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This joke gets its giggles from a classic bit of wordplay, specifically a pun on the phrase "dead-lines." The setup leads you to think about the literal lines or boundaries of the incredibly straight and well-constructed Roman roads. The punchline then cleverly flips that expectation, using "dead-lines" to refer to the modern concept of due dates or completion times, implying the Romans were perhaps not so great at hitting those. It's the unexpected twist from physical lines to temporal ones that makes the humor land.
Historically, the Roman Empire was indeed famous for its engineering marvels, and their road system was a prime example. Roman roads were incredibly well-built, often straight, and designed for efficient travel across their vast empire, connecting everything to Rome itself, as the saying goes. Many sections of these ancient roads are so durable that they are still visible or even in use today. So, while their roads were certainly top-notch, the idea of them having "terrible dead-lines" for projects is a humorous anachronism, applying a very modern workplace frustration to an ancient civilization for a good laugh.