What are some tried and true methods that you use to communicate your IT strategy to build support and engagement? The sort of things that are part of your personal playbook because they consistently work.  Have you taken any unconventional approaches to communicating your strategy that have worked well?

Agree with the other comments, but would add my kind of "Recipe" for showing a technical strategy - small or large - and driving the right discussions.

I have a single slide/picture with the following components:

1) DRIVERS- name the drivers for the change or strategy (ie, revenue growth as a business priority, increased security risk as an IT priority...)

2) CURRENT STATE - where are we now, what challenges do we have?
3) TARGET STATE - where we want to go/ what we want to look like
4) ACTIONS to get from current state to target state

I usually build a "house" picture, where Drivers is the roof, Current State is on the left, Target State on the right, and Actions is in the middle of Current State and Target state

First and most important, and IT strategy should be aligned with the business strategy. That aids in the communication and engagement by making this about the business and not a siloed IT approach. Secondly, you need to give each staff member a line of sight on how their role/activity ties to the strategy. This gives them connection and buy-in to the strategy.  Finally, you need to communicate the status of the strategy at regular intervals and celebrate the success along the way.

When building an IT strategy, it's extremely important to involve your team and your business stakeholders. Listening to their views, acknowledging their concerns and paving a way forward. If the IT Strategy is built on the overall organisation strategy, it becomes easy to communicate and demonstrate to the executive team (as they have been through the overall strategy process before). A strategy is a collaborative exercise where the right people need to be involved to identify the current state and forecast the future state /roadmap. Executive briefings, vendor showcases, internal staff demos, etc. are some of the communication methods often used to present the strategy.