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There's no great trick to it, though it does help to avoid forcing the connector if it doesn't slot in easily, as this usually means you're using the wrong port or the cable is upside down.
Most modern machines offer a mix of connection types, so it's worth knowing which one you're dealing with. You might find a standard USB 3.0 port, a slimmer USB-C slot, or, on newer laptops, a Thunderbolt port capable of shifting data at remarkable speeds.