Question 1/20

Do you find too often you rely too much upon the knowledge of a few key individuals to maintain and improve your systems

Sometimes in an organisation there can be a few "gatekeepers" to critical systems and processes whom the business relies upon to operate successfully. Often these individuals will have a huge amount of knowledge stored in their minds which is not documented or accessible by others. In other situations it might be that there are too few people, sometimes just 1 or 2, that have the skills and experience required to manage these systems and processes.

Question 2/20

Do minor changes in business processes turn into significant IT projects which are time consuming and expensive

It is not practical for any company to have all their technology developed and maintained in-house as custom development. Custom development is expensive, often slow and of course requires a lot of ongoing maintenance. When we lean into the market for technical solutions, whether a SaaS solution or an ERP amongst many, there will be compromises in terms of what that software can do and how we would ideally like it to work. Sometimes a business can benefit from the speed and cost but also sometimes the lack of ability to control how that software works can begin to hold us back.

Question 3/20

Do you frequently end up with complex ongoing management and maintenance responsibilities for systems and software which was not expected

There are clear and obvious costs when first procuring technology or implementing our own systems, but over time these costs can snowball unexpectedly. It's not unusual for a solution that represented good value in the past to become wrong-sized in the future. Sometimes as our usage increases our costs increase. Sometimes as the demands we put upon our technology increase, the costs to improve that technology and maintain it can increase.

Question 4/20

Do you feel like your current IT architecture has evolved to become unnecessarily confusing

Working with third parties is an excellent way to achieve technology outcomes, but over time we can become concerned that we have become to reliant on that third party. This can create fears around price increases that we find hard to reject, changes in the operating model of that third party or an inability to align or motivate a third party towards our own goals and objectives.

Question 5/20

Do you feel like the burden of operational responsibilities on your technical team makes it hard to find time to address strategic improvements to your IT estate

Knowing where you want to be and the ability to get there are not the same problem. All businesses realise they must continue to change and pivot in order to keep up or stay ahead of the game. At times this can mean implementing new technologies or capabilities that we simply do not have the experience or resources to achieve today. Once we understand where we want to be, only then can we understand whether the team is able to get there without new skills training or fresh hires to augment them.

Question 6/20

Do you feel like you are missing out on the benefits of many modern technology concepts to drive your business forwards (e.g.AI, RPA, Microservices)

It is extremely common for all but the newest of organisations to carry old technology which underpins mission critical systems and capabilities.Over time legacy technologies can become significant anchors to our progress, but we can continue to view them as too expensive, too complex or too dangerous to touch. Organisations reach a tipping point where the benefit of tackling these millstone issues outweighs the negatives of doing so, but that does not always mean that moment is recognised or acknowledged.

Question 7/20

Do you feel you are missing out on a lot of the value of the third party tools and systems you use due to the lack of integration

This can be both a cultural or technical issue. A common example of this problem will be a member of the business asking for what outwardly seems to be a simple feature or capability to be implemented by IT, but then a lengthy and expensive scoping and development exercise begins. Maybe it is the instinct or passion of your development team to retain control over your systems or maybe it is because your systems refuse to play nicely with third party tools and solutions.

Question 8/20

Does your technology stack make it difficult to find and hire the right talent into your organisation

By now every company is aware of the importance of the data they hold in making good decisions and satisfying their target audience. With that said, many organisation know that there is a lot more value and opportunity in the data they hold to create success for the business. Whether that is in creating better user experiences, creating smarter supply lines, better forecasting for peaks and troughs or creating new business opportunities from the value of the data we hold.

Question 9/20

Do you feel there is a gap between the service and support your vendors or suppliers offer and that which you actually need

By now every company is aware of the importance of the data they hold in making good decisions and satisfying their target audience. With that said, many organisation know that there is a lot more value and opportunity in the data they hold to create success for the business. Whether that is in creating better user experiences, creating smarter supply lines, better forecasting for peaks and troughs or creating new business opportunities from the value of the data we hold.

Question 10/20

Do you feel your IT is able to flex for peak demand and contract efficiently during lower times of demand

It is common in organisations, for what the business perceives as a minor change in process or business need, for those changes to become significant project deliveries to undertake. Business processes, especially long running processes, often touch multiple systems or functional areas which translates to downstream impact on the resources and technology that support them. Delivery approach, system architecture, data architecture, API architecture etc also contribute significantly to the impact of these changes in delivery terms. More so in simpler process changes where their impact will be far more apparent.

