Here's how you can provide feedback on your manager's IT strategy while maintaining appropriate boundaries.

Start by immersing yourself in the strategic goals and objectives that your manager is trying to achieve. Recognize the challenges and constraints they face, such as budget limitations, technological capabilities, and organizational priorities. By appreciating these nuances, you can tailor your feedback to be constructive and aligned with the overarching goals, showing that you are invested in the same outcomes. This approach not only ensures your feedback is relevant but also demonstrates your commitment to the team’s success.

IT is imperative that you have a good relationship with leadership , understanding a problem is one thing but really knowing what their unmet need is as well as their vision clarifies why they say/do what the say/do. The Goals and Objectives need to be very clear thus do not relinquish the need to have clear KPI's by which to measure (and yes this is a great conversation starter to gain insights into that unmet need). Last but not least IT strategy always has multiple stakeholders , Align to them but focus on the sole responsible R in the RACI model that is also A (and that is typically CIO/CTO)

Gather specific examples and data to support your points, ensuring they are grounded in evidence rather than opinion. Structuring your feedback in a clear, concise manner will help you communicate more effectively. Consider using frameworks like the "SBI" (Situation-Behavior-Impact) model to articulate your thoughts. This preparation shows respect for your manager's time and thoughtfulness in your approach, reinforcing your professionalism and dedication to the team's objectives.

Choosing the right moment to provide feedback is as important as the feedback itself. Opt for a time when your manager is not overwhelmed with immediate tasks or crises. Ideally, request a dedicated meeting to discuss your observations, framing it as a collaborative effort to enhance the strategy. Avoid impromptu or casual settings where your manager might not be fully receptive. By being mindful of timing, you show respect for their schedule and increase the likelihood that your feedback will be considered thoughtfully.

IT strategy is al about the right thing at the right moment to solve the right issue...and it is not planned it is mostly reactive, thus your IT strategy should not be super detailed For example when IT strategy requires me to create a better process framework for ...(fill in anything after the dot's) I have created for myself a 'one size fits all' process framework...it is structured yet not detailed in such a way that I am stuck on the choice thus allowing me to talk about the boundaries of the process as the needs arise.

Use a positive, collaborative tone, focusing on potential improvements rather than criticisms. Highlight what is working well before discussing areas for enhancement, ensuring your feedback feels balanced and supportive. Avoid using confrontational language; instead, frame your suggestions as opportunities for growth and development. This approach helps maintain a positive relationship with your manager and underscores your role as a team player committed to mutual success.

As the saying goes, no pne has ever learned anything from listening to themselves talk. It can not be more true than in this instance. Ask questions. Use the questions to ferret out their reasoning. As questions to lead their thinking. Ask questions about how you can add value. Ask questions about needs for clarification. Ask questions to ensure alignment. Ask questions about impediments, challenges and aspirations. Ask..

IT strategy is by nature very technology driven and thus becomes also very resistant to change as technology is not people... Be the connecting factor to not let IT strategy be a technology exercise of functions and features that scares the bejesus out of the people!