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Tips & Tricks to Master Software Migrations - Part 3

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.


Andy Graham

Andy Graham has been working in tech for 30 years, with nearly 25 of those as a senior technology leader for some of the most preeminent fleet management organisations in Australia, New Zealand, and the UK. Andy has led several multimillion-dollar technology projects whilst remaining ‘hands on’, excelling in pragmatic problem-solving and managing complex technical scenarios. As a strategic systems thinker, Andy has also led the design and development of industry-leading software solutions, constantly driving innovation and efficiency in product development.

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