Have you ever successfully persuaded a highly skeptical executive to go along with a really ambitious strategy? How did you convince them that the investment would be worth it?

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Director, Strategic Security Initiatives in Softwarea year ago
Yes and No. Depends on the situation...
Senior Director of Engineering in Softwarea year ago
I didn't it by suggesting early and frequent check/inspection points.

Also, aiming to deliver value as soon as possible taking advantage of the pareto principle.
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Senior Director of Engineering in Softwarea year ago

*I did it

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Director of IT in Manufacturinga year ago
I have, and actually they just have to trust you, and you in turn have to prove that you were able to accomplish the task and prove the value over time.

Enterprise IT Manager in Services (non-Government)a year ago
Numbers.....lots and lots of numbers. If you can prove cost savings over time, that usually does the trick.  Proof of concept and documented case studies 
can help as well.
1
CTO in Bankinga year ago
1. Understand their goals and motivations (chances are one or some of these will be aligned to your strategy).
2. Understand why they are sceptical.
3. Ask questions to clarify 1 and 2.

4. With answers to 1 (that are aligned to your strategy) explain how your initiative moves the agenda along.
5. Show how you are going to deal with any impediments raised by 2.
6. Explain how you will take a fraction of the investment required to show early value and prove the concept in time boxed fashion without rising the entire investment.
7. Deliver!

2

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