the:
    1. deprecation of a legacy platform 
    2. an increase in revenue 
    3. a decrease in costs 
    4. the elimination of single points of failure 
    5. a combination of all of that or a myriad of other objectives  

Once you define your ‘north star’ stick to it and don’t deviate, regardless of what external or internal forces are trying to redefine the target.  If the project steering committee hasn’t approved a change in the success criteria, don’t let it happen by stealth. This won’t always make you popular but will make you successful. You must always be focusing on the big picture and not the minor skirmishes which you may encounter along the way.

Governance with Common Sense - good governance and guardrails don’t have to adversely impact execution speed - whilst robust governance is valued, it can also be balanced with collaborative, agile and efficient execution.  Try to thread this concept throughout the project management processes and remember that the team are there to deliver an outcome, not to become experts in creating pretty pictures, writing documents, and mastering spreadsheets.

This article was crafted exclusively by human expertise, without the use of artificial intelligence.

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