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.

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:

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.

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) -

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:

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.