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 Software, 10,001+ employees
Yes and No. Depends on the situation...
Senior Director of Engineering in Software, 501 - 1,000 employees
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.
1 Reply
Senior Director of Engineering in Software, 501 - 1,000 employees

*I did it

Director of IT in Manufacturing, 51 - 200 employees
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.

Director of IT in Services (non-Government), 201 - 500 employees
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.
CTO in Banking, 51 - 200 employees
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!

Chief Information Technology Officer in IT Services, 201 - 500 employees
Yes by gathering evidence and take time to understand concerns and listen actively to the executive's concerns and skepticism. 
Co-Founder in Services (non-Government), 2 - 10 employees
Use examples from real life or,kids family, etc 
CISO in Insurance (except health), 5,001 - 10,000 employees
The method I use in this instance and just about any instance where I would like strategy buy-in is to: 
1. Build a case for the strategy that outlines business outcomes. 
2. Document the strategy and how the strategy will be achieved and how success would be measured. 

3. Socialize the strategy to key stakeholders. 
4. Identify stakeholder supporters 
5. Allow supporters to evangelize the strategy
6. Pick the proper time to engage the skeptical executive 
Head of Transformation in Government, 501 - 1,000 employees
Agree with many of the responses. But 10 years ago, we did just this, modernising an entire business process and technology blueprint in 6 years. We were accused in planning stages and early pilots that what we were doing was  illegal, immoral and impossible. So you can imagine the executive sweat. Today it is status quo and people have forgotten the incredulity. 

1. Lots and lots of data and numbers (Leslie mentioned this). 
2. Very pretty slides, great communication, simple words, no jargon, and solid arguments rooted in strategy and providing them with their benefit in their words. (but include 2 or 3 spaghetti slides to illustrate the as-is mess, it really works regardless of the unreadability)
3. Persistence. Keep on going. Skirt the limits. Keep doing, keep arguing, develop thick skin and show results. Sometimes, people support the persistent.
4. Start small. I absolutely despise the phrase low hanging fruit. It illustrates a lack of understanding of how hard it is what we do. But do start small and show value early. 
5. Lobby. Lobby. Lobby. Build a guiding coalition. This is all basic change management. Read and apply Kotter, et altri.
6. Be radically transparent. Failure is failure. Don't whitewash it. If it is really an ambitious strategy, then you will fail. Fail honestly, fail proudly, and flush the detritus back into the wash cycle of 1 through 5 above. Persist. 
7. Believe in it. If you are just following best practice you will fail. Make it your heart. Bet your career on it. Live and die by the sword ;-)
VP of IT & CISPO in Finance (non-banking), 201 - 500 employees
I would suggest that you attack it in layers and if you can allow t he executive to influence the outcome. 

I start with musing out loud and getting their feedback.  
Then over time returning to it as a quick update from time to time. 
At each time I try to layer in what is in it for them, their department, for the company. 
If they show interest and wish to hear more, I give them more letting them know that we are on the journey together now. 
I lay in potential costs and benefits at a high level early but with more detail as we go.  Don't rush it. 
Over time I have found that the best ideas gain an organic business sponsor and if it doesn't it either isn't such a good idea or may fall into one of those things that you have to build a sandbox for them to understand.  

Hope that helps. 

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Chief Technology Officer in Software, 51 - 200 employees
My personal experience. 

I usually get the feedback and go back with data driven analysis providing details to cross leaders to understand the context and make decision basis data and and not gut feeling. 
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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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