The short answer
Stop presenting a finished direction and asking for buy-in. Start bringing key stakeholders into the problem before you have the answer. When they help shape the thinking, they stop being an audience you need to convince and become co-owners who want it to succeed.
You keep hitting a wall because you're arriving with a finished answer and asking people to sign off on work they had no hand in. Research on business and IT alignment consistently shows that the quality of communication and shared understanding — not the quality of the strategy itself — is what drives real stakeholder commitment. The process matters as much as the product.
Marcus Aurelius put it plainly: maintain your own purpose free from compulsion — and that cuts both ways. You can't force alignment by pressure or polish. Real alignment happens when everyone in the room feels they genuinely chose the direction, not that they were walked into it. Your job is to create conditions where they can actually choose.
This week, pick one executive or board member who is hardest to read. Don't show them a deck. Ask them one question: 'What would have to be true about our market for this product direction to be the obvious bet?' Listen. Take notes. Let their answer shape how you frame the problem to the next person. You're not collecting permission — you're building shared language, one conversation at a time.