This was several years back. Keep in mind that early in my career, my father had told me that doing a good job often meant doing what needed to be done in spite of your boss. And by that he meant that you can either make your boss successful and happy or you can run every decision by your boss. In which case no one is successful or happy.
I was working at the time for a Fortune 500 company and our CTO had signed up to deliver a big project for an important client with whom he had personal connections.

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A software developer shares a story about a project where the CTO's decision turned out to be a bad idea. The author and their team faced challenges with the vendor's 'product' and ultimately had to lie to the CTO to meet the project's launch date.

The One Where I Lie To The CTO

Its called “Managing Up.” A successful leader learns that they must manage in both directions.
In picking your battles,
<ul>
<li>asses the risk,</li>
<li>make a solid plan A and B</li>
<li>Throw in a bit of the “Scotty Principle”</li>
<li>execute.</li>
</ul>

So you lie about the milestones you were hitting because you already hit it ?