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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CIO in Education2 years ago

The Smart Classroom concept in 2018 which became a reality during the COVID period. My initial motivation for the initiative was a vision propelled by student needs and trying to find a way of accommodating them in their needs. The needs included ability to retrieve a lecture video if one missed a lesson, ability to attend a lesson from a place on convenience than a lecture room, and the convenience saving travel costs and other security matters that affect students on their travel to campus.

It was not an easy exercise as most executives were hearing this for the first  time and i had been in the employment for less than a year which could have compounded trust issues. I used the idea of lobbying with the relevant stakeholders individually in order to address their fears and concerns around the concept. I used the opportunity to share the evidence of information gathered from students that this is what the current generation of students prefer. they wanted some blended and learning conditions that accommodate their needs than old methods that compelled them to be physically in class. I managed to get support at individual level and proceeded to get my item on the agenda.

I presented this at a retreat in early 2018 and successfully got support and a budget. My institution was the first in Africa to implement the Smart classroom which became handy at the time of COVID and later in as student numbers were limited in classes due to conditions set under COVID rules.

Chief Information Officer in Education2 years ago

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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Head of Transformation in Government2 years ago

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 ;-)

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CISO in Insurance (except health)2 years ago

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 

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Co-Founder in Services (non-Government)2 years ago

Use examples from real life or,kids family, etc 

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