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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. 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 could benefit from external assistance.

1. Do business driven IT projects/initiativies 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, by answering the above questions, business leaders quickly come to clear view as to how they feel about their IT function. As a result, it becomes much easier to identify the next steps and their priority.
Finally, one of the first actions I take post this exercise, is run through the responses to these questions with the Head of the IT department. Comparing the results can demonstrate how well aligned the organisation is on this topic. 
I hope that the above may prove useful. Please feel free to add your own in the comments section below.
All the best.