How can you help the organization evolve with you when launching an initiative or strategy?

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Chief Enterprise Architect in Finance (non-banking), 10,001+ employees
There are a lot of pieces involved but the people aspect is key. We had to do a lot of socialization first on how we’ll organize and even on the vocabulary of our capabilities. That ensured everybody could speak the same language. It’s important to connect that with how you will plan your work and the budget you are planning to ask for around each capability. One angle was working with the PMO team for annual planning. For the engineering side, we helped to educate them on which technology tools they need in order to understand architecture.
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VP, Chief Security & Compliance Officer in Software, 1,001 - 5,000 employees

We’re working with our head of architecture to place architecture back in its rightful position. Because if the organization has strong architecture, there’s less of a driver for cyber security to intervene where there are poor configurations. So we are on a mission to shift left and ensure that architecture is leading that shift. 

Manager in Education, 501 - 1,000 employees
Any successful drive to change an organization relies on consensus-building, which is predicated on  transparent and regular communications.  It is crucial to understand the basis of change that one's initiative encompasses -- including any and all impacted stakeholders, who are necessary to build consensus --  so that the scale, scope, and context of said impact can be properly communicated.

Inclusive communication is not enough; one must also craft a compelling narrative that demonstrates the value inherent in the change.  This requires getting inside the heads of the stakeholders to ensure that one's messaging is relevant, well-targeted, and sincere.  It only takes a single dissatisfied stakeholder (of sufficient rank) to scuttle a well-laid plan!
CIO in Education, 201 - 500 employees
Learn the business, over-communicate and keep pushing. Pre-building confidence and relationships saves time too.
VP of IT in Education, 501 - 1,000 employees
One way is to bring in your experiences to share, be open, transparent and honest.  Encourage others to do the same.  Also one of the most important things that we as tech leaders can do is to check our Ego at the door.  Too many times I've seen ego halt or derail a launch of an initiative.  Be respectful, helpful and encouraging to those around.  Open mindedness is also important. 
Chief Technology Officer in Finance (non-banking), 11 - 50 employees
Stakeholder management. Understand what you are trying to achieve and how your project effects other stakeholders.
VP of IT in Real Estate, 5,001 - 10,000 employees
People and Communications are key. Clear communications on why and how are key to success, as it helps the fellow colleagues to understand the rationale and reasoning behind all these initiatives and strategies. 
Chief Technology Officer in Finance (non-banking), 1,001 - 5,000 employees
From the postings, I saw excellent suggestions about people, communication, and culture. Frequently I come across many talented consultants pitching textbook versions of ideas instead of ideas contextualized to the industry or even specific enterprise.  One shouldn’t hesitate to challenge experts to think through deeply within your company’s context.  Otherwise, what works in one vertical may not work in another. 
IT Operating Unit Director in Education, 10,001+ employees
Once the project is nearing production or launch, I prefer to do more listening than talking. At that point, taking action on the feedback you hear is going to be crucial to helping the organization evolve to help make it a successful outcome. 
VP( Network Engineering and Delivery) in Telecommunication, 10,001+ employees
Forming a guided coalition of change agents , by communicating and sharing the vision and mission of initiative or strategy. This helps in building necessary momentum as time passes by and helps in buying necessary mindshare.
COO in Healthcare and Biotech, 5,001 - 10,000 employees
The biggest keys are communication and change management.

An organization needs to know where it is headed: you can never over-communicate.

The other is a strong change management plan, which dovetails with communication through the organization.

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CTO in Software, 201 - 500 employees
Without a doubt - Technical Debt! It's a ball and chain that creates an ever increasing drag on any organization, stifles innovation, and prevents transformation.
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