There are two types of objective in the critical first 30 days, the short term ones that should be completed in the first week or so and the remainder that can take the rest of the 30 days. Those in the second category often need input from the short term objectives in order to proceed.
So, let's consider the short term ones first and for this to be most effective and expose the most effective, pragmatic outcomes, you need a mind set that you are an IT Assessor, here to watch and review as an outsider (at least initially anyway)::
1. Meet everybody in the department, the senior management, major customers and the key suppliers.
2. The questions that you ask each group are different. For example, questions to the internal IT staff could be: name 3 things that we do well and 3 that we don't, if you could change 3 things then what would you change and why etc. For the senior management, the questions revolve around what do they see as the most pressing issues and what success would look like. Prepare in advance a number of questions for each group and swap them around so that people don't know what is coming.
3. Review the product offering. This is not only from a technical viewpoint but also from a business one. Part of this is looking at competitors and their offering and analysing the differences. A review of the limitations of the architecture together with a review of the proposed development roadmap gives an indication of where the product is likely to end up over the next 12-18 months or so. This together with the competitiveness analysis can often provide several important building blocks for a strategic plan.
4. The final objective is to look for short, medium and long term differentiators between the current product offering and competitors. This is where the 'dreams' that have been pent up within the organisation are brought out into the cold light of day and dispassionately reviewed. At least one and usually several more of these make it onto the strategic plan, with a business sponsor for each one.
Having completed the early objectives, it is time to move on to the remaining ones. These will take the remainder of the 30 days and once defined and agreed with all parties will form the basis of a 'contract' with the business. Deliver on these short term and strategic goals whilst still maintaining a very high availability for the production systems and success is assured. That being said, changes occur all the time so being able to be flexible with the plans and understanding of the need to change them is also important. In fact, it is a good idea to review the plans at least once a month, ideally with all of the business stakeholders, to ensure that they are still right for all concerned.
The remaining objectives for the rest of the first 30 days, build on what has been discovered and understood so far. Those objectives are:
a. Continue putting together a tactical plan to address any time-critical issues and decisions. Merge this plan with the short-term objectives mentioned in (4) above. Review the merged plan for resource issues and budget constraints, and then schedule accordingly. Communicate and agree with the management team then cascade across the IT organisation, having got the 'buy-in' of the IT management team first. If possible, cascade across the entire organisation.
b. Use the medium and long term objectives from 4 (above) as some of the building blocks for a 2-3 year strategic plan. Add to the strategic plan any technology requirements that are necessary to deliver the plan as well as maintain very high levels of system availability. Again, communicate and agree with the management team the plan, then discuss with the IT management team before cascading across the entire organisation (or at the very least IT).
c. Conduct a review of the IT organisation from a structural perspective. Do this on your own, at least initially, in order to prevent staff from having unnecessary worry. However, if necessary, do get external help, particularly if partial or complete outsourcing is actively being considered. If IT is not really business aligned then fill some key positions with people from the business. Again, communication and agreement with senior management, IT management and all other concerned parties are vital for this objective to be achieved.
I hope that the above may prove useful. Please feel free to add your own thoughts in the comments section below.