10 questions to gauge if your IT needs help?

The reputation of an IT function can struggle for many reasons, ranging from an overwhelming workload or a rapidly changing market through to having significant technical debt or a lack of skilled technical staff. Nonetheless it can be hard to know if an intervention is necessary. Personally, I like clarity on which aspects may not be performing or if the needs of the wider organisation are being met, as often these aspects will drive any potential improvement programme.

5/20/20244 min read

10 questions from an external perspective

Below are 10 questions that I have asked many times over the years, to help business owners, CEOs and Chairs understand whether their IT department is a potential cause for concern.

1. Do business driven IT projects/initiatives feel like they are taking longer to deliver?

2. Does the IT function feel like it is no longer providing value for money?

3. Are the IT systems unreliable? If so, are they failing during core business hours?

4. Have any of the IT systems suffered a data breach or a security incident?

5. Does the IT strategy match and support the business strategy? Are they proceeding, on schedule, in lock step?

6. Does the Head of the IT department appear to need help and guidance in order to succeed?

7. Is the IT department demoralized? Is there an unusually high staff turnover?

8. Are any departments outside of IT running their own IT systems?

9. Does IT feel like it does not have a handle on the demand for changes?

10. Is there a particular IT project or initiative that is extremely late and over budget?

In my experience, the answers to the above questions enable business leaders to quickly come to a clear view as to how they feel about their IT function. As a consequence, it becomes much easier to identify the next steps and their priority.

One of the first actions I take post this exercise, is run through the responses to these questions with the CTO/Head of the IT department. Comparing the results can help all parties gauge how well aligned the organisation is on this topic.

Internal IT challenges

However, all of the above points focus on the external view of the IT department and whilst, clearly, this is important to understand, it is neither the only area for consideration nor is it likely to show any potential challenges first. In other words, if the situation has got to a point where outside of the technology teams can see issues then there is a very good chances that there have been problems inside those teams, bubbling away and getting worse for a much longer period of time.

Resolution expectations

This leads me to a further point in this type of scenario and that is around expectations on resolution. The truth is that even there are external symptoms, it can still take a significant amount of time and effort within the wider organisation before there are even discussions on what to do next. Indeed, once those discussions do start, it can also take some time before they are concluded and an action plan drawn up. Going back to my previous point around internal issues occurring long before external symptoms are visible, and now adding the length of time and effort required for the organisation to arrive at an action plan, results in those internal challenges (that are often the root cause) being heavily ingrained. As a result, it can take significant effort and change in order to bring a resolution to the situation. This is also one of the reasons why there is often need for change at all levels within the IT department, not necessarily personnel ones, but certainly cultural, procedural and possibly technical ones. In other words, if the action plan is to replace the incumbent IT leader and no more then there is a very real chance that the situation will not get better for some considerable time. That being said, it is often stated that the replacement IT leader should have the freedom to make the necessary changes as it is "on their head" so to speak. This is true but it is also true that time is of the essence in this situation and the better prepared and briefed the replacement IT leader is then the faster they can execute once in place. Personally, I believe that the numerous times when I have been that IT leader, it would have been most helpful to have gained a head start in my thinking. In fact, I mention this fact in another blog post What to do in the first 30 days of an IT turnaround.

Stakeholder Interviews and an IT Assessment

On that basis, there are few things the new IT leader can do, possibly before they even officially join the organisation, namely:

1. Conduct 1-2-1 interviews with the key stakeholders from the wider organisations

2. Conduct 1-2-1 interviews with their direct reports

3. Get an "off the record" view from their boss or the Board or both

4. Get an external view from any NEDs or other non execs and possibly investors

5. Use a trusted advisor to do an IT assessment or review and to highlight those areas that need the greatest attention and most importantly, suggest an action plan as to how to tackle them and in what order

Culture within the IT department

Finally, in departments where the culture may not fit well with both the wider organisation or the members of the IT teams, it is important to get as many data points as possible. In other words, be sure to go down as many levels of the structure as is practical in order to get insight from a wide spectrum of people. A culture can appear a certain way at one level and perspective and completely different from another. A great example is "Command and Control" can appear efficient and extremely well organisation from one viewpoint and utterly overbearing, demoralising and stifling of innovation from another.

If any of the above points resonate then please do feel free to get in touch. I would be delighted to have an absolutely no obligation, off the record chat and see if I can help.

All the best.