You need to think about the things that keep you awake at night. For most senior IT people these fall into 2 main areas. The first is being able to handle the peaks brought about by change and yet to deliver business as usual (your business SLA) while this is happening. The second is the constant change and evolution in technology and how to keep up with it to ensure you are delivering the best you can to your business. Outsourcing can help in both areas.
Flexibility and experience. An outsourcer will be able to deploy extra resources and experience for either short term initiatives, or to handle a widening of the service/technology mix as your business needs change. So, make sure you understand what else your potential partner does and who they do it for. Speak to their other customers. Ask why the outsourced, why they selected a certain partner, what their experience was (in relation to what they asked for and were prepared to pay for). Part of the advantage of building a strong collaborative long term relationship is that you can, in effect, take out insurance against the ramp up cost of future change.
Not all outsourcers deliver the same service ? but not all customers are looking for the same.
At one end of the scale is the commodity outsource deal. This is constrained, but cost-effective. You are buying a standard package and taking advantage of the economies of scale the outsourcer can provide by sharing resources (be it people, bandwidth, whatever) across multiple customers. Deviation from this is justifiably expensive since the outsourcer will not have made provision within their service model and charging for significant change. This is not to say that adding an extra server with a standard build, or more bandwidth should be a big deal. But adding a new OS or a different set of monitoring requirements to support, for example, a different application profile will entail real effort hours that the outsourcer will need to recoup. Also, the commodity support model may not be adaptable to fit your new business requirement, at least not at the price you are used to paying. For an outsourcer who is used to providing pile-it-high-sell-it-cheap services, this change may be as difficult for them to encompass as it would be for an internal IT function adopting a whole new technology set.
At the other end is a collaborative, bespoke personalised service that has been designed and built for you alone. Obviously more expensive, but the extra expense vs doing it for yourself could be justified by guaranteed provision of such things as 24*7 expert cover, emergency resources for incident and problem management, pre-agreed lead times for repeatable tasks, access to skills and experience either within their organisation or by having leverage over the big boys that you may not have. The outsourcers experience should be able to deliver change faster, but they should still not be expected to be able to turn everything around with no notice. To facilitate this they should be closely involved with your technical and business strategy so that they can plan ahead to deliver the expertise you need when you need it. Part of what I would insist upon from a collabortative deal is dedicated access to a named Service Delivery Manager who would not only report back on service as delivered, but also form a part of my strategic team.
All this contributes towards more effective delivery for you against your internal SLA?s to your business.
One thing you should not do.
The one aspect of the deal you should be wary of outsourcing is the overall architectural control. You should certainly use the skills and experience of your outsourcing partner to help you design your technology roadmap for the future. But you are the one who is responsible for delivery and you should ensure you have the right team to retain overall control, and awareness of what is being done for you by your outsource partner. In the unfortunate event of a severance of the relationship, you may need to have to pick it up and move it. You also need to be aware of what you have in order to perform due dilligence to ensure service quality and price remain competitive. While outsourcers should have an understanding of the market they work in, it?s not a guarantee that they will volunteer revenue threatening suggestions to you before they need to.
And something you could do.
You don?t have to outsource the lot. Consider co-location for your infrastructure, with a separate niche management company providing a managed service on top. If either falls by the wayside then the other is still there to support you in dealing with the problem. And you still own the kit of course.