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Director of IT in Services (non-Government), 11 - 50 employees
Global Director - Security in Telecommunication, 10,001+ employees
In my experience, a IT strategy has certain attributes that need to be considered and I summarized them here:

- a definition of the business demand first including the current state and the desired state with an appropriate rationale why these should happen, now.
- description of target state and a set of actions that will be taken to reach the desired results.
- a financial plan and budget spending roadmap to realize the changes
- people allocation to execute activity against the strategic aims

You need to be sure that the strategic planning process includes representatives from every department, and ideally should be led by your Chief Information Officer (CIO).
I hope that helps to start a fruitful discussion here.
CIO and IT Director in Telecommunication, 2 - 10 employees
We are currently evaluating IT Strategy by:
1.) Establishing standards
2.) Analyzing results
3.) Measuring performance
4.) Setting goals and making necessary adjustments.
Senior Director Engineering in Travel and Hospitality, 10,001+ employees
A same way we would look at any strategy. People, Process and Technology.

Are we engaging with the people better. First part being the customer - are they getting better value from whatever we are changing as a part of the IT strategy. Are they having a better experience.
Second part being the employee - is the strategy disruptive for the employees. If yes, what are the steps to help them be better at it. If not, is the strategy even setting the bar high.

Has the strategy improved the day to day operations? Have things been simplified? Is it eventually driving better value to everyone? Is it avoiding risk or is it mitigating one or is it adding new risks?

Similar to the process, is this something changing to ensure there is simplicity? Ease of hiring, ease of upskilling and last but not the least is it easy to maintain/sustain in the long run. 

End of the day, IT Strategy needs to either simplify or increase the value of what you deliver - to the customer, or to your employees!
Deputy Director of the CyberSecurity Department in Finance (non-banking), 201 - 500 employees
We are evaluating our IT strategy as follows:
1) achieving the stated benefits and outcomes
2) feedback from the business
3) performance control
Director of IT in Software, 11 - 50 employees
My IT strategy is strongly biased toward the security aspect of infrastructure which includes the purchase of new network infrastructure to replace any legacy hardware and equip my support team with relevant skills to manage and improve security. This includes setting aside 25% of our annual budget to fund and oversee the transition and avail onsite support for a smooth transition.
Director of IT in Services (non-Government), 5,001 - 10,000 employees
The most successful businesses in the world all share a similar trait: vision. Strategic planning is the method used to carry out that vision. If they want to build a strong, long-lasting company model, even the tiniest businesses must engage in some amount of strategic planning. Regardless of the industry they work in, those who are interested in business leadership will discover that adopting the four phases of the strategic planning process is crucial to success.

The four stages of IT strategic planning are as follows.

The process of acquiring, compiling, and evaluating information is called environmental scanning. It's a procedure that also gathers and examines pertinent data to find opportunities and dangers. You should, ideally, have a clear understanding of what needs to be addressed in order to achieve your company goals based on the data acquired during environmental scanning. Additionally, you can expand on what you've discovered to be effective thus far. Perhaps the most crucial step in putting a plan into action is to effectively communicate it in the first place. The long-term vision of the firm should be shared with and understood by the whole organization. Every firm should work to continuously improve, thus part of the strategic planning process is keeping an eye on things and making necessary adjustments.
Director of IT in Services (non-Government), 11 - 50 employees
For us, the main thing in the evaluation of IT strategy is how every aspect of the business from order processing to marketing can be streamlined and improved via efficiency savings. With global economic impacts, money-saving and efficiencies are key to business survival. If we can operate with less duplication, manual processing and manual intervention the better. 

By connecting various sections of the business using modern application methods we are able to improve efficiency. For example, we are utilising open API's from the various providers that we use to automate processes between systems thus reducing the manual input of staff. This also includes the adoption of new software that integrates with our existing platforms making for much speedier implementation and testing stages, together with easy user adoption of the new systems. 

We evaluate each system, application or provider by assessing how it will improve efficiency. The timescale of implementation and the overall impact on the day-to-day operation of the business. If it meets most of these requirements then it is deemed viable to put into a test and evaluate stage where it is normally run in parallel with existing systems until we conclude it is the right choice.
Group IT Manager in Manufacturing, 1,001 - 5,000 employees
Our IT Strategy is measured against delivery towards the Business strategy.  We did a COBIT review with the business leadership 2 years back and that gave us many areas to focus on and then this year we did a 360 with the business leadership again.  Each Executive up to the CEO was given some time with the IT Management team to unpack their frustrations with I.T. as well as their vision for how I.T. can assist them deliver the business strategy objectives and initiatives. 

From there we were able to evaluate what need to change. Now all we have to do is execute!
Director of IT in Manufacturing, 10,001+ employees
We evaluate based on how well it is supporting the current business model and future growth model, utilizing people, process, and technology. 

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