An Undisclosed Number of Tips for IT Strategic Assessments

Written by Tim Haight

I'm VP of Technology Services for CGNET. I love to travel and do IT strategic planning.

September 26, 2019

Anybody can do an IT strategic assessment and make recommendations. The trick is to get your recommendations accepted. This means really knowing what the organization wants and what it’s willing to accept. To achieve this, your communication has to be great, both in what you put out, but, more important, in what you take in.

I come at this as an outside consultant, but I think some of what I say applies to internal studies as well.

The basic idea of an IT strategic assessment is straightforward: Examine all aspects of an organization’s IT operation, compare that to best practices, and make recommendations, usually inside a roadmap for three to five years.

Organizations, however, can have lots of reasons for doing an IT strategic assessment. Some have a new president with different attitudes towards technology. They may want to focus on one part of their IT effort, such as implementing an important application or upgrading their infrastructure. Sometimes, they’re moving to a new office. Some have had some major IT failures or security issues they want to avoid in the future.

The Beginning is Crucial

So, lots of reasons, and it’s great to really understand them at the beginning. Sometimes, you will.  The universal goal of an IT Strategic Plan is to align IT’s activities with the specific goals of the organization, in the timeframe under discussion. Translating the broad goals of an organization into specific initiatives can be a challenge. If you find somebody within the organization who can be clear on this, be grateful.

Often, despite documents full of missions and objectives, and despite a talk with the CEO, you still don’t know the whole story. Talking to department heads is very important.

Your first point of contact, of course, are the people who hired you. Hopefully, these are the people who defined the project and who have been empowered to represent the organization to you. Good contacts are a joy to behold.

Spend enough time with them at the outset to define the research questions clearly. Draft some research questions and let your contacts revise them. You have your own ideas, and this is a good point to bring them up in the form of questions. Use the research questions to guide your creation of interview questions.


You can assess the current state of IT at an organization in many ways. I prefer gathering evidence from interviews. Interviews also uncover what people want.

Here are some don’ts about interviews: Don’t do surveys. Written surveys are too impersonal, but don’t even let your interviews behave like surveys. Please, not a long list of close-ended questions! But crucially, surveys make too many assumptions about what information you will get. The answers are too often determined by the questions.

I like guided, open-ended one-on-one interviews for managers and focus groups for the people in the trenches. Don’t put managers and assistants to be in the same groups. Prepare different questions for each department, based on how they might see the overall issues from their angle. Let people go on, answering several questions with one answer and perhaps not getting to some issues.

Interviews as Therapy

Most people love to give their opinions. Sometimes, talking about IT in an organization is a bit like therapy, particularly if people don’t feel they haven’t had much of a say about IT. If you simply pay attention to people and bring out their thoughts, you will get a good interview. You will, of course, pick the topics for them to talk about, although the ones they bring up spontaneously sometimes turn out to be the most important. Don’t try to show them how much you know or how clever you are. It just gets in the way of what you are trying to learn. Asking intelligent questions is enough.

Take good notes. It is so easy to forget important material. I’ve found that interviewees will tolerate my typing on a notebook computer during the interview. I’ve also found that telephone conversations can be as effective as face-to-face contact. With a microphone headset, this also gives you the opportunity to type.

The end of the interviews is a good time to write a needs assessment report. Submitting this for the client’s review, and getting feedback, ensures you’re on the same page. In general, both in this report and in the final report, good writing is essential. It needs to be clear, concise and a good read.

Project Management

In general, it’s a good idea to have weekly project management meetings with your official contacts in the organization. Do, however, let the clients make reasonable changes to this schedule. Their preferences are what matter, if meetings are still frequent enough to manage the project effectively.

Be sure always to keep to the schedule. There will be delays, but let them be caused by the client, not by you. The greatest source of delays will be scheduling the interviews. Many organizations we work with have people on the road more than half their time. Remember that phone interviews work and that you can talk to people on the road if they are comfortable with that.

The best tool for project management is a Gantt chart, or some other clear timeline, with the number of days and the dates for each task.

Some clients will have lots of delays. Tolerate this, but don’t let it allow you to get lazy. If you can do work ahead of time, do it. If the delays begin to endanger the project, bring up the subject in meetings.

Are You Still Reading?

There’s so much more to say about IT strategic assessments. We include security tests in our IT assessments such as vulnerability testing and evaluating threats to the organization’s attack surface. IT policies have to be analyzed. We suggest technologies and often specific products. At the end, we put together a final report, a roadmap and very often a presentation.

So come back for more. There’s so much more to do, and to avoid doing, that more posts will follow.



Written by Tim Haight

I'm VP of Technology Services for CGNET. I love to travel and do IT strategic planning.

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