Question 11/20

Do you find it a challenge to translate your business needs into technical solutions

When a company invests in a new software (e.g. Salesforce or Mulesoft), it is expected that there will be an overhead associated with that key investment. Frequently however organisations can discover that a range of other technologies were adopted in order to get those things to work, or just implemented by enthusiastic and well meaning team members along the way. Perhaps your organisation finds itself with a range of open source technologies which are unsupported at enterprise level which still require patching and updating to ensure continued operation.

Question 12/20

Do you often feel like your business is adapting to the technology rather than adapting technology to your business

Given business applications are rarely built to work elegantly with everything else, that vendors rarely look beyond an ability to connect to their application, that lots of commercial software developers write poor APIs and that all organisation have some legacy it is very difficult to deliver on elegant. Short of using an application monolith or a pure micro services approach, elegant probably feels unattainable for many organisations. Elegance through integration requires considerable capability in a what is already a challenging discipline.

Question 13/20

Does your business often encounter multiple competing visions / philosophies on how to achieve outcomes

As organisations continue to implement new capabilities, features and technologies, the responsibilities of an IT team can snowball. Whilst technology becomes smarter and in many ways more simple every day, it is also true that the range of demands placed upon our IT capability increases, often at a greater pace. This means at times an IT function can find itself so consumed by managing the "as is" state, that time cannot be devoted to the desired "to be" state of the business.

Question 14/20

Do you feel like the operational running cost of your existing solutions is too high

Implementing the latest concepts in technology can be an excellent way to gain competitive advantage in your space. Think about for instance what Netflix, Amazon or Uber achieve in their respective spaces by utilising technology which their competition has not. To answer this question think about your competition and consider whether your organisation is constantly playing catchup when it comes to adding new capability or whether you feel like you are ahead of the curve in your respective market.

Question 15/20

Do you feel you are over reliant on suppliers & third parties to maintain successful IT operations

When we purchase SaaS or ERP tools, often we buy them because we are focussed on some particular features or capabilities we desire. It is common to discover that there are a great many additional features that are desireable to our organisation, but the lack of experience with the tooling and the integration needs to make those features work can be prohibitive. This can leave organisations benefitting from only a relatively small percentage of the true power of our investments.

Question 16/20

Do you feel like you are missing critical roles and skill sets in your business to achieve everything on your roadmap

Finding the right people to work in our organisations can be one of the biggest and most important challenges leaders face. In IT this problem is amplified by the number of technologies we work with and the relative popularity of those technologies. Often organisations may find themselves wedded to obscure, niche or legacy technologies because the perceived pain to update or replace them is high, but this can lead us to a position where we fear losing critical internal resources because our ability to replace them is so severley restricted.

Question 17/20

Do you have legacy systems which have become too difficult or too expensive to replace

It is common to rely upon third parties for the successful operation of our IT systems and capabilities. Most third parties will of course promise to support and adapt to the needs of your organisation during the sales process, but it is common to discover that the actions behind the promises do not align. That is because third parties must provide services and support to many organisations at once whilst still working with a common operating model themselves.

Question 18/20

Do you find you have to resort to development where there should be simple off the shelf solutions to small problems

Many situations can create a surge in activity around your business, whether that be seasonal peaks, weather conditions, geopolitical events or viral media events. Ideally during these moments your systems can cope with the demand by self scaling to provide the additional capacity required, but frequently this is not the case. Similarly during your quietest moments, paying for high availability can be a waste of money when demand is at its lowest.

Question 19/20

Do you feel you are collecting and leveraging the business intelligence from the data your organisation holds

Failing to solve the business problem when implementing a technology, the business being underwhelmed by the solution delivered and complete failures in implementation affect all organisations at some point in time. Generally the resources involved in delivering those solutions look beyond their delivery for reasons why things go wrong. It’s human nature and generally those reasons have contributed to the failure. In some cases organisations that lack capability or maturity in capability practice avoidance because they know that it is beyond their capability. In a lot of cases organisations try and simplify implementations and do so to the extent that they minimise the value of the implementation to the business.

Question 20/20

Do you consider your current integration approach to be right sized and delivering sufficient value in relation to the integration problems you are solving?

There are as many ways to solve a problem as there are people trying to solve it. Each group of people have their own priorities, agendas and beliefs in how to solve a problem. Sometimes in organisations those beliefs in how to address a problem can clash or oppose one another. Sometimes an organisation can end up following multiple paths that do not necessarily compliment one another.